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Leonard was lucky in the Residential Living Lottery and got a single room
in Q Dorm in his freshman year. The odds were long and he was the first frosh
in seven years to his the mark, but he did get a room all to himself for his
first year in college.
He was lucky in another way as well. Q Dorm had four wings radiating out
from the corners of a central block which held each floor's bath/shower rooms.
Len's single happened to be at the end of one of the wings on the second floor.
This gave him a very nice view in two ways. One, out his windows, and the
other, down his hall: there were three other rooms in the wing and each of
those doubles were occupied by women. The whole dorm was co-ed but not in any
pattern. Just more of Leonard's luck that both upper-class choice and the
lottery had filled his wing with women.
Len was rather glad to get a single, even if it was half the size of the
normal room, because he was rather shy. He was happy to be at college but he
had been worried about living with someone he didn't know. Now, he would have
time to make friends and find someone to room with next year.
Actually, he got to know the six girls in his wing fairly quickly, which
surprised him. In 231 were Anne (a short, cute blond) and Debbie (a very tall
and willowy beautiful blond). In 232 were Georgette (an average (in most ways)
brunette) and Harmony (a compact, energetic bombshell with raven-black hair).
And, in 233 were Susie (another black haired woman with the biggest breasts
Len had ever seen) and Donna (another blond and the best looking of them all).
Len's room was 234.
The girls were all very easy-going and friendly, which helped Len get to
know them. They - all seven of them in the wing - became almost like a family,
and the four doors were seldom closed (though Len's was shut more often than
then others').
One day about a month after the first midterms of his college career, Len
was in the basement doing his laundry. The student handbook advised that one
shouldn't leave one's clothes unattended when doing wash. Len always followed
the rules, at least until he was sure enough to break them. So, there he was
in the laundry room, alone, studying Calculus and waiting for the wash to be
done.
Mid-way through his wash cycle, Len was joined by Getty and Harm who came
down and loaded up three machines with their combined loads. When they had
the machines chugging away, Getty sat down by Len and asked, "Len, honey, could
you do us a favor? Harm and I are watching this really rad movie and we don't
want to miss much more of it. Here's the quarters - could you put our clothes
in the dryers when they're done...?"
Len said, "Sure, no problem." He was happy to be a help and he would be
there anyway. Getty told him how to separate the loads for the dryers and what
settings to use. Then, after giving him a peck on the cheek, she and Harm
hurried back upstairs leaving Len blushing over his calc books.
Len loaded his own wash into a dryer then, 15 minutes later the girls'
loads were ready. He followed Getty's instructions and put the quarters in,
pushing the right buttons. He found himself lingering over one of the loads,
however - the one that contained the girls' frilly underwear. He took his time
moving that particular load, going piece by piece. His mind was intrigued by
the softness and sheerness of the fabric and, of course, the fact that each of
the garments had been in intimate contact with one of the girls from room 232.
Finally, the dryers were going and Len tried to go back to his calc. But,
his attention kept returning to the front-loading dryer where the lingerie
tumbled colorfully in the soft heat. Strange thoughts had been sown and were
beginning to grow.
Over the next five or six weeks, Len became the official 'wash-person' of
the wing. He got very good at making sure all manner of girls clothes got
clean and dry safely. The girls repaid the time he spent downstairs with
quarters for his wash and one meal a week at a nearby diner (the cafeteria
food being just as bad as college food is supposed to be). Len really
wouldn't have minded ding the girls' wash without the payment for two reasons:
first, he was very considerate and he could usually rationalize that he would
be spending all that time in the basement anyway either at his own laundry or
studying in the interruption free and quiet (enough) room; also, he was really
getting into the girls' underthings and now he was able to touch, fondle, and
(at times, very secretly) even smell the pre-washed items, which was payment
enough for him to have hand laundered each item on a rock by a stream as far as
he was concerned.
Even though his fetish, so newly discovered, was growing steadily, Len
didn't think of "borrowing" any of the apparel that so fascinated him until
very close to finals. Then, the end-of-term pressures that drove the whole
dorm into slightly weird behavior finally got to him. He had noticed, after
the early excitement of his fetish had passed, that he actually studied better
when in the company of the girls' underwear. So, during reading week he
thought to borrow a pair of red and black lacey panties from Donna's load of
wash.
That first pair of panties did indeed help him through finals. That
success led him to 'borrow' a pair every week, each time from a different girl.
