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**Transgender Stories** · 05-04-2016, 03:44 PM

Part 2

Enter Jaden

I went to high school as a freshman. The first day, I
met a guy named Jaden, who was about 6' 4" tall with sandy brown hair and
piercing blue eyes. I was 5'7" then and haven't grown since. Jaden was
trying out for the basketball team and I immediately decided that the
basketball team needed another trainer. The thought of wrapping those tall
hunks with tape was a perfect job for me. My interest in girls was just as
strong, but guys were easier to see naked in the shower (without getting
arrested). I went to see the coach and he immediately agreed, since his
previous trainer had graduated and he was looking for a replacement.

It was everything that I hoped it would be. Naked, athletic bodies
everywhere. Guys needing their muscles rubbed and little old me there to
oblige. I especially enjoyed it when Jaden got a pulled calf muscle and I
had to rub it down while he lay on his stomach. I got hard just looking at
him that way.

One Friday, after school, Jaden invited me to come over to his house for
dinner and a late movie. I told him that Uncle Hal and I played golf on
Saturday mornings. He said I could sleep over and his dad would take me
home the next morning. I agreed (thank you God) and met his family that
night. His father, Carson, was 39 and still in good shape. His mother
Jane was a beautiful woman with big tits and a great ass. I got aroused
watching her walk across the room.

That night was uneventful, although Jaden and I slept in the same bed and I
spent half of the night trying to figure out a subtle way to suck his big
dick. His cock was in proportion to his large frame. It was slightly
larger than mine and very thick. I just couldn't work up the nerve. The
next day, Hal didn't know what hit him. I was so horny, I fucked him
senseless.

Friday nights at Jaden's became a regular thing. He invited me almost
every Friday and I always accepted. By the fourth Friday, I was desperate
to try something. I brought over some of my father's port wine in my
overnight bag and talked Jaden into drinking some before bed. By the time
we went to sleep, he was definitely intoxicated. We went to bed about 1 AM
and an hour later I made my move. He had just turned over on his back and
was sleeping soundly. I reached down and slipped my hand in his briefs and
started stroking his cock.

Jaden started to writhe and moan but didn't open his eyes. I kept stroking
and he got so hard. I decided it was now or never and I moved down and
took his cock in my mouth. I didn't know what to expect and I was afraid
he would punch me. Instead he held my head and started thrusting into my
mouth. I really worked that cock over well. When I swallowed it all he
began rubbing my hair and groaning. I knew he would not last long and I
wanted it to be very special for him. I began bobbing and sucking,
stroking and milking him. When the first spasm erupted in my mouth, he let
out a very load groan. I was terrified that his family would hear him. He
bucked his ass feeding me his cum as his cock pulsed in my mouth. When he
finally finished, he whispered, "Thank you" and turned away to sleep. I
was confused, not knowing how he felt.

The next morning he didn't say a word about it and his father drove me
home. Hal and I had great sex that day, but I couldn't stop thinking about
Jaden's reaction. At school that week, he acted as if nothing had happened
and when Friday came, he invited me to stay over again. When I hesitated,
he winked at me and said "Bring the wine again." My dick got hard just
thinking about the night to come. As soon as we turned the lights out that
night, he slipped out his huge slab of meat and offered it to me. I
accepted it quickly and started working him over, rubbing his balls,
squeezing his shaft with my soft lips, and squeezing his ass with my hand.
After a few minutes, he pushed me away and asked if he could fuck me. I
tried to contain my excitement, but quickly agreed. I got a rubber from my
bag and slipped it over his thick shaft. I lubed my ass and his cock and
told him to go easy. I had never had a cock this big and I was nervous.

He was gentle as he prepared to mount me. He wanted me on my back so he
could watch my face and I was happy to oblige. He pressed his cockhead
against my tight hole and penetrated me carefully. My cock grew harder as
my ass stretched to accommodate his thick love log. He pushed slowly,
rocking a little, until his balls rested against my ass. He was going too
slowly for me and I hissed "Fuck my ass with that big dick, you stud." It
was corny but it got him going. Before long he was moving in and out like
a jackhammer and I was in heaven. My knees were pinned back against my
chest and his balls made a slapping sound as they bounced off my ass.

When he was ready to cum, I told him I wanted to eat it, but he really
wanted to shoot in my ass, so I let him have his way. When he shot his
load, I could feel it pulsing in the rubber sheath that was buried in my
ass. He let out a loud yell when he came and again I feared that everyone
must have heard. He fell on my chest and, to my surprise, kissed me
deeply, his tongue exploring my mouth.

When he rose, I thought he was going to sleep. Instead, he began stroking
my cock. Then, to my surprise, he took me in his mouth and started sucking
my dick. I was stunned, but very pleasantly so. He was not bad for a
rookie and he was able to take most of my cock without gagging. I was
eagerly awaiting my orgasm, when he pulled off, leaving me hanging (Ok,
standing straight up). Before I could protest, he leaned over and
whispered, "Please fuck me David. I need to know how it feels." He was
just full of surprises!

His big cock gave me an idea. I lay on my back with my head and shoulders
raised by pillows. I slipped on a condom and instructed him to straddle me
and place his sphincter against my cockhead. He pressed slowly against my
cock until, finally, the head penetrated his ass. I then moved forward
with my plan. By bending and pushing my shoulders forward I was able to
get the head of his prick in my mouth and suck it while he impaled himself
on my hot sausage. He was happily surprised and it took his mind off the
painful stretching his ass was enduring as he lowered himself on my log,

Once he had settled all the way down, with his balls resting on my stomach,
he began to buck forward, giving me more of his cock to suck. The feeling
on my cock was unbelievable. Hal was tight, but this was my first cherry
boy and the feeling was indescribable. The great cocksucking he was
receiving encouraged him to ride my cock and he really got into it. After
his sweet ass adjusted to my big anal invader, he really started to ride
me. I had trouble keeping his cockhead in my mouth.

After a few minutes of this he began to moan loudly then, with a yell, he
exploded in my mouth. His bucking pulled his cock from my lips and he
sprayed my face with his sticky, hot cum. That really got me going and I
shot a huge load in the condom that was lodged in his tight butt. He
removed the condom and licked me clean, then flipped over and prepared to
sleep. I curled up behind him, reaching around to fondle his big cock
while he drifted off.

In the morning I went to the bathroom that was connected to his bedroom and
climbed in the shower. A few minutes later, he climbed in behind me and
began to rub soap all over me. His cock rose and grew hard as a rock.
Without a word, I leaned forward and placed my hands against the tile. He
rubbed his cock with soap and placed it at my entrance. Leaning forward,
he penetrated my manpussy and began to ream me good. It was like a
wonderful dream. He held my hips and steadily slid his thick, hot slab of
cockmeat in and out of my steaming, tight ass. I began to push back to
meet his thrusts, forcing him all the way in as his balls bounced off my
backside. I began to talk dirty to him, telling him how big his cock felt
in my ass and urging him to fuck my ass like he would a girl's pussy. He
got very excited and told me that I was better than any girl he had been
with. When he came, I swung around and swallowed every drop. His groaning
was so loud that I was sure everyone in the neighborhood had heard.

After breakfast, his father and I headed out, but didn't go through the
usual smalltalk ("How's school?", yadda yadda, etc.). He was very quiet
and I got a strange, uneasy feeling. Finally he asked, "How long have you
and Jaden been having sex?" I just froze. I didn't know how to respond.
He finally said, "It's OK David, I'm not angry. I understand how it can
be." I started to mutter an apology, but he interrupted and said "When I
was in college, I had sex with men and women, but when I married Jaden's
mother, I decided I would forget about men forever. I have not touched
another woman or a man since, but when I heard the two of you going at it
through the door, some old feelings came back. I got so aroused hearing
the two of you that I went back to bed and fucked Jane like a madman. She
didn't know what hit her." I was amazed at the things he was telling me
and I didn't know how to respond. I just stared and waited for him to get
to the point.

Finally he asked, "Is Jaden gay?" I told him that both Jaden and I were
into girls too. That seemed to relieve him. Then he asked, "Was Jaden
your first man?" I told him that I had been with others (OK, I
exaggerated), but I wasn't about to tell him that I was on my way to fuck
my uncle who had been fucking me for months. He then told me that,
although he had never been with a man since he got married, he had always
felt that something was missing. I told him that I understood that
feeling. He then asked the $64,000 question, "Would you be interested in
doing something with me?" It felt strange to admit it, but I told him I
would love to suck his cock. He looked so happy, I almost felt sorry for
him. I leaned over and unzipped his pants. He looked like a deer in the
headlights. I reached in and pulled out his cock, which was six inches
soft. I started to stroke it and he almost drove off the road.

He suggested that we pull behind a shopping center that was not open at
8:30 on a Saturday morning. After we parked, I immediately took him in my
mouth and started working him over, sucking and licking while his cock grew
to its full eight inches. He was even thicker than Jaden. He was so hot,
despite having fucked his sexy wife just a few hours earlier. I knew he
wouldn't last long and, sure enough, he started breathing faster and shot a
string of cum straight down my throat. I kept sucking until there was
nothing left to swallow. He kept rubbing my head and thanking me, then
started the car and drove me home.

When we got there, he thanked me again and I went inside. When Hal
arrived, we drove off and he leaned over and gave me a big kiss. He pulled
back and looked at me with a shocked look. I realized that he could taste
the cum that Carson had just shot in my mouth and I was very concerned
about his reaction. He just grinned and asked me whose cock I had just
sucked. I decided to come clean and told him the whole story. He got so
hot that he made me blow him right there in the car on the way to the
motel. He kept kissing me to get another taste of Carson's cum. The sex
that day was hotter than ever.

After we had been at it for an hour, I was sucking Hal's cock and suddenly
I realized that a maid was standing across the room, staring at us. We had
not heard her knock and come in. She started yelling in Spanish and Hal
freaked. I could understand enough to know that she was going to tell the
manager. I jumped up and, in broken Spanish, asked her not to do it. She
calmed down and told me that she had never seen anything like this. I
noticed that she had a great body and started to get aroused again. When
she saw my cock harden, she started to laugh. I asked her if she would
like to stay and watch. At first she said no, but I talked her into it. I
think she was amused and intrigued at this point.

Hal had lost his erection so he started sucking my dick. The maid, whose
name I later discovered was Angie, sat in a chair and started to rub her
crotch. Before long, her hand was inside her panties, then the panties
came off. Remember that I had never been with a woman before and the sight
of her pussy lips made me so hot. I tossed her one of Hal's dildos and she
started fucking herself with it. Finally I couldn't stand it and I jumped
off the bed and knelt between her knees. She was so hot, she didn't even
attempt to stop me. I began licking her pussy and tonguing her and she
grabbed my head, pulling me closer. The pungent aroma of her cunt was
intoxicating and cuntjuice poured over my face. I motioned for her to show
me her tits and she obliged, taking off her remaining clothing. Her tits
were very large, at least a D cup. She kept yelling "Coma mi concha (eat
my cunt)"

Hal was tired of being left out and joined us, inserting his cock in my ass
and starting a slow pumping rhythm while I tongued and fingered her cunt.
I knew enough to know where her clitoris was and when I started working it
over with my tongue, she went wild. When she came, she covered my face
with pussy juice. Afterward, I asked if I could fuck her. She agreed and
slipped a condom over my cock. She knelt and started sucking me while Hal
continued to fuck my ass.

We finally moved back to the bed and she lay on her back and let me slide
my cock in her tight cunt. She was no virgin, but she was my first woman
and it was heavenly. There is something so soft and inviting about a
woman's love box. I fucked her in several positions, watching her cum
twice. Then we moved into a 69 with her on top.

Suddenly, Hal's cock appeared and slid into her pussy. I continued my
tongue work, licking her cunt and Hal's cock at the same time. I think
they both found this incredibly erotic. She really went to work on my cock
and I signaled her that I was about to cum. She pulled my dick out and
aimed it at her tits. I squirted a big load of juice all over her tits.
She then licked me clean and turned to straddle Hal. She leaned forward
and rubbed her tits in his face as he licked off my cum.

As she fucked Hal she kept trying to tell me something. She motioned at
her ass and said "Tome mi culo" over and over. I finally understood that
she wanted me to fuck her ass while she rode Hal's cock. For some reason,
I hesitated and she yelled "TOME MI ASNO." I decided that I had better do
it to shut her up. I lubed my cock and positioned it while Hal stopped
fucking. She was really tight, but not an anal virgin. It felt really
great with Hal's cock applying pressure through the walls of her hot, juicy
snatch. We managed to get a good rhythm going and the vision of her taking
us both and loving it was so stimulating. When I was ready to cum, she
motioned me to bring my dick to her mouth. She and Hal were both licking
me and when I erupted, they shared my cum. I fell back exhausted, then
started fingering her asshole, while she came. Hal followed quickly and
Angie and I shared his cum. We rested a few minute, then she had to get
back to work.

It was an amazing day. I've been involved in much more kinky sex in much
more bizarre circumstances, but this day was full of firsts - my first fuck
with Jaden, my first encounter with his father, my first time with a woman
including oral and anal, and my first male/female threesome. I loved
licking the two of them while he fucked her and I loved eating out her cunt
and sucking her tits. I was in a daze for a week. I thought that sex was
supposed to be like this and it changed my perspective on relationships. I
have never been in a monogamous relationship and probably never will.

**Transgender Stories** · 05-04-2016, 03:48 PM

Part 3

The following Friday, Jaden and I had lovely sex, with a new twist. Jaden
had purloined some stockings, a bra, and crotchless panties from his
mother's dresser. He asked me to wear them while we fucked and I agreed.
I loved imagining his mother in them and fantasized about fucking her and
sucking those big tits (Relax, you perverts, I never got to have sex with
her.). The feel of the stockings was incredible and I was amazed at the
way the bra made me wish I had big tits to fill those cups. I was a bit
uncomfortable with the way these feminine feelings crept in. It seemed so
natural.

That night, we finished with him in my ass. When he started to pull out, I
stopped him. I positioned us in a spoon position with his cock still
buried in my ass. I told him to leave it there and he did. I drifted off,
but awoke a while later to the feel of his hard cock sliding in and out of
my ass. He lifted my leg to get better penetration and really fucked me
hard. I loved every minute of it. My favorite part of the night was when
I fucked him, wearing his mother's lingerie. It was so erotic. I
realized, eventually, that he had a real hardon for his mother, but
couldn't admit it. This was the closest he could get to fucking her.

At breakfast, I kept staring at Jane and feeling guilty. I had fucked her
son, sucked off her husband, worn her sexy panties, and lusted over her big
tits. I just felt bad about it. Then Carson told Jane that he needed to
take their motor home in to have something done on it. He told me he would
drop me off on the way. Of course, even as naÃ¯ve as I could be at that
age, I knew something was up.

Their motor home was one of those really expensive types that cost more
than most homes. As soon as we pulled out of the driveway, I knew what he
had in mind. He finally worked up the nerve to ask if I would have sex
with him and I eagerly agreed. He told me that he had listened outside
Jaden's door while his son fucked me and had to fight to keep from breaking
down the door. He said he had gone back to bed and buttfucked Jane all
over the bed. I would have paid big money to see that. That's when the
idea hit me. I told him I would only have sex with him, if he could
somehow arrange for me to watch him fuck Jane's ass. He hesitated until I
reached over and stroked his dick. As I expected he caved in quickly. We
pulled behind the shopping center and climbed in the bed.

It was very hot with him because it brought out the lust he had kept
bottled up for 17 years. We did it all -- blow jobs, ass licking,
assfucking, 69, cum swallowing, etc. He couldn't get enough. His ass was
not as tight as Jaden's because he used one of Jane's vibrating dildos on
it when she was not around. Hal was out of town that day, so we had plenty
of time. I let him fuck me twice and swallowed his cum both times.

When we finished, he drove me home. On the way, I masturbated him and we
planned my voyeur party. We agreed that Wednesday would be the best time,
because Jaden would be at his regular Key Club meeting and Carson could get
me in position before Jane got home. I really believe that he was getting
aroused by the idea. Their bedroom had his and hers closets and he could
put me in his where I could have a good view of the bed with the door
slightly open.

Everything worked beautifully. I had to wait a long time because she
stopped at the grocery store on the way home, but when she got there, he
was able to get her aroused very quickly. This was always a "sex night"
for them because of Jaden's meeting schedule. Jaden couldn't miss because
he was the vice-president. They got busy immediately and it was everything
I dreamed it would be. Her body was exquisite and the sight of her sucking
his cock and her tits bouncing when he fucked her was priceless. I groaned
once, but she was moaning so loudly that she didn't hear me.

Finally he got her on her knees and slipped it up her sweet ass. Then she
stuck a vibrating dildo in her pussy. After a couple of minutes of
watching his big dick pound her ass, I shot a huge load all over the inside
of the door. I kept stroking as he fucked her and eventually started to
get hard again. When they finished, she went to take a shower. The sight
of her getting up with cum running down her legs and shining on her face
and tits was breathtaking and my dick got amazingly hard.

Carson opened the closet door and asked me what I thought. I told him that
he could fuck me any time he wanted. He saw my hard cock and went down on
me right there. I told him that I had to leave before she caught us. He
said that she always stayed in for at least 15 minutes and we could hear
the shower stop. I reluctantly let him continue, half-hoping that she
would catch us. I shot a load down his throat and hurried out. Afterward,
I felt very guilty about using Jane in that way. I decided I would never
do anything like that again.

The following weekend, he could not use the motor home story again so I
took him to my motel and fucked his brains out. Later that day, Hal made
me tell him about it while he fucked me. I got this brainstorm that we
should get together with Carson or Jaden, but Hal was reluctant. He was
afraid that word would somehow get back to my parents and he would be in
big trouble. I decided to let it go -- for a while.

I Get Caught and Make New Friends

On Moday, at school, this tall skinny kid named Bobby took me aside and
said he had something important to ask me. I didn't know him well, so I
was surprised when he asked "Are you a male prostitute?"

"Of course not." I said, half-stunned and half-angry, "Where did you get
that idea?"

"My dad owns the P______ Motel and I work there on Saturdays. I've seen
you there with different men and I checked the rooms when you left and
found used condoms. I know you're fucking around with these guys."

I knew he had me, but I didn't know what to say. Finally I asked, "Have
you told anyone about it?"

"No", he said, "I wanted to hear your side of it first."

"Well Bobby, I guess I don't have to tell you that I am bisexual and I have
to go to a motel because my parents would not appreciate me doing this
stuff at home. For what it's worth, I've had sex with a woman there too."
I don't know why I felt that I needed to add that.

"I can understand David, but you're going to have to do something for me to
keep me quiet."

How did I guess that was coming? When I asked him what it was, he said I
had to go to a movie with him on Saturday night. This seemed rather
innocent, so I agreed.

That week, I did not stay at Jaden's on Friday, because they were out of
town. Hal showed up with a surprise. He had been very excited about my
lingerie session with Jaden and he brought a really slutty whore outfit for
me to wear while we fucked. It had black leather boots, black fishnet
stockings, a leather waist harness that held my cock in place, and a black
boustierre He even had makeup, which he helped me apply. I was stunned by
the transformation and so was he. I actually looked kind of hot. He kept
calling me his pretty whore while he fucked my ass.

That evening Bobby and I met at the local mall. Then we got in his car (he
was 16) and he drove to an adult video store. I asked him what we were
doing there since we were underage. He told me the night manager was a
friend of his and he went inside alone. A couple of minutes later, he came
back out and we drove around behind the building to the delivery door. The
door opened and we went in. We went inside a small room and Bobby told me
it was a private viewing room. There was a large screen, a chair, and a
small padded bench in there. I was scared, but anxious to see what would
happen next.

