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Chapter III
The sunlight began streaming over the lake and into the bedroom at the top
of Hanover Towers. For those first few moments of existence, Jack was a
little foggy as to just where he was. That was, until he rubbed his eyes
open and smelled breakfast cooking.
He started to sit up, and a new
sensation between his ass cheeks helped even more to remind him of where he was, and more importantly, where he had been.
"Good morning Sugar," came a voice from beyond the bedroom door. "If
you're chilly, there's a robe and slippers for you inside the closet door."
said Toni. Jack stood up and took a step towards the closet. He was
definitely feeling the afterglow from his introduction to Flirtinis and
anal sex. Opening the door to the walk-in closet, Jack lays eyes on an
astonishing array of dresses, lingerie and other women's wear. There were
hundreds of pairs of shoes encircling the perimeter. Jack felt like he was
at an art exhibition.
'Look at that black sequin number over there. Ooh,
and that hot red mini-skirt on my right!' His mind was once again spinning
like a kid at a candy counter. "Breakfast is getting cold Sugar, and you
can't be very warm yourself," said Toni as she smiled at Jack in his
current state of undress. Jack turned around and blushed. "Here, this
should do for now," said Toni as she placed a pink satin robe on Jack.
Jack tightened the belt and then slipped into the matching slippers below.
The slippers had a slight lift to the heels, enough to remind him of his
fashion show the night before. Jack looked up at Toni and began to speak.
"So, last night..." Toni put a finger to his mouth and then embraced him in
a long kiss. "You should never have lengthy discussions on an empty
stomach. Let's talk over breakfast."
Jack followed Toni into the dining room and sat down at the table. Toni
brought out their breakfast and sat it down. She then brought out a
pitcher of what appeared to be some sort of strawberry fruit blend and
filled her and Jack's glasses. "Well, it's pink," said Jack, "but it looks
different then what we had last night." Toni laughed and informed Jack
that this was a part of her daily ritual. "This is a health blend that
I've drank for years. I'll switch off the flavors from time to time, but
strawberry/passion fruit is my favorite." "Now why doesn't that surprise
me," replied Jack.
He began to take a sip but Toni stopped him and said,
"Wait, wait. Let me propose a toast." "A toast over toast?" laughed Jack.
"A toast to health and beauty." smiled Toni. Jack smiled back and sipped
from his glass. "Delicious, Toni." With that, an awkward silence came
over the room.
Soon, Toni broke the silence. "I hope you aren't angry with me," she said
with a look out toward the lake shore. "Well, I must say that it, err, came
as a bit of a surprise. And might I add, not a small bit. You could have
just told me." "Oh sure, and see that look of shock and disgust on your
face right before you turned and head out the door? I know it was sneaky
and dishonest, but keeping it a secret was the only way I could make sure
that last night would turn out as spectacular as it did." Toni stopped. Turning around and smiling at Jack she said, "You did think it was
spectacular, didn't you?"
"Toni, it was incredible!" replied Jack. "I can't explain the multitude of
emotions I went through all night. I don't understand what's going on
enough to put it into words, but I just felt like something kept pushing me
to try things that I've never done before. To take risks. And it all paid
off. It certainly helped that such an incredibly attractive woman was
leading me down that path. Your beauty is enchanting and so inviting.
There were times last night that I almost felt myself being drawn to you by
your smile like a puppy on a leash."
Toni laughed as she refilled Jack's
health shake. "In fact," continued Jack, "I might even go so far as to say
I'm a little jealous of your beauty. I've never been what you would call
'handsome', so to see beauty on your level makes me slightly envious."
"What a sweet thing to say," said Toni. "I'm so glad you're not angry with
me. So you don't find me any less attractive knowing what's underneath
these panties?" smiled Toni. "24 hours ago, I might have felt different,
but last night changed everything. Remember, friends for life." said Jack
as he felt Toni's foot brushing up against his leg. "Girlfriends for
life," said Toni as she stood up and crossed over to Jack. "Just for the
record" she said, "I think you're incredibly beautiful. In fact, I think
we're both so beautiful that we should treat ourselves to a day out on the
town. Hit the spa, do some shopping. You know, girls day away!" "Sounds
like a plan, but first I need to get my car and I should probably wear
something a little less revealing then this robe and slippers," said Jack.
"Well the car is taken care of. I knew you would be in no shape to drive
last night, so I slipped your keys away from you earlier in the evening and
gave them to John at the bar. He drove your car to a secured garage on
Belden Street then grabbed a cab home." "Remind me in the future to guard
my pockets," commented Jack.