He kept his booty in the bottom of the back of his shirt drawer and made sure
that none of the girls ever had reason to go near the hiding place.
Most of the next term went by the same as before, but things changed
drastically around spring semester finals. Len had been eyeing and exquisite
set of shiny-blue lingerie - the whole works in a matched set, from bra to
waist-cincher, garterbelt, stockings, and panties - that belonged to Susie. Up
to that point he had taken only panties, nothing else. But he now felt like he
needed something more and that blue set seemed perfect: they even seemed to be
in his size!
Unfortunately, something like that lingerie was more easily noticed when it
went missing. Susie had already noticed the few panties that were missing from
her and Donna's laundry, and she had a really good idea who was responsible.
All she had to do now was prove it.
So, when the other girls took Len out for his weekly dinner, Susie stayed
behind, citing having to study extra hard for her final the next day. She had
managed to slip a bit of gum into the lock of Len's door so that she was able
to slip into his room and thoroughly search it. She turned up the lingerie set
as well as all of the missing panties - hers and Donna's, and what had to be
the other girls' as well. Thus armed with proof, she returned the room to its
pre-search state and waited for the girls to return.
The moment they got back, she called a conference in her room. Len had
work to do and so didn't feel excluded when they shut themselves in Susie's
room leaving him in his. Susie explained what she had found and asked, "What
are we going to do about it, huh girls?" There was alot of excited and
outraged chatter, then Debbie said, "You know, I've always fancied Len, but he
looks so - so pretty. I think he'd make a gorgeous girl, and he seems to like
our underwear already. Why don't we give him the chance to go all the way?
"Georgette, is your cousin going to be able to swing us that six-bedroom
house? Good. We'll get good ole Len to move in with us for the summer - he
hasn't found a place yet. Once he's there, I think we can persuade him to
dress how we want him to. Oh, I almost forgot. Anne, can your brother get a
large supply of female hormones for us? I think Len should really look the
part - he'll thank us when it's done."
And so it went. Next day, Debbie told Len that if he wanted to he could
move in with them when finals were over. Anne and Georgette would share a
room, leaving Len and the other girls a room apiece. Len agreed without the
slightest hesitation, overjoyed at being able to stay close to these beauties.
The day after their last final all seven of them moved into a very nice three
storey house. Len's room was larger than his dorm room, and it was the
smallest in the house. The kitchen was huge and the living room huger. Len
loved it and even more because the girls were there too.
The household got settled down within a week, and Len found his own
niche quickly. The six women all had summer jobs but he didn't. He had no
trouble paying the rent - he had a monthly stipend from his trust fund that
covered it and more - but he also had lots of free time. So, he fell into
taking care of the house. He was a passable cook, he knew (quite well) how to
do laundry, and he learned how to clean the house. His remaining time was
spent in front of the TV - or in his room dressed in 'borrowed' lingerie.
Even though he now had full access to the wardrobes of all six girls, he
still normally only tried on what the girls put in the wash (not limiting
himself to underwear, though) - cleaning the garment, trying it on, then
cleaning it again before putting it away. But there were a few times when he
just couldn't wait for the item to be put in the wash. He had returned all of
the things he had 'borrowed' over the school year, and now he often went into
Donna's drawer for that first pair of red and black panties, or into Susie's
for that blue lingerie set. The girls didn't wear these things often enough
and they gave him a special thrill to wear them. In fact, so far those two
were the only two 'outfits' he ever dared to jerk off in. Masturbation was
new to him and those two items really helped him get off. They were also his
downfall.
Three weeks into the summer, Len was in Susie's room putting on the blue
outfit. He had put on the bra (stuffed with panties) and the corsolette, and
was pulling up the tiny panties when he heard the front door slam. He was
paralyzed with fear - he had never dreamed of getting caught and now he had
no idea of what to do. Quick reactions might have kept his secret. Instead,
he just stood there, blue panties halfway up his thighs, as footsteps sounded
climbing the stairs and came down the hall. It could have been any one of the
girls, of course, but he had also left the door open so when Anne stopped in
the doorway and looked in, Len almost fainted.
In his mortal embarrassment, Len didn't notice that Anne was rather
startled by the size of his equipment. She got a grip on herself and said,
"What have we here, huh? You look almost girlish enough to be wearing that
lingerie - but not quite. Want to explain yourself, Len?"
