This story is not intended for commercial use and is not to
be posted at any other site without the author's
permission. This is not suitable reading for minors. Thanks
to Kelly Ann Rogers for her editorial assistance, as well
as Josie for allowing me to borrow her name. Josie swears
she's never lost at cards.
Unlucky at Cards --
"It's your deal." He flushed as he handed over the cards.
The blood was rushing to his cheeks. From drinking two
Brandy Alexanders? Possibly. Josh always looked like a
blushing bride whenever he drank alcohol. Also, whenever he
was embarrassed. And ironically, his face lit up like a
stoplight whenever he was trying to signal to a girl,
"let's go for it." Which was it this time? A little of
each. Josh was losing badly at strip poker.
True, if the goal of strip poker is exhibitionism, he
wasn't losing. Far from it, for the twenty-one-year-old had
by now taken off everything but his thong. Fashioned from
black Lycra, it announced itself - in silvery script - as
something to be worn by the "Macho Male." Yet it looked
like something for the "Fantasy Female," and Josh was
sheepish about wearing the thong - and nothing but the
thong - in front of Denise on their second date.
She was staring at the thong. Josh hoped she had x-ray eyes
to see how excited he was underneath it. He hadn't expected
to play strip poker; it had been her idea. And he hadn't
expected to lose almost every hand. Had he foreseen this
outcome, he would have worn plain cotton boxers. Indeed, he
had only worn the thong because in his experience he never
got "lucky" with a girl as beautiful as Denise, especially
on just their second date.
A blue-eyed blond with a turned-up nose, Denise was, at age
twenty, a disconcerting bundle of contradictions. Just five
foot two, a good four inches shorter than Josh, she looked
as wholesome as a soloist in a Baptist choir. At first
glance, she looked too chaste ever to have had sex. And
maybe she hadn't, for none of his friends, including his
two roommates (both obligingly visiting their folks on this
holiday weekend) had ever met a boy she'd dated. And yet
she was, like Josh, already a junior at Harvard Square
College, an institution renowned for its co-eds in search
of a MRS degree from a Harvard law, business or medical
school graduate.
She hadn't been acting like a virgin. She had grabbed his
hand as soon as the lights dimmed at the movie theater, and
had placed it on her pant leg. She squirmed so much that
Josh's hand had ended up high on her inner thigh.
Afterwards, she had invited herself back to his Somerville
apartment, ostensibly to teach him how to make a Brandy
Alexander.
At first, there had been enough light for Josh to see that
Denise's fleshy, inviting lips belied the innocence of her
nose and eyes. Her eyebrows were wickedly sculpted, and the
hoops dangling from her ears reminded him that she was all-
woman.
As the creamy drink warmed his insides, Josh found it
increasingly difficult to hide the physical fact that
Denise turned him on. That's why he was thankful when she
turned the lights low. Did she expect him to pounce on her?
Maybe. If so, she was disappointed because Josh didn't dare
make a move for fear of rejection. And arrest - he had so
little sexual experience he had no idea of what constituted
date rape. He figured it was wiser to let Denise make the
first move, as though she had not already.
Denise was in a quandary. After one drink, she could see
that Josh had no capacity for alcohol. And yet, drink did
not make him bold. She realized she'd have to make the
first move, and make it soon before he lost his
functionality, for she was determined to have sex with this
boy.
Why him? Because he was gorgeous, prettier than most of the
girls she knew. His long hair was almost as black as his
huge coal-black eyes, around which fluttered the longest
eyelashes she'd had ever seen on a boy. His delicate
features reminded her of a porcelain doll, and his ears,
his ears, were so tiny they were elfin. Compared to Josh,
most males looked gross and coarse. He was a genuine doll,
and she wanted to play with him.
They were both lounging on a shag carpet. It would be easy
enough to sidle into him, but how would he react? He seemed
so virginal that she worried about scaring him off. Indeed,
he seemed capable of fleeing from his own apartment if she
did not conduct the seduction at a pace he could handle.
They had to do more than talk, she recognized, for Josh
didn't know what to do with his hands other than to lift
his brandy cordial to his lips to gulp down nervously.
"Let's play poker," she'd suddenly said. Not until he'd
dealt the cards did Denise admit that she had no money to
bet.
"I'll stake you," Josh had offered, but Denise figured it
wouldn't be fun for Josh to win his own money; so she
suggested strip poker. Five-card draw with nothing wild.
Shyly Josh had agreed, but play did not commence until he'd
turned off the lights and surrounded the two of them with
candles, cleverly placed (he thought) to reveal much more
of her than of him. There would be plenty of light on both
their genitals when the time came, while allowing her to
take off her bra in the shadows.
Josh was sure that strip poker was inherently unfair to
women because their breasts were so much more private than
a man's chest. So he'd arranged the candles to ensure she'd
have some privacy until she had lost entirely. Yet she
almost never lost a hand.
Josh had deliberately lost the first two hands. "What the
heck," he'd thought. "It's only my sneakers, and I really
want to get her into this game." Sure, she'd suggested they
play, but Josh feared she'd chicken out if she had to start
the disrobing. But now that his feet were exposed enough to
feel the candles' warmth, he played to win. The only
problem was, he didn't. True, Denise did lose her shoes,
socks, jeans, and sweater, but not before he'd stripped off
his own socks, as well as Shetland sweater, his wide, red
leather belt, his pearl-buttoned Western shirt, and his
boot-cut jeans.
Only his thong remained, and Denise was dealing. As always,
she'd shuffled the cards like a Vegas card shark. He hadn't
seen hands move so fast since he'd lost track of the Queen
of Spades while playing Three Card Monte at the Greyhound
Terminal. Denise had won every time she'd dealt, with
nothing lower than three of a kind, and he was not hopeful
this time. She had the luck of the devil.
