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Extended Vacation
All stories on this web site are purely FICTIONAL. The people depicted within these stories only exist in someone's IMAGINATION. Any resemblence between anyone depicted in these stories and any real person, living or dead, is an incredible COINCIDENCE too bizarre to be believed. If you think that you or someone you know is depicted in one of these stories it's only because you're a twisted perverted little fucker who sees conspiracies and plots where none exist. You probably suspect that your own MOTHER had sex with ALIENS and COWS and stuff. Well, she didn't. It's all in your head. Now take your tranquilizers and RELAX.
Subject: NEW TG: An Extended Vacation
Date: Tue Jul 18 16:38:44 1995
This is a just finished transcription of a story I wrote several
years ago. I hope you all enjoy it. As should be obvious, it contains
adults doing adult things, and if you shouldn't be reading adult stuff,
then don't read this.
Feedback is welcome, and encouraged. Flames will be replied to
with logarithmically applied ire. Have fun, all!
Dafydd --Cheshire Cat-- Cyhoeddwr
[email protected]
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An Extended Vacation
by Dafydd Cyhoeddwr
copyright July, 1995
Charlie was a sophomore at Columbia University, located in upper
Manhatan. He had spent a year and a half there (minus summer break
back home in Colorado), and had never been farther off campus than the
corner restaurant. His roommage this year, Stan, had told him all
about the wonders of New York City, but he had simply always been too
busy to go see it beyond a view of the skyline from the high rose
dorm. Until now.
It was spring break, a mild early April week, and Charlie had
almost $1200 to his name with which to take a week's vacation. He
turned down several offers to go skiing, or to Florida: he figured his
bankroll would last all that much longer right here in the city, where
a subway could take him back to the dorms at any time to sleep.
After seeing Stan off to Florida and saying goodbye to Linda,
his girlfriend of the moment who was going to Arizona for Break,
Charlie took a subway to the Port Authority on 42nd Street. There were
a lot of things that New York City had to offer, but Charlie wanted to
check out the infamous 42nd Street first of anything. It was only the
middle of the afternoon, but the neon and flashing lights of the strip
still held lots of promise.
Charlie, whose experience with porn was limited to 7-11
purchases of Playboy and Penthouse, decided to see it all. He stood on
the corner of 7th Ave. and 42nd St. and planned to go into every store
and X-rated theater from 7th to 8th, back up the other side from 8th
to 7th, then the other half of the strip from 7th to 6th and back. He
was sure it would take a while, but he knew that the lights never went
out on 42nd Street.
He walked into his first dirty book store and began to peruse
the hundreds of magazines lining the walls. He had never suspected
there could be so many!
He glanced over the 'soft core' issues, then the 'hard core'
ones, with astonishing prices between $25 and $60 - just for pictures!
They showed anything and everything though, including things he had
never heard of, like TVs and TSs. He kind of skimmed over the male
mags section - he knew about homosexuality, but it kind of bothered
him.
He scanned the video tapes, the sex aids, the naughty lingerie,
blow up dolls, and lubes. Then, he went into the video booths section.
With a pocket full of quarters, he put at least two bits in each
machine, inundating himself with more smut than he had ever dreamed
of. He even braved the three male booths at the back, but only spent a
single quarter in each and saw very little - each had coincidentally
been rewound to the beginning and the most he saw was a guy jerking
off (and he tried to ignore the fact that this scene got him hard).
Once through the booths, Charlie went back out and bought a
soft-core mag about women with shaved pussies - he had decided to buy
something from each shop he entered - and left. About 45 minutes had
passed, but Charlie was having fun.
He took three hours to do the whole block down one side. he had
purchased a dozen mags, even one that was very hard core. There had
been only one theater on that side of the street, but he spent maybe
15 minutes in there. He noted what the name of the movie was though
("Blue Ice"): he had really enjoyed the part had seen and intended to
see more, either by returning to the theater later in the week, or
buying the video if he happened across it.
He took a break for a meal at the Arbys in the Port Authority,
then it was back up the other side of the block. Things began to get
strange, though, when the second book shop he came to was all-male.
It wasn't all that different, really. The magazines were all
male, as were the books and videos, and the 'toys' were all gay-male
oriented - fancy men's briefs, male blow-up dolls, all kinds of dildos
and suction pumps, and not an artificial vagina to be seen. He went
back into the video area and actually watched a few scenes in each
booth, and he didn't feel quite as put off as he had before. In fact,
he was beginning to decide that homosexuality wasn't disgusting at
all.
After buying a hard-core mag on the order of Puritan, called
Stroke, Charlie went to the next establishment which happened to be a
strip joint. He paid $6 to get in, and took a set in the second row
about three quarters of the way along the long runway that ran out
into the room from the stage. The theater/bar was very sparsely
populated, most of the patrons being in either the first or second
rows and well apart from each other.
Just a few seconds after Charlie sat down, the lights went out
and a spotlight centered on the stage. An announcer said, "And now,
the Star Shiner Theater presents: Little Miss Cindy!"
A cute, short blonde appeared in the spotlight, dressed in a
short frilly dress, holding a teddy bear. Then music came on, hard
rock with a driving beat that Charlie could feel in the center of his
chest, and the 'little' girl began to bump and grind like no little
girl should know how to do.
Charlie watched the little girl/sexy woman strip all the way
down to just a little black g-string, then walk jauntily off stage
amid cries of 'More, more!' and 'Take it all off, babe!' Cindy had
barely vanished through the back curtain when the announcer came back
on the PA with, "Next for your enjoyment, our very own cheerleader,
Lyla!"
