Jason was getting frustrated. The embroidered jacket was chafing, the
bar scotch he'd ordered was watery, and he was sweating in the rubber
pants. What the hell he thought, I may as well enjoy my drinking, if I
can't enjoy the bl**dy party. He poured his drink into an abandoned
margarita, and caught the bartender's eye. "Double shot of Macallan,
neat," he ordered. The bartender, a bored-looking gorilla in a nun's
habit, said, "Top shelf is four bucks a shot," waited for his reaction,
and when he said nothing, turned to pour.
Jason had come to the Hallowe'en party alone, as a last resort, knowing
full well he would most likely remain alone. He looked around the
party, noting the many couples that had formed since the masquerade
dance had begun. It looked like yet another lonely night out of years
of lonely nights.
Earlier, things had looked promising as several attractive women had
shown interest in his flashy costume. But right on cue, his insecurity
had caused him to stammer, to blurt meaningless and silly things, and
one by one, they had disappeared into the crowd, only to be glimpsed
later hanging on the arm of another, apparently more confident man, or
in some cases, woman.
It was hard to tell, with some of the costumes.
Shit, why couldn't I have been born gay, he thought. At least, there
seem to be a lot more men here than women with a fetishistic bent.
His hopes rose again when a young woman in an outrageous blonde wig and
1920's flapper dress walked up to him with two glasses of champaign.
She looked like a gangster's moll from a movie.
"Hoy they-uh," she said. He grinned. She even had the accent down pat.
"Hey, baby doll," he said in his best imitation of Al Capone.
She frowned slightly then brightened. "Oi loik ya cawstume, where'd ja
Once again, he tried to concentrate on what he would say. She was a
knockout, he just _had_ to get it right this time. For the s*******nth
time tonight, he heard a friends advice in his mind. "Just be
yourself. People can sense when you're putting on an act." He tried
He dropped the "gangster" accent and smiled in what he hoped was a
winning manner. "Well, I rented the jacket, hat and shoes, but I
already had the rubber pants. Where did you find that outrageous wig?"
Thirty seconds later, he stood morosely wiping champaign from his
jacket, amazed to discover that not only had her accent been real, but
the wig was not a wig, and her head was as empty as her glass was now.
She was not The Woman.
'The Woman' was a sort of fantasy he'd entertained since puberty. He
sat down at the cash bar, and thought back to his high school days, to
his first and only great love.
When he was about eighteen, and noticing girls in a big way, he'd made a
pass at the sexiest red-headed girl in school, Mandy. This was a bold
step for him, since he'd always had trouble talking to girls. It was
discouraging, actually, for his swim-team body and cute looks tended to
attract quite a few potential dates and even bed-mates. The problem
was that Jason Stewart was not just a jock. He was smart, and he knew
it, and he just couldn't relate to 99% of the girls at school, despite
the urging of his percolating hormones. To be sure, there were a few
smart girls at his school, but they dressed like bag-ladies, and their
personal grooming habits would have shamed a wino. There appeared to
be no females there with good looks, good taste, and intelligence in
the entire city of St. Louis.
Moreover, his social skills seemed somehow lacking when dealing with
girls- they seemed to him almost an alien race, with quite different
needs and goals than he. Due to an early divorce, Jason had grown up
without a father, and somehow his mother had never graced him with any
After two years of unsuccessful attempts at conversation with
empty-headed Madonnawannabes, and a few aborted dates, he overheard a
conversation between his chemistry teacher and Mandy Rafool. She was
discussing the relationship between what she had learned in physics
class to the current discussion of valences in chemistry. He would
never have imagined! He had seen her around for quite awhile and like
every other guy in school had been fascinated with her pretty face,
tight jeans and sweaters, and astonishingly mature body.
And like every other guy in school, he had noticed that she was
conspicuously without a boyfriend. But he'd assumed from her good
looks and her retinue of bimbettes that she was yet another bimbo
herself. She was two years older than he, a senior, a cheerleader and
she seemed like a daddy's-little-girl type who never lacked for
anything, yet he had fallen hard, and he resolved to win her heart.
For the next six months he secretly bought all the magazines the girls
at school seemed to worship, and studied. In s*******n, he learned how
a 'real cool dude' walked, talked, and dressed. In Young Model, he
read about the things every teenage girl supposedly wanted in a
boyfriend. In Cosmo, he discovered what sort of sex 'every'
sophisticated, mature woman 'wants to have'.
And, finally, after screwing his courage to the sticking point, he'd
asked her for a date.