He told me to sit and he entered a code from a piece of paper. Suddenly an
adult film came on with a guy fucking a girl in the ass. I couldn't help
but think of Angie and wonder where she went. I had not seen her since
that day at the motel. I would have asked Bobby, but I didn't want to get
her in trouble.

I started to get hard watching the film and then a new character appeared.
It was another guy and he slid in behind the first guy and slid his cock up
the guy's ass while he was still fucking the girl in the ass. For some
reason, I had never considered that position, but I found it incredibly
erotic.

Suddenly Bobby got up and slipped his clothes off. I almost fainted when I
saw his cock. This skinny kid had an enormous slab of beef hanging from
his crotch. It was soft and it must have been almost eight inches long and
three inches wide. It looked so out of place on that skinny body. He
started to stroke it and it must have been almost ten inches when it got
hard. It never got above parallel to the ground because it was so heavy
and his balls looked like oranges.

I was starting to feel a little strange because he had not told me what he
had in mind. That big dick was certainly worrying me, but it was
intriguing at the same time. He said "Watch this." and turned toward the
wall and stuck his finger through a hole that I had not noticed before. I
had no clue what he was doing until I saw a 6-inch cock slide through from
the next booth. Bobby immediately went down on it and started sucking it
like a baby. It was so odd to think that some anonymous man was in the
next booth getting his dick licked by an anonymous tongue in our booth.
Bobby stopped briefly and handed me a condom and some lube. He motioned
for me to fuck his ass and I was ready, willing, and able. I slipped in
easily and started a steady rhythm while he continued to suck the other
guy. Soon the mystery man exploded in his mouth and he shared some with
me. It was sticky and not too salty.

Bobby then had me stick my cock through the hole. I did so reluctantly, a
little afraid of what might happen. I expected a hand or mouth to greet
me, but instead I felt the unmistakable feel of a woman's pussy enveloping
my cock. Bobby got down behind me and started licking my asshole while
this woman squeezed my cock with her pussy muscles. Then I felt a tongue
on my cock, licking me and the woman's cunt at the same time. It was
fabulous. I was feeling sensations everywhere and then Bobby really
surprised me. He stood and placed his cockhead against my sphincter and
pressed forward. I felt intense pressure but it wouldn't penetrate. He
tried a couple of times, then started inserting fingers up my ass. I
moaned loudly as he inserted the fourth finger.

Then he pressed his cockhead forward again and penetrated with his huge
mushroom. I grunted, feeling like I had sat on a telephone pole. He let
me rest briefly, then pushed a few more inches in. Thank God he had put a
lot of lube on the condom. He stretched me to record widths and took my
breath away as he plunged in further. When he finally bottomed out, I
thought his cock was in the back of my throat. It was so intense that I
almost forgot about the cunt that was massaging my cock and the tongue that
was bathing it.

Suddenly the pussy and tongue were gone and my dick stood harder and higher
than ever. I then felt a new tighter grip on my cock as someone was
inserting it in an asshole. I reached through the glory hole with my
finger to rub her pussy and touched balls instead. It was a man's ass and
the woman started licking my cock as he fucked himself on my stiff shaft.
Bobby started moving his cock in and out of my ass slowly, pushing me
deeper in the man's ass. I heard moaning from the other booth and the
woman stopped licking my cock. I could feel a pulsing around my cock and
heard sucking sounds. I realized that he was coming and she must have been
swallowing his jism. This was so kinky not seeing the other couple.

Bobby was moving faster now and I was starting to feel a buzz in my balls.
The feeling was still intense, but very exciting. Bobby called me his
bitch and, for some reason, it excited me. The mystery man started fucking
himself even harder on my cock as Bobby picked up his pace. Being the meat
in this sandwich was fantastic. I finally couldn't take anymore and
started humping faster. The mystery guy, pulled off and the woman
swallowed my cock. The man then started licking the shaft while she sucked
the head. I exploded in her mouth and then they switched so he could
finish swallowing my cum. It was an incredible orgasm. I must have pumped
a gallon of cum. Then Bobby started short-stroking and blasted his load up
my ass. I could feel the heat of his semen as it filled the tip of the
condom. He kept stroking for a while then slumped on the bench. I turned
around, my ass feeling so wide open from the huge cock that had
bitch-fucked me. I carefully removed the condom and emptied it into my
mouth. Then I leaned forward and kissed Bobby, sharing his cum with him.

There was a knock on the booth door and I was frightened. I pictured the
vice squad at the door. Bobby laughed and opened the door and in walked
two gorgeous women, both in short skirts. I was very excited, but did not
understand what was happening. Bobby noticed my confusion and laughed
loudly. He finally told me that they had been in the next booth. I was
relieved but wondered, out loud, where the man had gone. One of the women
laughed and lifted the skirt of the other woman, revealing a 6-inch cock.
I was astounded and aroused at the same time. I had heard of shemales, but
had never seen one, even in pictures. She (he?) was very attractive and
had big tits. It was fascinating and I studied her carefully. She
introduced herself as Shelly and introduced her friend as Sapphire a
stripper at the club next door. I stupidly lifted her friend's skirt just
to be sure. They both laughed.

Shelly said she could just eat me up and proceeded to prove it by going
down on me. Bobby rubbered up and planted his cock in Sapphire's cunt.
They shifted with him laying on the bench while she rode him "cowgirl". I
lay on the floor and Shelly moved into a 69 position so I could taste her
big clitstick. We really went at it and eventually we both got a mouthful.
I sat back and rested, watching Bobby and Sapphire go at it. Shelly moved
me to my hands and knees and slipped on a condom. Her cock was already
hard again. She called me "pussy boy" and slipped her cock up my ass.
After Bobby's big log, I wasn't sure that I would feel it, but my ass had
closed a bit by that time and Shelly's cock felt wonderful.

Sapphire then had an inspired idea. While she sat on Bobby's schlong, she
had me straddle the bench and buttfuck her while Shelly slid behind me and
mounted me. It took a while to get everyone positioned well, but it was
very erotic and worked fairly well. When Shelly got close, she moved
around and exploded in Bobby's mouth and on his face. Sapphire leaned
forward and licked his face clean. Then Shelly moved in and started
licking both of the cocks that were buried in Sapphire. That caused us to
cum much sooner and I ripped off the condom and shot my load on Sapphire's
ass and pussy, covering Bobby's cock in the process. Then I moved down and
licked it all up. Bobby pulled out and I removed his condom and slipped
that huge member in my mouth. I worked up and down the shaft with my
tongue and lips. When I deep throated him and took the whole thing he
blasted me with his load. He was so deep that most of it went down my
throat immediately. I pulled off halfway and tasted the rest.

Bobby told me that no one had ever taken even close to that much of his
cock. He was amazed and very pleased. By now it was getting late and we
said goodbye to the ladies and left. When we came around to the front of
the place, the evening manager was waiting for us. Bobby pulled up and let
him in the backseat. He introduced himself as Jim and told me that he had
watched most of the action through a peephole. I was a bit irritated until
Bobby said that it was part of the deal to get us in. I asked him what the
rest of the deal was. He pointed to the backseat where Jim's cock was
waving in the breeze. He told me that I could do the honors or drive while
he did. I told him that I couldn't drive yet and he said that it would
have to be me. I would have been really angry, but Jim was very attractive
and had an uncut cock, which I had never had before. I climbed over the
seat and started to kiss him, but he pulled away. "I don't go for that
stuff," he said, "I'm not a fag." I was stunned and didn't know what to
do. "I just let queers suck my cock and I fuck them." Talk about major
denial. I really didn't mind, but his attitude pissed me off and I decided
to do something about it. I told him to take off his pants and underwear
so I could do it right. He reluctantly did so and I started sucking his
cock. It was strange the way his foreskin moved back and forth but he
really got into it, grabbing my head and facefucking me hard with his
6-inch cock. I moved my hand to his balls and rubbed them as he moaned
deeply. Then I snuck a finger to his asshole and pushed. I managed to get
an inch up his ass and he came unglued.

"What the fuck do you think you're doing bitch?" he screamed. "I'm not
into that shit." Then I said, "You are if you want me to finish." He was
pissed. "Bobby, get back here and suck my cock. This queer wants to make
me into a faggot too and I ain't goin' there." Bobby laughed and said,
"Jim, it's time you faced the fact that when you have sex with men, you are
at least bisexual." Jim looked as if Bobby had just cum in his mouth. He
couldn't speak.

Finally he started to cry and said "My father always said I would turn out
to be queer. Then I came home early from school one day and found him
getting fucked in the ass by a queer that lived down the street. That
bastard made me this way. I can't help myself." This whole evening was
just full of surprises. I told him to calm down and I hugged him while he
sobbed. This had obviously been building for a long time. We drove him
back to get his car and we never finished the sex. He kept apologizing and
told Bobby he was still welcome in the booth any time. When Bobby dropped
me at home, he told me that I was welcome to join him anytime and he would
love to join us for a threesome at the motel sometime. I told him I would
think about it and kissed him goodnight.

I finally did introduce Bobby to both Hal and Carson. They both agreed
since he already knew their names from their credit card receipts and
hadn't told anyone. Neither of them let Bobby fuck them with that monster
cock, but he fucked me several times. Then Bobby's father sold the motel
and moved to Birmingham, Alabama and Hal was transferred to Atlanta. Bobby
eventually moved to San Francisco because the scene in Birmingham was not
conducive to people with his proclivities.

**Transgender Stories** · 05-04-2016, 03:54 PM

Part 4

I Get a Girlfriend (and more)

My dad got me a car - a brand new Mustang Cobra and I had
a lot more freedom. I also got a lot more attention from girls. I was at
a school dance and a stunning girl came up to me and asked me to dance.
Her name was Dannie (Danielle) and she lived a few blocks from me. I had
met her a month earlier when her family moved into the neighborhood. They
invited the neighbor kids to a pool party so Dannie could make friends
quickly. I didn't think she even noticed me. I spoke to her father more
than I did her. She was a beautiful redhead and had a great body. Her
tits were D cup (at 16) and she had light blue eyes.

We danced a slow dance and she was really holding me close. I wasn't sure,
but it felt like she was rubbing her breasts against me intentionally. We
danced several times, all slow dances, and she asked me to take her home.
I quickly agreed and when we got to her house, she invited me in for a
swim. I told her I didn't have a suit and she said I could borrow one from
her dad. I agreed and her dad was very nice about loaning me the suit. We
went for a long swim and she turned the lights out on the patio. She
kissed me and we necked for a while. I wanted to go further, but this was
new territory for me. I had never had to do the romance thing before.
Jaden always said I gave off a strong sex vibe and Hal agreed when I told
him. They both said I had a real feminine side. That night with Dannie, I
was a different person.

We began dating and my Friday nights changed dramatically. I was always
out with Dannie on Fridays, so Jaden and Carson were cut off. After a few
dates, I made my move with Dannie and she responded eagerly to my advances.
We had sex in her pool the first time. It was very erotic knowing that her
parents were only 50 feet away while she sucked my cock and I ate her hot
cunt. I fucked her once that night and was amazed to find that she was a
virgin. Despite that, she was a fast learner. We worked hard to find
times and places for sex and eventually she let me fuck her in the ass.
After that, she couldn't get enough. She also learned to swallow cum and
deep throat. When I taught her to do it, I told her that I learned from
watching a previous girlfriend. We managed to have sex about twice a week.

Jaden was getting more than a little testy about getting cut off, but he
understood. We managed to fuck occasionally on weekends when his parents
were out of town. I always wore makeup and lingerie when we had sex and he
loved calling me bitch, cunt, slut, and whore while he pounded my ass or
filled my mouth with his hot cum. One Saturday, I forgot I was supposed to
pick up Dannie early and Jaden had just fucked me and cum in my mouth when
I remembered. I barely had time to change and rush over to her house.
When Dannie's father answered the door, he looked at me strangely as he
invited me in. I didn't think twice about until I went to the powder room
and looked in the mirror. There on my cheek was a bit of cum and I still
had lipstick and mascara on. I was sure he didn't see the cum or didn't
know what it was. The lipstick and mascara were hard not to notice.

I washed up and came back out, wondering what he might say. He wasn't
around though and Dannie came down and we left. We had to go to a motel
that night to fuck after the movie. I was fucking her ass when she started
to laugh. I asked her what was so funny and she told me that she had
caught her father fucking her mother's ass a couple of days before. She
said they were very cool about it because they were always so open and
accepting about sex. I told her that they might not feel that way if they
caught me fucking her in the ass. She laughed and said that they knew we
were having sex. I laughed, but then realized that she was serious. Then
I panicked. I thought I was a dead man, but she said that they were cool
about it. I had trouble believing it, but she assured me that it was OK.
She told me that they belonged to a swingers' group and had even hosted a
party once while she was at her grandmothers' house for a visit. Her
parents had not told her about the swingers' group, but their housekeeper
spilled the beans. Her father is a well-known surgeon and I was surprised
that he would risk his reputation like that. It's amazing to me the risks
people will take to satisfy their desires, me included.

The next day, I stopped by to return the swimsuit that I had worn home that
first time and had promptly forgotten about. No one answered so I walked
around to the pool and saw her father tanning. I said hello and he shook
my hand. I handed him the suit and he told me to put it on and join him.
I asked where Dannie was and he told me that she had gone shopping with her
mother and wouldn't be home for a while. I decided I should be diplomatic,
so I put on the suit and joined him by the pool. He handed me a gin and
tonic and I took it, a little surprised, considering my age.

After a bit of small talk, Howard said "My daughter tells me you are great
in the sack." I dropped my jaw and my drink at the same time. When I
reached to pick up the pieces, I cut my hand. He told me to follow him
inside so he could put a bandage on it. I tried to apologize about Dannie
while he put the bandage on but he said "David, Dannie is very much like
her mother, a very sexual young woman. It's perfectly natural. Her mother
and I are very open sexually. In fact, we have sex with other couples.
Does that surprise you?" "Yes it does," I lied. I decided to be bold and
asked "Does Dannie's mother have sex with other women or just men?" "This
intrigues you doesn't it David?" he asked knowingly. "Yes she does, it's
very erotic. I love to watch her with other women or have sex with another
woman while she joins in." I decided to really push my luck and asked "Do
you have sex with other men too?" He looked serious for a moment and said
"No David, I never have, although I am interested. Carol doesn't want me
to. I know that sounds odd, since she has sex with women, but she said it
would really bother her. Some of the guys in the group do have sex
together and she doesn't like it. She won't do a threeway with two men if
they are doing things with each other." The conversation had definitely
gone way beyond anything I would have expected.

"David, how long have you been having sex with men?" he asked. My jaw
dropped again and I said "Where did you get that idea?" He told me that he
had noticed the makeup the other day. I tried to make something up
quickly, but he stopped me and said "David, don't worry about it. I won't
tell Dannie. I don't think she would be any more open to it than her
mother." I decided to come clean and I told him that I did enjoy sex with
men occasionally. He laughed and said that I should be more careful about
the makeup and that he was probably the one father that would have let me
in the house. I laughed, thinking about Carson, but didn't say anything.

We went back to the pool and he asked me to put some suntan oil on him. It
seemed like an odd request, but I decided to do it since he had been so
understanding. I put it on almost everywhere, admiring his great tan and
decent physique. He was in pretty good shape and he looked younger
than his wife. I began to get suspicious when he slipped
off his suit and lay on his back. He said that he wanted to get a full
body tan. He encouraged me to do the same. I told him that Dannie and
Carol might come home and see us. He assured me that they would be gone
for hours so I reluctantly went along with it.

I lay on a lounge chair and he got up to fix us another drink. As he
walked over and back, I fixated on his nice ass and his luscious cock. It
was one of those big veiny ones and his pubic hair was shaved, making it
look even bigger. I started to get hard and I covered myself with a towel.
I was very embarrassed. He sat next to me on my chair and handed me my
drink. As I took a sip, he lifted the towel and saw my big, hard cock. He
rubbed it and said "I see why Dannie likes you so much. This thing must
really do a number on her." I was perplexed by his attitude toward his
daughter, but I was so excited I quickly forgot about it. He started
stroking me and I moaned anxiously. He leaned down and kissed me deeply
while continuing to stroke my big cock. I was so hot I would have done
anything for him.

"David, I want you to suck my cock and let me fuck you," he said "Will you
do it?" I didn't respond. I just reached out and grabbed his big dick.
He smiled and helped me up. He walked to the edge of the pool and sat with
his legs dangling in the water. I dove in and stood between his legs. I
licked his asshole while I stroked his cock - then finally took the head in
my mouth. I gave him an incredible blowjob with lots of deep throat action
while I fingered his asshole. He kept rubbing my head and calling me his
"sweet little cocksucker" and his "oral angel". I thought it was strange
the way he treated me like a girl, but I actually liked it.

When he finally came, I swallowed some and let the rest run down my chin.
He leaned over and licked it off, tasting his own cum. He said it was his
first taste. We swam for a while and he picked me up and carried me around
in the pool. He kept kissing me and calling me "sugar" and "honey". It
was exciting. When he got hard again, we went inside to his bedroom and he
put some of Carol's sexy lingerie on me from their swinger parties. She
had all of the usual "whore" clothes. He also helped me put on makeup, a
necklace, and earrings, then kissed me and carried me to bed. He laid me
on my back and prepared to mount me in the missionary position. He put a
condom on and lubed me good with his fingers. Then he slowly pushed his
way inside my ass, being careful not to hurt me. He rested on his elbows
as his hips bucked up and down, burying his big cock deep in my ass. He
leaned over and wrapped his tongue around mine and kissed me deeply. He
never broke his rhythm as his balls slapped my ass and his cock explored my
inner warmth. He kept telling me how wonderful my tight cunt was and how
much he loved fucking it.

Then suddenly he got up and went to a dresser and came back with a long,
thick double-headed dildo. He lubed it and stuck it up my manpussy. He
said he wanted to see how far it would go in. It felt great, but started
to hurt as it went deeper. I had no idea how far it could go. When he hit
a certain point I yelped and he stopped. When he measured it, it was
almost 14 inches in. I asked him not to go that deep again and he promised
he wouldn't. Then he did something more unexpected. He stuck one end of
the dildo in his own ass. He said he had done it before. We scissored
each other and pushed it up both our asses. I had about ten inches up me
and he had about eight and our balls were rubbing each others. We then
started bucking against each other. It was so sexy.

We then got on our knees and reinserted the double cock. We faced in
opposite directions and fucked each other with the dildo. It was
impressive how much he took considering he had never been fucked by a man.
He then removed the dildo and asked me to lie back again, which I did.
Instead of fucking me more, he straddled me and sat on my big dick. He
started bucking on me, really riding my cock. For an anal virgin, he could
really take it. He must have used those dildos a lot. Suddenly, his cock
erupted, spewing cum all over my face and chest. For a second orgasm, this
was a lot of cum. I licked some off my face as he slowed his pace on my
cock. He swung around, removed my condom and took my cock in his mouth. I
moved him over me so I could clean his cock while he blew me. A minute
later I nearly blew the back of his head off with my orgasm. He gagged on
it but kept sucking till he swallowed it all. Meanwhile I finished my cock
lunch.

We went back to the pool to wash off. He slipped on a condom and picked me
up, face-to-face as I wrapped my legs and arms around me. We were almost
chest-deep in the pool so there was not much weight on his arms. I leaned
back to give him enough angle and he sat me on his cock and proceeded to
impale me all the way. Then he bounced my butt all over the pool, calling
me his "anal princess" and "sweet cunt girl" -- names that sound sexier in
the heat of the moment. He came up my ass then removed the rubber and
swallowed his own cum. I asked him to share and he kissed me, giving me a
good load of my own.

