A young man goes to a bar to celebrate his birthday, but the
birthday surprise he gets wasn't exactly what was on his wish list.
hope you like it just a little whimsicle story i came up with, love to
hear what you think. thank you GadgetGurl, my beta.
this is an original fiction, charactors are my own
Jason's First everything
Imagine if you will a young man; sitting in a bar for the very first time after
coming of age, ordering his first adult beverage, celebrating his birthday by
himself as he nursed the drink in front of him.
He noticed a very striking woman at the end of the bar, staring at him with
piercing golden brown eyes. Her hair was long, wavy, and sparkled with black
highlights. It was hard to tell while she was sitting, but she seemed small,
maybe 5’4” or so. She had a slight build with what looked like nubs for
breasts, which was fine with him. He was more of an ass man. She was
wearing a slim black dress that hugged in all the right places. He glanced at
her shyly, trying to watch her without getting caught.
Aftera couple of drinks he began to get bolder, looking at her outright but still
sober enough to avoid her gaze.
The woman tired of the teasing glares. Picking up her almost empty drink and
walking over to him, she lifted a leg to sit on the bar stool next to him, asking
him to buy her another drink.
He was well aware of the slit that went high on her thigh, showing all of her
leg as she sat. Obliging her, he bought her and himself another round.
She had a deep, soft, seductive voice; they talked about this and that and how
he’d come to be celebrating his birthday alone.
She asked him if he would like to go to her place to have a
“private”celebration. He agreed. Like a gentleman, he turned, slid off his own
stool, and put his hand out to help her off the stool she was sitting on, slightly
wobbling in the process. Not surprising; he had 3 hard drinks in him.
He followed her out of the bar and to her car. Getting in, he had no cares about
whether or not she was capable of driving.
They got to their destination safely and walked in; well, he was stumbling a
little, but he managed to follow her to the elevator.
While waiting in the elevator, as it ascended the multitudinous floors, she
pressed into him, letting the top of her thigh brush against him. His manhood
springing to action, a slight pant escaped his lips as he looked down into her
hypnotizing golden brown eyes.
Drunk,and now horny, he bent the short distance to place his lips on
hers.Being a virgin, he wasn’t quite sure what he should or shouldn’t do. As he
lifted his lips from hers the bell of the elevator rang, signaling the elevator had
stopped at their floor.
She grabbed his hand and pulled him to her apartment door. Opening thedoor
she held both his hands, yanking him through, spinning them both around so
she could close it behind them.
She stared up into his dazzling emerald green orbs, she was stunned frozen in
the place she stood.
Aftera minute she placed her hands on his chest, pushing him...no, guiding
him backwards. He didn’t stop till his knees hit the couch, causing him to fall
backwards. The woman knelt gracefully, her hands on his legs. They slowly
glided up his thighs to stop at his belt buckle, expertly undoing the belt and the
The young man only saw the silhouette of the woman in an unknown light
source glowing in the apartment. She tugged gently on the pants, bringing
them down enough to expose his generously large member. He could see a
smile and a surprised look on her face.
“Oh, so big. A splendid surprise…” she commented in a seducing tone. Her
voice was deep, rich and seductive, and made the dribbling member twitch.
Lowering her head, she seized his rock hard member in her mouth, licking and
Being a virgin, he all too shortly said he was going to come. Not caring, she
swallowed all he had to give.
Practically stuttering in awe and embarrassment, the young man apologized
and confessed that this was his first time.
“Well, happy birthday to me for being your first,” she said with a generous
Kissing him deeply, allowing him to taste himself upon her lips, she felt him
wince a little at the unfamiliar taste of come mixed with alcohol. But being the
horny virgin that he was, he took her into his mouth. He’d heard from a friend
that when kissing like this, you were meant to suck on the tongue.
Which he did, although quite messily. The woman took it in stride; taking
control of the kiss, she guided him to duel with her tongue, to move it around
in a dance of pleasure. Before he knew it he was hard again.