Sure enough he'd lost again. The thong would have to go. To
hide his embarrassment, Josh hummed a few bars of "The
stripper" as he took it off. Maybe he should have tried
the national anthem instead, for his penis reacted to its
unveiling by standing at attention. Impressively. So there,
he was buck-naked!
Had Denise seen his erection? Indeed, she had. She was
staring hungrily. "Enough's enough," he thought, as he
futilely attempted to drape his flagpole with the thong.
"The game's over," he announced, "and I lost. Big time."
"It's not over," she said, "which means you're cheating by
trying to cover yourself up. You can't start putting your
clothes back on until the game is over, and it's not over
until I'm as naked as you. You do want to see me without
any clothes on, don't you?" Her voice said she wanted a
'yes'.
"Well sure. It's only fair that I see as much of you as
you've seen of me," he gulped.
"You mean, as much as I'll be seeing of you, don't you? The
rules say that you can't put anything back on. And you
better not! You have a lot to show off!" She leered.
Josh turned beet red. The thong slipped from his hand. Once
again he revealed himself to be ready and eager for a
sexual romp.
"Here," she held out her hand. "Give me your thong. No way
I'm letting you put it back on before the game is over."
He did. As she fingered the nylon pouch, she teased him.
"Oh wow," she said. "I wish I had panties as sexy as your
thong. You boys are sure lucky; you can wear almost
anything these days." As she reluctantly put the thong
down, she became aware of its scent. "Oh, cool!" she
purred. "You use Obsession. I've got a bottle of it at
home. I think it's super that Calvin Klein invented a scent
that a guy and his girl ... friend can share. Talk about an
awesome time to be alive!"
"Uh, Denise, there's a problem. Now that I've lost all my
clothes, what can I bet with?" Josh hoped she'd think of
something sexual, like a blowjob for him or a pussy licking
for her. Indeed, it was the expectation of sexual favors
that had kept him in the game. Certainly, if their roles
were reversed, Denise would soon be learning what a wild
imagination a totally, absolutely aroused twenty-one-year
old male can have.
What could he bet with? Which part of his naked body would
he have to use? "Your tongue," she said. "If you lose,
you're going to have to use your tongue."
His tongue? Josh reveled in the possibilities. Would he
have to lick every inch of Denise's body? Or just her toes?
His imagination freely roamed over her body - until Denise
spoke.
"Josh, I want you to use your tongue to talk about
yourself."
"Huh? Why do you want to talk? I thought we were ... past
talking."
"In strip poker," Denise said, "You've got to reveal
something when you lose. So from now on, whenever you
lose, you'll have to tell me a secret about yourself. A
sexual secret."
She'd put the emphasis on "sexual" but Josh's mind was
still worrying over that word "talk": Women! Why did they
pry so much? Why did they always want to talk when men
wanted to act? And they always seemed to get their way.
Somehow they were the ones to set the rules.
Josh wasn't happy with the new rules of the game, but eager
to see Denise nude in the candlelight, he agreed to them.
After all, he only had to win three more hands to see
everything.
This time Denise decided to throw the hand. She wanted Josh
to stay interested in the game, and figured he would if she
exposed her bra. So she threw away two aces to draw to the
inside of a three card straight.
When she lost to Josh's pair of deuces, she stripped off
her extra-large pink tee shirt with such exuberance that
Josh thought, "Cripes, she's an effin' exhibitionist after
all! It must have been killing her to win so many hands."
This thought gave away to another, as her bra came into
view: "Fantastic! She's wearing pink satin. That's got to
be the most beautiful bra I've ever seen. Look at the white
lace trim! I've died and gone to heaven. In that bra,
Denise looks like an angel. God, I wish I could touch it
now."
Denise could see that his interest in strip poker had
revived. Indeed, his whole body visibly tingled. It was
time for her to win again, and as she was dealing this
time, her luck returned just enough for her to beat his
full house, aces and eights. Josh couldn't remember the
last time he'd seen anyone with four queens in straight
draw poker. He sat slack-jawed for a moment.
"You must be the luckiest person on earth," he said, now a
bit suspicious.
"You're darn right I am," Denise replied. "After all, I'm
here alone with an incredibly handsome guy who's wearing no
clothes and is about to tell me all about himself. It's
time for you to make good on your bet with a secret."
Warily -"What do you want to know?"
"I want to know ... about your first kiss. When was it? Who
did you kiss? What was it like? Did you fall in love with
her? You have to tell me everything or you're not playing
fair."
"I was twelve."
"Ah puppy love! What was her name?"
He mumbled something. She couldn't make it out. So she
asked again. "Come on, Josh, you lost the hand. You have to
tell me everything about your first kiss. I want to know
the name of your first sweetheart." She put her hand on his
knee to encourage him.
"He wasn't my sweetheart. It was nothing like that."
"He? You got your first kiss from another boy!" Her voice
rose with tension. "You're not gay, are you?"
"Oh God no," she prayed. "Don't make him gay. Why do they
always have to be gay?" Then, before he could answer -
"Cause if you're gay, it's cool. Some of my best friends
are gay. Steve doesn't have a boyfriend right now, and
you're definitely his type."
She was talking super fast, her nerves getting ahead of
her. She ignored Josh's attempts to interrupt until she was
halfway through an offer to arrange a blind date with Steve
that Josh finally broke through: "I don't want a date with
Steve! I'm not gay! You're the one I want to see ...
naked." He looked down, turned his head in the cutest way,
and blushed.
"Then why did you kiss a boy?
"I didn't kiss him. He kissed me!"
"What kind of kiss was it? Did he give you some tongue?"