We got cleaned up and had another drink. By the time the ladies arrived,
it all seemed like a wonderful dream. I got dressed and Howard said he
wanted to treat Dannie and I to dinner. He handed me $500 and whispered,
"Take her to a nicer hotel and get room service." That night we had
lobster and great sex at the Albion in South Beach. Her mother was pissed
when we got home at 1:00 AM but Howard calmed her down and said he would
have a chat with me. When I left, Howard walked me out and got in the car
with me. "Carol thinks I'm scolding you, so look penitent." he said as he
pulled out my cock and stroked it. "I want to see you again if it's OK."
I agreed and asked if he would be interested in meeting the guy who fucked
me the day I showed up in makeup. He said he would love that.

The next Saturday afternoon, Dannie and Carol went shopping again and Jaden
and I came over for some fun with Howard. Howard and Jaden really hit it
off and we had a great time. They put me in one of Dannie's short skirts
and halters and took turns fucking my ass against a wall with the skirt
flipped up. They kept switching off like a tag team wrestling match. We
fucked in every possible combination. My favorite was when I fucked Howard
while Jaden reamed me out good. I must have swallowed six loads that day
and I came three times, once in Jaden's mouth and twice in Howard's. That
night, thanks to Howard, Dannie and I went out in style again and I fucked
her ass just like I fucked her Dad's. It was surreal. What was it about
me that brought out this hidden side of men -- men who were happily married
for years? Howard said I should have been born a woman because I made him
feel the way he felt toward women. Based on my experience, about 10% of
the population is gay and another 40% is bisexual under the right
circumstances. I am constantly astounded by the seemingly straight guys
that end up in bed with me, with their cock buried in my butt.

For the next few months, my dance card was pretty full. I continued to
have sex with Dannie, Jaden, and Howard as often as possible. Bobby came
for a visit and we ended up having sex with Jim at the video store. He had
finally admitted his bisexuality and was making up for lost time. He even
let me fuck him once. After that I stopped by the store occasionally for a
quick fuck or a blowjob. Even Uncle Hal came to town every couple of
months and reamed me out for old time's sake.

**Transgender Stories** · 05-04-2016, 03:56 PM

Part 5

I Take One for the Team

I was still the trainer for the basketball team. I traveled
with the team, but we usually came back the night of the game on a school
bus. One time we went to a tournament in Orlando and stayed overnight at a
decent hotel. Jaden and I managed to room together, so things looked
promising. After curfew, one of the guys snuck out and used a fake ID to
buy beer and several of us gathered in a room and proceeded to get wasted
(We bought a lot of beer.). By about 3 AM, all but three of the guys had
gone to bed and I was pouting and passed out on the bed. When I woke up,
Jaden was pushing his cock in my mouth and I smiled and started to suck on
it. He lay on his back and I stripped and started deep throating him.
Suddenly I felt another cock rubbing my crack. I spun around and
discovered that the other three guys were still there (they had hidden in
the closet) and were all wearing condoms and jerking their cocks. I looked
back at Jaden, feeling very hurt that he would do this to me, but I
realized that he was too drunk to think clearly. I figured I had better go
along with things or it might get ugly.

I got some lube and filled my ass with it. The first guy to mount me was
Levi, the starting center. He was a 6'7" tall senior, black, with a very
thick seven inch cock. I convinced him to go slowly and, thank God, he
did. That thick slab really stretched me wide, but felt great after the
initial shock. He started rocking in and out and talked constantly about
that "sweet ass" and what a "hot cunt" I was. Meanwhile, Jaden shot a big
load in my mouth. I decided, at that point, to teach Jaden a little
lesson. After I filled my mouth with his cum, I leaned down and kissed
him, feeding him his cum. The other guys started teasing him about being a
cocksucker.

I got Levi to lie down and let me straddle him. While Levi continued to
pound my ass, Jeff came over and fed me his cock. Jeff was a forward,
about 6'4" and his cock was longer than Levi's but narrower. When I deep
throated him, he got weak in the knees and fell, but recovered quickly.
Levi kept shouting orders - "Suck that cock" and "Ride that black snake".
I motioned the third guy, Reston, to come closer. Reston was the backup
center, 6'6", black, and huge. He must have weighed 240 and it was all
muscle. His most impressive muscle was his huge cock. These tall guys
sure had big ones and his was the biggest - 9 inches and as big as my
wrist. I started switching between he and Jeff, sucking them deep and
licking their balls.

Suddenly, Levi screamed "I'm cumming, take it bitch." I jumped off and
dove for his cock. I ripped off the rubber as the first shot hit my face
and I swallowed him all the way. He moaned and fucked my face. He just
kept shooting and shooting his white jizz in my mouth. It looked sexy
seeing that white cum on that dark cock. I licked it good and clean and
prepared to take Jeff in my ass. He put me on my back and said "I want to
see your face while I ream that tight ass." Jeff's cock pierced my
sphincter and he immediately got a hard, fast rhythm going. Reston sat on
my face looking at Jeff and told me to lick his asshole. His long cock was
practically hitting Jeff in the face. I figured Jeff would be pissed and
do something about it. I couldn't see with my mouth on Reston's asshole
and my tongue buried up his ass, but I suddenly heard the unmistakable
sound of cocksucking. I pushed Reston's butt up and saw Jeff sucking
Reston's cock as he reamed my ass. This was getting more interesting all
the time. When Jaden saw what Jeff was doing, he walked over and planted
his mouth on Levi's soft cockmeat. Levi started shouting "Suck my big
black cock, Jaden. Make me cum." Jeff turned me over on my knees and
started to plow my ass. Reston slid beneath me and I swallowed his big
cock. I was getting so hot watching Jaden suck Levi, while I got it from
both ends. Then it got better.

Reston suddenly started licking my balls and Jeff's cock as it reamed my
ass. Jeff went nuts and started really pounding me hard. Then Reston took
my cock and began sucking it. I was now in total bliss. He sucked like a
pro and I was ready to blow a load. I warned him that I was coming and he
pulled off, letting it flood his face and chest. This got Jeff so hot that
he pulled out, removed the condom, and shot a load all over my back. Then
he leaned over and licked it up.

With my ass available, Reston slid around and mounted me, slipping that
black tree trunk in slowly but surely. Thank God he went last, because he
was really stretching me. I looked over and saw Jaden getting fucked in
the ass by Levi while Jeff sucked his cock. I couldn't believe what I was
seeing. These big macho guys would never do this sober. I didn't have to
worry about them telling everyone after what they were doing.

Reston finally pulled out and I swallowed his cock and his load. I was
pretty tired and sore by then so I laid back and watched the action. Jaden
took Levi's load up the ass and Jeff took Jaden's load in his mouth. The
grand finale was when Levi sucked Reston's cock to life again and swallowed
his cum. It was the only time that Levi wasn't barking orders at someone.

The next morning I woke up and the guys were still there. I went to take a
shower and Jaden joined me for a morning fuck. When we came back into the
bedroom area, Reston and Jeff were in a 69 and Levi was fucking Reston. I
finally reminded these guys that they had a game to play in about four
hours. They finished and showered. When they got out of the shower, I
started sucking each of their cocks. Then I stopped and I told them, I
would eat their cum on the bus that night if they won the game.

They played better than they had all year and beat a team with a much
better record. The coach was very pleased and Jeff told him it was all due
to a new physical therapy routine I was doing for them. The coach looked
clueless but thanked me. What a moron. That night, on the way home, we
sat way in the back of the bus and I sucked all four guy's cocks and
swallowed their cum. The coach was surprised to see half of his team in
the back of the bus and yelled "You guys stop playing with your peckers
back there." and laughed. Little did he know. The rest of the way home I
fondled their cocks.

After practice, blowjobs became a regular part of my therapy on the guys.
We had a private room with a massage table and the guys always had tight
muscles after practice, especially between their legs. Another guy, Cal,
had figured out what was going on that night on the bus and threatened to
expose us unless I sucked his cock - which I did. He never knew about the
after-practice sessions and I didn't tell him. I was already doing a
blowjob or two every day after practice and didn't need any more customers.

One day the assistant coach called me into the head coach's office. He was
a recent college grad, about 24, named Phil. He wanted to be called Coach,
but everyone called him Phil. The head coach had left for the day. He
told me that he was going to have to get a new trainer to replace me. I
was shocked and I asked him why. He said that he had found out about my
after-practice activities and couldn't keep me around. I asked if the head
coach knew and he said no. I asked him what he was going to tell him and
he said he wouldn't tell him if I quit. I said I would quit on Monday.

That evening, I told Jaden what happened and he laughed. It was not the
reaction I expected and I asked him why he was laughing. He said that Phil
had tried to get something going with him and Levi and was just jealous
because he hadn't succeeded. On Monday, I stopped by to see Phil and told
him I would be happy to quit, if he did too. He got angry until I told him
what I knew. Then he got scared. He begged me to keep quiet. I told him
I would if he gave me a blowjob. I was really enjoying this a little too
much. He agreed, but I told him I was kidding. He actually seemed
disappointed. There is nothing worse than someone who victimizes someone
else for doing exactly the same thing that they are doing (or in Phil's
case, trying to do).

Jeff and Levi graduated that year, but I did get to have sex with them a
couple of times before the year was over. Reston moved after basketball
season and I never saw him again. Before he left, I let him fuck my ass
and I swallowed his cum. He was an amazing physical specimen.

**Transgender Stories** · 05-04-2016, 03:57 PM

Part 6

My Transformation Begins

I was still dating Dannie
and seeing Jaden, Carson, and Howard when time permitted. But one thing
had changed. I began wearing women's lingerie much more often. I wore
crotchless panties during all my male encounters. One day, I was at
Dannie's house and Howard was fucking me on the pool table. I had on some
of Carol's sluttiest lingerie, including leather boots and crotchless
panties. We were shifting into a new position when I saw Carol standing a
few feet away with a stunned look on her face. I felt sick inside and knew
this was not going to turn out well. Howard didn't see her and said "Move
your ass bitch, I want that sweet cunt of yours right now." Carol
shuddered when she heard that and screamed "You unbelievable bastard. Get
out and take your girlfriend with you." I was even more concerned with
where Dannie was. Fortunately, she was still shopping with her friend Pam
and had not come home yet. Howard scrambled to his feet and tried to
reason with her, but it was no use.

She divorced him and made Dannie stop seeing me, but she never told Dannie
the whole story. She couldn't tell anyone else without risking her own
reputation and future alimony. Dannie was close to her father and it
really tore her up inside. I felt guilty and angry at the same time. Why
was it OK for her to have gay sex but not him. It's such a double
standard. I also missed Dannie a lot. I was surprised to find that I
missed holding her and talking to her as much as I missed the sex. A
couple of times we snuck off to our old motel and had sex, but it wasn't
the same. She was constantly worried that her mother would find out.

The next shoe dropped when my father passed away. He had surgery for a
gall bladder problem, got a bad infection, and just couldn't beat it, even
with IV antibiotics. I was very shook up. I had always been afraid that
he would find out about me and now I would never know how he would feel
about it. I decided to tell my mother a few weeks after Dad died. She
just smiled and said "David, it's OK, you're father and I knew for a few
months. He took it hard at first, but decided to let you figure out what
you wanted." I should have told him myself. After that, I decided to just
be myself. I grew my hair longer so that I could look feminine or wear it
in a ponytail when I wanted to look more masculine (lots of guys were doing
it then). I started wearing crotchless panties and stockings under my
pants, even at school.

When I took my pants off in gym class, it created quite a stir. Guys were
calling me faggot and pussy and the instructor told me not to wear those
things anymore. The principal talked to my mother, but she refused to make
me stop. I told everyone that I was bisexual, but they still called me
faggot. Dannie put two and two together when she stopped by Howard's
apartment unexpectedly and found me there in a robe. Howard and I were
fucking each other on a regular basis. I told her the whole story and she
took it very well. She said it would just be too strange having sex with
someone her father was screwing and we stopped getting together for sex.
We still talked occasionally and got along well. She was an angel.

I lost the trainer spot, but I was tired of the responsibility. The new
players were so straight-laced and Jaden was no longer playing. He had to
downplay his relationship with me, but we still got together and had sex
when we could. I had just turned 18, so no one could really say much about
my sex life anymore. The strangest thing was the way some of the girls
reacted to my new image. The girls with a reputation for being sluts
seemed to be more attracted to me. I didn't quite understand it, but I
liked the attention. One girl, Judy, had once gotten wasted and sucked off
five guys at a party. She was really nice looking and someone took a video
of her doing it. She was flashing her tits, rubbing her pussy, and getting
her face covered in cum.

She started having lunch with me every day along with her friend Heather.
Heather was notorious for getting caught in auto shop after school getting
her ass fucked by the shop teacher. He got fired and she got suspended
until her parents threatened to sue the school. They were so intrigued by
my lifestyle and wanted to hear every detail which, of course, I couldn't
tell them. One day after school, they pulled up beside me at a light and
motioned for me to follow them, which I did. They drove to Heathers house
and invited me in. I was worried because some of the parents were not
happy with their kids hanging around me. Heather told me her parents were
in Jamaica so I changed my mind quickly.

Heather opened the bar and we all had a drink (or two). She put on some
music and Judy started dancing in front of me. As she swirled around she
started taking off her clothes. I was mesmerized. She had nice tits, not
huge, but big enough and her ass was a work of art. I felt a pair of
breasts press against the back of my head and turned to see Heather,
already nude. Her tits were very large and very shapely. She was just
slightly overweight, but she really looked sexy. The girls took my hands
and led me to Heather's bedroom. I was so hot and hard, I thought I was
going to cum in my pants.

The girls stripped me and laid me on the bed. Judy started sucking my cock
(of course) and Heather planted her steaming cunt on my face where I
proceeded to work her over good. Heather was gushing cuntjuice everywhere
and writhing like a snake. She kept telling me how good it felt. Judy was
a talented cocksucker (lots of practice, I guess) and had me hard as a
rock. Finally Judy couldn't stand Heather's moaning any longer and made
her switch. Heather was not as good as Judy at cocksucking, but did manage
to take all of my cock. Judy was just as juicy as Heather and screamed
even louder.

Heather decided to sit on my cock, but I had not remembered to get condoms
and told her so. She laughed and reached in her dresser, pulling out a big
box full of condoms. She covered me and climbed aboard. The girls were
facing each other, each riding me hard. Then they started rubbing each
other's breasts, kissing, and tonguing each other. It was so hot to watch
when I could catch a glimpse. Judy's pussy was blocking my view most of
the time.

I finally shot a load up Heather's pussy and the two of them cleaned my
cock with their tongues. While I recovered, they got into a 69 and went at
it like bitches in heat. Judy reached out to stroke me and I got hard
again quickly. Judy told me to fuck her and Heather would lick us both.
They stayed in their 69 and I fucked Judy for a while. Then I started
fucking Heather again. Finally, Heather asked me to fuck her ass and I
kindly obliged her. Her ass was really tight and I had trouble getting my
cock inside her. I finally broke through and gave her a world-class
buttfucking while she sucked and licked Judy's cunt and ass.

After a while the girl's switched and I pronged Judy's sweet asshole.
Heather jumped up and got a strap-on dildo and positioned herself to fuck
Judy's pussy while I reamed her butt out. As experienced as I was
sexually, I was discovering a whole new world of sexuality that evening.
These girls were just doing what every guy at school would do if they could
- have wild sex anytime they wanted.

We went at it for a couple more hours, trying lots of combinations. My
favorite was when I fucked Heather's sweet ass and Judy did me with the
strap-on. Before she fucked me, they dressed me in slutty clothes and put
makeup on me. When I left, they were cunt-to-cunt with a double-dildo in
their asses. I got together with them several times, but always together.
They were inseparable (attached at the hip, or near there). Every time we
got together they came up with something new. I even watched them pee on
each other. I never could get into that, but it was hot watching them do
it.

Heather told me to keep the clothes, because they were a little tight on
her since her tits had gotten so large. I decided to wear them home, still
in makeup. I really looked hot. It was dark out and I stopped at a light
and some guys pulled up beside me and started whistling and asking if I was
in the mood for some fun. I asked them what they had in mind and one of
them said "You". I told them that I was probably not the kind of girl they
wanted and they insisted I was. I decided to blow their mind so I raised
up and flashed my cock. They freaked out and sped away. About that time
the police lights came on behind me and the officer pulled me over.

He told me that he had seen me flash those guys and was going to have to
book me for indecent exposure. I was really scared and very shaken. He
made me lean against the car and he frisked me. He ran his hands up my
legs which I thought was a little ridiculous since I was wearing a short
skirt and stockings. When he got to my crotch and found my cock, he
laughed and said, "I thought that's what I saw. You sure scared those
smartass little bastards away." I was really confused now. What was going
on?

"I'm going to have to give you a field sobriety test" he said and placed
his middle finger against my asshole. He inserted it up to the knuckle,
then removed it and said "Looks like you've had a couple of stiff ones.
I'll have to give you a breathalyzer test." At that point, I realized he
was just taking advantage of me. I'm sure he thought this was a funny,
sexy come-on, but I was so shaken that I was not amused. He told me to get
on my knees and swallow his probe, but I told him I was really not in the
mood to continue this game. He realized I was irritated and apologized
profusely. He said that he had misread the situation and apologized two
more times.

By then I had calmed down a bit and started to feel sorry for him because
now he was scared. He asked if I wanted him to follow me home to be sure
that those guys weren't waiting to get back at me. I told him if he really
wanted to make it up to me he could take me for a spin in his patrol car.
I told him that I had always wanted to ride in one. He agreed and we got
in and took off. He introduced himself as Jack. He said that he and his
last partner had been fucking each other until someone found out that his
partner was gay. After that he was abused to the point that he had quit
the force, leaving Jack with no partner temporarily. As we turned down a
dark street, I leaned over and unzipped his pants. He was shocked but
excited as I pulled out his cock and started to lick the head. He looked
for a place to stop but couldn't find one. I took his stiff member in my
mouth and started to fuck it with my mouth. He was getting desperate to
stop and pulled behind a supermarket.

We got into the back seat and I kept working on his cock. It had reached
its full height now and I asked him if he had a condom. He grinned and
pulled one out. When I slipped it on him, he almost came in my hand. I
laid flat on my stomach and he climbed on top of me and lifted my skirt. I
helped him position his cock and he eased it inside my ass. Thank God for
lubricated condoms because we had no lubricant. He started slowly pumping
my hot, steamy ass, telling my how tight and soft it was on his stiff
shaft. He was getting close to coming when another squad car pulled up and
the officers shined a light in.

Jack freaked out. "If they catch me fucking a boy, I'm dead meat. I'll
have to leave the department". "Don't worry" I said, "Pretend I'm a girl
and let me do the rest." The officers opened the door and one of them said
"Hi Jack. Is this your idea of community relations?" "My car broke down
and this sweetie was taking me home." I said in my most feminine voice. "I
was just thanking him.".

"You have an interesting way of showing your gratitude ma'am.", he said.

"What is your name and how old are you?"

"My name is Tess", I lied. "and I'm eighteen, but I left my license in my
car."

"Do you do this a lot young lady."

"Only for hot studs like Jack - and you sweetie."

"Are you one of those girls that likes uniforms?"

"I sure am lover and I'd love to suck your cock."

He looked around nervously, turned to his partner, and asked him what he
thought. His partner said "Only if I get a turn.". I told him he would
definitely get his turn too.

Jack was relieved and started to get hard again. He stuck his cock back in
my ass as the first cop stuck his cock into my mouth. I proceeded to suck
both of the late arrivals to roaring orgasms, swallowing both. I kept some
of their cum in my mouth and when they thanked me and left I kissed Jack
and shared their cum with him. He got so excited he pulled off the rubber
and added his load to the mix in my mouth.

Jack told me, if I ever got into trouble with the cops, to ask for him and
he would take care of it. He took me back to the car and I drove home. On
the way I still had the taste of three cops in my mouth. It was delicious.