She stood, pulling her dress up enough to straddle his legs. In an instant his
member was guided into a very hot tight hole. He moaned loudly but strained
to keep from getting louder. The woman impaled herself on his cock and
hissed, moaning in pain and pleasure as the oversized member entered her.
Arching her back, tossing her head, she grabbed the young man’s
head,bringing it to her neck. He began to suck and nibble on the tanned skin
under her jaw as she moved up and down, impaling herself on his hardness,
moans and pants bursting from her mouth. He himself wasn’t much quieter.
Gasping at the her tightness, he was barely coherent enough to wonder if all
women were like this; this tight, hot, pulsating hole, sucking him in, squeezing
Off in his own little world of pleasure, he almost missed the woman tensing as
she hissed she was coming. It caused her to tighten even more around his
cock, forcing him to spill his virgin seed deep within her. She collapsed on his
chest, breathless, trying to regain control over herself. When she was able to
talk again she raised her head, kissing his lips passionately.
“Thank you. That was great.”
“Ain't I supposed to say that?” he asked with a smile. She grinned and rose off
of him, his now flaccid member slid easily from her body. She pouted at the
loss of it and walked off to the other room.
Sated,drunk, and on the verge of passing out, he vaguely saw the woman
return, kneeling once again in front of him. He then felt something cold on his
member. Then there was darkness.
** * * *
When he woke up the next morning he’d been cleaned up, and there was a
blanket over him. His mouth felt pasty from the alcohol. He tried to moisten
his mouth with his own saliva until he noticed a glass of water on the coffee
There was also a note. I think you will need these. Two pills sat next to the
glass. He picked up the pills, popping them into his mouth and chasing them
down with a deep gulp of water.
Now fully awake, he looked around at the unfamiliar surroundings, trying to
recall the evening. Slowly at first, he remembered the bar and the beautiful
woman. Then things got a little foggy, like how he’dgotten to the apartment.
But he vividly remembered the evening’s activities and he smiled, both from
embarrassment and the knowledge that he was no longer a virgin.
“Finally awake? How’s the head?” A sensually deep, but strangely familiar
voice spoke next to him. He saw a slender man in boxers walk past him to the
Struggling to keep his composure, he apologized for crashing on the couch
and introduced himself as Jason.
The slender man said his name was Casey, and he looked familiar to
Jason,who just figured that he’d met him last night and couldn’t remember.
Casey was short for a man, about 5’6”, with short,dirty blonde hair. It was the
eyes, though, that got him. They were the same as the woman from last night,
the same golden brown color. He thought that maybe the guy was her twin or
Jason asked him about the woman from last night, if she was still sleeping.
Casey looked at him, puzzled at first. Then he began to laugh, and the more he
thought about it, the longer he laughed.
Jason was getting annoyed now. “Mind letting me in on the joke?!” he asked
grumpily. He was irritable with his hangover and couldn’t understand why the
man was laughing.
Casey apologized, trying to get himself under control. Once he managed to
stop snickering he walked over and knelt in front of Jason, hands on his knees.
Jason sat further back into the couch, wondering why the guy had his hands on
In a calm (well, as calm as he could be after laughing uncontrollably) voice,
Casey said, “I thought you knew, why else would you be there?” There
meaning the bar. He stared Jason in the eyes for any acknowledgment that he
Jason stared back, puzzled by the comment. “Knew...what?” he asked slowly.
Casey paused, trying to find the right words to explain to the boy that the
woman he slept with last night had, in fact, been Casey dressed in drag.
He began with a question. “Do you know what kind of bar you went to last
Jason looked confused. “Yeah, a bar that you drink at!” he answered.
Casey pushed harder. “Yes…it’s a bar where you drink. But do you know what
kind of bar it was?”
Jason still didn’t understand the difference and he stated as much, getting
annoyed at the questions.
Casey looked down, shaking his head back and forth. “Oh boy,” he
murmured.“It’s better to show you, ‘cos you won’t believe me otherwise.”
Standing gracefully, Casey walked back to the other room only to return
moments later, still in boxers but now sporting long, wavy black hair. He was
poised, ready in case the young man on the couch reacted with any violence or
Jason saw the movement out of the corner of his eye and turned his head to
look at the sight before him. Eyes opened wide, jaw slackened in total
disbelief, he stuttered, words failing him.