"Yeah," Josh admitted. "I thought I'd gag! I can still
remember it. He had a tongue like a Komodo lizard. He stuck
it way down my throat. And he kept it there forever! I was
really uncomfortable. I'm not gay." He shook his head from
side to side for emphasis.
"So what were you doing alone with a gay boy? And why did
he think you wanted to be kissed? Why wasn't he afraid
you'd hit him or tell all your friends about him?" Denise
was suspicious. Something didn't add up.
"Mike's not gay either. Jeez, he's always got a girlfriend.
Even when he was fourteen. That's how old he was when he
kissed me."
"Josh, I hate to be the one to be the one to tell you, but
any boy who sucks face with another boy isn't straight.
Maybe those girls are just cover, whether they know it or
not. Did ... did he ask you for sex?"
"Well yeah, but there was no way I was going to have sex
with a boy," Josh said loudly. Much more quietly, he added
"then."
"Well, whatever your little friend Mike claims to be now,
he was definitely into cock when he was fourteen."
"That's not true! There's nothing queer about Mike. He's
the straightest guy I've ever met. I don't want to spread
false stories about him, especially considering ... that he
never talked to anyone about that kiss. I haven't neither,
'till now."
"Let me see. Mike's not gay, never was. Yet he soul-kissed
you. Was it a pity kiss? Did he kiss you because he thought
you were gay, and needed cheering up? Come on, Josh, lots
of boys have their homosexual stage. They grow out of it.
If you were gay at twelve, that's cool - just as long as
you like girls, or at least one girl" - she blew him a kiss
- "now."
"What the heck. You might as well know. Mike kissed me
because he thought I was a girl. It was an innocent
mistake. Neither of us was, or is, gay. There's no way Mike
would knowingly kiss another guy. No way, no how."
"He's not gay, but he's blind? How could he mistake you for
a girl?"
"Easily," she thought, as she caught Josh's eyelashes
fluttering in embarrassment. "It wouldn't take much to make
you look like a girl. A little bit of lipstick and some
strategic padding. That's all it would take, even now. And
at twelve? You sure weren't more rugged-looking then."
Josh blurted out the truth. "He thought I was a girl
because I looked like a girl. I was wearing a dress. It was
powder blue, with puff sleeves, and white stitching and
buttons. I had on patent leather Mary Janes, and ... you
may as well know it all, because you're bound to ask, light
blue cotton panties and a matching bra, pink lipstick,
makeup, and a powder blue hair band. I even had blue
earrings, clip-ons. They were star-shaped."
There -- it was out. She was silent, inscrutable, shocked.
He had left nothing to the imagination. Or had he? Yes, he
had. He might as well spare her the trouble of asking.
"Yeah, Mike thought I was a girl because I was pretending
to be one. I told him my name was Josie. He still jokes
about it - you know, calling me 'Josie' - whenever we're
alone together. He always thought it a hoot that I had
fooled him so easily. He said he'd be more careful in
future. He treated the whole thing as a big joke, when he
found out the truth a couple of weeks after he first kissed
me."
There was a prolonged silence. Then Denise asked, "Are you
a transvestite, Josh?" She stared intently at his inviting
erection for a few moments, then looked up into his eyes.
"You're not going to have the operation, are you? I hope
you never do." She looked distressed. "You've got ... a lot
... to lose. You stayed hard even when I asked if you were
gay. But do you like wearing ... drag? 'Cause if you do,
that's cool."
"No, I'm not a transvestite, and I don't go around in
women's clothes." Josh was frustrated; this was going from
bad to worse. "I pretended to be a girl named Josie because
I didn't have a choice. I couldn't let him know I was a boy
...," his voice rose, "not dressed that way! So I had to
pretend to be a girl. It wasn't my fault he was turned on
by the way I looked. I thought he'd stop at holding hands.
How was I to know he'd kiss me?"
"Why were you dressed like a girl? Did you ... do you still
... want to be female?"
"I'm quite happy being a guy, thank you. It was my mom who
made me dress up like that. It was all her fault that I
wearing a dress, and panties, and everything when Mike and
his mom came over to visit."
Denise's eyes went wide: "She's not one of those mothers
who wished she had a daughter instead of a son, is she? I
saw a show about them on TV once. You poor dear. Was your
mom like that?" Her hand was once again on his knee, this
time in consolation.
"No way. My mom already had a daughter. Sandra's my younger
sister. She's a year younger than me but we were always
about the same height. Girls grow faster than boys, you
know."
"I know. So why did mom put you in a dress?"
"It was going to be Sandra's dress - a surprise for her
twelfth birthday. Mom was making it from a pattern. God,
she loved to sew when we were young. Mom wasn't sure about
the fit. I think she'd never made a dress with an empire
waist before, and so she badgered me to try it on so that
she could make some adjustments."
"Were you eager to try it on? You can tell me. I'm cool."
"Eager? No way!. I made my mom promise to take me to Red
Sox game - seats behind first base - before agreed to wear
the dress for her."
"Well, that explains the dress, but the rest? Were the bra
and panties your idea?"
"You're kidding, right? It was mom's. And she would never
have had me put them on had Sandra not been growing up so
fast. She had just recently hit puberty. Mom had me put on
the bra and panties so she'd know how the dress would hang
on Sandra, now that she had small breasts. I know, I know,"
he said, putting up his hand to hush Denise before she said
anything. "I've not explained how I ended up in makeup or
got my hair styled."
"No, not yet," Denise replied. "I can't see why you needed
to put on lipstick, earrings, or a hair band in order for
your mom to see how a dress would look on your kid sister.
I bet you and your mom got carried away. You both wanted to
see how feminine you could look."