**Transgender Stories** · 05-04-2016, 03:58 PM

Part 7

The Next Step

Eventually, I persuaded my mom to help me find a
doctor to discuss a real transition to a more feminine form. I was tired
of having no breasts and all that body hair was a pain to keep shaved. The
first two doctors would not even discuss a partial transition and insisted
on a very prolonged process including 3 months of therapy, 18 months of
living as a woman, then hormones and surgery. I finally convinced the
third doctor that I didn't need therapy because I had essentially lived as
a woman, albeit a bisexual one, for a very long time. He agreed to begin
hormone treatments and I got electrolysis for a quick solution to the hair
problem. The breasts would have to wait a while. My mother refused to pay
for that - she couldn't bring herself to take that step while I was still a
student. My father had left me an education trust that would pay for an
expensive private university, but if I got scholarships, I could keep the
money. I had already cinched over $30,000 in scholarships with my 3.9 GPA
and my 1455 SAT score, so I knew I could eventually afford the breast
implants. What I didn't tell the doctor was that I did not intend to ever
finish the job. My goal was to become a woman in every way except for
removing the penis. I had to maintain a fully functional cock.

Judy and Heather noticed the changes in me before anyone else. They loved
the softening effect, the lack of body hair, and the change in my voice.
They started dressing me and taking me to places normally reserved for
women. I was excited to see that no one paid any attention except the men
who hit on me. Heather was pissed when a gentlemen she had her eye on
asked me out. I told him I was in a relationship so Heather finally got
her man. Based on her accounts, she got her man three times, then shared
him with Judy..

My last semester, I couldn't wear dresses, but they didn't complain about
the undergarments anymore. I still got some harassment, but that slowly
subsided. Jaden stopped getting grief for hanging around me and he and I
continued to have the occasional roll in the hay. Carson had not had sex
with me for months since I spent so much time with Howard and the girls.
One day I went to see Jaden, actually hoping to see my favorite lady, Jane.
Neither Jane or Jaden was home, but Carson was there, cleaning out the pool
house which had gotten some water damage in a storm. When he saw me, he
gasped. He couldn't believe how feminine I looked, especially with my
short skirt and a man's shirt unbuttoned and tied, exposing my sexy tummy.

He kissed me deeply and squeezed my ass, causing us both to harden down
below. He told me that Jane and Jaden had gone to Boca Raton to help
Jane's mother move some things into a storage unit. Carson had stayed
behind to work on the damaged pool house. I was surprised when he told me
that he had company coming by. He was hesitant to tell me that it was a
new male lover he had found. I assured him that I was not jealous and was
happy that he was able to find a way to meet his needs for male sexual
contact. He told me that he had gone to a club in South Beach, while Jane
was out of town, and had met Greg in the restroom. They danced for a while
and things got hotter. Greg kissed him and stroked his cock while they
danced and then went to a hotel with him for a few hours of hot sex. I
told him I was very happy for him and assured him I would vacate before his
lover arrived. Suddenly, he had a brainstorm. He wanted me to watch them
while they had sex, like I had done with him and Jane. I told him that I
didn't feel comfortable with it anymore. Then he came up with another idea
that I did like.

When Greg arrived, I was watching from inside the main house. He was tall,
with dark hair and a fairly muscular build. Carson had told me that he was
28. His ass looked great in his tight pants. Carson hugged him and led
him inside the pool house. I went to the pool house window and peeked
inside. They talked briefly, then Greg undressed revealing a thick,
circumcised, six-inch cock. Carson went down on him and adjusted their
position so I could watch him suck and he could see me watching. He was
really working on Greg's cock, deep throating him over and over again.

Suddenly Carson, jumped up and pointed at the window, yelling something
that I couldn't hear. He ran out and grabbed me dragging me forcefully
inside. Greg was freaking out and Carson screamed "You little peeping tom
bitch, what do you think you're doing watching other people's private
affairs?" Greg was scared of what Carson might do and said "Maybe we
should let the cops deal with her, Carson."

"Exactly what would I tell them Greg? She was spying on me and my male
lover? Are you crazy?"

"Ok, calm down Carson"

"No Greg, I think I'm going to teach this little cunt a lesson that she
won't forget."

"Carson, I won't be involved in beating up a teenage girl."

"Shut up, Greg. I'll handle her."

Turning to me he yelled "Get on your knees, cunt." He was very convincing
and I followed his lead. "Unzip me and take out my cock you little whore."
He said forcefully. I was getting hot and had to work hard to appear
scared. "Ok" I said and pulled out his cock. "Call me master, you little
cunt." he barked. "Yes master" I responded, "What are you going to do to
me master?" "I'm going to do what I please, slut, now suck my cock." "Yes
master" I said and began to blow him tentatively. "Take it all, cunt" he
said and grabbed my head shoving his cock down my throat. I pretended to
gag and I could see Greg's cock beginning to harden. Carson got on his
knees and continued to feed me his cock very forcefully. He turned to Greg
and said "Get behind her and fuck her pussy."

He looked scared and said he couldn't do it. Carson yelled "You do it you
cocksucker or I'll never see you again." "Good bluff" I thought to myself
as Greg moved behind me, stroking himself. "Lift her skirt so I can see it
go in." Carson ordered. "Tell him you want that cock, cunt." he barked.
"Please don't look under my skirt master" I begged, trying not to laugh.
"Why not?" Greg said curiously. "Please don't fuck me, master." I moaned
pitifully. By now Greg was very curious and raised my skirt for a peek.
"Oh my God, Carson. This she is a he." "Really?" Carson asked and looked
for himself, feigning surprise at my large package. "That's even better.
Fuck the bitch's ass" Carson said to Greg forcefully. Greg was now hard as
a rock and slipped on a condom. When he started fingering and lubing my
ass, I pretended that I couldn't take it. "Please stop, master. Don't
shove that thick cock up my tight little asshole. I can't take it." I
begged. By that time, he was too far gone to care and he placed the head
at my entrance and pushed. I squeezed my muscles making it very difficult
for him to penetrate me. It finally slipped in and he started working it
up my steamy tunnel. I slowly stopped squeezing and he kept pushing.
Before long, I was fully mounted and he started a steady rhythmic fucking
motion sliding almost out then smoothly back in, slapping me with his
balls.

About that time, Carson yelled "Take my cockjuice you cum-swallowing
whore." and shoved his cock in to the limit spewing semen in my mouth and
throat. I was really getting off on this scene and Greg was giving me a
great assfucking. He held my hips firmly and "stirred" my ass with his
sweet sausage. Then Carson surprised us by moving into a 69 position with
me. "Clean up my cock, bitch while I taste your big clit." he ordered. I
was happy to oblige and Greg started moaning as Carson licked my balls and
his cock. Greg started panting and grunting as his orgasm approached.
Just before Greg blasted my ass, Carson pulled his cock out, ripped off the
condom, and took Greg's cock in his mouth. Greg humped his face and
showered his mouth and face with thick, white semen.

Next, Carson laid me face up on a workbench he had set up and my legs and
head hung over each end. Carson asked Greg to suck him hard again and Greg
obliged. Then Carson rubbered up and slipped his cock in my ass to the
hilt. Greg walked around and shoved his still-dripping cock in my mouth
and said "Suck it, boy toy:". He was really getting into the spirit now.
I let him use my mouth as a fuckhole, milking the shaft as he fucked my
face. They got a good rhythm going and took turns calling me "cunt",
"slut", and "whore". It was kinky, but fun for me.

Greg pulled out suddenly and climbed on top of me, slipping a rubber on my
cock. Then he faced me and sat on my big dick, slowly sliding down my
shaft and rocking to loosen his tight hole. Carson had a great rear view
as he continued to pound my boycunt with his big prong. He fondled my
balls as Greg rode my fuckstick. I can't imagine a more sexually-charged
environment and we all were feeling it. Greg leaned forward and forcefully
stuck his tongue in my mouth tasting the mix of his and Carson's cum that
remained. The scene was so erotic that I started to cum. Greg jumped up
and removed my condom and ate my cum as Carson pumped my load in his mouth
with his right hand. Then Carson and Greg moved around and pumped their
second loads into my open mouth.

They left me on the table and sat down to rest. Carson had another
brainstorm and used a curtain pull to tie me up with my legs spread, feet
on the floor, bent over with my stomach flat on the workbench. He said I
would be their fuckhole for the evening and they began working on the pool
house. They would work for a while then one or the other would see me, get
horny, and come fuck my ass. They each fucked me twice more, then 69ed
each other to orgasm right in front of me. I had cum twice while they
fucked me and Carson gave me one final blowjob. It was getting late and
Greg was starting to come back to his senses, worried about what I might
say. When Carson broke down and told him the truth, he was angry and
relieved at the same time. He started to apologize for the harsh
treatment, but I told him it was sexy knowing that Carson would not let it
go too far.

Greg invited us both to a party being held for Gianni Versace (such a
tragic loss) the next night at someone's home in South Beach, but Carson
could not go. I accepted eagerly and went with Greg as his date. Elton
John was there and I got to meet him. It was exciting as hell and the
large crowd was very eclectic. There was great food and wine and a lot of
sexy men and women. I went dressed as a woman and was surprised to find a
hot-looking woman goosing my ass on the terrace. I asked her how she knew
I was a man and she said that she didn't, but that would eliminate the need
for me to wear a strap-on. I told her that I was there with Greg and she
told me to bring him along. I found him and told him what had happened.
He had met another sexy guy and brought him too. The first two bedrooms we
found were occupied with other people having fun, but the second group
invited us to join them. It was a sexy couple and things got very wild.
However the wildest part was when Julianna, the girl from the terrace, took
off her thong and revealed a gorgeous seven-inch uncut cock. I almost came
when I saw it. She had beautiful tits, a pretty feminine face, a hot ass,
and a beautiful cock.

The sex that night was great. Rona, who turned out to be the only real
girl in the bedroom, ended up getting fucked in every orifice repeatedly
and she loved every minute of it. I got my share too with every cock
finding its way into my mouth and ass. After Rona and her date Garrett
left (both with a mouthful of cum and sore asses), the others started
passing me around taking turns reaming my ass. I fucked Julianna once and
I loved reaching around to rub and squeeze her tits or stroke her big dick.
I came like a firehose in Greg's mouth. We didn't leave until 2 AM and
when Greg dropped me off at home he sucked me off in the car before I got
out. When I came, it was almost painful. He was almost as insatiable as
me.

Graduation was almost a welcome relief. I was accepted at a medium-sized
private school in Coral Gables that has a great football team (no more
hints). That summer was a bit of a sexual blur. Between Howard, Jaden,
Carson, Greg, and all of Greg's friends, I was very satisfied. I was also
happy about staying close to home so I could continue to see my sexy
companions. Since freshman were required to stay on campus, I was assigned
to a dorm - a male dorm. Things got dicey immediately. My new roomie
freaked out when he realized I was going to be living as a woman. He asked
to have me removed and the university was at a loss as to how to handle it.
The situation was resolved quickly when another student volunteered to room
with me. I insisted on meeting him and was pleasantly surprised to find a
very nice, attractive, seemingly intelligent senior business major (like
myself). He was quite wealthy, coming from a well-to-do family and having
inherited a great deal of money when he turned 21. Because he was a
senior, and school contributor, he had a special room with two separate
bedrooms, a private bath, and a small living room.

During the fraternity / sorority rush period, I was surprised to receive
two rush party invitations. The first was from a sorority, when a member
saw me on campus and thought I was a woman. This sorority was known for
its attractive women, so I was very flattered. Of course I declined. An
informal gay fraternity also approached me and I accepted their party
invitation. I had visions of interesting fraternity parties. When I
arrived at the party I was only mildly surprised to find that my new
roomie, Gary, was a member. The party was a bit subdued, but everyone was
nice. I realized that many of the members were either recently out of the
closet or firmly entrenched in public. Most of them had had very little
sexual experience. Also, they did not want to call attention to the small
house for fear of harassment.

The hazing was somewhat predictable, childish stuff, until the final test.
The last night, we were forced to kneel blindfolded and naked in the living
room and perform oral sex on various vegetables and fruit, then identify
it. When we got to the obligatory cucumber, it was about ten inches long.
I heard gasps when I deep throated it and closed my mouth with it inside.
Needless to say, I was quickly a popular member of the fraternity. That
night, back at the room, Gary told me that the cucumber stunt had raised
some eyebrows and hardened some cocks too. I reached over and rubbed his
and asked him what he had thought of it. He said his reaction was pretty
much like the one he was currently having, a very stiff cock. I asked him
if he would like a private demonstration and he responded by dropping his
pants and briefs, revealing a very thick, six-inch love log. I removed my
skirt and top, leaving me in crotchless panties and a lacy padded bra.
When I took his cock in my mouth I realized that he was not experienced.
When I finally took it all the way down, he came in my mouth almost
immediately.

"Can you teach me to do that?" he asked earnestly. "Certainly." I said and
proceeded to give him a cocksucking lesson, with my cock being the final
exam. He did well after a few gags and coughs and the occasional biting.
When he got the hang of it, he really got into it. He sucked me to a
roaring orgasm, then kept it in his mouth until it hardened again and
sucked another load out of me. I was very pleased with my roomie. We
slept in his bed that night and I let him fuck me (another first for him).
I sucked all of his cum from the rubber, and he was riveted by that. The
next morning we showered together and he fucked me again, then sucked me
off.

After that night, things got more interesting at the frat house.
Apparently, Gary became a convert and went forth to train others. By the
next big party, the gang had gotten a bit more daring. Almost every senior
and junior member invited me to a bedroom for some private time. I took
one guy up on it and we had a grand time. My feminine undergarments got
him so hot that he let me fuck him then cum in his mouth. We were gone for
about an hour and a half. When we came back to the party, several guys
were naked and in various sexual groupings. Some of the guys got scared
and left. One guy was on his back, getting fucked, and asked me to suck
his cock. I slid over him and got into a 69, taking his massive meat in my
mouth. He was, by far the largest one there - over 9 inches and quite
thick. He reminded me of Bobby and the night in the video booth.

He sucked me well and I deep throated him over and over until he shot the
biggest load I'd ever taken. It poured into me and ran down my chin. This
caused the guy fucking him to explode and I got some of his load too. I
slipped around and took his place, fucking my new friend until his cock got
hard again. Then I slipped a condom on him and sat on his giant schlong.
It was painful, but so worth it. When I lifted up, his giant dick rubbed
my thighs. Before long, I shot a load on his face and chest and he caught
a few drops in his mouth. He continued stretching my anal cavity, sliding
in and out, squeezed by my tight boycunt. I milked his stiff shaft and
started talking dirty to him. When I begged him to "fuck me like a cheap
whore" he suddenly exploded in ecstasy. I milked every drop into the
condom, then slipped off and drank it. People all over the room were
oohing and ahhing over that. His name was Gil and I decided he was going
to be a close friend.

About once a month we had a party like that and word spread to other
schools. We eventually had a challenge football game and party with a
similar group from Florida State and a group from the University of
Florida. The parties quickly degenerated into major sausagefests with lots
of good fucking and sucking. I came up with a clever way to meet everyone.
I laid on my back on a table with my head hanging off. Then the guys
formed a line and I gave everyone a quick deep throating. There were over
thirty guys there that night and I got a taste of them all. Three of them
were so excited they shot a load in my mouth. After I gave Gil a few
sucks, I told him to fuck me while I sucked the others. While I did the
remaining cocks, Gil reamed out my ass good then fed me his cum.

When I was done sucking, the boys brought out a surprise for me - a real
girl, totally nude. It was supposed to be a joke, but she was a real "fag
hag". She was very attractive and had huge tits. She sat on my face and
sucked my cock like a pro. Then she told me to fuck her ass like I would
one of the guys. I gave her a very sensual fucking with lots of rubbing on
her tits and ass. She moaned continuously. When I got close, she put my
cock between those big jugs and titfucked me to an orgasm, most of which
she got in her mouth. I found out later that she was a hired stripper.
She gave me her card and said I could have a freebie anytime I wanted. I
got together with her twice after that and buttfucked her both times.

**Transgender Stories** · 05-04-2016, 04:01 PM

Part 8

The Butterfly Emerges

When Gary heard that I was planning to get breast implants, he got very
excited. The thought of me with big tits was very exciting to him, since
we now slept together anytime we weren't sleeping with someone else.
Occasionally, we even shared lovers. He loved the idea of squeezing female
breasts while stroking a male cock. I told him I had to wait until the
next semester for my semiannual trust fund disbursement, but he wouldn't
wait. He insisted on paying and I reluctantly agreed.

Over the Thanksgiving holiday period, I finally got my implants. By the
beginning of the next semester, the healing was virtually complete. My new
large-C-cup tits gave me a 38 inch bustline to go with my 26 inch waist and
36 inch hips. I wasn't sure how my friends would react to seeing me in the
flesh, but the results were shocking.

Suddenly, guys that I had always thought to be straight were swarming
around me. Other than the surprise between my legs, I was a total female.
I began wearing low-cut tops to show off my new friends and it drove men
wild. All of my old sex buddies were constantly after me to see them and
they couldn't take their eyes (or hands) off them. Heather and Judy almost
sucked my nipples off in a marathon day of sex at my dorm. They loved my
new tits. Gary loved titfucking me and squirting cum on them for me to
lick off. Everyone wanted to suck my tits and they loved the feel of them
rubbing their backs when I fucked them.

Howard and Jaden loved me in my black, crotchless tights and boustierre. I
surprised them one day, meeting them both at Howard's place, dressed as a
young schoolgirl with the short plaid skirt and long, white socks. We
played a little game of headmaster and assistant disciplining the naughty
schoolgirl. They spanked my bare ass, then made me suck their cocks while
wearing the outfit, minus the panties. They fingered my girlish asscunt
and then rubbed my big clit under the skirt. Finally they unbuttoned my
top, removed my bra, and bent me over the desk and gave me a "special
punishment", taking turns to apply it. Finally, Howard was giving me the
punishment and Jaden gave him a little of his own. I watched him impale
Howard in a mirror and I shot cum all over the desk shortly after. They
made me lick it off the desk, then suck theirs up too. I loved that day.

Things were a bit awkward with Gary for the most of the semester. He felt
more possessive after the implants because he had paid for them. I had no
intention of being monogamous and it led to a bit of tension. I offered to
pay him back, but he refused to accept it. Finally he came around and we
resumed sleeping together (or not sleeping). Before he graduated and left
Miami, I spent a whole weekend saying goodbye. I fed him, bathed him,
pampered him, and screwed his brains out repeatedly. He would be walking
across the room and I would go to my knees and suck him off on the spot. I
fed him chocolate sauce from my nipples and licked whipped cream (and his
cream) from his cock. Every time he got hard, I offered an orifice or hand
for his pleasure. When the weekend was over, I slept over 18 hours to
recover.

Just When I Thought Things Couldn't Get Stranger

During the summer following my freshman year, I bumped into Dannie at
Howard's place (he was out). She had heard about my implants from Heather
and she had to see them, so I showed her. She lifted them felt of them,
but lingered a little longer than I expected. Suddenly she leaned over and
started sucking my left breast. I was shocked and it took a lot to shock
me by this time. She said that she had been experimenting a bit with
Heather and found breasts very enticing. I had this stupid notion that I
had turned her into a Lesbian. She assured me that she still liked sex
with men and to prove it she pulled off my skirt and panties and devoured
my cock. "I've missed this so much" she moaned while licking and stroking
me. "No one has ever fucked my ass the way you do." I was shellshocked by
this unexpected, but not unwelcome, sexual assault.