“Y-Y-you! H-Her! Same...how?” He scrambling to the other end of the couch,
anger rising. “You tricked me!”
“No, I didn't! You were the one stupid enough to come into a gay bar!” Casey
Jason stumbled off the couch, walking around the Casey like he was a viper
ready to attack, giving him a wide birth. He thought the man would strike out
at him, trying to catch him to keep him from leaving. Making his way to the
door, Jason stumbled to open the locks. He looked back, making sure the guy
was not following him, and left.
Jason was numb, feeling like he had been violated. He made his way home
and immediately went to the shower. When he was done he sat on his
bed,wearing only a towel wrapped low around his hips, wondering how he had
gotten himself into that situation. He had never been to a bar before, let alone
a gay bar. How was he to know?
Now he knew why the men had been looking at him. She was beautiful, Jason
thought...no, he...for a guy, he was beautiful. Jason began to remember the hot
moist mouth on his cock, how tight it had been, how she... no, how he rode
The towel around his hips grew tight as his member hardened at the memory.
He wondered why; he wasn't gay...or was he? He tried to rationalize his
feelings by remembering that he’d thought Casey wasa woman. But the more
he thought about it, the more he realized that he was no longer freaked by the
reality of it, that in itself freaked him out more.
Pulling the towel from around his waist, he took his now rigid member in his
hand, wrapping his fingers around the good sized length. He began to pump, at
first remembering the image of the woman, her long wavy black hair, the
golden brown eyes that hypnotized him.
Then the image morphed into the man with dirty blonde hair, the slim, almost
naked body he’d seen that morning. He imagined that same head bobbing on
his member, as the black-highlighted head had done the night before. His
orgasm exploded from his body, racking his nerves. It was...intense, more so
** * * *
Jason spent the next week analyzing his thoughts and feelings regarding the
encounter, and what he had done and imagined after. Yes, he’d been shocked
to find that she was actually a he, and even more shocked that he could
masturbate to the man’s image afterwords...and several times during the past
Finally, he decided to pursue the curiosity he felt at why he was not disgusted
by it. Jason decided to seek Casey out, to see if he himself was indeed actually
gay or not.
He waited outside the bar to find her...him, too embarrassed to go back inside.
He waited outside for several evenings, looking for the she-male Casey,
wondering if she would come as a man or a woman. If Casey came as a man,
would Jason recognize him?
What Jason didn't know was that Casey had more than one wig, so he had no
idea the man was there. But Casey recognized the young man standing across
the street staring, taking notice of who was coming and going.He realized
every once in a while Jason would show recognition of a person only to slump
back against the wall, looking disappointed.
Casey decided to have some fun with Jason. He was wearing a fire-red curly
wig with large, black-framed sunglasses, even though it was dark out. His
body was sheathed in a hot red, skin-tight mini dress that zipped from the
bottom to the top with a sparkling red heart zipper pull.
Casey walked over to Jason, leaning against the wall next to him. “I've notice
you hanging around the past couple of nights, who are you looking for?
Maybe I can help?”
Embarrassed, Jason said he wasn't sure. He didn’t know if Casey was still
Casey when she dressed up, even though the name was ambiguous.
Casey (in disguise) told him she was a regular at the bar, and that she knew
just about everyone. She asked him to describe the person he was looking for.
Jason thought for a second, looked over at the woman, wondering if she was a
They sure made for some beautiful women. Even though they were guys.
He began describing the person he was looking for. “She has long wavy black
hair that sparkles, about your height, your build.” The woman was looking at
him through the large rimmed glasses as Jason continued to ramble about the
mystery lady's beauty.
“Her eyes are the most dazzling I've ever seen. They’re an amazing golden
brown; a person could get lost in those eyes.”
Casey was amazed and flattered by Jason’s ramblings. He looked down as he
took off his sunglasses, slowly raising his head to look at the young man.