"I don't know. Maybe my mom was curious - she kept saying
that she never realized before how much I looked like
Sandra. But I would never have allowed her to make me look
so much like a girl if she hadn't started crying."
"Started crying? How come?"
"She said she'd messed up. The dress was too drab, and
Sandra would hate it. It was the wrong color, the wrong
fabric. Everything about it was wrong. I told my mom that I
thought the dress looked great, and that the only reason it
looked plain was because I wasn't wearing makeup and fancy
shoes like Sandra would."
"That's when she decided to make you look as much like a
girl, as much like Sandra as possible?"
"Yeah. And when she was done, she started crying again."
"How come? Does your mom suffer from PMS?"
"I don't think so. Anyway, how would I know at age twelve?
She told me she was crying because I looked so beautiful -
that was the word she used - and so she knew that Sandra
would too. She said Sandra would love the way she looked in
the dress. Then my mom started kissing and hugging me like
I was a four-year-old. I can still remember how embarrassed
I was. Having your mother treat you like a baby when you're
twelve years old is almost as bad as having a boy kiss you
because he thinks you're a babe." He shivered at the
memory.
"Okay, I guess I understand how you ended up dressed like a
girl. But why were you still dressed that way when Mike got
there?"
"Because of lunch. I was famished. The fitting had taken a
lot longer than my mom had expected. It was almost two
o'clock. I was complaining so much about being hungry that
my mom had me sit in the kitchen, still in my dress, while
she made us tomato soup and a grilled cheese sandwich. I
was still eating it when Mike and his mom got there."
"You mean they dropped in without calling first? Your mom
didn't expect them? I bet she did. The timing is
suspicious. She wanted Mike and his mom to see you in a
dress. Yup, that's the way it played out."
"No, it wasn't like that. Mom swore that she had no idea
Mrs. Meyers would drop by with Mike in tow. If she had, mom
would never have answered the door. But Mrs. Meyers was
selling cosmetics, brushes and Christmas ornaments door to
door. They knew each other from church. She'd recently lost
her husband. Lung cancer, I think. He didn't have any
insurance, and so mom felt like she had to buy something."
"Why was Mike tagging along?"
"Well, he wasn't really. He was on his bicycle. He had been
riding around looking for his mom because he hoped she'd
have enough money after a morning of making house calls to
pay him his allowance. He wanted to go to 'Jurassic Park'.
It turns out she did have the money for his allowance, and
it was enough for the two of us to get in."
"Don't tell me you went to the movies with Mike!"
"Well, it was entirely his idea. He just marched into the
house, unasked, and found me hiding in the kitchen. I think
it was lust at first sight,'cause he insisted we go to the
movie together as soon as he saw me."
"You didn't have to go."
"Yes, I did! We're talking about Jurassic Park! The best
movie ever made for a twelve-year-old boy. God, I dreamt
about raptors for months! And Mike said he could sneak me
into the theater, even though I wasn't thirteen yet. I had
to go. I just had to."
"So you went to a movie dressed like a girl when you were
twelve? Josh, that doesn't sound like the sort of thing a
normal boy would do. You're sure you're not a transvestite?
Or maybe you were then and outgrew it?" She hoped.
"Nobody could have recognized me. It was perfectly safe,
except that Mike was all hands. He even put his hand on my
bare leg. Every time a dinosaur came onto the screen, he'd
whisper, "You must be scared. Don't worry; I'll protect
you. Then he'd squeeze my leg, or my hand, or my arm."
"You let him get away with that? No wonder he soul-kissed
you!"
"Well, I was na?ve. What did I know? Anyway, he was better
behaved the next time."
"The next time? You saw him more than once? Don't tell me
that Mike and Josie went out more than once."
"We went out two more times, and I wore Sandra's clothes
both times. Why not? He took me to the movies! And it was
fun being with him, except for the kissing. I didn't like
that. Our third time together ..."
"You mean your third date together, Josie."
"That's Josh to you, Dennis. Yes, it was our third date. He
wanted to do more than kiss. When he started putting his
hands down my tee shirt, I slapped him. And that was that.
No more dating. No more Josie."
"He came by a couple of weeks later to apologize. That's
when he discovered the truth about Josie. He wasn't too
happy about it at first. But suddenly he started to laugh.
We both had a good laugh. He even thanked me for slapping
him. He said he was so turned on that day that he would
probably have kept going for the orgasm even after he'd
discovered I was a boy. He always says that the slap kept
him on the straight and narrow."
Josh laughed nervously. This was no time for Denise to
think too much about the story he'd just told, so he said,
"Hand over the cards. It's my deal. And I'm going to win
that bra from you. I mean, I'm going to get that bra off
you."
Denise looked at him skeptically. "That's quite a story,
Josh. Here are the cards, but before you deal them, I've
just got to know. Have you ever been Josie since that
slap?"
"What a silly question! I told you - I'm not a
transvestite. Josie was an accident and she stayed around
just long enough to get into three hit movies for free. I
swear that Josie is long gone. You don't have to worry
about Josie. She'll never be back."
"That's good news. So deal. I'm going to win this time and
get another secret out of you. But I don't expect it to be
as amazing as the first one. That was truly an original."
Josh lost with a Queen high.
"Now you have to tell me about the first time you had sex.
I'm not asking about kissing or running the bases. I'm
talking about a home run. Who did you score with first?
What was ... her name? It was a 'her', right?" She crossed
her fingers.
Josh turned fire engine red. He looked away as he said, "It
was a guy. It was the only time I ever had sex with a guy.
Just the one time. And I'm certainly not going to do it
ever again. It's not that I'm homophobic, mind you, but I
dig chicks ... er, young women."
"Let me see if I understand. The first time you ever had
sexual intercourse, you did it with a guy? Let me make sure
we're talking about the same thing. I'm talking
penetration. Are you saying that one of you screwed the
other up his ... well you know," she said blushing
furiously.