She went to the bathroom and came back with lube and a condom and got
herself ready for an anal intrusion. She pushed me on the carpet and
straddled my waist. With little preparation, she impaled herself on my big
cock. While she bobbed up and down on my cock, she rubbed my tits and
called me her "sexy bitch". I was so aroused. I had missed her
tremendously and this was so exciting. She jumped off and got on her hands
and knees and said "Screw my hot ass, Tess.". I loved it when she talked
dirty and used my new name. She kept telling me to rub my tits on her
back. I discovered later that Heather used a strap-on on her ass and
rubbed her big tits on Dannie's back.

I was just about to cum when I felt something on my ass. I turned and saw
Howard rubbing my ass with his hand. "Doesn't anyone in this family
knock?" I thought to myself, but said nothing. Dannie's head was down and
she didn't know he was there. He took out his cock, put on a condom and
slipped his cock in my ass. I tried to stop him without alerting Dannie,
but he was determined. This was really getting high on the "weird scale".
I continued to fuck Dannie's ass, but every time she opened her mouth, I
cringed. "I love it when you stick that big cock all the way up my ass,
baby" she hissed. I had no choice with Howard slamming my ass forward so
hard.

Finally, she looked back and spotted an extra leg back there. "Who is
that?" she asked, urgently. "It's Dad baby, don't stop." Howard replied.
"This is freaky.", she said firmly, but kept fucking. When she came, she
squeezed my cock so hard that I exploded in her ass. When she finished she
rolled over and watched her father fucking her ex-boyfriend. I couldn't
imagine what was going through her head until she started fingering her
pussy and moaning softly. Only sex can make people act this way.

When he came, I swallowed it all. She was tempted to kiss me and have a
taste, but couldn't go that far. We all sat quietly for a few minutes, no
one knowing what to say. I sensed that Howard had always been attracted to
his daughter, but didn't dare act on it. I think he saw this as a way to
have sex with her without physical contact. I thought it was a bit odd
that Dannie didn't bother to cover herself afterward. Maybe she was
attracted to Howard as well. Dannie left shortly after, but I stayed to
have more sex with Howard. He seemed much more aroused than usual after
the earlier scene. He fucked my ass all over the bed, riding me so hard.
I finally just laid flat on my stomach and raised my ass slightly so he
could pump my ass as hard and fast as he wanted.

The next day, I went over to Heather's apartment and, when I knocked, she
yelled for me to come in. When I entered her bedroom, she was in a 69
position with someone that I assumed was Judy, although I could not see her
face. Heather looked up and asked me to fuck her ass, so I stripped and
slipped on a condom. When I got on the bed and prepared to mount her ass,
she raised slightly and I realized that the recipient of her cunt juices
was not Judy, but Dannie instead. I wasn't prepared for that and my cock
deflated as the shock set in.

Dannie reacted quickly, saying "Let me help with that." and taking my cock
in her talented mouth for a quick blowjob. I became hard again quickly and
Dannie helped me insert myself into Heather's sweet asshole. Dannie moved
slightly so that she could lick my cock at the same time she licked
Heather's cunt and asshole. It was tremendously stimulating. We kept at
it a while and Dannie and Heather both had major orgasms. Dannie's face
was covered in cunt juice. When I finally pulled out to shoot, Dannie,
took me in her mouth and Heather swung around to lick the shaft. They
shared my load, then kissed deeply, mixing their cunt juices with my cum.

We rested and Dannie and I talked a bit. She admitted that the session the
day before had been very arousing and that she intentionally stayed with
Heather, when Heather mentioned that I was coming over. She said that
there was no way we could have a relationship, but she would love to have
sex with me once in a while. I told her I would like that and we kissed
deeply. The taste of everyone's juices lingered in her mouth and it was
very titillating. Judy came by later and we had a great time. The girls
got into a three-way daisy chain and I took turns fucking them and licking
their asses.

A couple of weeks later, I stopped by unannounced to invite Jaden to a
party that night. Nobody answered the door, so I walked around to see
whether he was swimming. I didn't see anyone, so I started to walk away.
As I turned to leave, I heard a loud groan and knew it was Jaden
immediately. He was in the poolhouse, so I walked over to see who he was
fucking. I peeked in and saw something that freaked me out for life.
Jaden was on his hands and knees and Carson was giving him a royal
assfucking. I had never considered this as a possibility and I was shocked
and aroused at the same time. I fought my desire to barge in and join
them. I did jerk off while I watched and left a puddle of cockjuice behind
when I left. I don't know what would have happened if I had joined them.

I was supposed to meet Greg at the party, but he arrived late. He didn't
tell me what the situation was with the party. He only told me that it
would be very interesting. Most of the attendees were in their thirties
and forties, lots of couples. There were probably 20 people there, with
twelve men and eight women (and me). I had a drink and mingled talking
with a nice couple in their early thirties. Suddenly, the guy (Karl)
started to fondle my ass. He said, "Your ass is really firm, do you work
out?" "Yes", I replied, expecting his wife (Susie) to object, but she
turned the other cheek (literally) and asked "Do you enjoy anal sex?" I
wasn't sure if they knew my "status" but I decided to go with it. "I love
a nice, juicy dick up my ass." I said. They both smiled and said "Please
party with us first.". At that point, I realized that this was a swingers
group and was very excited.

Couples and threesomes began to pair off and they led me to large sofa in a
corner and began to disrobe. Clothes were starting to come off all around
us and the lights were dimmed. I was nervous about their reaction to my
"special equipment" and when Karl gave me a deep kiss, I got concerned (and
aroused). Susie removed my top and bra and started sucking my tits and
rubbing my ass under my skirt. I got on my knees and started to suck
Karl's cock and he started licking her pussy. I moved to his balls and
started licking and sucking them. He was really getting hot and started
tongue fucking Susie hard, making her squeal with pleasure. I then licked
his asshole and he begged me to tongue it good. I inserted my tongue a bit
and wiggled it. His asshole was not that tight, leading me to believe that
he was no anal virgin. I stuck a finger in and started to fingerfuck him.
He moaned and said "Fuck that ass baby. Oh, I wish we had a dildo handy."

That was my cue and I slipped off my skirt and panties, revealing my long,
hard cock. They both went after it at once, licking and sucking it like
they were starving. Karl whispered in my ear "Please fuck me with that big
cock. I need it bad." He leaned over the sofa, on his knees and Susie
sucked me and licked his ass. She helped me slip on a rubber and insert my
cock, stroking me as I penetrated his tight hole. Then she straddled his
back and pressed her cunt in my face. I licked and tongued her as I
steadily fucked Karl's luscious, hot sheath. Susie was very short (4'10")
and her tits were very large (DD), so they hung just over my head as I ate
her pussy. Occasionally, I reached up and squeezed or rubbed them. After
a few times, I felt something wet in my hair, and reached up to see what it
was. I tasted it and realized it was milk. She was lactating and for some
reason, I found that incredibly erotic. I lifted my head up and sucked her
tits, tasting her milk and getting her very hot. Finally she told Karl to
move and stuck my cock up her ass. Karl, feeling left out, moved behind me
and started licking my ass. I told him to get a condom on and give my ass
what it needed. He smiled and, in a flash, he was balls-deep in my butt.

We fucked and sucked each other in several positions until Karl gave me a
deep kiss, then left to join two guys who were fucking a pretty brunette.
I last saw him sticking his cock up one of the guys' ass. Susie asked if I
would like to play with her and another woman for a while. I quickly
agreed and she said she would bring her over. She told me that the woman
had gone through a nasty, protracted divorce which was finalized recently
and she was sowing her wild oats and would love to have sex with a shemale.
I went to get a drink and felt a hand on my shoulder. I turned and it was
Susie and standing beside her was none other than Carol (Dannie's mother
and Howard's wife) who had caught Howard and me on the pool table. I
braced myself for a major scene, but instead she said "Hello Tess, Susie
tells me that you are quite the little sex machine. Would you like to
party with us for a while?" It suddenly occurred to me that she didn't
recognize me. I knew the changes were significant, but this was proof that
my transformation was complete.

Carol was a sexy woman - not in Jane's league - but pretty and shapely. I
followed then to a semi-private alcove with a long, wide, upholstered bench
about the size of a twin bed, but a bit longer. Susie had Carol and I lay
on our backs with our heads at opposite ends. She then inserted a
double-headed dildo in my ass and Carol's pussy. We then moved closer
until our asses were almost touching. I must have had 10 inches in my ass
and she had about 7 inches in her cunt. We scissored each other and began
to fuck each other with the dildo. I couldn't help but remember the time I
had done the same thing with her husband. Susie straddled my face and
started rubbing her hot pussy on my tongue, then leaned over and licked my
balls and Carol's cunt as we rocked against each other. After Susie and
Carol came (I almost drowned), we shifted and Carol fucked Susie's pussy
with a strap-on while I fucked Susie's ass. Then I fucked Carol's pussy
while they 69ed. When I came, Carol sucked my cock and shared my cum with
Susie. About that time, another guy walked by and Susie passed some cum on
to him with a big kiss. It was wild to see a total stranger tasting my cum
that way. He introduced himself simply as the Cockmaster. Susie whispered
in my ear that he really deserved the title. Carol excused herself and
joined another twosome, licking some blonde's pussy. Cockmaster certainly
had impressive equipment - a gorgeous dick, about 8.5" long and thick.
Cockmaster sat down and began sucking my cock, then we shifted into a 69.
Suddenly, I felt a knock at my backdoor and felt Susie penetrate me with
the strap-on. "I'm getting you ready for his big dick." she said smiling
mischievously. Finally, his cock was fully erect and he asked if he could
fuck my ass. I didn't respond except to push him on his back and mount
that big fella. It was so thick that I had to work it in slowly.
Eventually, I was resting against his pubic hairs with that big monster
stretching my sphincter to its limits.

I started to rock on it when Susie straddled his torso and planted her ass
on my cock. I was a bit awkward at first, but we worked out a rhythm.
Cockmaster put a pillow under his head so he could lick her pussy as she
rode my log and I rode his. Susie came two more times and slipped off
before I shot a load on his chest. She leaned over and licked up my cum,
again sharing it with Cockmaster. That really got him hot and he bucked my
ass hard. He picked me up, still perched on his rod and walked around the
room pounding my asshole repeatedly. Susie followed us around as he
introduced me to various people, still reaming my ass. It was very erotic.
When he was ready to cum he went to the middle of the big room and shot a
gallon of cum in my mouth. It was like a firehose and it ran all over my
face and tits. He also shot a little on my dick. He then laid me on my
back, and several people began licking his cum off of my body. One cute
raven-haired beauty with big tits (Andrea) licked my cock clean and
fingered my ass. Her boyfriend, Rusty inserted a finger alongside hers and
together they fingerfucked me. My cock didn't respond quickly, so Rusty
decided to fuck me instead. He raised my legs and buried his sweet cock in
my butt. Meanwhile, Susie and Andrea got into a 69 right beside us. I
reached out and stuck a finger in Andrea's cunt. It was surprisingly tight
for a girl that hung out with a crowd full of big cocks. She moaned and
started fucking herself on my finger. She finally told Susie to stick a
finger in her pussy and told me to stick mine in her ass, which I gladly
did. She almost broke my finger when she started bucking and writhing
against it. Rusty was giving me a nice fucking. He really knew how to
stimulate my ass by rubbing his cockhead against my prostate. I told him
he could shoot in my mouth, but he wanted to fill the rubber in my ass.
After he came, he removed the condom and poured his cum on Andrea's
asshole. He then instructed me to lick it off. When my tongue, hit her
asshole, she went nuts, groaning and writhing. Poor Susie was getting
pummeled as she licked Andrea's cunthole. Finally, I slipped on a rubber
and planted my cock in Andrea's amazing ass. I have never felt an asshole
so tight, not even on an anal virgin, but she acted like it was nothing.
She was pushing back harder than I was pushing forward. Rusty began eating
Susie's pussy, taking her mind off the woman who was rubbing her face so
hard with her cunt. Andrea's ass was like a wonderland of stimulation.
She squeezed and milked me, changing angles and pushing back to meet my
thrusts. I came much quicker than usual and squirted my load into Susie's
mouth. Andrea came one more time, then rolled off, allowing Rusty to kiss
Susie and get his share of my jizz. I lay on the floor hugging and kissing
Andrea as we rubbed our sweaty breasts against each other. At the group's
next party, I met two guys and they persuaded me to let them both fuck my
ass simultaneously. Their cocks were both about six inches long and not
tremendously thick so I agreed. It took some effort, but they finally got
both dicks in and gave me a solid assfucking. After they finished and I
ate their cum, the older one sucked my cock, followed by the younger one,
who got my load. I was struck by the way they never touched one another.
After we finished, they revealed that they were father and son. It seems
that the father had suspected that the son was bisexual and brought him to
Miami to one of the wild clubs. They both ended up sucking cock that night
and the father had his answer. From then on they made regular trips to
Miami and had sex with men and tgirls. This was their first attempt at a
double anal scene and I was glad they chose me. It was exciting,
especially when they alternated moving in and out. I became a regular at
these parties until a big scandal erupted and we had to stop having them.
Apparently, one of the women brought her 15 year old daughter (she looked
25) and let her join in the fun. I'm glad I didn't have sex with her,
although those who did said that she was certainly no virgin. I saw her
take on two guys in every possible combination, including getting her ass
fucked. She also ate pussy twice, including her mother's.

**Transgender Stories** · 05-05-2016, 12:17 AM

Part 9

I Find the Pot of Gold

Right after I started my sophomore year, my fraternity decided to go to one
of the hot clubs in South Beach. The club had the usual mix of gays,
straights (men and women), bisexuals, transsexuals, and transvestites. It
was a real freak show and I was certainly not out of place there. I danced
with my fraternity pals, got fondled a bit in the crowd, and ended up
fucking a bisexual guy in the lady's room while his girlfriend watched and
instructed me (and nibbled my tits). Girls were peeking over the stall and
cheering as she reached under and stuck a finger in my butt, then stuck it
in her boyfriend's mouth to suck. One girl climbed over and started to
suck my buttfuck's cock. His girlfriend got bent out of shape and made her
leave. Eventually, I came in his mouth and walked back toward the dance
floor.

This nice looking guy, about mid-thirties, was watching a girl dance and
walked right into me. He was very embarrassed and offered to buy me a
drink to make it up to me. We hit it off immediately and had a couple of
drinks . He told me his name was Rod and I told him I
had several friends with the same name. I was drinking White Russians and
he told me he had never had one. I told him I loved to taste White
Russians and feel the cream run down my throat. I saw a bulge growing in
his pants and told him that I thought there was something alive in his
pants. He got very embarrassed - it was just adorable.

He told me that he had just moved to Miami from New York to run the Miami
office of a major investment banking firm. His office managed the South
and Central American territories as well as South Florida. They were very
involved in dotcom IPOs. At that point I was far more interested in his
dick going up than the NASDAQ index. I asked him if he had ever stuck a
large amount in Fannie Mae and his cock grew even larger. The double
entendres were getting him hot and he finally asked if I wanted to put my
money where my mouth was. I whispered in his ear "I'd like to put your
dick where my mouth is." He almost sprayed his shorts. He asked if I
would like to come back to his waterfront townhouse and I quickly accepted.
It wasn't until I got in the car with him that I started to wonder whether
he knew I was a tgirl. He leaned over and kissed me, fondling my breast
and I quickly forgot all about telling him.

We pulled out of the parking lot in his Mercedes convertible and headed
toward his place. I leaned over and nibbled his ear, fondling his johnson
at the same time. It was an impressive bulge and I wanted to free it from
its constraints, so I unzipped him and worked it out. It stood high and
proud in the night air and I started to stroke it to full attention. It
finally stopped growing at about eight inches and I leaned over and licked
the head. He moaned deeply and pushed the head into my mouth. My red lips
worked up and down his shaft for about a minute, then swallowed him all the
way. That was all he could take and he blasted my mouth with his sticky
cum. I swallowed it all and he thanked me profusely. The rest of the way
to his house, I kept my head in his lap and his cock in my mouth as it
dripped cum. He stroked my hair and said sweet things as his cock began to
harden again.

We pulled into his garage and went inside his beautiful townhouse. The
view was beautiful and the upstairs terrace was surprisingly private. He
opened a bottle of Caymus Special Selection cabernet and I knew enough
about wine to recognize that he was trying to impress me. I lay back on a
cushy chaise lounge on the terrace and sipped the luscious wine as he
rubbed my shoulders. He leaned over and kissed me intensely and I moved
his hand to my breast. He removed my top and began to caress my breasts
and suck my hard nipples. I pulled him back up and opened his fly to get
at his sweet cock. I moved him behind my head and had him lean over so I
could take it into my mouth as his balls dangled against my nose. The
aroma was intense and musky. He lasted longer this time and started to
moan loudly as his orgasm approached. Just before he came I put the head
in my wine glass and he shot a torrent of cockjuice into my remaining wine.
When he finished, I sucked him dry, then drank the wine with his cum
swirling in the glass. He looked on in amazement and said "You are the
sexiest woman I have ever seen. I'm going to give your pussy my special
oral treatment." I started to panic again realizing that he really did not
know.

I really have to tell you something." I said urgently as he pulled my skirt
down. My cock was tucked between my legs and he had a baffled look on his
face as he stared at my pubic area. He spread my legs and I braced myself
for an angry reaction. My big cock sprang up and he slipped off the chair
and landed on his bare butt. "What the fuck is that?" he asked in a
stunned voice. "At least he isn't hitting me." I thought to myself. "What
kind of girl are you?" he asked, though he already knew. "I don't believe
it, a real live shemale. The ones in the films are so ugly, but you are
gorgeous." "Ah ha" I thought, "He watches shemale films." Suddenly it
occurred to me, "He wouldn't have been in that club if he hadn't been
interested in the wild side of life." I asked him whether he wanted to
continue and he told me that he was a bit freaked out. He said he had
never had sex with a shemale or a male but had watched a couple of shemale
films out of curiosity.

I told him I would call a cab if he wanted to stop. He glanced at my empty
wine glass and smiled. He got up and brought more wine, filling my glass
and telling me that he would be happy to add cream later if I wanted more.
I licked my lips and slipped a condom on him. I told him I wanted him get
on top of me and mount me like a woman. I raised my legs and spread them,
giving him easy access to my ass. He got some lube and inserted a finger
in my ass. As he stroked my butt with his finger, his other hand moved
cautiously to my cock, rubbing it carefully. Next he rubbed my balls
tentatively, like a child with a new toy. I begged him to stop teasing me
and give me an assfull of cock. He slid between my legs and guided his
cock to my tight entrance. I told him to prong my ass good and he eased
the head inside. It felt so good as it started to slide up my chute,
making my cock tingle and my nipples harden. I squeezed his shaft with my
butt muscles and he moaned like he was in pain. He placed his lips on my
nipple and sucked me gently as he smoothly stroked my ass. He rubbed my
other breast, then squeezed it gently, fucking me in a deep, intense way.
When he started to cum, I ripped off the condom and swallowed his cock,
taking his load in my mouth and purring. Then I drank more of the fabulous
cabernet and swirled the cum and wine together in my mouth. He surprised
me by kissing me and tasting the sweet mixture of cum and wine.

He had just had his third orgasm and he was a bit winded. He lay on
another chaise and caught his breath and I lay beside him, taking his cock
in my hot mouth, sucking very softly, getting the last few drops of cum.
My cock was near his face and he started to touch it again, studying it
carefully as it grew long and hard. I moaned and he licked the head very
carefully, as if he was afraid he would break it. I think he was working
up the courage to cross that threshold and, finally, he took my cock in his
mouth. After a bit of trial and error (and some painful nicks with his
teeth), he started to figure it out. He couldn't take more than half, but
my moans guided him in his quest to improve his oral skills. He really
went at it and soon I was ready to blast off. I told him I was about to
cum and he grabbed a wine glass and stuck my cock in just as I shot a huge
load. I really filled the glass with cum as he stroked my shaft, milking
more juice into the glass. He poured more wine in the glass then offered
it to me. I was a bit disappointed, but drank about half. He redeemed
himself by drinking the rest and licking his lips. He smiled and said
simply, "Thank you my love, it was wonderful and enlightening."