She'd accepted! Actually, when he first spoke to her she'd laughed and
walked off with her friends, but then right after school, he had found
her sitting on the hood of his car. She told him she was sorry, that
she'd actually thought him cute when they first met, but his inept
approach had 'f***ed' her to rebuke him, lest her girlfriends think her
'easy'. Considering how she domineered her peer group, he thought it
more likely that she only feared a loss of control, but didn't dare
risk such a rebuke. He was in love... or lust, which was about the
same to him at that age.
"Well, aren't you going to drive me home?" she'd demanded. At last, he
had thought to himself, a girl who takes the lead. As they talked,
sitting in his car in front of her house, he discovered with delight
and a certain relief that she did have a brain after all. The vast
majority of the attractive girls, at least, seemed to believe that
brains and education were anathema to becoming a model, which every one
of them except Mandy seemed to want. She told him she was getting
straight A's except in Home-Ec, which she loathed, and that she had
already decided to become an investment broker!
He asked her why she had no boyfriends, why she had picked him. Her
reply astonished, and then warmed him. It seemed that she too, was
turned off by empty-headed football jocks suffering from what she
called testosterone poisoning. She seemed surprised and delighted that
he was on the swimming team, yet was also an intelligent student. Then
she shocked him by revealing that she had not only dated a few of those
football jocks, but had sex with several, and found them to be boring,
At his stunned look she added, "Oh, don't look so shocked. There's
nothing wrong with having sex early, although you could never prove it
by those immature fools I run with. I'm not stupid, I use condoms, I
play it safe.
Besides, I've seen the way you look at my body, you know damn well
you'd give your left arm to get in my pants..." here she reached over
and squeezed his crotch, nearly causing a minor traffic accident,
"...and who knows, maybe you will, if you're good to me."
Jason's brain was yelling, "DANGER...DANGER, Dr. Smith! Cockteaser
ahead!" but he suppressed its voice easily and told himself she really
meant it- she was just a very bossy girl...er, woman, he corrected
She turned out to be a rather f***eful lass indeed. Fortunately for
Jason's grades, she shared no classes with him, but when they passed in
the halls, she surreptitiously blew him kisses, or licked her lips
lasciviously when no-one was looking. She insisted on meeting him
after school every day, and that he drive her home. He lived for those
drives, as they talked about their passtimes and interests, the other
k**s at school, and frequently about sex. She seemed quite
knowledgable on that subject, and astonished him with her frank,
technical descriptions of what seemed to him bizarre yet tantalizing
Finally, on Friday, she informed him that he would pick her up at seven
that night to go to Angelo's for dinner. Angelo's was a restaurant &
nightclub, rather pricey for k**s their age, but his part time job at
Radio Shack had allowed him to save a tidy bundle. He felt a moment of
pride at being able to wine and dine the sexiest girl in school.
It was rather a relief actually, not having to worry how to persuade
her to go out with him. All she required of him was a "yes".
When he picked her up, he discovered that she challenged the
conventions of fashion as well. He got to her house early and after
waiting nervously on the porch for several minutes, he rang the bell
precisely at seven o'clock. She opened the door within seconds, and
breezed right past him toward the car. He could only stare after her
in shock. When she realized he wasn't following she turned, staring
back at him with hands on hips, looking at him silently as if to say,
'Well, aren't you coming?' He continued to stare for a moment, than
slowly walked up to her, his expression of slack-jawed astonishment
slowly turning to one of frank admiration as he boldly looked her up
and down. The temperature of the warm June night suddenly rose several
"Buy you a drink, senor?" The voice at his shoulder snapped Jason back
to the present. A huge woman, no, a transvestite, in a tight red
flamenco dress was standing next to him.
"Umm, no thanks. I mean, no offense, but your eyes are the wrong color
for me." The flamenco dancer pouted and flounced away. Jason sipped
his scotch, closed his eyes and thought back to that first, incredible
For their trip to the club, she had worn an outrageous shiny rubber
miniskirt in hot pink that fit like a second skin. If that wasn't
enough, she had topped it with a tight-fitting jacket of white patent
leather, accompanied by fishnet stockings and pink patent spike heels.
She wore no blouse under the jacket, and if she wore a bra, it must
have been quite low-cut, as her burgeoning cleavage was plainly
displayed in the neckline. His first reaction was that she looked like
one of the hookers on Main Street, or a heroine from a B-grade movie,
although unarguably sexy!
"My god Mandy," he said, "you look delectable!" She grinned a wicked
grin. "Yes, I know. I take it then that you like my tastes."
She even sounds like a b-grade movie, he thought. He convinced his
eyes to stop exploring her body, to meet her gaze. "Mandy, I LOVE the
way you look...it's just that... I guess it's a bit of a shock. At
school, you never wear anything more provocative than a tight
sweater...do you dress this way every time you go out? Don't you get a
lot of flack from your parents?" He realized he was gushing and shut
up, coloring slightly.