The woman who appeared next was tall, brunette, and filled her
white sweater to overflowing. Charlie sat forward on his seat as she
began to do a few cheers: Lyla bore a vague resemblance to his
highschool girlfriend, who had also been a cheerleader. Soon, the
music changed from marching-band to hard rock, and again Charlie could
feel the beat in his sternum. He watched avidly as the beauty shed
article after article of clothing - sweater first, then halter top,
and after a bit of bouncing and shaking, her lacy bra. Her body was
lithe and lean, and her breasts were full, fine, and just ripe enough
to sway as she danced rather than bobbing all over the place. Next,
taking even more time, she removed her skirt, then her shoes and
socks. Next to last, she removed her short shorts, inching them down
her golden thighs until she was grinding her way around the stage in
only her lacy purple panties.
Charlie was almost on his knees at the edge of the stage by
then. Lyla was just so gorgeous! All-over tan, compact and lithe,
glistening with sweat from her performance which she truly seemed to
be enjoying.
After dancing in just panties for several minutes, she stunned
many of the patrons, Charlie included, by slowly slipping down her
purple panties, baring her mostly shaved cunt to the cheers of the
whole room. She took the wisp of cloth from around her ankle, twirled
it for a bit while she posed proudly, fully naked in the spotlight,
then flipped her panties into the audience: right at Charlie! The
startled youngster caught them in his lap and stared at them for a
moment. As the music shifted, his attention was drawn back to the
stage and he slipped the panties into his pocket almost automatically.
Lyla, still totally nude, danced back onto the main portion of
the stage where she picked up two props that had mysteriously appeared
there - a chair and a hot dog and bun. She dragged them halfway down
the runway, set the chair down and sat on it, and began to eat the hot
dog in little nibbling bites. Sounds of a football game momentarily
replaced the rock music and Lyla mimed watching the game for a few
moments. Soon, though, her free hand began to roam around her thighs
and then her bush, and she began to pant around her snack as her
fingertips caressed her pussy. She extracted the un-touched hot dog
from the half-eaten bun and began sucking on it as the music faded
back in. Then, amid appreciative cheers, she slipped the hot dog out
of her mouth and into her cunt.
Charlie couldn't believe his eyes! He watched avidly as Lyla
fucked herself with the hot dog, getting more and more turned on,
squirming her hips and lolling her head back and finally gasping
loudly as she orgasmed. And Charlie (and half the audience) gasped as
well - and he felt the wet warmness that told him he had joined Lyla
in her orgasm.
Lyla spent a moment draped limply over her chair, then rose,
bowed to the thunderous applause, tossed the well used wiener into the
audience (but not to Charlie this time) and hurried off stage. The
clapping and cheering went on for a while, but when the announcer
introduced 'Marvelous Melanie', Charlie slipped away from the stage in
search of a restroom.
He found one by the exit, went in and locked the door. He
stripped off his pants and sticky underwear. He tossed the jockeys -
there was no way he coudl wear them. He cleaned up his crotch, and
then his jeans, leaving a large wet spot on their front. He figured he
could wait out the spot drying in a video booth next door, but wearing
wet pants would be very uncomfortable without something between him
and them ... and then he thought of Lyla's panties.
He fished them out of his pocket and held them up. They were
skimpy and very feminine, but he figured they would fit. He held them
to his nose briefly and inhaled Lyla's heady scent, then slipped the
silky things up his legs and around his loins.
They fit, if a little snugly. And they felt wonderful - slippery
and soft against his cock, balls, and ass. He stepped into his jeans,
checked the look in the mirror, covered the wet spot with his bag of
smut, and left the restroom and the theater. He went into the next
bookstore, scanned through the mags and videos, got $5 in quarters,
picked a video booth and went in. He spent all $5 watching a movie
about a guy bartending at an orgy and all the action that went on.
When he came out, his pants were dry. He returned to the front of the
store, looked the books and magazines over again, and bought one about
one woman servicing three men, and continued his slow trek up the
block.
The rest of the shops on that side of the street were normal
book shops. Charlie went in and out, totally unfazed any more by the
pornography so displayed. He had become used to it. He bought a
different book or magazine in each one, some hardcore, some soft, some
gay and some straight. He reached 7th Ave. and paused for a moment. It
was very late he knew, sometime after midnight, but the two block
strip of 42nd street was as bright and active as ever.
As he paused, he thought briefly about the underwear he had on.
He had been aware of them since he had put them on - soft and
slippery, confining but sensually pleasant as he walked; and they sent
amazing feelings through his cock as it erected and deflated during
his magazine-browsing or video-gazing. He wondered if that was why
women really wore such nice underwear - not to entice men, but because
it felt so nice.
He pushed such thoughts to the back of his mind and crossed the
avenue. Three more book stores and he came to another theater. He paid
the admission fee and went in to find another stage and runway
arrangement surrounded with seats, with the rest of the large room
filled with tables surrounded with chairs - much like the first
theater/bar he had gone into. To his slight surprise, this time there
were almost as many women scattered among the seats and tables as men.
Charlie took a seat at one of the tables a little way from the
runway and waited. A low level of talk pervaded the room - there were
several single and mixed gendered groups of people chatting between
shows. He observed and eavesdropped while waiting, and found the
conversations very entertaining.
Finally, the lights dimmed and the audience quieted quickly. An
announcer said, "Ladies and gentlemen, please welcome our resident
cowboy, Tex Rex!" The audience cheered, music came on, and out of the
curtains at the back of the stage danced a tall blond man dressed like
a cowboy.
Charlie watched his first male stripper with a gaping mouth. The
dancer was lithe and muscular, with an oiled and gleaming body beneath
his clothes. Charlie felt himself responding the man way down deep -
most specifically, he felt himself erect in Lyla's panties.