Jason wasn’t looking at the woman as he spoke, but as he turned to say
something else about the person he was looking for, he had to do a double take
at the eyes that were now looking up at him. He grew quiet, slowly realizing
whose eyes he was looking into. Now at a loss for words, he just stared at the
face, the eyes of the woman/man he now recognized.
“It's you!?” That was all he could say.
Casey voice was slightly dull. “Yup. I've noticed you been here a few times.
Didn't know you were looking for me?”
“Why? After that night I thought you would never come this way again,”
Casey asked, sounding more interested.
Jason looked down, feeling guilty about the way he’d acted. He apologized,
telling Casey how shocked and embarrassed he’d been,and that he had no idea
that he’d gone into a gay bar. Finding himself with another guy for his first
time had been a little more than he could handle at the time. He also confessed
that after he got home, he’d realized he wasn't as freaked out about it as he
acted.Confessed that he was very attracted to Casey, and that he thought that
maybe it meant that he was gay too.
Casey stared at him for a short while, assessing the young man before
him.Then he told Jason to go home or to a straight bar to pick up a real
woman. He turned and started walking away.
Jason grabbed his arm to stopped the small figure of a man from
leaving.Casey turned and looked pointedly at the hand on his arm in a silent
command to let go. Jason slowly let go, but didn’t remove his hand in case
Casey decided to walk off again.
“Why would you tell me that?” Jason inquired, looking at him intently.
“You're not gay. You're just attracted to the illusion of the woman before you,
not the person I am.” Casey said it objectively, turning towalk back to the bar.
Jason once again grabbed at his arm, turning him completely around so he
could grab hold of the other arm as well to keep Casey from leaving.
“Let go of me!” Casey commanded.
“No, listen to me. I'm not attracted to how you're dressed. Granted, as
beautiful as you are, it's not the image I see when I remembered you.When
thinking of you this past week it's not the image of a woman with black hair
that I see, but of the mostly naked man with dirty blonde hair I saw the
morning after.” Jason was pleading his case,hoping Casey would see the
sincerity in his face.
When Casey made no effort to leave, but stood there staring at him, Jason took
the risk of bending the short distance to place a sweet, chaste kiss upon the
petite man's painted lips, pulling back to see Casey's reaction.
Taking a small step into the young man, Casey raised his arms. Jason let go of
his soft grip on the man's arms, allowing them to move. Casey placed his
hands around the back of Jason's neck, pulling him down to his level to place
a kiss of his own on Jason's lips, holding him there. He then slid his tongue
out across the young man’s lips, surprising Jason momentarily. But Jason
opened his mouth, allowing Casey to explore the cavern within and letting his
own tongue greetthe soft, warm appendage. He closed his eyes, enjoying the
feeling and the emotions it stirred within him.
After a couple of minutes of dueling tongues Casey pulled away to look at
Jason, wanting to see what expression he held on his face. Jason slowly
opened his eyes. They were glazed over with the growing lust the kiss had
stirred in him. Casey, being satisfied with the honesty the face held, took hold
of Jason's hand, pulling softly but firmly.He started walking backwards with
the young man in tow, and then turned to watch where he was going, pulling
Jason walked quietly, watching the figure in front of him, the slight build, slim
waist, and firm, round butt swaying in front of him, hypnotizing him further.
Lust was growing, and he wanted to reach out with his free hand for the hip
rocking in front of him.
Before he found the courage to reach and touch the red clad figure it stopped.
Jason looked up to see Casey standing next to his car,opening the passenger
door, and it took Jason a minute to realize he was supposed to get in. Mentally
shaking his head, he moved to get into the car. As he walked the couple of
steps to the waiting car seat, Casey let his hand slide across Jason’s stomach
when he passed. Jason paused for a second to look at Casey through lust-
glazed eyes, wanting to take him now, but he turned and slid into the car.
Casey closed the door behind Jason and retreated around to the driver’s side.
Jason watched as Casey’s beautiful, naked leg stepped into the vehicle,
followed by the graceful body that sat next to him, and then the other leg. The
hem of his dress hiked high on his thighs, causing more lust to stir in Jason’s
chest and a twitch in his member.