He invited me to spend the night and I gladly accepted. His bedroom was
gorgeous and we both fell asleep quickly, in the spoon position with his
arm draped over me. About 3 AM I awoke to feel his hard cock rubbing my
naked ass. I grinned and asked if there was something he wanted. "Please"
he begged, "I need to feel it again." I got a condom on him and slid back
in the spoon position. I raised my top leg and he helped me hold it up as
he slid his big log back up my asscunt. I rubbed my nipples and stroked my
cock as he got into a steady rhythm, riding my butt and stretching my tight
tunnel. Finally he blasted a load up my ass, then slipped off the condom
and started to toss it. I grabbed it and drained it into my mouth,
swallowing most of it. Then I stuck my tongue inside it and got the rest.

I leaned over and kissed him and he grinned. "That was so hot, baby. You
are amazing." "Thanks lover." I replied and turned over to get some sleep.
"Sweetie, are you awake?" he asked and I turned to see what he wanted. He
told me that he had been watching me as he fucked me and was very curious
about it. I knew where this was headed and I got very excited. He finally
worked up the courage to ask me to fuck his virgin ass and I agreed,
quickly. I got him on his knees and lubed him and a fresh condom. I
worked a finger in his ass and he started having second thoughts. I
assured him I would go slow and eventually worked the head of my cock past
his tight assring. He started to panic and I leaned over, rubbing my big
tits across his back, then reaching around to stroke his cock. Amazingly,
it started to get hard again, just minutes after his fourth orgasm of the
night. Very impressive.

I worked it in slowly and he finally started to get more comfortable. I
wanted to give it to him harder, but I knew better. Eventually, I picked
up the pace, getting into a good rhythm, slow but steady. He was hurting,
but loving the way it filled him and the feel of my hand stroking his dick.
He wanted to see my face so we flipped over and he straddled me, sliding
down my big rod and fucking himself quickly. He started bouncing rapidly
and stroking his cock hard, then leaned forward to kiss me and rub my
nipples. I was really ready to shoot and he told me to shoot it on his
cock. I slipped out and turned to spray his cock and balls with my hot
jizz. After I covered his package with my cream, I went down on him and
swallowed his cock, eating my cum. Shortly after, he deposited another
creamy treat down my throat and kissed me to get a taste.

About 9 AM, I awoke to a kiss and breakfast in bed. He made wonderful
omelets with croissants, bacon, marmalade, and amaretto coffee. While I
ate, he washed my feet and massaged them with ginseng oil. Next, he sucked
my toes, giving me a major hardon. He asked how I liked the coffee and I
asked for some cream. He started to move toward the kitchen and I told him
I would rather get mine fresh from the source. He grinned and crawled up
to my face where I slipped his cock out of his briefs. I covered it with
marmalade and pounced on it, sucking him really hard and tasting the sweet
gelatin on his cock. I bobbed rapidly up and down till his moan grew
louder and I knew it was about to explode. I pulled it out and aimed it at
my coffee cup where he erupted with a massive load. I don't know how he
had that much after the previous night. I stirred it in the coffee and
sipped it, licking my lips and kissing him.

After I finished the coffee, I went to shower and get cleaned up. His
shower was huge and had a porthole with a view of the water. I was really
enjoying the warm water cascading off my face and over my tits. Suddenly,
I felt a pair of hands on my ass and smiled, knowing what was coming next.
I leaned forward, placing my hands on the wall and spreading my legs. I
reached back and put soapy water in my ass and on his condom-covered cock.
He entered me slowly and gave me a lovely morning ass fucking, ending it
with another luscious load of cock nectar. I hugged him and rubbed my
soapy body against him, my tits caressing his chest and my cock rubbing his
tight tummy. He groaned and hissed "Fuck me again. I need my ass fucked
again. Please give it to me." I was happy to oblige and slipped on a
rubber. He assumed the position, and I rode his ass to a mind-blowing
orgasm.

He and I became regular sex partners and he invited me to move in with him.
I told him that it was important to me to get a degree and declined his
offer. However, I did allow him to help me with financial advice.
Eventually he helped me use some of my college money to invest and managed
to get me in on some of the IPOs his company was doing. My $5000 initial
investment quadrupled with the first IPO (thanks to the internet boom).
Then we did several more and each time my return was unbelievable. It
doesn't take long to build a huge amount of money with that kind of return.
By the seventh IPO, I had over $12 million dollars and he told me to stop
and smell the roses. He knew that the gravy train was going to end and he
didn't want me to lose my money. Even now, he manages my money and it has
grown to over $14 million under his expert handling.

After a couple of years in Miami, he was promoted and transferred back to
Wall Street. Fortunately he was visiting me when the Trade Centers fell.
He said I was his good luck charm and I know that he was mine. He gave me
passion and friendship, a love of fine wines, and financial freedom.
Whenever he is in town or I am in New York, I clear my calendar for him.
It may be hard to believe, but I am far more grateful for the love and
friendship than the money. Rod is a special man.

**Transgender Stories** · 05-05-2016, 12:19 AM

Part 10

My Junior Year

By my Junior year, I had bought a nice home in South Beach with a good view
of the water. It became party central for my fraternity friends and every
weekend was a scene of wretched excess. I did not allow drugs in my home,
so that eliminated the really bad crowd. However, some of the guys were
bringing some rough trade to the parties. The tattoos and piercings were
growing exponentially and the sex was getting rougher. It was a sea of
cock rings, ball gags, butt plugs, and dildos. One night my Uncle Hal
showed up unexpectedly. I had not seen him since the hormones and implants
and when I answered the door, he asked for David. Then, he remembered my
new name, and asked for Tess. I decided to tease him a bit and told him I
would look for her. I told him to have a seat on the sofa and his eyes
grew wide at all of the hot male flesh before him. I walked into the
bedroom, careful not to step on anyone, then returned and sat by Hal. I
told him that Tess was occupied and would be out soon. I moved closer to
him and stroked his thigh and his package stirred in his pants. I took his
hand and moved it up my thigh until he found my package and he quickly
heated up. I had his cock out in no time and gave him a spectacular
blowjob, loving every minute as he splattered the roof of my mouth with his
special sauce.

When I finished, I moved to his ear and whispered "Just like old times,
Uncle Hal." He almost fell off the couch. He kissed me and told me how
happy he was to see me again and how exciting my new body was. It was then
that I knew my transformation was complete. I worked on his cock some more
to get him ready for my friends. Then he dove in with gusto and had a
sausagefest with the guys. My big boy Gil wanted to fuck him but Hal
couldn't handle it so I let Gil ream my poor little butt while Hal sucked
me off. When Gil blew his load, he showered Hal's face and mine too. We
then kissed and licked each other, each getting a mouthful of Gil's
joyjuice. There were 11 guys at the party that night and I fucked, sucked,
or got fucked by 8 of them.

Hal spent the weekend with me and we made up for lost time. I invited
Howard over and they took turns reaming my ass, then fucked each other's
brains out. The best part was when Howard had me on a table fucking me and
Hal straddled my cock and sat on it, riding me to a great orgasm while
Howard bathed Hal's ass cheeks with cum. We then licked Hal's ass clean
and I tongue-fucked him to another raging hardon. Then Howard and I 69ed
while Hal mounted me and rode my steamy tunnel hard. When Hal came he
added his cock to Howard's in my mouth. My lips hurt as the two cocks
stretch my mouth wide open. I couldn't hold Hal's cum and it ran down both
dicks. Howard was so excited by this that he shot another load in my
mouth. I removed the cocks and cleaned them up, resting until the next
round. It was a wonderful weekend.

-----------

Jaden stopped by to see me that semester. I hadn't seen him since I caught
him having sex with his father. I was a bit uncomfortable and then Jaden
said that he knew why I hadn't called him. He said that he had seen me
that day, but didn't want his father to know. I laughed and told him that
I had been having sex with Carson too and that Carson knew about the two of
us. He looked agitated at first, but finally laughed at the irony. I
asked him whether it was a one-time situation and he reluctantly admitted
that it had become a regular thing. He said that his father had called him
David a couple of times during sex, causing him to wonder whether something
was going on.

I became very aroused and suggested that we invite Carson over. He was
reluctant, so I went down on him and tongued his ass. I described what we
would do together and he finally let the little head make the decision. I
called Carson and invited him over. Jaden had told me that Jane was at her
mother's for an overnight visit, so I knew the coast was clear. Carson
agreed to come over and about an hour later, the doorbell rang. I yelled
and told him to come in. He asked where I was and I told him to come to
the bedroom. When he walked in his jaw dropped as he saw me with Jaden's
big cock buried in my ass. It didn't take him long to realize that he had
been set up.

He was out of his clothes in a flash and had his cock in my mouth almost
immediately. It was ironic that the member of the family that I wanted to
have sex with more than any other was the one that wasn't there. I still
got hard just thinking about Jane's big tits and shapely ass. Carson and
Jaden worked me over for a while - then Carson slipped behind and filled
Jaden's vacant slot with a hot beef injection as Jaden continued to slam my
bouncing butt. Jaden's dick got noticeably harder when Carson rear-ended
him. Jaden came first filling the condom in my ass with his hot juice.
Carson followed with a roaring orgasm that covered Jaden's back. I began
to lick it off and Carson went down on me, getting a load of his own. I
was relieved that everything was now out in the open and we could enjoy
each other as a group. We fucked and sucked each other for hours, then had
dinner and came back to my place for more fun. Before Carson left that
night he and Jaden took turns fucking me against a wall. Jaden spent the
night, but was too tired for another go. I woke him the next day by
sucking his cock, then let him bury his big love log up my ass in the
shower. Just like old times.

-----------

The upperclassmen on campus had learned about me and had either stopped
hitting on me or, in a number of cases, started fucking me. So I was
surprised, one day, when a couple of guys from the football team struck up
a conversation with me, behind the library as I walked by. They were both
black and very muscular. One was a second-string defensive lineman named
Al, about 6'5" and 280 pounds. His hands were as big as my head. The
other guy was a well-known offensive player, who is now in professional
football. I can't say more without revealing his identity (let's call him
Ted).

They told me how hot I looked in my short skirt and asked if I wanted to go
out with them that night. I made sure that I had room to make a quick exit
and asked them if they knew about my "special circumstances". They assured
me that it was ok and asked again about having an evening with them. I was
intrigued, but reluctant. I had trouble believing that these two guys were
into tgirls. Lust got the best of me and I finally agreed. They told me
to be ready at 8 PM.

They picked me up in a BMW 740 (can you say NCAA violation?) which Ted was
driving. We went to a club in South Beach and danced for a couple of
hours. They both were quite amorous on the dance floor, rubbing my ass and
fondling my tits every chance they got. I finally needed some relief and
invited them back to my place. They were ready to roll immediately and
broke records getting to my place. We went inside and had a drink - then
things started to get interesting. I sat on the sofa and they sat on
either side of me. I started feeling their cocks and then things escalated
quickly. We were naked in seconds and they both had nice, big cocks
hanging between those muscular thighs.

I went down on Al as Ted rubbed my ass and tits. I shifted and started
sucking Ted's cock for a while. This went on for a while, until Al asked
if he could fuck me. I quickly agreed and got a condom on that black
anaconda of his. I started to get on my knees, when suddenly Al picked me
up and turned me to face him. He had his hands cupping my ass and holding
me up as I wrapped my arms around his neck and my legs around his waist. I
leaned back a bit to give him a better angle and groaned as he penetrated
me with that thick slab of meat. He started walking around the room,
carrying me and bouncing me on his big dick. His strength was as
impressive as his big dick and he began to talk to Ted.

"This girl has the tightest ass, Ted. You gotta get some of this." he
hissed.

"Put her down Al so she can suck my cock."

"Not yet, I wanna fuck her against the wall"

With that he pressed me against the wall and pounded my ass, his balls
slapping me with every thrust. I decided to take a chance and I kissed him
deeply. He met my tongue with some tongue of his own.

"Come on Al, I need some of that hot mouth or manpussy. Share that hot
little cunt with me."

"Alright man, hold tight a minute."

"I've been holding it. Now I need me some ass. If you don't share, I'm
gonna fuck your big black ass."

"That sounds good, baby. Get a wrapper on and fuck me while I ride this
shemale's ass."

I couldn't believe my ears or my eyes as Ted, slipped behind Al and buried
his big boner up Al's muscular ass. This was obviously not their first
time. Eventually, Ted had a go at my ass as I sucked Al's cock. They
started carrying me around and fucking me again, passing me back and forth
like a cheap whore and bouncing my tired ass all over the house. I
swallowed massive loads from both of them, then fucked Ted while Al fucked
me. Before they left the next morning, they took turns fucking each other
and both fucked me again. Every time I see Ted on television, my ass
tingles. I never had another go with him, but Al came by two other times
and fucked me all over the house. He really stretched my butt wide.

Through Al, I met a gorgeous black girl named Jaleen. She had huge tits,
at least DD, and an ass that curved beautifully down to her long, slender
legs. Her face was lovely and her lips were full and luscious. She knew
about Al's proclivities and enjoyed the scene. She and I got together a
few times and had mindblowing sex, fucking and sucking each other
senseless. I once ate her pussy until she had five orgasms. Then I fucked
her pussy, ass, and mouth. She loved to talk during sex, calling me her
"hot white assmaster" and begging for me to "bitch-fuck" her. She asked me
to call her things like "black bitch", "ebony whore", and "ass-fucking
cunt". It really got her hot. When she came, she really sprayed my face
with cum. I returned the favor, fucking her huge tits and spraying her
face with my white jizz. Jaleen joined Al and I on his last visit and she
really got into it when I fucked his ass. She kept yelling, "Fuck that
tight black ass. Make him a black ass-fucking cunt like me." It was very
erotic.

Jaleen worked at the library and I stopped by there one day and fucked her
ass in a storage closet. She screamed so loud that we got caught by her
supervisor. He was pissed until she offered to suck his cock too. He got
very cooperative after that and blew a load all over her face. I offered
him my mouth or ass, but he declined, saying that he wasn't quite prepared
for that. After that he asked Jaleen about me all the time. Finally he
worked up the courage and asked her to bring me by after they closed one
night. He really plowed my ass that night as Jaleen sucked a big load out
of me. When he came, I swallowed his load. Jaleen was my kind of girl and
I miss her sweet ass and hot pussy.

**Transgender Stories** · 05-05-2016, 12:20 AM

Part 11

Maddie and Sandy

My Senior year was pretty hectic. I was focusing more on academics because
I wanted to graduate with honors and I was also tutoring some underclassmen
who needed help. One of these was a Junior named Sandy. Sandy was an
attractive girl with a great body. Every time I worked with her, my cock
would get hard under the desk. She knew I was a tgirl and eventually
started asking questions about it. I didn't mind sharing, but the
questions eventually turned to sex and specifically to my preferences. She
finally confessed that she was bisexual and very attracted to me. Needless
to say, the tutoring stopped immediately and the sex began. During that
first night, I fucked all of her holes and she came at least four times.

Throughout my Senior year, I continued to have sex with Sandy. Every time
she expressed a new fantasy, I made it come true. When I told her about my
father-son double anal session, she begged me to help her try it. I
invited a hot guy named Randy over and within minutes we were both buried
in her hot ass. She loved it, but mentioned that she would have loved it
even more with a cock in her mouth. The following week I invited Randy
again and he brought his friend Jack. Sandy finally got her wish and we
even added a dildo in her pussy. She was truly insatiable. I wanted to
try double anal too, but their cocks were so big, I thought better of it.
Randy was about 7 inches and Jack was about 6.5 inches and they were both
very thick. I fucked both of them and they both rode my ass hard, each
giving me a couple of tasty loads.

Through Jack, I met another tgirl named Maddie, who worked at a local club.
Maddie was so feminine it was hard to believe that she was a tgirl, until I
finally got a look at her cock. I had not seen a cock like this since
Bobby moved away. It is almost 10 inches long and gets hard as a rock. We
instantly became best friends and began a sexual relationship that is still
going strong today. Together we have had some amazing sexual adventures,
but I'll cover those in more detail later.

My house had become the epicenter of trisexuality in South Florida. Almost
every night Sandy, Maddie, and one or two horny guys would join me in a
myriad of sexual configurations. One guy described my house as
Disneyworld, except with better rides. He certainly rode me enough times.

One night, a guy named Phil was in from out of town and came over with one
of our regular guys. Phil lived in Atlanta and told us about a sex club
that he had started there. The members were all men, except for a couple
of tgirls. He said that they had weekly parties at his place and would
love to have Maddie and I join them the following Saturday night. Maddie
already had plans, but I eagerly accepted. I flew in on Friday and spent
the night with Phil. We slept together and had great sex, but little did I
know what was in store for the next night.

The typical attendance at the parties was about seven people, but this
night was different. They were initiating a new member and 10 members
showed up, including Phil and one tgirl. Phil asked if I was ready to go
through the initiation ceremony and I asked what was involved. He told me
that new members had to offer their ass and mouth to every member that was
in attendance and swallow one load of cum from every member. I almost came
just thinking about it.

Not wanting to waste time, I stripped immediately and got down on all
fours. In seconds, everyone undressed and a guy with a thick eight incher
was sliding up my butt. He was a sensitive lover and caressed my tits as
he slowly moved in and out of my red-hot asshole. The sensation was
incredible as he nibbled my neck and slowly, steadily gave my ass the
stroking it craved. Finally, he was ready to shoot and I stripped the
condom from his cock and buried his cock down my throat as I licked his
balls. The first two shots of cum almost went through the back of my head.
Then I pulled back and took the rest on my tongue. Instead of swallowing
it, I held it in my mouth as the next guy began to insert his six inches of
thick cockmeat in my well-lubed ass. When he was ready to cum he added his
load to the cum that was still in my mouth. I then opened wide and
swallowed every drop.

The tgirl was next to invade my nether regions, flipping me onto my back
and sliding her thick seven incher up my hot ass. She was a wonderful
lover, sucking my nipples and kissing me deeply to get a taste of her
predecessors deposits. She finally reached her limit and sprayed my mouth
with a lovely load of hot juice which I happily swallowed.

The rest of the night was a steady stream of hot cocks filling my steamy
hole, followed by a tasty deposit in my mouth. Phil was next-to-last and
gave me a lovely fucking and a huge load of manjuice. The finale was the
most amazing of all. His cock was the biggest I had ever seen. He said it
was 11 inches, but I think he was being modest. It was extremely thick as
well and it took almost 5 minutes for him to work it all the way in.
Fortunately he was sensitive to his lover's needs and started a slow and
deliberate fucking motion which caused me to erupt with a huge orgasm. The
tgirl was there in a flash to swallow most of it. This sensual screwing
went on and on for 20 minutes in three positions, ending with me on top.
When he came, I pounced on his cock and swallowed all 11 inches and got
every drop of his big load.

After I swallowed the last load, everyone stood around me and applauded.
Phil told me that I was now an official member of the club and I could now
choose anyone in the group to fuck. I was torn, given the gorgeous group
of men who had just taken my sweet hole for a ride. I finally decided to
fuck Mr. Bigcock (David) since he had just given me so much pleasure. He
graciously accepted and sucked my cock until I got hard again. I put him
on his back on a low table and slipped my cock slowly up his surprisingly
tight chute. He begged me to give it to him hard so I obliged with a major
ass pounding. By the time I came in his mouth, I had pounded that warm
moist slot for a good 15 minutes. At that point, I was exhausted, but I
was persuaded to try one more encounter. The other tgirl (Andrea) laid on
the table and I moved into a sixty nine position with her. Phil moved
behind me and slipped his luscious rod up my well-fucked ass. At the same
time, Jerry, a gorgeous young guy, slipped his lovestick up Andrea's
lovehole. Andrea and I pleasured each other as the guys gave us both
something to smile about. It was a great way to wrap up the evening.