Released by her words, Len collapsed on the bed and began to cry. It took
Anne a while to get him to tell his story and he didn't stop crying until very
near the end. Anne, who was more than a little aroused by Len's kinky, half
dressed state, was comforting and understanding rather than stern or angry.
She said when he was through, "Well, I understand about this sort of thing, but
stealing is wrong. You should have asked Susie to borrow her lingerie instead
of taking it, not to mention all of the other stuff. I'll have to bring this
up tonight and see what the others think."
This caused Len to start crying again and Anne finally said she'd be as
gentle with the news as she could and be on his side that night. She left him,
suggesting he get dressed. She wend back to work and Len finished his
housework in worry and fear.
After dinner, Anne kept the others at the table when everyone was done
eating. She gently explained what she had found when she had come home earlier
to pick up something for work, and what Len had explained to her about it. The
silence of the others at the revelation should have warned Len that this wasn't
a total surprise to the girls but he was too worried about the outcome to
notice subtleties.
As usual, Debbie spoke for the group. She said, "Well, Len, this is very
serious. But we are friends - I don't think any of us will insist that your
punishment need be severe. In fact, I think you might even enjoy what I have
in mind.
"As is most fitting, the punishment will fit the crime. A cure or kill
solution. Len, from now until school starts, you will be dressed as a female
from the skin out at all times. There will be surprise inspections conducted
by any one of us - if you are caught in any sort of man's clothing you will be
spanked severely. On the other hand, you can count on our help in keeping you
properly feminine. Anne, if you would do the first honors?"
A full ensemble was quickly assembled in Len's room and Anne closed the two
of them in. She said, "Strip, kid. We'll start from scratch."
Len was very shy about removing his fruit-of-the-looms but Anne finally got
them off of him. She again surveyed him in the buff and was still impressed.
She thought she could detect a hint of feminization about him already - the
hormones had been only working for three weeks - but she had no real idea of
his condition before the hormone treatment began so she couldn't really tell.
She helped him into the blue set of lingerie he had been caught in, making
sure to fondle his hefty cock as she tucked it away between his legs to
present a correctly flat aspect in his panties. When he was fully dressed in
the sexy underwear, Anne was further impressed - even without makeup Len looked
remarkably feminine.
She said, "You know, Len, you look really good dressed like that. Pretty,
even. Sexy, too." She walked over to him and pressed herself up against his
front, then reached up, drew his head down, and kissed him.
Len was overwhelmed. He felt very good just wearing the lingerie and even
better when Anne complimented him in it. Then, when she kissed him, he...he
was blown away! He'd never been kissed before. Anne was hot, beautiful, and
kissing him: he didn't know what to do.
So, Anne took charge. She continued kissing him and began to caress his
body, especially his tucked away cock. Naturally, Len's organ began to respond
by trying to erect, which caused a bit of pain due to its positioning. When he
began to squirm, Anne said, "Oh, poor boy. Let's free that rod of yours so it
can be happy." She pulled his panties off, releasing Len's cock which took
advantage of its freedom by erecting fully. It stood over 9 inches out of the
nest of light brown pubic hair at his crotch. His balls, naturally hairless,
hung large beneath it, all framed by the garter-straps depending from the
corsolet he wore.
Anne dove onto Len's cock, inhaling it half way down her throat on the
first bob. She proceeded to give len the first blow-job of his life, and it
was an event to remember. Len had nothing to compare it with but he was still
sure that Anne knew what she was doing. She lavished her attention all over
his groin, licking and sucking cock and balls and skin as well. Midway
through, Len's knees gave out and he sat down hard on the bed. Anne followed
him and continued her work, finally being rewarded by Len's orgasm and what
seemed like a quart of cum.
She kept licking and sucking even after Len stopped cumming, cleaning every
last drop of jism she could find away. When she was done, Len was hard again,
sitting there staring in a stunned fashion at Anne. She stood, looked at the
beautiful figure of Len half lying there in lingerie and hard cock, and began
to disrobe.
Len just continued staring as Anne removed her blouse and skirt, revealing
a familiar set of bra and panties in lacey green. Then, she removed first the
bra, revealing her beautiful breasts, and then her panties, showing Len his
first live cunt which also happened to be shaved. Naked, Anne advanced on Len,
taking hold of his throbbing rod and caressing it. She said, "Scoot back a bit
and make yourself comfortable."