'Tex Rex' stripped down to a very tiny and well packed g-string,
then bumped and ground along the runway for a few more minutes while
the audience - mostly the women, but some men as well - cheered and
egged the man on. Finally the dance was over, and 'Tex' danced his way
back through the curtain. The next act was a woman who didn't take it
all off, and the next was one who did, although she didn't play with
herself quite as graphically as had Lyla. After she was gone, the
announcer introduced another male - Bruce.
Bruce was compact, hard, and very agile. He danced out of his
clothes and then for a while with just an impossibly bulging g-string.
Then, in response to the increasingly raucous urgings of the audience
he removed that last wisp of clothing too.
Charlie gasped at the sight of his first real live cock: it was
huge! Bruce had just a sparse frame of brown-blond pubic hair around
the base of his huge prick, and his balls were plump and bare. The
sprinkling of curly hair went perfectly with the rest of his sleek,
hairless body, forming an erotically perfect picture.
Bruce began to dance again, with more restrained body motions,
though his hands went into second gear. Using his own spit as
lubricant, he proceeded to jerk himself off as he danced.
The audience went wild at Bruce's display, cheering and
screaming, and rushing up to me edge of the runway. They all (those by
the runway) extended their hands, eager for a touch or a stroke. Bruce
allowed each one a single sample, men and women alike. Charlie was
further impressed.
Eventually, Bruce drew away from the hands and began moving his
own faster and faster. The music sped up and intensified as Bruce drew
closer and closer to orgasm. Finally, with a body-wrenching spasm,
Bruce shot his rather copious load out into the audience causing a
furor of ecstasy as everyone (nearly) scrambled to get some. Both
Bruce and Charlie made their respective exits during that mad
scramble.
Charlie decided to let his feelings and reactions to Bruce and
the whole spectacle percolate in his subconscious while he continued
his trek. Two stored later, he found himself in a bookstore with an
extra feature. Down a flight of stairs was a set of booths and a stage
enclosed by tiny cubicles. The neon signs advertised 'Live Nude Girls'
and '25? Stage Show', with gas tube silhouettes of women blinking
away. Curious, Charlie went down and found that each of the larger
booths was really two booths put together, with a woman in lingerie in
one half, connected by a window through which the customer could watch
her touch herself and talk from the 'safety' of the other booth. It
seemed a little silly considering the kind of shows going on down the
street, but then again, at least this was one on one almost-contact,
and there were quite a few different women to choose from.
He got 'one free visit' with a very pretty blonde who slipped
out of her green teddy as soon as the curtain between the booths slid
up, and who kept trying to get him to alternately unzip, and put a $10
bill in the little slot so they could have more time together. He was
too nervous to do so, standing there almost in public only inches (of
plexiglass) from a naked stranger, and he was glad when the phone
clicked off and the curtain went scrolling back down, separating the
booths again.
Charlie wandered around the booths ogling the beauties who stood
in their lingerie in the doorways of their booths and attempted to
entice him into their cubicles. An announcer indicated a change of
shows, and Charlie, not knowing just what that meant, noticed that one
of the lingerie-clad women left her booth and went over to the other
structure in the basement, which turned out to be a revolving stage
surrounded (almost) by tiny booths with a door on one side and a very
small window over a coin box on the other. The woman went in the door
to the revolving stage as another woman came out (that door being the
only place there wasn't a tiny booth), and Charlie took his place in
one of the booths and dropped quarter after quarter into the coin box
to keep the little curtain raised and his view of the slowly revolving
stage clear. The cute blonde rolled around on the stage, playing to
each open window as she revolved to face it, stroking her breasts and
her groin with her fingers and a dildo she had brought along, making
lascivious suggestions to each watcher in turn.
Eventually the blonde went back to her booth, and Charlie took
to walking around some more, trying to get up the nerve to go into the
booth of a gorgeous black-haired woman whose name plate (on her booth)
said she was 'Lilune'. She had an exotic look about her that fit the
name, but he couldn't quite bring himself to step into the other half
of her booth. He was sure he would be as embarrassed as he had been
with the first woman, and somehow he didn't want Lilune to see him
like that - to think him slow, or stupid.
He watched two more stage shows, both very exciting and both
quite draining on his supply of quarters. When the second one was over
he finally girded himself up and went over to Lilune's booth.
He entered the customer's half of the double booth and locked
the door. He followed the sign's instructions and put three tokens in
the little box (each of which had taken 2 quarters to get in the
machine outside). Apparently the token deposit of $1.50 simply
indicated to Lilune that she had a customer. He fingered the $10 bill
he had ready in his pocket while he waited for the curtain to rise.
It began to slide up with an electronic whine, and he picked up
the phone in preparation. When the curtain had cleared the 5-foot tall
plexiglass window, Charlie took his first close-up look at the
beautiful and exotic Lilune. She was tall and slender (except where it
counted - her breasts and hips were invitingly ample) with long
straight black hair down to her ass. Her face, the most striking
feature about her, was vaguely oriental, very oval with huge violet
eyes and full red lips. Her body was concealed (sort of) by a very
lacy and frilly red teddy over what seemed to be very tight black
bikini briefs.
Her voice was musical as she said over the phone, "Hi there,
stud. My name's Lilune. What's yours?"
"Uh-um, Cha-Charlie."
"Hi, Charlie," she said with a smile that might have looked
tired and practiced if Charlie hadn't been so dazzled. "Have a five or
a ten to put in the slot so we can have more time together?"
Charlie fumbled the bill out of his pocket and into the slot,
and watched Lilune dial up 30 minutes on the large timer by the
separating wall.
"Okay, all set," she said. "Now, want to see me undressed,
Charlie?"
"S-sure!"
"Fine, but only if you show me something, too. First, I'll take
my teddy off, and then you take off your shirt and pants. Don't worry,
your door won't open while the curtain is up, and you've got your own
manual lock on it as well, I see. Your things will be perfectly safe."