Andrea and I slept with Phil that night, but we were too tired to do
anything. The next morning we climbed into his gigantic Jacuzzi tub and I
let Phil fuck my ass while I sucked Andrea's cock. My ass was still a bit
sore from the night before, but it still felt good. After I swallowed both
of their hot cumshots. I gave Phil's butt a smooth, steady ride and shot
my load on Andrea's face. Andrea and I hit it off so well that she agreed
to come back to Miami with me and spend a few days at my place. On the
flight back, we got under a blanket in the back of the first class cabin.
She slipped a dildo in my ass and gave me a good reaming. I thought that
no one had noticed anything, but before we landed, a sexy male flight
attendant slipped me a note. It read "Loved the show. I would love to
join you for a private performance. I am at the _____ Hotel tonight.
Please call me.". As I left the plane, I brushed against him and squeezed
the bulge in his pants and winked. I showed the note to Andrea and she was
more than willing to join in.

My Love of Public Sex Begins

That night, we called Kyle (not his real name) at his hotel and invited him
to join us at a club in SoBe. He eagerly accepted and we met him there.
Inside the club, we danced and talked for a while, then moved to a darker,
more private area. I surprised Kyle by reaching under the table, unzipping
his fly, and stroking his cock. He jumped and spilled his drink in his
lap, mostly on his cock. Before he could get a napkin down there to clean
it off. I ducked under the table and took his cock deep in my mouth and
sucked it clean. He was terrified that we would be caught and couldn't get
comfortable enough to cum. I finally got him to relax and then I slipped a
condom on him, lifted the back of my skirt, and impaled myself on his
rock-hard rod. He was still scared, but I began to squirm on him and his
fear turned to lust. Andrea moved around to sit beside us and began to
stroke my cock. The top of my cock was sticking up above the tabletop and
I began to get concerned that we were being a bit careless. These clubs
expect a certain amount of this behavior to go on, but there are limits.
About that time, a waiter approached the table to see if we needed more
drinks. I tried to pull my cock down, but it was impossible to hide it.
As the waiter cleared our previous drinks from the table, he spotted my big
cock. Instead of making a scene, he actually reached over and stroked it a
couple of times, smiled, and licked his lips. I do love this town.

After that we knew we had carte blanche and we took advantage of it.
Andrea went down on me while I continued to ride Kyle's fuckstick. When
Kyle told me he was close, I went down on his sweet cock and got my first
cum cocktail of the evening. It would not be my last. We decided to
adjourn to my place and, as we left the club, I whispered in our waiter's
ear "Come by later and I'll show my gratitude." and I gave him the address.
He joined us about an hour later and we had a fantastic time. My friend
Maddie came by too and we had a respectable orgy. Everybody got a chance
to sink their cock in my velvet tunnel and I tasted everyone's cum before
we were done. The next two times I went to that club, I managed to get the
waiter's cock down my throat and get a sperm cocktail.

When I turned 21, I began to frequent the clubs more often and became
bolder about public sex. One night I was at one of the clubs that has a
very crowded balcony area and I was standing in a very crowded spot,
leaning over the rail watching the hot bodies squirming below, when
suddenly I felt a hand on my ass. It was so crowded that I couldn't turn
all the way around to see who it was. At first, I thought it was an
accident until a voice whispered in my ear "Don't turn around." Then a
pair of hands reached under my short skirt and squeezed my ass. If I
hadn't harnessed my cock earlier, I would have had a large bulge in the
front of my skirt. I spread my legs a bit, to give him better access and
he got a finger about an inch up my lovehole. I reached into my purse and
pulled out a small bottle of lube and slipped it behind my back. The crowd
was so packed that I really had trouble even handing him the lube. He
reached under again and inserted a lube-coated finger all the way into my
ass. It was so hot. I reached behind me to feel his bulge and was
surprised to find that his cock was not only out but was covered with a
condom. I had to admire his nerve. Since I couldn't spread my legs very
far, I tried to compensate by bending over the rail a bit further. He
pressed forward and tried to penetrate me without success. His cock was
long enough, but my legs were just not spread enough. The woman to my left
began to notice that I was trying to get more room and she glanced over.
She actually did a real doubletake and smiled broadly. She pushed her way
to the left a bit and smiled again as I spread my legs a few more inches.

That did the trick and my mystery man's cock slid smoothly up my tunnel of
lust. In order to avoid attracting attention, he pretended to move with
the music, like everyone else on the balcony was doing. The sensation was
intense and he was getting harder by the minute. The girl to my left kept
glancing over and laughing. She leaned over and asked "How big is it?" I
told her that it was hard to tell, but I would guess about 8 or 9 inches.
I leaned over and asked her what he looked like and she looked stunned.
She said that she assumed we were a couple being kinky. While she and I
chatted, he continued to slip me his big schlong. It was surprisingly
arousing talking to someone about what I was experiencing as it happened.
I asked if she would like to participate and she said yes. I told her to
reach over and squeeze his cock as it came out of my honeypot. When she
did it, he moaned loudly and began to move faster. In less than a minute
he exploded in my ass, filling the condom. He leaned forward, kissed my
neck and said "Thank you, Angel.". I leaned forward, trying to catch my
breath, then turned to look my lover in the eye. I was stunned to find
that he was gone. My new friend to the left said that he just tucked his
condom-covered cock in his pants and knifed his way through the crowd. She
told me he was a nice looking guy and surprisingly tall for an Asian man.
I was shocked to hear that he was Asian. I had no idea. The rest of the
night I looked for a tall Asian guy, but never saw one.

Since that time, I have been fucked dozens of times in public places. I
started going to Haulover Beach (clothing optional) and got to know some of
the lifeguards. The first time I appeared there in the nude, it raised a
lot of eyebrows (and a few cocks). Some of the people were rude and
disapproving, but my lifeguard friends protected me, especially the two
that fucked me at night on the lifeguard stand. Once, I pitched a small
tent and a horny young man fucked me senseless as people walked by. After
he came in my mouth and on my tits, I let the cum run down my chin and my
stomach. I left it there as we came out of the tent and walked along the
beach. Guys were falling over themselves trying to get a better look to
see whether it was what they thought it was. I made a point of licking it
off my chin and then my tits. After that, I couldn't walk 50 feet down the
beach without getting hit on. Surprisingly, a lot of couples came on to me
after that. I hooked up with a hot couple there and had a lot of sex with
them until they were transferred to Greece. She loved watching me fuck him
and always 69ed with him while I drilled his ass.

**Transgender Stories** · 05-05-2016, 12:21 AM

Part 12

Invasion of the Tgirls

In the late 90's, SoBe became the hip place to be and gays and bisexuals
began arriving in droves. Tgirl films were becoming very popular and many
American and Brazilian tgirls found a comfortable, accepting environment in
SoBe. I came on the scene at a time when gorgeous tgirls were on every
corner. Needless to say, I got to know many of the girls from the sex-film
industry. While I hated the people that used them for money, I loved
spending time with the girls. Most were only trying to make money for
their hormones and the inevitable sex change operation. Many of them
supplemented their film income with money made as a prostitute. I felt bad
for them, because their reasons were so different from most male and female
prostitutes. They couldn't keep jobs because they couldn't identify
themselves as females under the law. Their medical expenses were not
covered by insurance. As someone who was financially independent and not
interested in going through a sex change, I had never considered the
problems they faced.

The ones who were moving toward a sex change did not appear to be attracted
to other tgirls and didn't seem to enjoy sex very much, but the ones who
liked being a tgirl were generally insatiable sex hounds. The Brazilian
girls were the wildest and they could really take an ass pounding. Brazil
is the center of the cosmetic surgery universe and, despite the macho
culture, tgirls are more accepted there than they are in most parts of
America. It was not at all unusual for a guy to take a tgirl to dinner in
a restaurant in Rio. After hearing so much about it, I decided to see for
myself.

-----------

I went to Rio at Carnival along with Maddie and one of the Brazilian
tgirls. Her name is Doni, but she uses a different name in the movies.
She is a tall sexy girl with a large cock, a pretty face, and gorgeous
breasts. She loves to top and bottom in he films and looks great doing it.
She took us to a beach party the first night, where everyone wore masks and
very little else. What little they were wearing came off shortly after
sunset, but the masks remained and the sex began. Initially, it was
relatively normal, with men fucking women and the occasional gay or Lesbian
pairing. There were several tgirls there and we started pairing off.
Doni, Maddie, and I got a hot threeway going with Doni fucking me as Maddie
slid her giant rod up Doni's hot ass. Eventually, the "straight" people
gathered to watch and a couple of guys asked if they could join us. We
eagerly agreed and began coupling in various configurations.

After that, the dam broke and everyone was fucking everyone that they
bumped into. I fucked men, women, and tgirls in every combination and was
mounted a dozen times. Some guys just wanted to slide their cock in for a
few strokes and some wanted to feed me their hot load. My favorite part
was when two guys laid on their backs and positioned their bodies so that
their cocks were sticking up together. I straddled them and slid down on
both cocks at once. Just to make it more interesting, the wife of one of
the men managed to straddle him and impale her ass on my hard dick.
Finally, Maddie stuck her giant pole in my mouth and began to face fuck me.
The sensation in my love chute was so strong that I had trouble
concentrating on the lovely girl who was riding my cock like a maniac. She
was rubbing her clit and squealing as she continued to push back forcing
every inch of me up her vise-like asshole. I usually last forever before I
come, but she was so tight and energetic that I just exploded, filling the
condom with hot juice. She leapt off me and jerked the condom off. She
sucked my balls dry and cleaned my cock. Then she swallowed the contents
of the condom. What a hot slut she was! As she swallowed my cum, Maddie
filled my mouth with one of her trademark huge cumshots. Shortly after,
one of the guys in my ass filled his condom with creamy cum. I pulled his
condom off and shared it with the hot babe. When her husband was ready to
cum, he shot a little in her mouth and the remainder in mine.

I invited others to share their cum with me and it turned into an oral
gangbang. Every time a guy got close, he slid his shaft between my hot,
moist lips and I swallowed every inch and every drop that followed. I lost
count of the cocks I sucked, but Maddie said it was over twenty. It's a
good thing I got a lot of exercise that night, because 20 orgasms are equal
to 720 calories of protein. Next to Phil's party, that was the most I had
been fucked in one evening and definitely the most cocks I had either
fucked or sucked. Before we left, several guys and tgirls laid me on the
sand and shot their loads all over my body. Then they licked up every
drop. I shot about a gallon of cum in the mouth of a tgirl who was licking
my cock.

When they finished, I went into the ocean to clean up a bit. One of the
tgirls came with me and I let her fuck my tits and feed me her cum. At
that point, I was exhausted and I pulled Maddie and Doni off of each other
and we went back to our villa. On the way, Doni fucked Maddie in the back
seat. And I thought I couldn't get enough.

Celebrity Lovers Let me start by saying that I would never identify a lover
or do anything to jeopardize someone's career. When SoBe became a hot
spot, a lot of American and foreign celebrities either bought homes there
or visited regularly. A lot of those celebrities are either gay or
bisexual. The availability of tgirls was a major attraction. My first
celebrity encounter was a total surprise. I have never been starstruck and
I don't get weak in the knees at the sight of a hot movie star. I was with
some friends at a club, when another member of the party arrived with a
well-known Hollywood hunk in tow (we'll call him Fred). This guy was
married to a gorgeous star and had a long history of dating hot looking
women. He also had children. The minute he laid eyes on me he began
coming on strong. He was sexy and charming, but I was sure he did not know
that I was a tgirl. He finally said that he would like for me to join him
and a friend at his suite. I assumed that it was the girl that he arrived
with (not his wife), so I reluctantly agreed. Before we left, I asked if
he knew about my special circumstances. He said that one of the others at
the club had told him. When we left, the girl did not join us. Instead, a
hot looking stud that I didn't know came with us. His name was Jeff. We
rode in the back of Fred's limo and things got started quickly. As we
sipped champagne in the limo, each guy sucked on one of my nipples.
Eventually, Jeff worked his way down to my cock and began to give me a hot
blowjob. Meanwhile, Fred slipped his impressive cock out and fed it to me.
Before anyone came, we arrived at the hotel, pulled ourselves together and
moved the party to Fred's suite. It was a huge suite with many rooms, and
an unusually large bed. We piled in and began a wild night of fucking and
sucking. My favorite part was fucking this movie star stud up his tight
ass while Jeff gave my ass a lovely dose of cockmeat. We finally passed
out around 4AM, with Fred's cock still buried in my ass.

The next morning I awoke with Fred's limp cock still resting against my
butt and Jeff's cock in my hand. I started to get up when I noticed that
we were not alone. A gorgeous woman, in a very expensive dress was at the
foot of the bed watching me and I jumped, waking Jeff, but not Fred. "Hi
Mary", Jeff said and rolled back over. Mary (not her real name) said
"Jeff, aren't you going to introduce me to your friend?" Jeff said "Tess,
meet Mary, Mary meet Tess." and rolled back over again. I suddenly
realized that she was Fred's movie star wife, and that she was not upset by
what she was seeing. She immediately undressed and asked if I liked girls
too. Before I knew it, she was sucking my cock back to life. I shifted
around to 69 with her and woke Fred in the process. He smiled and said "Hi
honey. I see you met Tess." With that he slipped on a fresh condom and
slipped his hot cock slowly up my ass.

We found a great rhythm and I eventually shot a load in Mary's mouth. I
warned her but she never backed off, taking every drop. I continued eating
her sweet pussy and she went through three orgasms while Fred continued to
pump my shapely butt. When he got close, I slid his silky shaft in my
mouth and moved my lips slowly down his shaft until I had every inch. Then
I began to lick his balls. Mary shocked me when she moved behind him and
stuck her tongue in his ass. That put him over the top and he sprayed my
tonsils and tongue with steaming jizz. Mary wanted a taste so I let some
run down my chin and she licked it off.

We rested a bit, then I lubed Jeff up and slid my cock up his tight ass,
waking him suddenly. I didn't realize that Jeff had never been fucked
before. I offered to stop, but he told me to leave it, but go slow. He
was a real trooper as I gave him a slow, smooth fucking. He became a fan
very quickly, despite the pain of his first anal invasion. After I came,
Fred fucked him too.

We spent the whole day in bed, except for a lunch break which was delivered
by room service. Even during lunch, Mary was horny. She had asked for a
whole zucchini and then sat in her chair pumping her pussy with it, then
feeding pieces of the cuntjuice-covered cylinder to all of us at the table.

I have to admit that I was intrigued by her beauty and distracted by
memories of her movies and the various scenes that came to mind as I
engaged her in lusty interaction. She is a stunning lady and even more
beautiful than she appears onscreen.

After lunch we had more sex and I was exhausted when I left that evening.
It was an illuminating day and it wasn't long before I realized how
incestuous the Holloywood scene really is. About three days after this
encounter, I got a call from a Hollywood agent, asking if I would be
available for a date with one of his clients. The client was a well-known
action star who was frequently linked with very attractive starlets. I
told the agent that his client could reach me at one of the local clubs and
forgot all about it. That Friday night, I was at the club when I noticed a
big hubbub at the entrance to the club. A couple of minutes later, one of
the waiters told me that _____ was in the club and was looking for me.
This guy was quite the muscle-bound star and not known for his stunning
intellect.. I was actually ambivalent about meeting him and did not
respond initially. Eventually he tracked me down and asked if he could
talk to me privately. I agreed and we moved to a private area. He
apologized for the "star treatment" and said that he was a bisexual who had
to keep up appearances for the sake of his career. He had heard about my
session with Fred and Mary, who were frequent sexual partners and wanted to
meet me.

I appreciated his honesty and was attracted to him despite my disdain for
his macho bullshit films. He was very charming and somewhat shy at the
same time. I asked what he liked to do and he said that he really just
wanted to be fucked and to swallow my cum. I took him back to my place and
asked Maddie to join us. That night we took turns fucking "Mr. Macho" and
draining our cockjuice in his slutty mouth.

This encounter led to more encounters with Hollywood stars, most of which
would be household names to John Q. Public. The one thing I learned was
that these people were desperate to take a walk on the wild side. They
were so tired of living up to their image that they would do anything to
live out their fantasies with a hot shemale like me. Some of them were
probably not even bisexual. They were just desperate to try something new.

During that time, I had sex with three Oscar winners, two Emmy winners, and
two Grammy winners. I fucked three of them and was fucked by the rest.
They were all concerned about their image and will remain anonymous as far
as I am concerned. Eventually, I managed to avoid further contact with the
Hollywood crowd and was happy to be out of that scene.

My Political Connections

During the insanity of the 2000 presidential elections, a lot of political
operatives came to Florida to ensure that their side got a fair shake.
Most of those guys focused their attention on Tallahassee and the
incredibly biased actions of Ms. Hughes and her band of Republican stooges.

Some of these guys came to Miami to monitor the activities of the recount
squads, an activity that was incredibly tedious and boring. By the time
these guys finished a day's work, they were ready to unwind. I bumped into
a couple of these guys at a SoBe club and spent almost two hours listening
to their tales of how they were screwing the opposition.

The two guys I met were mid-level operatives who had aspirations of living
in Washington and being influential lobbyists. I got tired of the boring
recap of their activities and told them so. I began to make my exit when
one of them begged me to stay. In his intoxicated state, he described his
desire to have sex with me and swallow my cum. Given that he was a major
hunk, I decided to see this through. His friend was in shock but joined us
at my place.

By now, you have probably guessed that I love a man's cock. I love
everything about them - the way they look, feel, taste, and smell. I love
they way they feel in my hand, my ass, between my tits, and especially
sliding down my throat and spewing jets of hot cum. In my sexually active
history, I had seen dicks of every shape, color, and size imaginable, or so
I thought.

That night I experienced the most amazing cock I have ever laid lips on.
Mr. Stud Politico (Hunter) and his buddy Cam joined me at my place and I
immediately went for their cocks. When I pulled down Hunter's Calvins, I
was speechless. His cock was a respectable length, soft and grew to an
impressive seven inches as it hardened. The amazing part was the
thickness. It was as thick as a Coke can. I tried, in vain, to get it in
my mouth, but couldn't get past the tip. I wanted to suck it so badly, but
simply couldn't make it. He was so horny to be fucked, but I just had to
get that thing up my ass. I lubed my butt with a ton of lube and finally
got a big condom on him.

His friend was mesmerized by the sight of me straining to get that monster
up my ass. It took ten minutes to work it in all the way and I was gasping
for air as I began to move slowly up and down on it. It hurt a lot, but
felt so intensely hot at the same time. After a few minutes, the pain
subsided and I began a slow rhythm milking the giant pole that had my ass
stretched beyond all reasonable limits.

At this point, Cam regained his senses and managed to get his sexy lovelog
balls-deep in my mouth. It was all I could do to suck him with the intense
sensation going on up my hot ass. Then Cam got adventurous and
repositioned us so that Hunter was reaming me doggie style. The he moved
behind Hunter, slipped on a condom and slid his hot dick up Hunter's tight
ass. Hunter was so aroused, he began to pound me even faster, finally
moaning that he was going to cum. I swung around, slipped the condom off
his monstrous meat and slipped the tip in my mouth as he began to squirt
massive amounts of jizz on my tongue. The quantity was amazing. It just
kept coming and coming, filling my mouth and running down my chin. It was,
by far the most cum I had ever taken in one orgasm. Before I could
swallow, Cam stuck his cock in my face again and I took it all the way
down, coating it with Hunter's jizz. Then Cam began to shoot his steaming
load and I swallowed every drop. Then I sucked all of Hunter's sperm off
his cock and licked his balls clean too. Cam licked some of their combined
cum off my chin and tits.