Len slid his ass back on the bed and Anne followed him, retaining her hold
on his cock. When he was centered better on the bed, Anne pushed his torso
down so he was lying flat and straddled his thighs, still holding onto his
cock. Len could just barely see the inner pinkness of her cunt as the position
of her legs spread her outer lips slightly. He hoped that Anne wasn't just
teasing him with promises of further pleasure.
She said, "Len, honey, are you a virgin?" After a pause, Len nodded shyly.
"Fine. I'll be gentle. You're in for a real treat, kid, a real treat." With
that, she rose up on her knees far enough to position her cunt over his cock
and then began to lower herself slowly down onto it.
Len nearly went out of his mind as Anne sank slowly onto his cock. The
warm, tight wetness felt so incredibly wonderful that he berated himself for
hot seeking out sex long before. He lay back, closed his eyes, and just let
himself feel.
Anne was going wild herself. Len's cock was huge and filled her
wonderfully. At first, he just lay there making her do all the work. But
eventually the pleasure of his first fuck forced his body to respond and he
began pumping his hips in perfect rhythm. His eyes remained closed but his
hands rose and blindly found her breasts, beginning to fondle them almost
absently. Anne smiled - Len seemed to be a natural lover and he would swiftly
improve with practice and a little guidance.
Time seemed to slow down for the two lovers as their pleasure built higher
and higher. Anne's orgasms fired off one after another, but her pleasure
didn't diminish at all. And, the fire in Len's loins just kept building higher
and higher, seeking release. After an eternity, Len clasped Anne's breasts
tightly and thrust his hips upward as a scream escaped his lips with his
orgasm. Anne's cries of ecstasy were more subdued but as heartfelt as her cunt
spasmed around Len's pulsing rod. That final orgasm seemed to last as long as
the rest of the fuck, but at last they relaxed into sleep in each others' arms.
Very swiftly, any slight resentment Len might have felt about his
'punishment' vanished completely. For one thing, he found that he really loved
women's clothes - all of them, not just underwear. And he really did look good
as a woman. He quickly learned how to apply the proper makeup for any
occasion and how to make either his own hair or a wig look properly feminine.
He really got into his female role - the girls took to calling him Jane, a name
he liked. They taught him how to act feminine - voice, walk, mannerisms, etc.
Within a month Jane nee Len was almost perfectly female.
The other major reason Len-Jane went freely - eagerly, even - along with
the girls' punishment was sex. Anne spread the word about how good Len was in
bed and the other girls were quick to confirm her estimation. Len-Jane was
soon hard put to be able to sleep alone. He was 'on call' at all hours - the
girls had been forced to work out a schedule to sleep with him. One would come
home at lunch time for a quick but loving roll in the hay, another would get to
play before dinner and a third after. On weekends he had the pleasure of
orgies with from two to all six of the girls, depending on their own other
commitments.
Time soon came round to the return to school. About the same time, Jane
(no longer Len) began to notice the finally visible effects of the hormones
she had been taking every day, thinking they were vitamins. One morning while
showering, he suddenly realized that he was able to cup a small handful of
flesh about each nipple. A critical examination in a full-length mirror
revealed subtle changes only detectable upon close scrutiny (with an old
photograph to hand). He noticed, finally, how much his waist had narrowed
(helped both by the hormones and the corsets he normally wore) and how much his
hips had flared. His ass was now fuller and teardrop shaped, very feminine.
There were further even subtler changes - a softness of skin, a loss of
muscle tome, an alteration of bodily contours so that even his face, arms and
legs looked more feminine. His hair had grown amazingly rapidly and was now
shoulder-blade length. He was actually pleased that he looked so much like a
girl even naked - three months of enforced femininity had altered Len into Jane
very thoroughly. The only male think left in Jane was his 9+ inch cock and his
enjoyment in using it.
He confronted the girls with his discovery and his glad acceptance of it.
The girls were thrilled that he wasn't angry. They celebrated his new fully
female status with a wild and exciting orgy. And when it was over, they began
planning for the future.
They made arrangements to keep the house for as long as they wanted it.
Donna managed, by seducing one of the University's programmers, to get all of
Len's records altered to fit Jane allowing her to 'return' to school. And,
eventually the girls introduced their new sister to the joys of a man in bed -
and they all lived happily ever after.