He was finding it hard to breathe as he stared at the figure next to him.
Closing the door and starting the engine, Casey pulled out of the parking lot,
driving the short distance to his apartment. Jason was in a lust-filled stupor
and he paid no attention to anything other than Casey, not even when the car
pulled into the parking garage, or even when Casey turned off the engine. It
was only after Casey had stepped out of the car and leaned down to ask if he
was coming that he paid more attention to his surroundings.
Blinking his eyes, he turned and exited the car, walking quickly to catch up to
Casey, who had already started towards the elevator. Once in the elevator,
Casey turned to Jason and pinned him against the wall with his small but
beautiful body, one hand on Jason's hip, the other on his shoulder, pulling him
down to once again kiss him into another lusty haze.
They barely heard the ding of the elevator announcing their arrival to their
floor. The doors opened, but just before they closed again a hand blocked them
and they flew open once more. Guiding Jason out of the elevator, pulling him
by the hand, Casey once again walked backwards, keeping his eyes on
Jason blindly followed, seeing only the object of his desire in front of him.
Casey stopped front of a familiar door, letting go of Jason’s' hand long enough
to get his key out of his handbag to unlock it. With the door opened, he
grabbed hold of Jason's hand to guide him into the apartment, closing it
He didn’t turn on any lights, knowing the way by heart. He pulled Jason
behind him, down the entrance way, through the living-room, and past a door
into his room. The only light filtering into the room was from the glow of the
full moon streaming through the opened curtains, making it almost as bright as
Casey released Jason’s hands only to place his them on the buttons of his shirt,
unbuttoning one at a time, keeping his eyes glued to Jason's emerald greens.
Jason was in his stupor again. He reached up to Casey's hair, pulling the wig
off, surprising Casey.
“I want to see you, only you,” Jason hummed out.
Smiling, Casey continued with unbuttoning Jason’s shirt. Once opened he
placed his palms on Jason's stomach, causing the young man to twitch and
gasp at the touch. Casey watched his own hands glide up Jason’s stomach,
over every muscle that twitched and tensed under his fingers, and up over his
pecs, continuing across to his shoulders and down his arms, sliding the shirt
off to the floor. Filling his eyes with Jason's body, hands caressing muscle and
skin that heated under his touch.
Jason watched Casey's eyes as they roamed over his body. It almost made
himself-conscious, but he was fascinated by the look on Casey's face.
Daring to touch Casey, his hand reach for the sparkling heart that dangled
from the zipper pull of the dress, pulling it down to reveal what he desired. As
skin became visible, his member twitched and wept. The zipper glided farther
down to reveal no boxers, but a pair of black silk underwear. The dress fell
open when the zipper ended
Staring at the contours of this body, his member pulsed. Sliding his fingers
under the shoulders of the dress, he pushed them off, and like Casey he guided
the garment over his arms to fall to the floor.
“Beautiful,” he stated, looking over Casey’s body. Glancing up to Casey's
eyes, he saw a stunned look there.
Bending down, Jason kissed Casey. This time it was his tongue that glided
over the painted lips, waiting for permission to enter, which Casey gladly
gave. Chaste at first, their dueling tongues become fast and frantic, both of
them beginning to pant.
Casey reached for Jason’s buckle, pulling on the tail of the belt to release the
little bar that held it in place, pulling it open to get to the button hidden
beneath. Once the button was undone the zipper ripped open with little effort.
As Casey worked on the jeans, Jason stepped out of his shoes. Casey pushed
the jeans and boxers down to pool at Jason's feet.
Jason pulled away from the heated kiss to look around the room, and spotting
what he was looking for he pushed Casey back, stepping out of his clothes as
he stepped closer to his goal.
Allowing himself to be pushed back, Casey felt the bed at the back of hislegs.
Stepping out of one shoe, he lifted his leg up to the bed bending it to go onto
his knee. Lifting the other leg, he let the shoe drop off his foot to the floor.
Now on both knees, he pulled Jason with him as he sat back on his heels.