"Now, as for the choice of couture, that is a
little more challenging. Your clothes from last night are still dirty and
the pink satin robe would be a little chilly with the lake breeze being as
it is this time of day. I have a possible solution if you're open to it,"
said Toni. "Last night when you walked out in that teddy and those heels,
I did a double take. You looked natural and comfortable, had it not been
for that blushing boyish face and your raging hard-on, I would have sworn
you had been in heels before." Jack turned red in the cheek again and
said, "Well, I've put them on once or twice just out of curiosity, but I
never walked in then before last night. And I have worn panties before,
simply as a turn on for other dates that I've been with."
"I see," said Toni. "Well follow me and lets play dress up. We need to
find you something that will at least get us down to the spa." Jack paused
after one step. "You mean, go out in public dressed as a woman?" he said
with a slight quiver in his voice. Toni turned around, looked at herself
and then at Jack. "Is there something wrong with that Sugar?" she said.
"Well, no, of course not for you. You look like, well I should say you
have the, well...." Toni stopped Jack mid-sentence. "If you don't like the
way you look when I'm done with you, then we'll think of another plan. But
just allow me to work my magic and then tell me what you think." Toni
smiled and grabbed Jack by the hand and led him into the walk-in closet.
She turned around to untie the belt on the robe, and noticed that it was
sticking out in front. "Well, something tells me that you're not totally
opposed to this idea," Toni said as she tickled Jack's hard cock with her
index finger.
She looked Jack over and then turned her attention to the
lingerie and other fashion. She then handed Jack a powder blue satin bra
with matching panties and garter belt. After that she gave him a pair of
light tan sheer panty hose with straps. "Take these over to the bathroom
and put them on. I'll meet you there with the rest. Oh, and be careful
with the hose. Roll the on slowly so you don't get a run in them." Jack
stared down at the lingerie. "Well, come on, we don't want to miss our
appointment at the spa!" Jack looked up at Toni who smiled and blew him a
kiss. He was caught up in the wind of the kiss and hurried over to the
bathroom. He started with the bra and then the panties and garter belt.
He noticed that these panties had the same snap combination as the ones
Toni had on the night before. By instinct, he tucked his cock and balls
into the satin sack and pulled back on the material until he snapped it
into place. He rubbed his right hand down the front of his crotch and
looked in amazement at his reflection in the mirror. His cock had
magically disappeared. With each additional item, a new feeling of
exhilaration and warmth swept over his body. He finished by putting on the
hose. He went slowly as instructed by Toni. He couldn't get over the
feeling of the nylon rubbing up against his smooth legs. He stood up
snapped that straps into place along the garter belt. Just as he snapped
the last one, Toni walked in.
"Ooh! You look so hot Jack. Maybe we don't
need to go to the spa after all," she laughed. "No, you've gone to this
much effort, I don't want this beauty just wasted on me." She handed Jack
a black leather mini-skirt and an ivory beaded button down blouse. This
was topped off with a shiny gold jacket. "Oh wait, you're going to need
these first." Toni placed two silicone breast forms inside Jack's bra.
"These work great. I used to use them before mine grew in," said Toni.
Jack buttoned the blouse over the bra and then stepped into the skirt.
Toni placed the gold jacket on Jack and stood back. "Still needs
something," she said. "Wait right here." Jack had to laugh at the notion
that he might be considering going anywhere but there at this point.
"O.K. Sit down on the stool and turn and face the mirror." As Jack
followed Toni's orders, Toni lifted up a knob on the counter edge and
transformed the countertop into an instant cosmetics shop. She saw the
shock in Jack's eyes and said, "Don't worry, you just need a little bit to
make this work. She applied a little powder, a little blusher, a few
swipes of the mascara brush and a light pink lip-gloss. Toni then opened
up a box and pulled out a blonde wig, brushed it out and placed it on
Jack's head.
"Sugar! Take a look at yourself and tell me you don't like!"
Jack timidly stood up and faced the full-length mirror. "I, I, ..." he
stammered for words and his next breath. "I look beautiful!" Jack turned
to Toni and hugged her. "You are amazing Toni," Jack said. "What's a
girlfriend for?" Toni said with a wink and a smile. "Now step into the
shoes and lets get going." Toni handed Jack a pair of 4 inch gold
stilettos that matched the jacket. After he put the shoes on she
handed him a matching purse. "Open it up!" Toni said. Inside were a gold
necklace and two gold hoop earrings. "You can never have enough
accessories Sugar," Toni laughed.