Josh knew by now that she'd want all the details. So to put
all his cards on the table, so to speak, he confessed, "I
was the one who took it up the rear. But I swear I didn't
like it. God, it was painful! And I would never have agreed
to it if I hadn't been blind drunk. Anyway, he wasn't going
to take no for an answer. He said if I didn't put out, he'd
throw me out of his car and make me walk home alone. I
couldn't do that, not in the condition I was in."
"You mean you were too drunk? That's why you let a guy
screw you?"
"Well, no, not exactly. "I couldn't walk home because ...
because ... because I was dressed like a ... a girl." That
sentence was hard to get out. Denise blinked hard, but
didn't otherwise react. Josh rushed to explain. "We were
parked by the sea at Revere Beach. I couldn't walk around
that area in a dress after midnight, at least not in a
mini-dress. I would have run into big trouble for sure. I
was dressed like a ... French maid."
Josh was staring at his feet, so Denise studied them too.
"Yup," she thought. "You're blushing from head to toe."
She then fixed him in the eye and said, "Josh, you told me
that you haven't been Josie since you slapped Michael. And
now you tell me you had sex with a boy just three years
ago. And you were dressed in a chi-chi maid's outfit! You
have some explaining to do, Josh Andrews!"
She spoke so harshly that Josh's erection for the first
time declined an inch from the perpendicular. She looked
angry. He had to salvage the date, and he couldn't think of
anything else to do except tell her the truth. Surely she'd
understand how he'd been tricked into that outfit.
He began, haltingly at first, then with more assurance when
she didn't interrupt. "Bart was the guy's name. He went to
my school, but the only class we shared was gym. I should
have realized he was gay when I first caught him checking
me out in the showers, but he had quite a reputation as a
stud. So I didn't give it any thought. I wasn't even
suspicious when he started hanging around me. There was
always a good excuse, 'cause we seemed to have a lot in
common. We liked the same movies, played the same sports
and video games, and liked the same type of pizza, deep
dish with extra cheese."
"So he became your boyfriend," she said. Or was she asking?
Josh couldn't tell for sure.
"That's not how I saw it. He was just one of the guys. But
we spent a lot of time alone together. I guess he thought
we were dating. But I swear I wasn't aware we were doing
it. Josie, she dated boys. But there's no way that I would
... knowingly."
"So how did he get you into a dress?"
"Bart tricked me, the bastard. He took advantage of the
annual slave auction. My school held one each year to
raise money for a worthy cause. Each year's a different one
selected by the pep club."
"Pep club?" she interrupted. She didn't know what it was.
"Your school must have had a pep club; most high schools
have one. That's the student club that stages pep rallies
to cheer on the varsity teams, that organizes fund-raising
drives, and generally tries to promote school spirit. At
our school it was a big honor to be in the pep club. You
had to be nominated by two of the existing members."
His face said he wanted to be asked, so she did. "Were you
on the pep club, Josh? I just know you were. I bet you were
one of the players at your school."
Josh beamed. "Yeah, I was on the pep club. I was nominated
because I was captain of the cheerleading squad."
"Don't tell me you were a cheerleader! You wore one of
those tiny skirts and did a lot of somersaults so you could
show off your panties? Because if you did, there's no way
I'm going to believe you're not a transvestite. Come on,
Josh! Get real!"
Josh's face turned an angry red. "I did not wear a skirt,
tiny or otherwise. I wore trousers like the other three
guys on the cheerleading squad. There was nothing sissy
about us. We did a lot of heavy lifting, especially when
the team built pyramids. Only a real man could hold up
under the weight of two girls, like I did."
"Sorry. I was just teasing. Why on earth did you want to be
a cheerleader?"
"I thought it would be a good way to meet girls. After all,
the girls outnumbered the guys on the squad more than two
to one."
"Did you?" Did ya meet a girl while you were cheerleading?"
"Well yeah. But that's another story. I thought you wanted
to know about how Bart double-crossed me."
"I do. You were saying something about a slave auction. Is
that what you were? A sex slave? You weren't in handcuffs
or anything like that, were you?"
"Of course not! Like I was saying, we did it to raise money
for the food bank. Members of the pep club were auctioned
off to the highest bidder. We'd be a slave, which normally
meant carrying around somebody's books, doing their chores
at home, or cleaning out their locker. The geeks would be
bought by someone who needed to install some new hardware
or software on his computer. I was up for sale. It was
embarrassing. There were only three students who wanted me
for a slave, and Bart quickly shut down the bidding with
his $20. That may sound like a lot of money ...."
"Isn't it?"
"No, it isn't!" He sounded bitter. "Most students were
selling for forty or fifty dollars. I still can't figure
out why there was so little bidding on me. It's like there
was a conspiracy against me. There were a lot of knowing
looks being exchanged whenever Bart bid. The auctioneer was
the football coach. I thought I'd die when he complained
about the low bid. He said that even the sorriest specimen
should bring in more than twenty dollars. He said he
wouldn't let me go for twenty bucks.
"We're talking about a worthy charity," the coach said;
"One of you must care enough about the needy to pay forty
dollars for Josh."
"I stared at my friends imploring them to reopen the
bidding. I even mouthed the words 'I'll pay you back,' to
my friend Chuck; but I guess he didn't see me. He was too
busy whispering to Bart."
"Couldn't you have bid the money yourself?"
"No, that would have been totally humiliating. So I looked
over to Bart and used my eyes to plead with him to raise
his bid. He smiled. I nodded. Then he made his move: 'I'll
pay $100 for this slave ..."