FIN
in Q Dorm in his freshman year. The odds were long and he was the first frosh
in seven years to his the mark, but he did get a room all to himself for his
first year in college.
He was lucky in another way as well. Q Dorm had four wings radiating out
from the corners of a central block which held each floor's bath/shower rooms.
Len's single happened to be at the end of one of the wings on the second floor.
This gave him a very nice view in two ways. One, out his windows, and the
other, down his hall: there were three other rooms in the wing and each of
those doubles were occupied by women. The whole dorm was co-ed but not in any
pattern. Just more of Leonard's luck that both upper-class choice and the
lottery had filled his wing with women.
Len was rather glad to get a single, even if it was half the size of the
normal room, because he was rather shy. He was happy to be at college but he
had been worried about living with someone he didn't know. Now, he would have
time to make friends and find someone to room with next year.
Actually, he got to know the six girls in his wing fairly quickly, which
surprised him. In 231 were Anne (a short, cute blond) and Debbie (a very tall
and willowy beautiful blond). In 232 were Georgette (an average (in most ways)
brunette) and Harmony (a compact, energetic bombshell with raven-black hair).
And, in 233 were Susie (another black haired woman with the biggest breasts
Len had ever seen) and Donna (another blond and the best looking of them all).
Len's room was 234.
The girls were all very easy-going and friendly, which helped Len get to
know them. They - all seven of them in the wing - became almost like a family,
and the four doors were seldom closed (though Len's was shut more often than
then others').
One day about a month after the first midterms of his college career, Len
was in the basement doing his laundry. The student handbook advised that one
shouldn't leave one's clothes unattended when doing wash. Len always followed
the rules, at least until he was sure enough to break them. So, there he was
in the laundry room, alone, studying Calculus and waiting for the wash to be
done.
Mid-way through his wash cycle, Len was joined by Getty and Harm who came
down and loaded up three machines with their combined loads. When they had
the machines chugging away, Getty sat down by Len and asked, "Len, honey, could
you do us a favor? Harm and I are watching this really rad movie and we don't
want to miss much more of it. Here's the quarters - could you put our clothes
in the dryers when they're done...?"
Len said, "Sure, no problem." He was happy to be a help and he would be
there anyway. Getty told him how to separate the loads for the dryers and what
settings to use. Then, after giving him a peck on the cheek, she and Harm
hurried back upstairs leaving Len blushing over his calc books.
Len loaded his own wash into a dryer then, 15 minutes later the girls'
loads were ready. He followed Getty's instructions and put the quarters in,
pushing the right buttons. He found himself lingering over one of the loads,
however - the one that contained the girls' frilly underwear. He took his time
moving that particular load, going piece by piece. His mind was intrigued by
the softness and sheerness of the fabric and, of course, the fact that each of
the garments had been in intimate contact with one of the girls from room 232.
Finally, the dryers were going and Len tried to go back to his calc. But,
his attention kept returning to the front-loading dryer where the lingerie
tumbled colorfully in the soft heat. Strange thoughts had been sown and were
beginning to grow.
Over the next five or six weeks, Len became the official 'wash-person' of
the wing. He got very good at making sure all manner of girls clothes got
clean and dry safely. The girls repaid the time he spent downstairs with
quarters for his wash and one meal a week at a nearby diner (the cafeteria
food being just as bad as college food is supposed to be). Len really
wouldn't have minded ding the girls' wash without the payment for two reasons:
first, he was very considerate and he could usually rationalize that he would
be spending all that time in the basement anyway either at his own laundry or
studying in the interruption free and quiet (enough) room; also, he was really
getting into the girls' underthings and now he was able to touch, fondle, and
(at times, very secretly) even smell the pre-washed items, which was payment
enough for him to have hand laundered each item on a rock by a stream as far as
he was concerned.
Even though his fetish, so newly discovered, was growing steadily, Len
didn't think of "borrowing" any of the apparel that so fascinated him until
very close to finals. Then, the end-of-term pressures that drove the whole
dorm into slightly weird behavior finally got to him. He had noticed, after
the early excitement of his fetish had passed, that he actually studied better
when in the company of the girls' underwear. So, during reading week he
thought to borrow a pair of red and black lacey panties from Donna's load of
wash.
That first pair of panties did indeed help him through finals. That
success led him to 'borrow' a pair every week, each time from a different girl.