Lilune slipped out of her red negligee slowly while Charlie
reluctantly unbuttoned his shirt. She was free of her red wisp of
cloth before he had removed his shirt, so she just stood there,
caressing her very ample breasts and making encouraging remarks while
he finished the agreed upon disrobing. "Nice pecs, stud," she said,
"and well defined abs, too. You take good care of that trim body of
yours, don't you, Charlie? I like a man who cares about his body."
He unfastened his belt and began to push down his pants when he
remembered what was under them - Lyla's panties! He almost balked
until Lilune said, "What fetching underwear, Charlie. I love it - its
your color."
Blushing slightly, Charlie pushed his pants over his hips and
stepped out of them. He hung them on the hook by the door that already
held his shirt, and stood before the window dressed only in hugely
bulging purple lacy panties, and his tennis shoes and socks. Lilune
gazed at him appreciatively and said, "Oh, yes! Very becoming, very
erotic. Now, I want you to promise me something, you sexy stud.
Promise me that no matter what happens next, you'll stay here and do
your best to cum for me."
Charlie, very puzzled by Lilune's request but equally elated by
her praise and eager to please her, said, "Sure, I promise Lilune. I
will."
"Good," she said. She turned around, wiggled her hips a bit at
him, and then slipped her panties off, showing Charlie her very
rounded, luscious ass. "Ready?" she asked, and turned around before
Charlie could answer her.
Since he had already seen the rest of her, Charlie's gaze went
first to Lilune's crotch - and that was when the promise she had
extracted made sense. For exotic Lilune was even more exotic than he
had thought - she wasn't even really a she! There, at the base of a
smooth and totally hairless abdomin was a hefty and half hard cock and
a plump set of pink and also hairless balls. Lilune was a he!
Charlie was staggered. He had never heard of anything like what
faced him now through the window. It - he - she - he? - was so far
beyond what was Charlie's norm - even the supposedly oh-so-expanded
norm that was the result of the day's experiences - that he almost
couldn't function. Lilune didn't try to say anything - she just calmly
stroked her cock and fingered her left breast and waited for the shock
to pass.
Finally, when she detected the first signs of Charlie's
recovery, Lilune said, "Hey, stud, remember the promise?"
Charlie blinked and said, "Uh ... um, I'm sorry, Lilune, you
just ... startled me. I ... I ..."
"It's okay, stud. I'm used to this reaction. But you promised to
cum before you left - and we only have 15 more minutes. I can see
you're not too startled to be hard. Make use of that wonderful
erection under those panties. Come on, you can do it. I'll help."
And she did. After the first minute or so, it got easier. Lilune
was really beautiful, cock and all, and Charlie found himself,
encouraged by her practiced monologue, really getting into the
masturbation - and Lilune.
They both made it last, but not too long. Ten minutes later,
both shot rather copious wads against the plexiglass amid gasps of
ecstasy.
When they calmed down, there were still 5 minutes on the clock.
Charlie cleaned himself up - there were tissues in a little dispenser
just for that purpose - and put his clothes back on while Lilune did
the same only much more languidly. As he was tucking his shirt in,
Lilune said, "Charlie, if I asked you out after my shift, would you
accept the invitation?"
Charlie, who wasn't experienced enough to be cynical about the
request, thought a moment. He felt his cock begin to stiffen again in
his panties, and when he realized why he said, "Yes, I would. I really
like you, Lilune, and I'd be happy to spend some more time with you."
"Wonderful!" Her smile was no longer tired or artificial. "I get
off at six - be by the front door then and I'll meet you shortly after
the hour."
"I'll be there, Lilune, eagerly waiting."
Time was almost up and Lilune pressed herself to the glass.
Charlie, a bit more warily, pressed his lips to hers across the glass,
and stroked where her nipple pressed itself flat. He smiled when he
thought he detected an enlarging bulge in her tight black briefs. As
the clock ticked away, they said their goodbyes, "... until later."
***
As soon as the curtain had separated her from Charlie, Lilune
picked up her phone again. She was really interested in Charlie but
she also knew that if he decided to skip out on her, he was too good
to let walk away. She pushed a button and dialed a two digit number.
When the ringing was answered, she said, "I need a mark tailed -
observation only until six am. Description: six foot, medium-long
blond hair, wearing jeans and a blue and white polo shirt. He has a
large brown bag. If he doesn't return here by 6:30, detain him - I
think he'll make good material for the Market."
Her instructions were confirmed and she hung up. She really
hoped that Charlie came back - she was sure she could convince him to
come into her line of work fairly easily. And have *so* much fun while
she did, too!
***
Charlie left the store in a daze and entered the next one. He
went through the racks of magazines and books and this time actually
paid attention to the material in the Transvestite and Transexual
section. Intrigued and very interested, he thumbed through the
magazines and perused the books. He ended up buying six mags and four
books, and he found his cock so hard after that that he had trouble
walking into the next store.
Two more bookstores later, he came to another theater. He went
in and watched about half of a feature, but his attention really
wasn't on the screen. He was thinking about Lilune - about her breasts
and mostly about her cock. He was very confused by his reaction to her
body. After all, he had never had any homosexual feelings before! And
now, first those dancers, and now Lilune ... he just didn't know what
was going on inside of himself any more!
He finally left the theater no closer to understanding himself
or Lilune because he had no watch and was worried about the time.
One more bookstore (and two magazines) and he was finished. He
got the time - almost six - off of a bank sign on a cross-street and
headed back to the store where he was to meet Lilune. He stood by the
front door and looked in the shop window for a long time (shorter than
it seemed, of course) until he felt a touch on his shoulder. He
whirled in startled surprise and stared directly into Lilune's very
violet eyes. She smiled at him and stood on tip-toes to give him a
peck on his lips. Charlie was overwhelmed by her presence - the
nose-to-nose sight of her, her fragrance (which was heady enough to
make his knees weak); just everything! He impulsively hugged her, then
stepped back a pace and looked at her. The tube top and jeans she wore
looked fantastic on her, and Charlie couldn't detect the slightest
hint of what was between her legs.