"Everyone applauded wildly because he was offering a record
price. Then Bart set his condition: 'but only if he agrees
to be the maid for my birthday party tonight.'" He asked me
point blank: "What about it, Josh? Do you have enough
school spirit, enough charitable instincts, to wear a
maid's costume and serve cokes and burgers at my party?"
"I looked over to the football coach, hoping he'd rule the
bid out of order. But no such luck! The coach told the
crowd, 'Let's thank Bart Jimson for his magnificent show of
civic-mindedness. Everyone applauded; then he turned to me
and asked, 'So how about it, Josh Andrews, do you agree to
a harmless masquerade to help out the underprivileged?'"
"I never got a chance to answer, 'cause Chuck yelled out
'Of course, he will. Josh is cool.' After everyone did
three cheers for Bart and me, I was committed not only to
wearing a maid's outfit but to having my picture taken in
it for the school newspaper and yearbook."
"That must have been especially embarrassing, Josh,
considering what happened to you later that day."
"Yeah, and they've still got the photo up at the pep club -
for inspiration, they say. Can you believe it? You can see
I'm wearing panties." He was dejected.
"That picture should make you proud, Josh. It tells all the
world you raised a hundred dollars for charity by being a
good sport."
"Well, maybe. But I wasn't happy being a maid. I was
shocked when I first saw the costume. I had no idea if
would be so skimpy. I felt more naked in it than I feel
right now."
"How many kids were at the party?"
"There were about fifty of them, and they were all - both
sexes - calling me Fifi and treating me like a girl ... and
of course, like a maid."
"Okay that explains how you ended up in a maid's outfit.
Black satin with white frilly trim, and black fishnet
stockings, right?"
"Yeah, unfortunately." He studied his own crossed legs.
"I understand why you dressed up like a maid, but why
didn't you change into your regular clothes - into long
pants - before you started for home? Why were you still
dressed like a maid in Bart's car? Weren't you worried
about being stopped by the police?"
"Of course I was. But I had no choice. Chuck drove off with
my clothes. He thought it would be a great joke. That's how
I ended up dressed like a French maid in Bart's car. He was
supposed to be driving me home. Instead he parked at a
secluded spot near Revere Beach and he said he couldn't
take it any longer. He just had to get his rocks off. He
accused me of being a cocktease. He said - can you believe
it? - that I wiggled my ass seductively whenever I was
around him. I did it all the time, he claimed - and not
just when I was Fifi."
"You admit that you were walking like a girl when you were
serving them as a maid? You were prancing around when you
were Fifi? That doesn't sound very hetero to me, Josh."
"I wasn't mincing because I wanted to," Josh rebutted. "I
had no choice, not with three-inch heels. I would have
fallen over had I tried to walk like a guy. Besides,
whenever I took a normal stride, my dress rode up and
they'd see my panties. So I took baby steps, and my butt
did, I admit, wiggle a bit. But it wasn't something I
wanted to happen. And he was definitely hallucinating - he
actually was popping something, maybe Ecstasy - when he
said that I was constantly bending over, needlessly, to
show off my rhumba panties. I don't think I was, but when
you're serving drinks and snacks, you're bound to bend over
sometimes. Right?"
"I guess. But if you weren't coming on to him, why did he
think you wanted to have sex with him? Or with any guy?"
"I don't know. Maybe he was ... projecting. He's gay, so he
thinks everyone else is too. He wanted my bod, so he
figured I must want his. Besides, he was high on something.
He couldn't think straight." Josh giggled at his own joke.
He giggled alone.
More somberly - "Anyway, he insisted I go down on him. Then
he cornholed me. I had to let him. There was no way I was
going to try to hitchhike home from Revere Beach dressed
like a French maid. I would never have got out of that part
of town alive."
"You didn't have much of a choice, I admit. Did you turn
him into the police? You should have. Or were you too
embarrassed to report him?"
"I wasn't going to tell anyone about what happened, least
of all the police. Of course, I didn't want anyone to know
that I'd been dressed as a French maid named Fifi when I'd
lost my cherry. Or that I'd lost it to a guy! Anyway, I
didn't want to get him into trouble, cause he was my
friend."
"You mean he still was?"
"Well, yeah. He apologized the next day for taking
advantage of me. He said he was high on poppers. So I
forgave him. We remained friends, at least for a while."
"You didn't continue to have sex with him, did you?"
"No, of course not! I'm straight. We never talked about
that night again. It did bug me, however, whenever he
called me Fifi, which he'd do when he was high on
something."
"He called you Fifi? Did he call you that to humiliate
you?"
"Not exactly. Bart was so dense he actually thought I liked
the name. He called me Fifi when he was trying to get
something on. Of course, nothing ever happened - not after
that first and only time."
"Is that why you stopped being friends - because he
wouldn't stop calling you Fifi? Or was it because he kept
coming on to you?"
"No. He was easy to push away. And he only fifi-ed me when
we were alone. Whenever he called me Fifi, I'd glare at
him. If he didn't get the message - you know, that I didn't
like the name -- then I'd just shrug and let him babble on
about Fifi. Jeez, I wasn't going to lose a friend just'
cause I didn't like his nickname for me."
"Why then did you stop being friends?"
"Because of the Christmas present he gave me - some bell
bottom jeans with unusual gold stitching, a cloth belt - it
was blue and yellow ... pastels -- and a light blue tank
top. I loved the outfit - especially the tank because it
had this magnificent gold sun on the front. Wow, did it
ever radiate! It was awesome. I loved the outfit so much I
wore it the first day back to school after Christmas."