Jack clipped on the earrings and Toni
helped him with the necklace. "Now we're ready to seize the day!" said
Toni. "Carpe Diem!" said Jack. "Carpe Dior!" replied Toni. They giggled
as they strolled onto the waiting elevator that would begin their journey
into the city. Toni smiled at Jack as the elevator descended downward.
Only a few hours ago, she was heading up this elevator with some guy named
Jack in a mid-priced suit and virgin Flirtini buzz going on. Now she was heading down the same elevator and into town with her girlfriend who is
decked out in gold and black leather. She knew that her smile could work
on the occasional waiter or police officer, but this? Toni smiled at Jack
who beamed back. She then pushed the stop button on the elevator. In
plain view of the early Saturday morning bustle of the city, she pulled
down her skirt and pulled down her panties to reveal her throbbing clit.
"There used to me running a little late at the spa." she said before
kissing Jack on his shiny pink lips. Without hesitation, Jack got down on
his knees and put his cute, moist lips on Toni's clit and began to lick at
the pre-cum that had gathered at the tip. Soon his lips encompassed her
head. Jack had never had his mouth on another cock before, but some force
guided him every step of the way. It was like getting back onto a bike, or
stepping back into stilettos. Toni thrust her cock into Jack's eager mouth
and fucked his face until she was ready to explode. Toni grabbed Jack's golden hair and pulled his face closer until her cock was deep inside
Jack's throat. "Ooh baby, I'm going to release it!" and with that, Toni
coated Jack's mouth and throat with her seed. Jack swallowed it all and
came up for air. He then proceeded to lick off the remaining juice from
Toni's clit and pulled her panties and skirt back up.
They embraced again
tongue-to-tongue. After falling away from the long embrace, Jack opened up
his purse and pulled out his compact mirror and pink lip-gloss. After
touching up, he smiled at Toni who was doing the same and then pushed the
go button. The elevator reached the basement where Toni and Jack stepped
out and got into Toni's convertible. Toni put the hood up to protect
Jack's golden hair and headed into the city. Jack looked at the clock on
the radio and saw that it was only 10:02 am. 'I can't imagine how this day
will get any better than this' he thought to himself. Toni took her
luscious hand and nails off the gear shift and placed it down Jack's skirt.
Seize the day, indeed.
The sunlight began streaming over the lake and into the bedroom at the top
of Hanover Towers. For those first few moments of existence, Jack was a
little foggy as to just where he was. That was, until he rubbed his eyes
open and smelled breakfast cooking.
He started to sit up, and a new
sensation between his ass cheeks helped even more to remind him of where he was, and more importantly, where he had been.
"Good morning Sugar," came a voice from beyond the bedroom door. "If
you're chilly, there's a robe and slippers for you inside the closet door."
said Toni. Jack stood up and took a step towards the closet. He was
definitely feeling the afterglow from his introduction to Flirtinis and
anal sex. Opening the door to the walk-in closet, Jack lays eyes on an
astonishing array of dresses, lingerie and other women's wear. There were
hundreds of pairs of shoes encircling the perimeter. Jack felt like he was
at an art exhibition.
'Look at that black sequin number over there. Ooh,
and that hot red mini-skirt on my right!' His mind was once again spinning
like a kid at a candy counter. "Breakfast is getting cold Sugar, and you
can't be very warm yourself," said Toni as she smiled at Jack in his
current state of undress. Jack turned around and blushed. "Here, this
should do for now," said Toni as she placed a pink satin robe on Jack.
Jack tightened the belt and then slipped into the matching slippers below.
The slippers had a slight lift to the heels, enough to remind him of his
fashion show the night before. Jack looked up at Toni and began to speak.
"So, last night..." Toni put a finger to his mouth and then embraced him in
a long kiss. "You should never have lengthy discussions on an empty
stomach. Let's talk over breakfast."
Jack followed Toni into the dining room and sat down at the table. Toni
brought out their breakfast and sat it down. She then brought out a
pitcher of what appeared to be some sort of strawberry fruit blend and
filled her and Jack's glasses. "Well, it's pink," said Jack, "but it looks
different then what we had last night." Toni laughed and informed Jack
that this was a part of her daily ritual. "This is a health blend that
I've drank for years. I'll switch off the flavors from time to time, but
strawberry/passion fruit is my favorite." "Now why doesn't that surprise
me," replied Jack.
He began to take a sip but Toni stopped him and said,
"Wait, wait. Let me propose a toast." "A toast over toast?" laughed Jack.