Lilune said, "Well, come on, honey. I know a little coffee shop
that has wonderful sandwiches even this early. Lets brinner -
breakfast-dinner - okay?"
The meal was wonderful, and during it Lilune skillfully drew
Charlie's life story out of him. She also made it clear that she
intended to show him the inside of her bedroom, which helped to keep
him responding eagerly to her questions.
Almost before he knew it, Charlie was in that bedroom, watching
Lilune disrobe again. He was sitting on her king-sized bed and Lilune
was doing a sexy, erotic strip-tease for him to the perfect music.
Charlie was all but drooling as he watched her bare her considerable
charms, and his cock was straining in his pants, staining the purple
panties he wore with flowing pre-cum.
Lilune had even changed her lingerie after work, so when she was
down to just her underthings, they were new to Charlie. The music
changed and she began to dance even sexier and slower as she stripped
out of her filmy lingerie. First her breasts were free - creamy and
large as ever. Then her legs - long and shapely even without heels and
stockings. Garter belt and waist cincher vanished, and finally she
slipped down her panties and revealed to Charlie's avidly staring eyes
her handsome cock.
Charlie was so fascinated by that cock that he fell off the bed
and onto his knees before it and reached out to touch it, but Lilune
backed away smiling. She said, "Get naked first, young stud. Then you
can have all of me."
The music was still playing, and inspired both by Lilune's just
concluded performance and the shows he had seen earlier in the day,
Charlie did a clumsy but enthusiastic (and not totally charmless)
striptease. His showing off excited both Lilune and himself so that by
the time he was down to his underwear, the front of the strainingly
stretched purple panties was soaked with pre-cum and Charlie was on
the teetering verge of orgasm.
The tape ended as Charlie was posing in his briefs, and Lilune
clapped and cheered Charlie's performance. She said, "You know, you do
that with an amazing amount of promise. Have you ever considered doing
exotic dancing professionally? You'd clean up, you know."
Without waiting for Charlie to answer, she knelt before him and
freed his straining, hefty cock from its silky, sticky, purple prison.
Lodging the waistband of the panties under Charlie's balls, she opened
her mouth wide and ingested Charlie's cock straight to the root. There
wasn't going to be much she would be able to do before Charlie's
excitement got the better of him, so she made the most of what she
could get. When Charlie came, both of them were well satisfied for the
moment.
Lilune vacuumed Charlie's cock clean with her mouth and slipped
it back inside his panties. "Come here, stud, and do whatever you want
to me, or with me. Get to know my body - I want us to be very good
friends and good friends must know each other."
And Charlie spent the next 45 minutes doing just that. He was
fascinated with her body - so lusciously feminine yet sporting a
healthy, hefty cock and balls. He made absolutely sure, by dint of
long, thorough, and careful search, that there was no other masculine
feature on her body: sure enough, she was (nearly) all woman, and
magnificently so! Her skin was soft, smooth, and hairless, unblemished
and beautiful. Her breasts were full and resilient, and looked to his
untrained eye perfectly natural (to be fair, he had seen his share of
artificially- enhanced boobs in the magazines he had browsed through).
She was fit and healthy (again, in his untrained opinion), with sleek
muscles under her soft skin that helped her to attain her perfect
shape. Charlie probed and explored her from head to toe, and first
skipping her crotch but only to save it for last.
When he had finished his explorations of the female parts of
Lilune's body, Charlie focused all of his attention on her cock. It
was hard and throbbing by the time he got to it - his intense
explorations had aroused her nearly to the bursting point even though
he hadn't so much as brushed accidentally against it. Even in its most
rampant state, Charlie was amazed by the fact that it still looked
perfect on her otherwise female body. He spent a few minutes
delicately touching the tool and the surrounding flesh, but something
drew his mouth almost automatically to the man-spear, and soon he was
felating his first cock ever.
Lilune, realizing Charlie's inexperience, became an active
participant again, directing Charlie's efforts to please her. He
proved a very apt pupil - it was obvious that Charlie's zest for the
subject helped enormously!
Charlie threw himself into the blow job body and soul - his
world narrowed to Lilune's hips. Her verbal assistance was assimilated
subconsciously, reinforced by either her heightened response or the
easing of his own discomfort. Her physical assistance was also
accepted without question - again, there were positive reinforcements
to prove the usefulness thereof. Little by little, Charlie was
educated in the fine art of the blow job by a master/mistress, and it
was a lesson that would stay with him forever.
Gradually, Lilune's role returned to primarily passive as
Charlie mastered technique after technique. And soon the pleasure that
Charlie's actions were generating drove her right into orbit. Charlie
had learned enough to keep her there for a good long time before
allowing her to cum, filling his mouth to overflowing with her sweet,
tangy, and even subtly feminine semen (not that he had any way to make
that comparison - then, anyway). Charlie drank it down as fast as he
could, then licked up the drops that had leaked out of his mouth. When
he pulled up off of Lilune's beautifully hairless cock, he looked into
her eyes adoringly, as if silently thanking her for showing him
Nirvana. Finally, he rolled away from her to give himself some time to
recover.
"Well, stud," she said, "I've seldom had a blow job as expert as
that one from a beginner. I'm both impressed and well-sated, so I
think the next move is once again yours." Lilune sat up and reached
into her bedside table, retrieving a small tube of ointment. She
continued, "Take this K-Y and grease up your cock, and then I'll show
you how to fuck my ass."