"However, I stopped wearing it," Josh said ruefully, "when
one of girls took me aside to ask why I was wearing 'girl's
clothes.' I denied I was, but she had the Macy's catalog in
her school locker. And sure enough, everything came from
the Junior Miss department. I could have died when she said
that several of the girls knew, and she didn't know whether
or not they'd told their boyfriends. I was furious. So I
broke it off with Bart, and I never again wore that outfit
outside my house. Boy, was I mad."
She thought for a moment about his story, then asked, "Did
you and Bart ever kiss? And did you do it more than once?"
"Well, yeah. That night in the car, he made me kiss him.
More than once. But I didn't enjoy it. I kissed him because
that was the only way to stay in his car. I promise you we
never kissed again. He'd beg for a kiss, but he never got
another one. I don't kiss boys - not when I have a choice
in the matter."
"Well, I'm not so sure about that. I've been quizzing you
about your sex life, and so far all you've done is talk
about the boys you've kissed. I want to know about the
girls - if there were any."
"Of course there were. I'm a normal guy. I like girls. I
love girls." That's what he said. But did he really mean
it? Something was going wrong: he was declining 30 degrees
from the perpendicular. Perhaps, Denise thought, there had
been too much talking.
Of course there had been too much talking. Guys want to
gape, not jaw. If this evening were going to get back on
track, it was time for Denise to lose a hand. As she
wasn't dealing, the only way that Denise could guarantee
she'd lose was to ask Josh if he'd make her a Brandy
Alexander.
Naturally he agreed; he was anxious to end the
interrogation. Besides, he needed a drink.
As he glided to the kitchen, the candlelight revealed his
profile. Denise watched him closely. She was marveling at
his erection, when she caught a glance of his chest - just
enough to see that he appeared to have big pecs. "He must
work out," she decided. Her body tingled. She felt moist.
Her body was yearning for his.
She had gotten herself so hot that she had trouble
concentrating on the next hand; she almost won it. But at
the last second, she remembered to hide the Queen of Spades
and declared a busted flush. Josh won, to his surprise,
with two pairs - sixes and nines.
It was time for the unveiling. Denise positioned herself so
that the flickering candles highlighted her bust. Then,
slowly, seductively, winsomely, she reached behind her back
to unfasten. She twisted seductively, as she watched Josh's
eyes follow the bra as she slowly led it slide to the
floor. His eyes paused, and then moved upward to stare
rapturously at her pear-shaped breasts. They quivered. He
quivered. She quivered. They shared the knowledge of
desire.
"He's at least a bisexual," Denise decided.
Josh lost the next hand. Denise was taking no chances, so
it wasn't even close. She was in such a hurry for
enlightenment that she never even turned over her King-high
straight. It didn't matter. Eager to confess, Josh never
asked to see her cards.
"Your first kiss with a girl. You must tell me about it. I
want all the details. Start with her name."
"Cynthia -- her name was Cynthia. We were both thirteen at
the time. She invited me to spend the weekend at her
cottage in New Hampshire. That's where it happened - the
kiss."
"Josh!" Denise's voice rose. "You're not trying to tell me
that you were alone with a thirteen-year-old girl for an
entire weekend? That's hard to believe. Where were her
parents?"
"At the cottage, of course! We were well chaperoned. Her
parents weren't thrilled about my being there. In fact,
they were shocked out of their gourd when they saw my
mother drive up with me. If my mother had actually been
listening to them, instead of daydreaming about one day
owning a cottage of her own, I'd have gone back to Boston
with mom. But she blithely drove off, leaving me with two
irate lesbians."
"Lesbians? Are you saying Cynthia's parents were both
women?"
"Yeah. Her father deserted the family when Cynthia was
four. Her mom Cheryl and Cheryl's girlfriend Beth raised
her. I think that Beth was the 'other woman' who broke up
the marriage. At least, she always knew what she wanted,
and she wouldn't take no for an answer."
"So let me see if I've got this straight. You've just been
left for the weekend with your girlfriend and her two
mothers?"
He nodded, so she continued the summation. "And Cheryl and
Beth can't stand boys. Or was that all males? Yes, the
latter? Well how did your survive the weekend? You must
have -- you're still here. And I can see that Beth didn't
castrate you."
He looked nervously to the left, to the right, to the rear
- every direction but Denise. She waited, knowing that he'd
eventually untie his tongue. He wanted to tell all. She
could see that. But what was the big secret this time?
Another dress. Another feminine identity. Another girl's
name. Jennifer. That's what he said - Jennifer.
"There was only one way they'd let me stay the weekend. I
had to forget I was a boy. Cynthia had misled them, Cheryl
said. She'd done it deliberately, according to Beth. They
couldn't abide boys. If I wanted to spend the weekend at
the cottage, I'd have to pretend to be a girl."
"At this point," Denise replied, "Most boys would have
called the women's bluff or their own mother on the
telephone. Why didn't you phone up your mom and beg to be
rescued from two man-hating lesbians?"
"I couldn't. She went to a religious retreat for the entire
weekend."
"Well, there must have been someone else you could have
called. I'm sure there must have been a relative or the
father of a friend who would've rescued you if you'd called
for help. A lot of people think it's child abuse to force a
boy to dress up like a girl, never mind pretend to be one."
"I thought of calling up Chuck to arrange for my rescue. I
even thought of simply forcing Cynthia's mom drive me to
Chuck's, so I could beg his parents for asylum. But I
decided to stay."
"What on earth for? Were you actually looking forward to
being a girl for the weekend? I bet you were, Josie."
"It was because of Cynthia. She said she was thrilled at
the idea of having a girlfriend at the cottage. She begged
me to stay, to be Jennifer. She said that was her favorite
name. "Please be Jennifer, please, please, pretty please.'
She went on like that for the longest while. But I was
adamant. 'No way,' I kept saying, no matter how often she
said 'Yes, way!'"