"A toast to health and beauty." smiled Toni. Jack smiled back and sipped
from his glass. "Delicious, Toni." With that, an awkward silence came
over the room.
Soon, Toni broke the silence. "I hope you aren't angry with me," she said
with a look out toward the lake shore. "Well, I must say that it, err, came
as a bit of a surprise. And might I add, not a small bit. You could have
just told me." "Oh sure, and see that look of shock and disgust on your
face right before you turned and head out the door? I know it was sneaky
and dishonest, but keeping it a secret was the only way I could make sure
that last night would turn out as spectacular as it did." Toni stopped. Turning around and smiling at Jack she said, "You did think it was
spectacular, didn't you?"
"Toni, it was incredible!" replied Jack. "I can't explain the multitude of
emotions I went through all night. I don't understand what's going on
enough to put it into words, but I just felt like something kept pushing me
to try things that I've never done before. To take risks. And it all paid
off. It certainly helped that such an incredibly attractive woman was
leading me down that path. Your beauty is enchanting and so inviting.
There were times last night that I almost felt myself being drawn to you by
your smile like a puppy on a leash."
Toni laughed as she refilled Jack's
health shake. "In fact," continued Jack, "I might even go so far as to say
I'm a little jealous of your beauty. I've never been what you would call
'handsome', so to see beauty on your level makes me slightly envious."
"What a sweet thing to say," said Toni. "I'm so glad you're not angry with
me. So you don't find me any less attractive knowing what's underneath
these panties?" smiled Toni. "24 hours ago, I might have felt different,
but last night changed everything. Remember, friends for life." said Jack
as he felt Toni's foot brushing up against his leg. "Girlfriends for
life," said Toni as she stood up and crossed over to Jack. "Just for the
record" she said, "I think you're incredibly beautiful. In fact, I think
we're both so beautiful that we should treat ourselves to a day out on the
town. Hit the spa, do some shopping. You know, girls day away!" "Sounds
like a plan, but first I need to get my car and I should probably wear
something a little less revealing then this robe and slippers," said Jack.
"Well the car is taken care of. I knew you would be in no shape to drive
last night, so I slipped your keys away from you earlier in the evening and
gave them to John at the bar. He drove your car to a secured garage on
Belden Street then grabbed a cab home." "Remind me in the future to guard
my pockets," commented Jack.
"Now, as for the choice of couture, that is a
little more challenging. Your clothes from last night are still dirty and
the pink satin robe would be a little chilly with the lake breeze being as
it is this time of day. I have a possible solution if you're open to it,"
said Toni. "Last night when you walked out in that teddy and those heels,
I did a double take. You looked natural and comfortable, had it not been
for that blushing boyish face and your raging hard-on, I would have sworn
you had been in heels before." Jack turned red in the cheek again and
said, "Well, I've put them on once or twice just out of curiosity, but I
never walked in then before last night. And I have worn panties before,
simply as a turn on for other dates that I've been with."
"I see," said Toni. "Well follow me and lets play dress up. We need to
find you something that will at least get us down to the spa." Jack paused
after one step. "You mean, go out in public dressed as a woman?" he said
with a slight quiver in his voice. Toni turned around, looked at herself
and then at Jack. "Is there something wrong with that Sugar?" she said.
"Well, no, of course not for you. You look like, well I should say you
have the, well...." Toni stopped Jack mid-sentence. "If you don't like the
way you look when I'm done with you, then we'll think of another plan. But
just allow me to work my magic and then tell me what you think." Toni
smiled and grabbed Jack by the hand and led him into the walk-in closet.
She turned around to untie the belt on the robe, and noticed that it was
sticking out in front. "Well, something tells me that you're not totally
opposed to this idea," Toni said as she tickled Jack's hard cock with her
index finger.
She looked Jack over and then turned her attention to the
lingerie and other fashion. She then handed Jack a powder blue satin bra
with matching panties and garter belt. After that she gave him a pair of
light tan sheer panty hose with straps. "Take these over to the bathroom
and put them on. I'll meet you there with the rest. Oh, and be careful
with the hose. Roll the on slowly so you don't get a run in them." Jack
stared down at the lingerie. "Well, come on, we don't want to miss our
appointment at the spa!" Jack looked up at Toni who smiled and blew him a
kiss. He was caught up in the wind of the kiss and hurried over to the
bathroom. He started with the bra and then the panties and garter belt.