Charlie took the very greasy gel and smeared it all over his
cock. Following Lilune's next instructions, he knelt behind her
repositioned body. She had exposed her hairless ass to him by getting
on her hands and knees at the edge of the bed, and Charlie proceeded
to apply some more K-Y to the whole delectable ass crease she so
presented.
That done, he put the tube aside and aimed his cock for the tiny
pink star of her rosebud. He was an anal virgin in all senses, but he
knew Lilune knew what she was in for. Trusting her expertise and her
instructions, he touched her ass hole with the head of his cock, the
gripped her hips hard and pushed steadily and evenly with his own
hips. There was a bit of resistance at first but soon her body opened
up and his cock sank quickly into the hottest, tightest love canal he
had ever imagined. Linda had never been so tight, and his high school
girlfriend Martha, who as a virgin had been almost as tight, had never
been so hot. Compared to the only two women he had ever fucked, Lilune
was heaven!
This time, Charlie needed no further instructions from his
lover. His body knew how to fuck, and thanks to Linda who wasn't
exactly shy in bed, he knew a bit about pleasing a body with his cock
as well. It was somewhat different fucking an ass, but only in the
details, and the tricks Linda had taught him to satisfy her worked on
Lilune with only minor modifications.
As soon as his rhythm was established, he let his hands wander
over Lilune's body. He played momentarily with her resurrecting cock,
but didn't linger there (he had an idea of what came next, and he
didn't want to delay that by making Lilune's cock cum prematurely).
Mostly, Charlie played with Lilune's breasts, adoring the firm feel of
her globes as he plundered her ass.
Again, he used techniques learned at Linda's hand to keep
himself from cumming too fast, prolonging both their pleasure. When
finally he shot, Lilune cried out as well in obvious orgasm, but her
cock remained dry and hard.
They separated slowly, and laid next to each other, panting and
recovering. After a few moments, Lilune asked, "Ready to feel what I
was just feeling?" Charlie gazed deeply into his lover's eyes and
nodded dreamily.
Charlie assumed Lilune's position - on hands and knees at the
edge of the bed. Actually, he folded his arms around a pillow and
rested his head on it so as to be completely (as near as possible)
comfortable. He watched in fascination as Lilune used the K-Y to
grease her cock. Then, following her suggestion, he closed his eyes
and concentrated on his ass as her fingers slowly rubbed the gel
around his ass hole, and then began to penetrate it with her fingers.
She went slowly, tenderly, and erotically, and Charlie's cock began to
erect as he concentrated on the pleasure she was beginning to
generate.
The greasing process took much longer this time. Lilune worked
her fingers against his ass hole, massaging the muscle, opening it up
little by little. She inserted her fingers - one at a time until she
was pumping three in and out at once. She kept up a running commentary
in a lilting, sing-song tone that did as much to relax Charlie and put
him at ease as the slow preparations did. Finally, he was as ready as
she felt he needed to be, and she set the tube of K-Y aside. She stood
between his legs and stroked his ass and back, and asked whether he
was ready to be fucked. His dreamily murmured, "Uh huh," signaled the
next phase.
She took up the same pose as he had - standing facing his ass
with her hands firmly on his hips. She expertly positioned her cock at
his back door, pressing just enough so that she knew he could feel her
presence. She said, "Okay now, stud, this *is* going to hurt for a
bit. I'll go slow and easy, but your body has to adjust to my
equipment and there will be pain until it does. My advice is to just
try to stay relaxed, push your anal muscles at me to keep from
tightening up too much, and then just stick it out. Bite the pillow,
scream if you want to, but trust me - it *will* feel better, lots
better if you just last through the pain."
Charlie digested Lilune's advice from his near-blissful relaxed
state. He trusted Lilune at this point more than he trusted his
mother, and he knew that there was pleasure on the way, eventually.
Lilune paused long enough to be sure her words had sunk into
Charlie's brain, and then she began her slow, cautious entry into
Charlie's virgin ass. She pressed steadily and firmly against his
strong sphincter muscle, achieving entry far more easily than she had
expected. Charlie gasped, with a bit of a whimper, as her cock head
passed the ring of muscle. His pain was evident in the rigidity of his
shoulders, the whiteness of his knuckles, the expression on his face,
and the way he was biting the pillow his head rested on. Lilune
recalled her first few times well, and felt sorry for the boy, but she
also knew what the reward for perseverance was, so she was sure he
would forgive her.
She kept up the pressure, moving in slowly but steadily. Charlie
broke out in a sweat from the pain, and the cries in the back of his
throat grew more audible as she reached the halfway mark. She halted
her movement, pausing to allow Charlie's body to catch up. When his
fingers began to unclench, she started moving in again. His fingers
clenched even tighter, but almost immediately loosened again. Slowly,
as she worked the other half of her manhood into Charlie's ass, he
began to sense the pleasure welling up behind the pain of being
stretched farther than he ever had before. Slowly, inch fraction by
inch fraction, the pain subsided and the foreign stimulation of his
anal passage began to excite him. His shoulders relaxed, his fingers
flexed, his face unscrewed, and he spit the pillow out of his mouth in
order to sigh with a tiny bit of pleasure. As if it knew before the
rest of him, his cock began to erect again, after having shrunk
totally when the pain began.
Lilune didn't pause again until she rested her smooth pubic
mound against Charlie's ass-cheeks. Charlie gasped, lifting his head
from the pillow in ecstasy as he felt the full length of Lilune's
manhood buried inside of him and the contact of her skin against his
butt. His pleasure wasn't only from the undeniably wonderful feeling
of the cock up his ass, but also due to the fact that it was Lilune, a
'woman', who was fucking him. It was the almost-role-reversal that
added to the thrill, that made him groan from deep in his soul in
ecstasy.