She smiled wryly at him and ticked off her reply on her fingers.
"First: I dress the way I dress at school in order to identify with
those little idiots who follow me around like puppy dogs. I give them
something to look up to, they give me a certain cachet of
respectability, helping me to get on the cheerleading team, the school
newspaper, the yearbook staff, student council, and so on. That stuff
looks great to college scouts, after they finish examining your test
scores, of course.
"Second: no, I don't always dress this way when I go out, only when I
want to reduce my date to a drooling blob of lust." She grinned
"It's working, believe me," stammered Jason,
"..third," Mandy interrupted, "no, my parents don't mind much at all..
you should see some of the things THEY wear.
"and fourth, are we going to dinner, or not?"
During dinner, while his head was reeling from her fantasticly clothed
figure, her slightly musky cologne, and two glasses of wine, she
whispered to him in no uncertain terms what she expected of him later.
Jason was in pubescent heaven. His erection had not subsided since
she'd opened the door, and she certainly wasn't helping with her
thoroughly lurid account of the things she wanted to do to him. If she
weren't so straightforward and bossy, he thought, I'd think she was the
biggest tease of all time.
By the time dessert had arrived, she had removed a shoe, and was
massaging his uncomfortable bulge with her toes, the concealing
tablecloth keeping their secret. When she put her shoe back on and
began squeezing his crotch between both heels, he thought he would
explode. He didn't want to cream in his pants, but he didn't want to
make a scene, either. The whole time, Mandy kept up a stream of
innocuous conversation that for Jason, became increasingly difficult to
When they got to the car, she leaned back against the car, inviting him
into her arms. For a few seconds, Jason hugged her gently, as if
afraid she would break. He kissed her hesitantly, just before they
both threw decorum to the wind, each grabbing the other fiercely,
smothering each other with their mouths, their toungues.
Jason squeezed her ass and pulled her tightly to him, marvelling at the
unusual feeling of the smooth, pliant latex covering her muscular
cheeks. Mandy responded by pushing her hand down his pants.
Jason felt her hand around his erect shaft, and suddenly knew that they
would not be getting home at the hour he'd promised his mother. He
drew his head back, looked her in the eyes. "I think we'd better go
Mandy had him drive to the outskirts of town to an abandoned farmhouse
she knew about from some previous amorous adventure. The entire way,
she was melted against him, rubbing his skin with her hands, and
distracting him from driving in general. Soon she had opened his fly,
and had scooped everything out. Jason tried to think of something to
say, but was overcome by the unique sensation of SOMEONE ELSE handling
his cock, softly squeezing his balls. He tried to concentrate on the
road, but when she pulled him into her mouth, for the second time that
week, he almost drove off the road. "Ah!
..ahhh" was all he could say.
"Relax," she said, releasing his cock for a moment, "you drive the car,
and I'll drive you." She again bent to her task. During a moment's
clear thought, he realized she was quite good at it. Every time he
felt ready to come off, she either slowed down or stopped altogether,
moving her attention and tongue to his balls, or neck, or earlobes.
Only once did she come up for air, to give directions.
When they finally arrived, Jason pulled out a large picnic blanket his
mother kept in the trunk, "for road emergencies". He'd decided that
this was a road emergency. In seconds, Mandy had him down on the
blanket on his back, her legs astride his hips, and her hands pressing
his shoulders into the soft earth. "You're a virgin, aren't you?" she
asked softly, smiling gently down at him in the pale moonlight.
Despite his embarrassment, he couldn't break her gaze. "Umm, yeah," he
Softly, she stroked his face. "Heyy.... heyyy," she cooed, "it's
alright! Everyone's a virgin some time in their life. You just sit
back and enjoy the ride. If you feel like doing something, say so, or
just do what comes naturally. Now then..." She squirmed backwards
enough to get at his belt and stood suddenly, unceremoniously yanking
off his pants. "There! Now we're getting somewhere," she exclaimed,
grabbing at his underwear. When she had him totally nude he protested,
"Hey, wait a minute, I'm not wearing a stitch, and you're still
dressed! That's hardly fair."
Mandy stood astride his chest, looking down at him feigning a hurt
expression. "Don't you LIKE the way I'm dressed?" She ran her hands
over the thin shiny patent leather covering her breasts, turned to face
his feet, giving him an excellent view as she carressed her
latex-covered derrier. "Er, well, I didn't mean..."
"And besides," she added, bending to look at him between her knees as
she positioned herself above his head, "I'm not wearing any panties."
So saying, she knelt astride his chest, pinning his upper arms under
her shins, and squatting directly over his face.
To Be Continued...