Jason crawled onto the bed and wrapped an arm around Casey's waist, the
other on the bed to use as leverage. He pulled Casey farther up the bed,
allowing Casey’s legs to unfold out from beneath him.
Resuming their heated kiss, Jason's hand began to roam over Casey’s body
and up to the beautiful man’s face, cupping a cheek. Jason carefully lowered
his body down onto the smaller one beneath him. Casey's legs parted to allow
Jason to lay between them as he slowly ground his hard member into Jason's
Jason’s hand glided down Casey's side, dipping between their bodies and
tentatively touching Casey's member, not sure of what he was doing.Casey
arched slightly to coax his member into Jason’s trembling hand. When that
didn't work he slid his own hand between their bodies, taking hold of Jason's
hand and pushing it to his own erection, pulling the silk underwear down to
expose his flesh.
Jason, still unsure, wrapped his fingers around the hardened flesh, hot with the
lust that was pulsating between them. With a slide of his hand Casey moaned
softly through his lips, and Jason gained confidence from the encouraging
sound. He continued to pump at the member between them as Casey writhed.
Casey rocked his hips in rhythm with Jason's hand, and Jason slid his lips
from Casey's mouth to his earand neck, where he sucked and nipped at the
Before long Casey's moans grew louder. He panted with every thrust of his
hips into the hot hand that stroked his ridged member.
“AAAHH!!”Arching his back, he felt hot liquid fill the space between their
glistening bodies. Casey jerked with a couple of involuntary spasms before his
body collapsed back onto the bed, breathing hard.
“Oh…my god…” he panted out.
Jason looked into Casey's face. He had his neck stretched up and his
eyesclosed. Jason leaned in to kiss Casey’s chin, and Casey lowered his head,
kissing Jason on the lips.
After coming down from his explosive orgasm, Casey straightened one leg the
other bent he pushes his foot into the mattress to push Jason over, rolling on
top of him. Straddling Jason’s hips, he pulled the silk underwear from the back
to the side to expose the crevice of his ass. Scooping some of the wetness from
his stomach, he used it to lubricate his tight entrance, before reaching down
between his legs to hold Jason's hard flesh. Slowly, he impaled himself onto
the large, wonderfully ridged member, hissing as it entered him. Jason moaned
at the tightness and heat that suddenly enveloped him.
Casey slowly glided up and down the hard shaft, eliciting exotic sounds from
Jason, only having had sex one other time, found it very hard to control his
movements. Wanting to move faster, he bucked his hips to gain momentum.
Not wanting the young, inexperienced man to get overly excited, Casey
disrupted the rhythm of the movements and put his hands on Jason's stomach,
trying to control his urges to buck up.
“Oh…god!” Jason exclaimed.
“Slow down…let it last…” Casey tried to soothe Jason, but he was too far
gone with excitement. Casey dropped back into rhythm, letting Jason slam
into him from underneath. Casey moaned through grittedteeth.
“CASEY!” Jason cried out as his boiling passion filled the hot cavern above
him. Casey was surprised to hear his name cried with such passion, and he
stared at the young man beneath him.
At that moment he fell in love with the convulsing young man. Lying on top
of Jason, still connected, neither of them moved, not wanting to disrupt the
connection as they both slipped into an orgasm induced slumber.
Waking about an hour later to Jason's now again, fully erect member still
inside him, they made love again for quite a bit longer than the first time. They
took their time, rolling around the bed, taking turns as to was on top. At one
point Jason, who was now on top, stopped his movements to look Casey in the
eyes. Giving him a chaste kiss, he pulled slightly away from the beautiful face
with a serious look.
“I think...I love you,” he said, his voice just above a whisper.
With a relieved look Casey rolled them over to be on top again (his favorite
position). He looked into Jason's eyes with the same serious expression on his
“I know...that I love you,” he stated in a louder, more confident voice. He
leaned down to kiss Jason, his kiss was not as chaste as Jason’s had been.
Hungrily he kissed Jason, increasing his movements as he moaned into the
kiss.Jason moved in sync with Casey and before long they both cometogether,
crying each others names out loud.