Taking his groans for what they were - complete acceptance of
being fucked - Lilune began to fuck. Long slow strokes in and out that
had Charlie clenching the pillow again, but this time in ecstasy.
Slowly gaining speed, she fucked Charlie for as long as she could hold
herself back. When she finally sent wave after wave of scalding sperm
to flood his bowels, Charlie responded with an orgasm of his own: his
first totally anal orgasm ever. When both were over their moments of
maximum pleasure, they collapsed onto the bed, lying entwined and
slowly easing into sleep
***
The next week was the happiest one Charlie could remember ever
spending. The first four days involved almost non-stop fucking with
Lilune (well, not really, but it was close enough). After that, she
had to go back to work for 8 hours a day, but she pulled a few strings
and got Charlie tickets to shows and plays regardless of their normal
availability (he could have made a bundle scalping good seats to sold
out performances!), which kept him occupied with the mysteries of New
York City while she was on the job. Of course, she made up for the
time they had to spend apart, so that Charlie was almost glad for the
chance to rest when she went to work.
Beyond keeping her new stud well satisfied, Lilune worked on him
subtly but steadily to consider giving up his college career for her
own line of work. She was very good at it - she had lured four other
young men into the world of sex-for- pay, although with Charlie there
was far more personal attraction present than ever before. She was
desperate to win Charlie over, because she had no intention of letting
the 'trade' lose a piece as fine as he, and she really didn't want to
have to resort to the other methods available.
Fortunately, Charlie was responding. Lilune had repeatedly
remarked on how easily the right people could make money in the
'trade', and how Charlie was one of those 'right people'. It was
certainly a huge change to make, but there were several things that
actually made him seriously consider it. And one large thing was that
he was sure that if he went back to Columbia and his planned future,
he would never see Lilune again except perhaps across a plexiglass
window with a timer regulating their conversation. He was drawn to
Lilune like he had never been drawn to anything in his life, and he
wasn't sure he wanted to give her up.
On the Saturday seven days after his vacation had begun, Lilune
convinced Charlie to give exotic dancing a try at a club she knew that
had an amateur night. Almost to his surprise, Charlie agreed. After a
little coaching, Charlie and Lilune went down to the strip club - the
same one he had seen Bruce do his special dance in. That made him a
tiny bit nervous, but a large bit inspired.
A nerve-wracking 30 minutes were spent in one of the
cubicle-sized dressing rooms assigned him. Lilune did her best to keep
him loose - she knew quite well how jittery a person could get before
a performance. He was given his first cue, and went nervously to wait
in the wings for his turn on stage. After a last minute inspection of
his uniform, Charlie made ready to go on. The 'cool down' period was
over and the audience was settling down as the lights dimmed. The
announcer said, "And now, the Purple Tassel Lounge's Amateur Night
presents a true first timer! Give it up for Chris the Cop!" Cheering
rose, the stage floods came on, and music began. Charlie took a deep
breath and walked out on stage.
He was dressed as a traffic policeman, white gloves, gold
braids, and all. He walked out to center stage and took up a position
with his back to the audience. The music changed to soft rock with
city sounds mixed in, and Charlie mimed directing traffic. The
background rock increased in tempo until finally it changed into hard,
driving rock and Charlie ceased miming and began dancing, finally
facing the audience though not really looking at them.
He danced to the best of his untutored ability, and was pleased
to realize that he was enjoying himself thoroughly. He got into the
music, and he imagined that he was dancing to excite Lilune, which
provided the incentive needed to get over his stage-fright - in fact,
he forgot about the audience completely, for a little bit anyway.
Piece by piece, Charlie removed his uniform until he was down to
the traditional g-string and a lot of glistening flesh. His cock was
hard and straining at the skimpy garment, which was making him very
uncomfortable. So he did what he hadn't really been planning on doing
- he stripped it off and danced totally naked for the remainder of his
music track. He struck a dramatic pose as the final drum crashed and
when the music died he could hear the crown roaring and cheering like
mad. He held his pose for a moment, then turned and paced calmly and
proudly back to the wings, buns flashing at the crowd. Lilune was
waiting for him with open arms and all kinds of congratulations, and
as he fell into her embrace, he made up his mind about his future.
Lilune was ecstatic when she heard his decision. She had turned
another one! She called her contacts as soon as she got back to
*their* apartment. There were details to arrange - Charlie would need
a new face and a new identity if he was going to go into the 'trade'
right here in NYC, so close to his former residence. And Lilune had no
intention of letting anyone steal Charlie back to the 'mundane'
existence of college and 9 to 5 jobs.
Lilune's contacts worked fast. Within two weeks, Charlie signed
papers that legally changed him into Mark Chesterfield, a name he had
already begun using when he danced (Chris was too close to Charlie,
but he liked Mark even more). Another four weeks had passed, with him
dancing four nights out of seven, and already beginning to rake in the
cash from his up-front employers as well as the under-the-table
'performances' he was taking on, when he took a little vacation. A
trip to a discrete hospital later, and his face was no longer
recognizable as Charlie's, though the changes had been subtle and had
left him even more handsome. Charlie was finally completely gone.
Lilune was very proud of her convert, but she wasn't quite
through with Mark yet. She had brought Charlie a long way from college
student to stripper and prostitute, but there was another step she
still wanted to go. With someone she wasn't so close to, she might
have just gone ahead and taken the last step without the subject's
knowledge, but she saw Mark as more than just a mark or a target. She
wanted to entice Mark into willingly taking that last step on his own.
She tried for four months to subtly hint what she wanted for
him, but even though Mark was no longer a naive college boy, he wasn't
quite as worldly as he maybe wished he was and he never quite caught
on to what she was getting at. Finally, she decided to be direct but
not forceful, and hope that gentle persuasion would work.