He kept his booty in the bottom of the back of his shirt drawer and made sure
that none of the girls ever had reason to go near the hiding place.
Most of the next term went by the same as before, but things changed
drastically around spring semester finals. Len had been eyeing and exquisite
set of shiny-blue lingerie - the whole works in a matched set, from bra to
waist-cincher, garterbelt, stockings, and panties - that belonged to Susie. Up
to that point he had taken only panties, nothing else. But he now felt like he
needed something more and that blue set seemed perfect: they even seemed to be
in his size!
Unfortunately, something like that lingerie was more easily noticed when it
went missing. Susie had already noticed the few panties that were missing from
her and Donna's laundry, and she had a really good idea who was responsible.
All she had to do now was prove it.
So, when the other girls took Len out for his weekly dinner, Susie stayed
behind, citing having to study extra hard for her final the next day. She had
managed to slip a bit of gum into the lock of Len's door so that she was able
to slip into his room and thoroughly search it. She turned up the lingerie set
as well as all of the missing panties - hers and Donna's, and what had to be
the other girls' as well. Thus armed with proof, she returned the room to its
pre-search state and waited for the girls to return.
The moment they got back, she called a conference in her room. Len had
work to do and so didn't feel excluded when they shut themselves in Susie's
room leaving him in his. Susie explained what she had found and asked, "What
are we going to do about it, huh girls?" There was alot of excited and
outraged chatter, then Debbie said, "You know, I've always fancied Len, but he
looks so - so pretty. I think he'd make a gorgeous girl, and he seems to like
our underwear already. Why don't we give him the chance to go all the way?
"Georgette, is your cousin going to be able to swing us that six-bedroom
house? Good. We'll get good ole Len to move in with us for the summer - he
hasn't found a place yet. Once he's there, I think we can persuade him to
dress how we want him to. Oh, I almost forgot. Anne, can your brother get a
large supply of female hormones for us? I think Len should really look the
part - he'll thank us when it's done."
And so it went. Next day, Debbie told Len that if he wanted to he could
move in with them when finals were over. Anne and Georgette would share a
room, leaving Len and the other girls a room apiece. Len agreed without the
slightest hesitation, overjoyed at being able to stay close to these beauties.
The day after their last final all seven of them moved into a very nice three
storey house. Len's room was larger than his dorm room, and it was the
smallest in the house. The kitchen was huge and the living room huger. Len
loved it and even more because the girls were there too.
The household got settled down within a week, and Len found his own
niche quickly. The six women all had summer jobs but he didn't. He had no
trouble paying the rent - he had a monthly stipend from his trust fund that
covered it and more - but he also had lots of free time. So, he fell into
taking care of the house. He was a passable cook, he knew (quite well) how to
do laundry, and he learned how to clean the house. His remaining time was
spent in front of the TV - or in his room dressed in 'borrowed' lingerie.
Even though he now had full access to the wardrobes of all six girls, he
still normally only tried on what the girls put in the wash (not limiting
himself to underwear, though) - cleaning the garment, trying it on, then
cleaning it again before putting it away. But there were a few times when he
just couldn't wait for the item to be put in the wash. He had returned all of
the things he had 'borrowed' over the school year, and now he often went into
Donna's drawer for that first pair of red and black panties, or into Susie's
for that blue lingerie set. The girls didn't wear these things often enough
and they gave him a special thrill to wear them. In fact, so far those two
were the only two 'outfits' he ever dared to jerk off in. Masturbation was
new to him and those two items really helped him get off. They were also his
downfall.
Three weeks into the summer, Len was in Susie's room putting on the blue
outfit. He had put on the bra (stuffed with panties) and the corsolette, and
was pulling up the tiny panties when he heard the front door slam. He was
paralyzed with fear - he had never dreamed of getting caught and now he had
no idea of what to do. Quick reactions might have kept his secret. Instead,
he just stood there, blue panties halfway up his thighs, as footsteps sounded
climbing the stairs and came down the hall. It could have been any one of the
girls, of course, but he had also left the door open so when Anne stopped in
the doorway and looked in, Len almost fainted.
In his mortal embarrassment, Len didn't notice that Anne was rather
startled by the size of his equipment. She got a grip on herself and said,
"What have we here, huh? You look almost girlish enough to be wearing that
lingerie - but not quite. Want to explain yourself, Len?"