He noticed that these panties had the same snap combination as the ones
Toni had on the night before. By instinct, he tucked his cock and balls
into the satin sack and pulled back on the material until he snapped it
into place. He rubbed his right hand down the front of his crotch and
looked in amazement at his reflection in the mirror. His cock had
magically disappeared. With each additional item, a new feeling of
exhilaration and warmth swept over his body. He finished by putting on the
hose. He went slowly as instructed by Toni. He couldn't get over the
feeling of the nylon rubbing up against his smooth legs. He stood up
snapped that straps into place along the garter belt. Just as he snapped
the last one, Toni walked in.
"Ooh! You look so hot Jack. Maybe we don't
need to go to the spa after all," she laughed. "No, you've gone to this
much effort, I don't want this beauty just wasted on me." She handed Jack
a black leather mini-skirt and an ivory beaded button down blouse. This
was topped off with a shiny gold jacket. "Oh wait, you're going to need
these first." Toni placed two silicone breast forms inside Jack's bra.
"These work great. I used to use them before mine grew in," said Toni.
Jack buttoned the blouse over the bra and then stepped into the skirt.
Toni placed the gold jacket on Jack and stood back. "Still needs
something," she said. "Wait right here." Jack had to laugh at the notion
that he might be considering going anywhere but there at this point.
"O.K. Sit down on the stool and turn and face the mirror." As Jack
followed Toni's orders, Toni lifted up a knob on the counter edge and
transformed the countertop into an instant cosmetics shop. She saw the
shock in Jack's eyes and said, "Don't worry, you just need a little bit to
make this work. She applied a little powder, a little blusher, a few
swipes of the mascara brush and a light pink lip-gloss. Toni then opened
up a box and pulled out a blonde wig, brushed it out and placed it on
Jack's head.
"Sugar! Take a look at yourself and tell me you don't like!"
Jack timidly stood up and faced the full-length mirror. "I, I, ..." he
stammered for words and his next breath. "I look beautiful!" Jack turned
to Toni and hugged her. "You are amazing Toni," Jack said. "What's a
girlfriend for?" Toni said with a wink and a smile. "Now step into the
shoes and lets get going." Toni handed Jack a pair of 4 inch gold
stilettos that matched the jacket. After he put the shoes on she
handed him a matching purse. "Open it up!" Toni said. Inside were a gold
necklace and two gold hoop earrings. "You can never have enough
accessories Sugar," Toni laughed.
Jack clipped on the earrings and Toni
helped him with the necklace. "Now we're ready to seize the day!" said
Toni. "Carpe Diem!" said Jack. "Carpe Dior!" replied Toni. They giggled
as they strolled onto the waiting elevator that would begin their journey
into the city. Toni smiled at Jack as the elevator descended downward.
Only a few hours ago, she was heading up this elevator with some guy named
Jack in a mid-priced suit and virgin Flirtini buzz going on. Now she was heading down the same elevator and into town with her girlfriend who is
decked out in gold and black leather. She knew that her smile could work
on the occasional waiter or police officer, but this? Toni smiled at Jack
who beamed back. She then pushed the stop button on the elevator. In
plain view of the early Saturday morning bustle of the city, she pulled
down her skirt and pulled down her panties to reveal her throbbing clit.
"There used to me running a little late at the spa." she said before
kissing Jack on his shiny pink lips. Without hesitation, Jack got down on
his knees and put his cute, moist lips on Toni's clit and began to lick at
the pre-cum that had gathered at the tip. Soon his lips encompassed her
head. Jack had never had his mouth on another cock before, but some force
guided him every step of the way. It was like getting back onto a bike, or
stepping back into stilettos. Toni thrust her cock into Jack's eager mouth
and fucked his face until she was ready to explode. Toni grabbed Jack's golden hair and pulled his face closer until her cock was deep inside
Jack's throat. "Ooh baby, I'm going to release it!" and with that, Toni
coated Jack's mouth and throat with her seed. Jack swallowed it all and
came up for air. He then proceeded to lick off the remaining juice from
Toni's clit and pulled her panties and skirt back up.
They embraced again
tongue-to-tongue. After falling away from the long embrace, Jack opened up
his purse and pulled out his compact mirror and pink lip-gloss. After
touching up, he smiled at Toni who was doing the same and then pushed the
go button. The elevator reached the basement where Toni and Jack stepped
out and got into Toni's convertible. Toni put the hood up to protect
Jack's golden hair and headed into the city. Jack looked at the clock on
the radio and saw that it was only 10:02 am. 'I can't imagine how this day
will get any better than this' he thought to himself. Toni took her
luscious hand and nails off the gear shift and placed it down Jack's skirt.
Seize the day, indeed.