That night, she removed all of Mark's underwear, replacing them
in the drawer with satiny, sleek bikini panties. Too subtle or not,
this would at least begin Mark moving in the right direction, she
hoped.
When he arrived home, very late by normal standards but just on
time for him, he slipped out of his clothes and into bed with Lilune.
They made love with their usual ardor - Mark liked to use his last few
shows to work himself up for his homecoming. After the third mutual
orgasm, Mark slipped into sleep and Lilune took enough time to get rid
of the sexy but male undershorts that Mark had worn home before
following her lover into slumber.
Next day, when Mark roused himself enough to shower and dress,
he discovered that his male underwear had been replaced with frilly
and slippery feminine panties. The sight reminded him of what he had
been wearing when he had first met Lilune, and the circumstances
surrounding his getting, and then putting on those purple panties. As
nice as those memories were, he hadn't worn them or any other panties
since that night. But seeing that drawer full of lacy and delicate
items, he remembered the feelings those purple panties had generated,
caressing his prick and groin. Tentatively, he reached down and
selected a black and red pair and drew them on slowly. As they settled
around his waist, he felt a tingling in his cock and balls, and he
began to harden.
He wore the feminine briefs all day, except while dancing (they
didn't go with his costumes), and he even put them back on to wear
home. Lilune was waiting for him in the living room clad in one of
their favorite outfits: bra, waist cincher gartering stockings, high
heels, and no panties. Her endowment hung out between the garters,
framed perfectly by the cincher's satin and lace.
She said, "Hi, loverboy. Strip - I'm ready to do it here and
now!"
Automatically, Mark complied. He was out of his outer clothes in
seconds (a side benefit of his official, unorthodox job) and was
hooking his fingers into his underwear when Lilune stepped up to him,
pressing herself into his side and cupping his scantily clad genitals
in her hand. She rubbed his stiff cock through the panties and said,
"You look very sexy in panties, babe. Do you like to wear them?"
Mark gasped and sighed, and said, "Yes, love, very much,"
pressing his groin into her hand.
She said, "Would you like to be able to wear those and more, all
the time?"
Mark paused a moment before answering. Even though her hand's
fondling was making it a little hard to concentrate, he thought he
could see where this might be going. And a moment later, he realized
that he didn't mind. When he was sure of himself, he answered, "Yeah,
I probably could get into that real easy. What did you have in mind?"
Lilune snuggled against him again, kissing his neck and smiling
to herself. She pulled away just a little, so they were still in
contact, and said, "Well, there are two methods to that end, maybe
even three. The first is that you could just wear feminine underthings
under your male clothes, which is fine for you since you'd be feeling
it all the time, but I don't think I'd get all that much of a kick out
of it, since it would be mostly a secret. Also, you'd always have to
worry about being found out - being careful in the changing rooms, in
the bathrooms, all that kind of thing. I think that's really more
trouble than its likely to be worth.
"Your second option would be to become a transvestite: either
occasionally, or even all the time wearing women's clothes from the
skin out, including makeup and jewelry and all. And the third option
is to go one step beyond just dressing like a woman, and become like
me, a she-male. Either of those two options would thrill me no end,
Mark. And I think you would make a damn sexy girl, breasts or no
breasts."
Mark was silent for quite a long time. He had guessed right
(finally), and he wasn't bothered by the suggestions, but didn't want
to make his decision lightly. After all, his life had already changed
so much - from college student, proto-yuppie, to well-known stripper
and sometime prostitute! But he realized that he was so far from his
former career path that he didn't even need to wonder whether he
should deviate even further from it - that was pointless and stupid.
So, he thought about wearing just women's underthings. As Lilune
said, that might give him the thrills that these panties were, but
there were just too many problems. So what about dressing, either full
or part time? That had some appeal - he certainly wouldn't have to
worry about hiding his underthings, unless he made a really
unconvincing woman. Then again, even if he wasn't easily able to put
on a dress and makeup and look like a female, there was always the
third option - take steps to make the transition permanent, if only
half-way. Lilune had captivated him from the first moment he had seen
her, and the revelation of her cock had only added to her allure. What
if he could become such an enchanting creature as well?
After long thought, he said, "How would you like to have a
sister she-male as a lover?" Her delighted squealing, and the kiss she
gave him that knocked him over, were pretty good indications of her
answer.
***
The process was slow, made more so because they took no
shortcuts. First, they made sure that Mark was passable as a female,
and it turned out that Lilune was right - he was gorgeous in makeup
and a dress. Mark never suspected that much of the reason that was so
was due to the instructions Lilune had given to the surgeons who had
reconstructed his face to make Charlie vanish.
Hormones started next. Lilune had connections, and was able to
supply Mark with experimental hormones that were effective, and yet
wouldn't completely emasculate him. Fir the first six months, Mark
stayed Mark and danced every week even as his body began to change.
After that, he took six months off to let the changes shift him from
effeminate male to masculine female. His body reacted well to the
hormones, altering steadily into a very feminine shape: breasts
growing steadily, waist narrowing (with some help, both dieting and
corsets), hips flaring and ass plumping out (though not *too* much!),
arms and legs slimming down, skin becoming soft, hairless, and smooth.
His hair grew out beautiful and long. His face even managed to become
even more feminine, though even with before and after pictures it
wasn't easy to actually point out what the changes were and how they
made him more female-seeming.
At the end of that time, he went back to dancing, this time
under the name Kerry. The changes continues through the bulk of the
second year, completing the switch from male to female completely,
leaving only the still fully functioning cock and balls of
Charlie/Mark to indicate that she hadn't been born with the perfectly
female body she now had.
And Kerry was as happy as a mortal could be with her new life.
She blessed the day she had decided to spend Spring Break seeing what
the Big Apple had to offer, and the extended vacation it had begun.
-End-
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