Even after several minutes, my ass was still terribly distended, something
I had never experienced, even with the biggest cocks that had fucked me. I
finally got around to fucking Hunter's pussy ass and fed him a nice load
and by this time my ass had tightened up again. Hunter wanted another go
at it, but I just couldn't do it. Cam surprised both of us by volunteering
to ride Hunter's giant fireplug. It took us almost twenty minutes to
loosen Cam up enough to take it and even after he got all of it, he
couldn't take it. He rode it briefly, then I took it out and licked it
until I got another load in my mouth. This time it was a more normal load,
but really big for a second shot. I kissed Cam and shared it with him.

**Transgender Stories** · 05-05-2016, 12:22 AM

Part 13

I Take Several for the Team

A couple of years ago, I bumped into a bisexual friend, Kevin at a party in
a suite at the Fontainbleu Hotel. The party wasn't that hot, but Kevin was
with a friend who he introduced as Bill. I immediately recognized the guy
because he is a member of the Miami Dolphins and is a well-built white guy
who is definitely not named Bill. I said "Bill, I really enjoy watching
you on TV" and he laughed. He asked if I was with someone and I said "That
depends on you, sweetie". He asked if I wanted a cocktail and I said that
I enjoyed both. He laughed, then leaned closer and said that he did too.
I then suggested that we adjourn to a more private location and we went
downstairs and jumped in his Cadillac Escalade. I verified that he knew
just what kind of "girl" I was and he said that Kevin had introduced us
because he knew that Bill was interested in meeting a tgirl.

I leaned toward him and began to stroke him through his tight jeans. His
cock immediately hardened and I unzipped him and freed his gorgeous meat
from its cotton prison. It was about eight inches long and pretty thick
and I immediately got every inch of it in my mouth. He moaned loudly and
swerved wildly. Fortunately he got it under control and I began to bob up
and down his shaft, milking his meat and playing with his balls. As we got
close to his house he couldn't hold back any longer and exploded in my
mouth. I swallowed his load and cleaned his cock before tucking it back in
his briefs. After a minute, he recovered and invited me in. I accepted
and he came around, opened my door and picked me up. He carried me inside
and straight to the bedroom, stopping on the way to grab a bottle of
champagne from the fridge. He was so strong that he could carry me with
one arm.

In the bedroom, he removed my clothes and grinned like the cat that ate the
canary. Apparently, this cat wanted to eat the cock instead. He poured
champagne on my lovestick and went to work on it with an expert tongue.
Then he stuck it in his mouth and sucked like there was no tomorrow. He
continued to suck me as I moved around to get my hands on his revived tool.
He surprised me by saying he wanted to concentrate on me for now. He
continued to work my cock, then lubed my butt and slid the neck of the
champagne bottle up me pouring bubbly in my love slot. Next he moved to my
ass and licked me as Dom Perignon leaked into his mouth. It was very
erotic. I told him that the bottle was great, but I really wanted him to
slide something else up me. He didn't need another invitation.

He slipped on a rubber and mounted me in the missionary position. I put my
ankles back by my ears, giving him a wide open shot at my ass and he took
advantage of it, fucking me with long smooth strokes. He leaned forward
and kissed me deeply, probing my mouth with his tongue. Then he moved to
my tits and began sucking first one, then the other, making my balls
tighten and my cock stiffen even more. We fucked this way for about ten
minutes, then he flipped me on all fours and dicked me deep from behind,
reaching around to stroke my rock-hard cock. After a bit of this, he laid
back and I sat on his hard meat and slid down the pole. I rocked and
rolled on his dick making him moan hard as he fondled my breasts making my
nipples tingle.

Finally he picked me up, still impaled on his big dick, and I wrapped my
arms around his neck as he bounced my butt up and down, letting gravity
force me all the way down on him. He was so strong that he just put his
hands under my ass and fucked me on his pogo stick. I told him I was
thirsty and he started walking toward the kitchen still fucking me. I told
him that I was thirsty for some balljuice. He laid me on the breakfast
table and I leaned my head back over the edge, so he could fuck my mouth.
He began to pump my mouth pushing it way down my throat with each stroke.
Finally he couldn't take any more stimulation and he erupted cum in my
mouth - the hottest cum I've ever tasted. We went back to the bedroom and
rested awhile. I asked if he wanted to be fucked and he declined, but he
did give me a great blowjob, swallowing my load. I spent the night, and he
fucked me once more that night and again in the morning. He spent so much
time on my tits that they were really tender when he took me home.

After that he introduced me to some friends of his who invited me to the
next home game. One of them had a private suite at the stadium with a bar
and beautiful leather furniture. When I arrived, I realized that it was
nothing but guys. I had worn a really sexy outfit with a very short skirt,
anticipating that these guys had something interesting planned for me. I
was right.

There were four guys in the suite when I arrived. They asked if I would be
interested in some fun and I played it cool saying I wanted to watch Bill
play. They said that they had a more interesting game in mind. I finally
gave in to my lust and agreed to play. First they all stripped and then
helped me out of my clothes. They let me study their cocks, then
blindfolded me. The object of the game was for me to identify the guy by
using my hands, mouth, tits, or asshole on their cocks. Then it turned
into an orgy with cocks in my hand, then my mouth. They flipped me several
times, filling my ass with one cock after another. I had no idea which was
which and I didn't care.

While I was being fucked and sucking a nice cock, I heard the sound of guys
fucking somewhere in the room. It sounded like a lot of guys and I was
intrigued. Eventually a guy stuck a cock in my mouth that was obviously
larger than any of the ones I had seen. It was 9 or 10 inches long and I
deepthroated it several times, causing him to drop a nice load in my mouth.
The fucking and sucking continued until finally I had to rest. I slipped
off the blindfold and looked around, amazed to see 12 guys in the room
several of whom were getting their asses plowed or cocks sucked. I liked
the way they played games. I asked what happened to the guy with the huge
cock and they said he would be back. I sat and watched some of the game
and Vince, the guy who leased the suite came and sat by me. I stroked his
cock until it got hard again, then I wrapped it and sat on it facing the
field. It was fun watching Bill's sexy ass in his uniform while I got my
ass plugged with a sexy cock.

Eventually a waiter came in with some food and liquor and I was surprised
that no one seemed to care. He walked over and asked if I wanted a drink.
I said no and he suddenly unzipped his fly and whipped out a huge cock. He
said, "You seemed to enjoy drinking from this earlier." I couldn't believe
that the waiter had fucked my mouth too. "What the fuck" I figured and
grabbed his ass pulling his cock deep in my mouth. With my ass plugged and
my mouth stuffed with cock meat, I suddenly felt a pair of lips around my
cock. Then guy after guy took turns giving my cock a few sucks until
finally one of them got a mouthful of hot sauce. He walked over to another
guy and swallowed his cock leaving my cum on his dick when he pulled away.
Another guy sucked it off and deposited it on another guy's dick. This
went on and on until ever guy had tried some and finally the waiter got
some on his cock and fed it back to me.

After the game, we stuck around until Bill came up. I assumed he would be
exhausted, but he stripped and reamed my ass good while everyone watched
and applauded. When he came, I was ready to take it, but he stuck it in
Vince's mouth and shot the load down his throat. Vince sucked it like a
baby. Eventually everyone began pairing off in twosomes and threesome and
fucked and sucked for another hour, before leaving. Bill fucked Vince
once, then rested and watched me fuck a couple of guys. Three of the guys
got fucked bareback and took loads in their ass, something that I am too
afraid to do either as the fucker or fuckee.

I went to two more home games that year and got fucked senseless both
times. Eventually Bill let me fuck him at home, then again in front of the
guys. After he got a taste of it, he was insatiable. I couldn't go near
him without him asking to be fucked. When I was too tired to fuck, I would
use a vibrator on his ass. After the last home game, everyone in the suite
had a go at his ass. I finally decided not to see him anymore because he
had become a total bottom and I need a guy who can give as well as receive.
He eventually hooked up with a tgirl that I get together with occasionally.
When she and I had sex she would tell me about all the times she fucked
him.

**Transgender Stories** · 05-05-2016, 12:23 AM

Part 14

Fuckin' Chattin'

There is an old movie where a mob guy dresses as a woman and tells a doctor
that he "loves fuckin' chattin". Now I know how he feels. I first
discovered the chatroom at Planet-Shemale, then moved to the one at
Gay.Com. I discovered that I really enjoyed chatting with horny guys while
sitting on someone's cock. I found that with the right computer setup, I
could sit on a cock and squirm and still type fairly legibly. I can also
get my cock sucked. Now this has become one of my favorite pastimes and my
friends enjoy it too. We still have regular sex, but at least twice a week
I get fucked and/or sucked while chatting online. The only time I
interrupt is to swallow a load of cum. I find it difficult to see the
screen or type while a cock is squirting semen in my mouth.

I eventually tried phone sex and videocams, but the phone thing backfired
when a guy tracked my number down using a crisscross directory and showed
up at my house uninvited. I stopped the videocam, when pictures and
videoclips of me showed up on the web.

I did stop chatting for a few months because the private requests became
overwhelming. I know that all of you horny boys are just looking for a hot
shemale to fuck but I couldn't chat with a guy without getting seven or
eight private requests. It got to be too much. The interruptions made it
impossible to carry on a conversation. I've now learned a few chatroom
tricks which make it easier.

Greek in Greece

My friends who moved to Greece invited me for a visit to their villa on
Mykonos. I had been to France, Italy, and most European countries a few
times, but never Greece. I had always been intrigued by Greece, since it
was the home of Lesbians (Lesbos) and the place where Greek sex was made
popular. In olden days, the soldiers were accompanied by young men who
were used as a sexual outlet. Those who learned to use their asses to
apply pressure to the soldiers' cocks were well rewarded. While this is
obviously an outdated practice, it does make me horny thinking about a
Greek army unit using my ass for their daily pleasure. Yum!

When we arrived in Mykonos, Marco and Sara greeted Maddie and I warmly and
invited us to join them for a swim at a private section of beach below
their villa. Clothing disappeared quickly and we were swimming nude in the
Aegean Sea. Within minutes Marco's cock was in my mouth and Maddie's was
down Sara's throat. Shortly after that, we moved to their living room and
condoms and lube appeared. Marco was up my ass in a New York second and
Sara had her cunt impaled on my cock. After some maneuvering, Maddie got
her cock up Sara's butt and we both drilled her nether region as Marco
plowed my inviting tunnel.

After I took Marco's hot load up my ass, Maddie soon replaced his cock in
my ass and I shifted to Sara's tight ass. Marco let me suck the last drops
of cum from his cock and I kept sucking until he got hard again. He
decided to give Maddie's ass a spin and planted his sweet cock balls-deep
in her butt. When I came, Sara took my load in her hot mouth, then shared
it with me. I rewarded her by going down on her sweet pussy. I worked her
clit and tongued her steaming hole until she came, then kept going while
she had two more orgasms. Meanwhile, Maddie kept pounding my butt while
Marco drilled her slutty hole. They finally reached their limit and I took
both their loads within seconds of each other. The next few days were a
blur of their horny Greek bisexual friends, all of whom got a taste of my
cock or my ass. I highly recommend Mykonos for those who love the bisexual
scene.

After we left Greece, Marco and Sara joined us at a villa in the Bellagio
area of Lake Como. We rented the villa from a gay American couple who
billed themselves as the homos of Lake Como. They greeted us when we
arrived and we invited them to join us for dinner at a local restaurant
(they were hunks). After dinner and several glasses of Port, we went back
to the villa and sat on the terrace, overlooking the lake. Before the
evening was over, both of those hunks got to mount me and ride my ass.
They both had amazing staying power, fucking my slot over thirty minutes
each.

Scott's Yacht

One of my favorite places to have sex is on a large yacht. The motion of
the sea is very erotic and you can fuck under the sun or stars without
worrying about getting arrested. My friend Scott has a 120 foot yacht with
7 beautiful bedrooms. His first mate, chef and cabin boys are all sexy,
horny guys and his friends are some of the most sexually provocative people
I have ever met. One of our trips was particularly memorable. I flew to
the Bahamas to meet them and we sailed from there down through the islands,
finally stopping in St. Barts. Along the way I got to know the other
guests. I had brought Maddie and Sandy with me and Scott had one gay
couple (Gerry and Patrick), one bisexual couple (Harry and Carla), one
single bisexual woman (Paulina) and a tgirl (Millie). Things didn't get
interesting for a while, the first day, because everyone was sunning nude.
Eventually, however, several of us jumped in the pool and that many naked,
horny people in a confined space is bound to lead to sex.

It all started when Gerry and Patrick approached me and both began to
stroke my cock under the warm water. Being the shy, reserved young lady
that I am (stop laughing), I invited them to taste it. I sat on the edge
of the pool and they took turns sucking my shaft and licking my balls.
Others were watching and masturbating, when Maddie invited Millie to have a
taste of her huge cock. Millie jumped on it with tongue flying. Harry
couldn't resist Millie's ass as it wiggled in the water as she sucked
Maddie deep.

Harry quickly slipped on a rubber and within seconds had his thick
six-incher lodged all the way up her hot love chute. He moaned loudly as
Millie pushed her ass back against him. I motioned Paulina over and buried
my tongue in her cunt as she stood over me. She screamed in ecstasy as I
tongued her clit and cunt. Not to be left out, Sandy and Carla moved into
a hot 69 as Scott slipped his luscious, juicy cock up Sandy's butt.

The rest of that day and well into the night, we paired off in various
combinations. After dinner, I fucked Horst, the German chef and then let
him mount my horny ass as I took turns sucking off the cabin boys (Perry
and Max). Perry and Max roomed together and when no visitors were on
board, they spent their time fucking each other senseless or getting reamed
by Horst. Max told me that one day he was gone ashore overnight and Horst
was so horny that he fucked Perry six times and let Perry fuck him three
times. Perry said that he had trouble walking the next day. That's my
kind of crew.

Scott was the captain of the ship, as well as the owner, so he often had to
attend to things on the bridge and could not join us. His first mate,
Terry, was a bisexual guy and covered the bridge when Scott was joining the
party. Once, during the trip, I noticed that Scott and Terry were nowhere
to be found so I walked up to the bridge to check it out. When I arrived
and peeked in, Scott had Terry bent over and was fucking him incredibly
hard. Terry kept grunting and saying "Slam that cock up my ass babe! Give
this whore's cunt the hard fucking it deserves.". I caught Scott's eye and
he motioned me over. I slipped on a condom and lubed up. Scott said "Stay
there Terry while I get some more lube." As he slipped out, I slipped my
cock up Terry's hot, juicy hole and began to pound the hell out of him.

I slowed momentarily to let Scott slip on a fresh rubber and slide up my
slot. Then we got a great rhythm going with me getting the best of both
worlds. Eventually, Scott said he was ready to shoot and Terry pulled off
to get his load. The look on Terry's face was priceless, but he recovered
quickly. He slid his hole back down my cock and motioned Scott to feed him
his cum. Scott got creative and slid under Terry as Terry went down to his
knees. I moved back in and continued to fuck as the two 69ed each other to
huge orgasms. Cum dripped everywhere as the guys tried to catch it all.
When I pulled out to shoot, both guys got a facial and a mouthful of juice.
I licked the excess off of them and sucked the last drops that were still
dripping from their spent rods.

Later that night, my bedroom became a revolving door as half the guests
stopped by for a late night fuck. By the time we arrived in St. Bart's, I
had fucked everyone on the ship and had every cock in my mouth and up my
slutty ass. The beaches in St. Barts are clothing optional, but the tgirls
in the group still created a stir as we strolled past the naked tourists to
a private spot. Guys did double takes and two women licked their lips at
our big dicks dangling in the breeze. By the end of the day two couples
had wrangled an invite to the ship and that night I managed to get my cock
up all of their asses and I wasn't the only one. One of the women was a
gorgeous redhead with double D tits a tiny waist, and an ass that caused
heads to turn. She shaved her pussy and I must have spent an hour working
her into a frenzy. After her fourth orgasm, she begged me to fuck her ass
and I happily obliged. When I finished with her, I fucked her husband's
ass and shot a load in his mouth, which he shared with her.

As we sailed back to the Bahamas, I decided to move out to the front of the
ship and do my "King of the World" imitation from the bow. As I leaned
out, I felt a hand on my butt. I looked back and saw Harry and I smiled my
most inviting smile. Encouraged, he slid my thong off and slipped his
sheath up my ass as he cupped my big tits with his hands. He began to
slide in and out of my ass and I purred as the cockhead massaged my
prostate, making my cock stand out proudly. About ten minutes later, we
began to approach a cruise ship. Scott turned to give the larger ship a
wide berth, but the passengers on the port side of the ship got a wonderful
view of Harry plowing my butt as my cock waved in the breeze. They were
yelling and whistling as we passed, encouraging Harry to "pound that
bitch's ass".

Since that trip I have been on three other voyages with Scott, all of which
were a sexual free-for-all. Our next trip will be through the Panama
Canal. I hope that the guys who work the locks will enjoy seeing me get
fucked as we pass through because I intend to give them a show.

My Sexual Legacy

As we went through my journals to gather the information that went into
this book, we compiled some statistics. While I'm sure that the totals are
not totally accurate, due to my inability to recall all of the details of
some of my group sex scenes (even when I did the journal entries the same
day), they are probably not far off.

The stats as of August, 2004 are as follows:

Blowjobs given 12,153 Blowjobs received 7,214 Loads swallowed 9,786 Anal
received 9,622 Anal given 6,123 Female oral sex given 2,345 Female
intercourse given 1,643 Handjobs received 1,987 Handjobs given 2,456 Double
penetration received 2,765 Double penetration given 2,178 Total men 3,213
Total women 1,712 Total tgirls 134 Total encounters in clubs 653 Total
encounters on beaches 174 Total encounters in cars 1,198 Total times being
hit 3 Total times being verbally abused 18 Total white partners 2,622 Total
Hispanic partners 1,212 Total black partners 833 Total Asian partners 211
Total mixed-race partners 181

Landmarks where I've been fucked:

Eiffel Tower Empire State Building Staten Island Ferry Central Park Statue
of Liberty Carnegie Hall US Capitol Washington Monument Independence Hall
Old Faithful Half Dome Golden Gate Bridge Carnelian Room (San Francisco)
Grand Canyon (no, that is not another name for my ass) Royal Gorge Yankee
Stadium Shea Stadium The Astrodome Pro Player Stadium Orange Bowl The Forum
(LA) The Staples Center (LA) Santa Monica Pier The Hollywood Sign Mardi
Gras Float Coliseum in Rome Seattle Space Needle The Alamo San Antonio
Hemisfair Tower Carlsbad Caverns Sydney Opera House Great Wall of China Mad
Ludwig's Castle Red Square in Moscow Tower of London Toronto Tower Toronto
Skydome Hotel (at the famous window)

As you can see, I'm an equal opportunity fornicator and I could clearly be
classified as a sexual addict. However, I travel the world in private
planes and yachts, stay in luxury hotels, eat in the finest restaurants,
and have sex with very interesting people and I am almost never depressed.
I give money to worthwhile causes and do volunteer work fairly often,
something I highly recommend. Keep in mind that this was not my life
story, it was a sexual memoir for my life to-date.

I hope this has been entertaining for you. If you got off at any point
while reading it then I am pleased. I love to facilitate sexual pleasure
any way I can. Many people will be surprised at my life and some will
judge me harshly. To them I say, walk a mile in my shoes (or spend some
time up my ass) and you would probably see the world differently.

Goodbye and good sex.

**Serjosha69** · 02-01-2024, 02:43 PM

very nice story. I like it

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