Released by her words, Len collapsed on the bed and began to cry. It took
Anne a while to get him to tell his story and he didn't stop crying until very
near the end. Anne, who was more than a little aroused by Len's kinky, half
dressed state, was comforting and understanding rather than stern or angry.
She said when he was through, "Well, I understand about this sort of thing, but
stealing is wrong. You should have asked Susie to borrow her lingerie instead
of taking it, not to mention all of the other stuff. I'll have to bring this
up tonight and see what the others think."
This caused Len to start crying again and Anne finally said she'd be as
gentle with the news as she could and be on his side that night. She left him,
suggesting he get dressed. She wend back to work and Len finished his
housework in worry and fear.
After dinner, Anne kept the others at the table when everyone was done
eating. She gently explained what she had found when she had come home earlier
to pick up something for work, and what Len had explained to her about it. The
silence of the others at the revelation should have warned Len that this wasn't
a total surprise to the girls but he was too worried about the outcome to
notice subtleties.
As usual, Debbie spoke for the group. She said, "Well, Len, this is very
serious. But we are friends - I don't think any of us will insist that your
punishment need be severe. In fact, I think you might even enjoy what I have
in mind.
"As is most fitting, the punishment will fit the crime. A cure or kill
solution. Len, from now until school starts, you will be dressed as a female
from the skin out at all times. There will be surprise inspections conducted
by any one of us - if you are caught in any sort of man's clothing you will be
spanked severely. On the other hand, you can count on our help in keeping you
properly feminine. Anne, if you would do the first honors?"
A full ensemble was quickly assembled in Len's room and Anne closed the two
of them in. She said, "Strip, kid. We'll start from scratch."
Len was very shy about removing his fruit-of-the-looms but Anne finally got
them off of him. She again surveyed him in the buff and was still impressed.
She thought she could detect a hint of feminization about him already - the
hormones had been only working for three weeks - but she had no real idea of
his condition before the hormone treatment began so she couldn't really tell.
She helped him into the blue set of lingerie he had been caught in, making
sure to fondle his hefty cock as she tucked it away between his legs to
present a correctly flat aspect in his panties. When he was fully dressed in
the sexy underwear, Anne was further impressed - even without makeup Len looked
remarkably feminine.
She said, "You know, Len, you look really good dressed like that. Pretty,
even. Sexy, too." She walked over to him and pressed herself up against his
front, then reached up, drew his head down, and kissed him.
Len was overwhelmed. He felt very good just wearing the lingerie and even
better when Anne complimented him in it. Then, when she kissed him, he...he
was blown away! He'd never been kissed before. Anne was hot, beautiful, and
kissing him: he didn't know what to do.
So, Anne took charge. She continued kissing him and began to caress his
body, especially his tucked away cock. Naturally, Len's organ began to respond
by trying to erect, which caused a bit of pain due to its positioning. When he
began to squirm, Anne said, "Oh, poor boy. Let's free that rod of yours so it
can be happy." She pulled his panties off, releasing Len's cock which took
advantage of its freedom by erecting fully. It stood over 9 inches out of the
nest of light brown pubic hair at his crotch. His balls, naturally hairless,
hung large beneath it, all framed by the garter-straps depending from the
corsolet he wore.
Anne dove onto Len's cock, inhaling it half way down her throat on the
first bob. She proceeded to give len the first blow-job of his life, and it
was an event to remember. Len had nothing to compare it with but he was still
sure that Anne knew what she was doing. She lavished her attention all over
his groin, licking and sucking cock and balls and skin as well. Midway
through, Len's knees gave out and he sat down hard on the bed. Anne followed
him and continued her work, finally being rewarded by Len's orgasm and what
seemed like a quart of cum.
She kept licking and sucking even after Len stopped cumming, cleaning every
last drop of jism she could find away. When she was done, Len was hard again,
sitting there staring in a stunned fashion at Anne. She stood, looked at the
beautiful figure of Len half lying there in lingerie and hard cock, and began
to disrobe.
Len just continued staring as Anne removed her blouse and skirt, revealing
a familiar set of bra and panties in lacey green. Then, she removed first the
bra, revealing her beautiful breasts, and then her panties, showing Len his
first live cunt which also happened to be shaved. Naked, Anne advanced on Len,
taking hold of his throbbing rod and caressing it. She said, "Scoot back a bit
and make yourself comfortable."
Len slid his ass back on the bed and Anne followed him, retaining her hold
on his cock. When he was centered better on the bed, Anne pushed his torso
down so he was lying flat and straddled his thighs, still holding onto his
cock. Len could just barely see the inner pinkness of her cunt as the position
of her legs spread her outer lips slightly. He hoped that Anne wasn't just
teasing him with promises of further pleasure.
She said, "Len, honey, are you a virgin?" After a pause, Len nodded shyly.
"Fine. I'll be gentle. You're in for a real treat, kid, a real treat." With
that, she rose up on her knees far enough to position her cunt over his cock
and then began to lower herself slowly down onto it.
Len nearly went out of his mind as Anne sank slowly onto his cock. The
warm, tight wetness felt so incredibly wonderful that he berated himself for
hot seeking out sex long before. He lay back, closed his eyes, and just let
himself feel.
Anne was going wild herself. Len's cock was huge and filled her
wonderfully. At first, he just lay there making her do all the work. But
eventually the pleasure of his first fuck forced his body to respond and he
began pumping his hips in perfect rhythm. His eyes remained closed but his
hands rose and blindly found her breasts, beginning to fondle them almost
absently. Anne smiled - Len seemed to be a natural lover and he would swiftly
improve with practice and a little guidance.
Time seemed to slow down for the two lovers as their pleasure built higher
and higher. Anne's orgasms fired off one after another, but her pleasure
didn't diminish at all. And, the fire in Len's loins just kept building higher
and higher, seeking release. After an eternity, Len clasped Anne's breasts
tightly and thrust his hips upward as a scream escaped his lips with his
orgasm. Anne's cries of ecstasy were more subdued but as heartfelt as her cunt
spasmed around Len's pulsing rod. That final orgasm seemed to last as long as
the rest of the fuck, but at last they relaxed into sleep in each others' arms.
Very swiftly, any slight resentment Len might have felt about his
'punishment' vanished completely. For one thing, he found that he really loved
women's clothes - all of them, not just underwear. And he really did look good
as a woman. He quickly learned how to apply the proper makeup for any
occasion and how to make either his own hair or a wig look properly feminine.
He really got into his female role - the girls took to calling him Jane, a name
he liked. They taught him how to act feminine - voice, walk, mannerisms, etc.
Within a month Jane nee Len was almost perfectly female.
The other major reason Len-Jane went freely - eagerly, even - along with
the girls' punishment was sex. Anne spread the word about how good Len was in
bed and the other girls were quick to confirm her estimation. Len-Jane was
soon hard put to be able to sleep alone. He was 'on call' at all hours - the
girls had been forced to work out a schedule to sleep with him. One would come
home at lunch time for a quick but loving roll in the hay, another would get to
play before dinner and a third after. On weekends he had the pleasure of
orgies with from two to all six of the girls, depending on their own other
commitments.
Time soon came round to the return to school. About the same time, Jane
(no longer Len) began to notice the finally visible effects of the hormones
she had been taking every day, thinking they were vitamins. One morning while
showering, he suddenly realized that he was able to cup a small handful of
flesh about each nipple. A critical examination in a full-length mirror
revealed subtle changes only detectable upon close scrutiny (with an old
photograph to hand). He noticed, finally, how much his waist had narrowed
(helped both by the hormones and the corsets he normally wore) and how much his
hips had flared. His ass was now fuller and teardrop shaped, very feminine.
There were further even subtler changes - a softness of skin, a loss of
muscle tome, an alteration of bodily contours so that even his face, arms and
legs looked more feminine. His hair had grown amazingly rapidly and was now
shoulder-blade length. He was actually pleased that he looked so much like a
girl even naked - three months of enforced femininity had altered Len into Jane
very thoroughly. The only male think left in Jane was his 9+ inch cock and his
enjoyment in using it.
He confronted the girls with his discovery and his glad acceptance of it.
The girls were thrilled that he wasn't angry. They celebrated his new fully
female status with a wild and exciting orgy. And when it was over, they began
planning for the future.
They made arrangements to keep the house for as long as they wanted it.
Donna managed, by seducing one of the University's programmers, to get all of
Len's records altered to fit Jane allowing her to 'return' to school. And,
eventually the girls introduced their new sister to the joys of a man in bed -
and they all lived happily ever after.
FIN