"But you did stay, Jennifer. How come? The thought of being
a girl excite you?"
"That's Josh to you, Dennis. Only Cynthia can call me
Jennifer. Otherwise, the name is defunct, extinct, pass?,
no more. I relented because Cynthia announced - right in
front of her two moms, who were looking pissed off with me
- that if I agreed to be Jennifer, she'd give me a big kiss
- a sexy, romantic one, just like in the movies."
"I looked over at Beth and Cynthia expecting them to get
out a bullwhip to drive me away before I got a chance to
kiss their daughter. Instead, to my surprise, Beth smiled
for the first time. In fact, she laughed out loud. You'll
never believe what she said."
"I can't imagine."
"She told Cynthia she could kiss her girlfriends as much as
she liked, though there couldn't be any hanky-panky -
that's the word Beth actually used -- until she was much
older. So Cynthia had the green light to give me a sexy,
romantic kiss, so long as I agreed to be Jennifer while I
was at the cottage."
"A kiss? That doesn't strike me as a good enough reason for
a boy - for a normal boy anyway - to cross-dress. Admit it,
Josh - you like dressing up in women's clothes. You're a
transvestite or you were at thirteen."
"No, you've got it all wrong. You've got to look at
Cynthia's offer through my eyes, through the eyes of a boy
who'd never kissed a girl and was, after those dates with
Mike, wondering if I was gay. I was desperate to kiss a
girl because I needed to know if her lips would be sexier
than Mike's, her kiss more erotic than a guy's. I was
fighting for my masculinity; that's why I put on the
sundress. You've got to understand how I felt. Gay panic is
not a pleasant thing to experience."
Denise was boggled at the backwards logic of it all. "Let
me get this straight -- you spent an entire weekend in a
sundress so that you could prove to yourself that you
weren't a homosexual?"
"That's right. But I didn't wear a dress the entire
weekend. I was in shorts - they were a pukey pink - much of
the time, and I mostly wore a swimsuit."
"One piece or two?"
"Once piece since it made it easier to hide my true sexual
identity." He looked down at his lap. As Denise followed
his gaze, she couldn't help but notice that that his penis
was standing tall.
"Why would you bother doing that, Josh? Cynthia and her two
moms weren't going to be fooled."
"Maybe not. But they were furious the first time they saw
the outline of my balls. Cheryl took me to me to Cynthia's
bedroom, and showed me how to tuck away my genitals with
the help of some tape. She even lent me a couple of Beth's
breast forms - she was pretty flat chested - to wear. Then
she worked on my hair. I freaked when she brought out the
scissors. After the haircut, the makeup was relatively easy
to accept."
"Then what?"
"Then I got my first kiss from a girl. Cynthia was so
excited by the way I looked that she gave me a big wet kiss
right in front of her parents."
"So is that the kiss you'll remember for the rest of your
life?"
"No, that came the next day when Cynthia and Jennifer were
necking behind a clump of bushes. That's the day I knew for
certain that I was straight. It was Fahrenheit 451 with
Cynthia, but no more than 98.6 with Mike. I was hooked on
women for life."
"I'm glad to hear that. But what a strange tale! Was that
weekend the last of Jennifer? I hope so."
"Not exactly. She was around for one more week later that
summer."
"At their cottage? Again? But why on earth? If you're
telling me the truth, then you didn't need any additional
proof of your heterosexuality, at least nothing that
Cynthia was likely to give you while her two moms were
watching.
"I was thirteen, Denise. I had delusions. I thought if
Jennifer hung around Cynthia for an entire week, there
would eventually come a moment when I'd be able to get laid
for the first time. Sorry, I shouldn't have used that
expression. I figured that Cynthia was more likely to put
out for a boy if she could call him Jennifer while they
were having sex. After all, the apple doesn't fall very far
from the tree. With a lesbian mom, and being raised in a
lesbian household, I figured that Cynthia just had to be
gay. It made sense, then at least, that Jennifer had a
better chance to seduce her than Josh did."
"Josh, you should be ashamed of your stereotyping. Girls
don't end up lesbians just become they have lesbian
mothers. Sexual identity is a lot more complex than 'monkey
see, monkey do.'"
"You're right about Cynthia. She's already married and
pregnant for the second time. However, my plan didn't
entirely backfire. I got lot more experienced at kissing
and she even let me touch her breasts - you know, with my
hand under her tee shirt."
"And nothing more?"
"Well no, but that's not bad for thirteen. Right?"
"Maybe she would have put out a little more, Josh, if you'd
been dressed like a male? Ever think of that?"
"I don't know. I was pretty happy with the progress I was
making with Cynthia, and for a while her two moms even
seemed to like me."
"How do you know?"
"Well, Cheryl took me shopping. She said it was time that
Jennifer had her own clothes. She bought me a lot of cool
stuff."
"Don't tell me you actually liked buying girl's clothes?
That proves it: you're a transvestite."
"That's not true. Be reasonable. Wouldn't anyone who was
forced to dress like the opposite sex want to look his
best? No one wants to look like a nerd. Of course, I would
have much rather dressed like myself, like a guy, but if I
had to dress like a girl, I'd rather wear a halter-top than
a tee shirt. I simply look better in a halter top, or I did
when I was thirteen. Admit it, Denise, everyone wants to
look their best."
"I don't think I'd be looking for the most masculine
clothes I could find if someone forced me to dress like a
man," Denise replied.
"That's easy enough for you to say, Denise, since you're
already wearing the kind of shirts and jeans that were for
men-only when your mother was young."
He had a point, Denise decided, and so she let the matter
of the halter-top drop. Clothes didn't, she knew, make the
man - or woman. She was more interested in what went on in
Jennifer's head than in what went on her body. So she
asked, "Didn't you find it weird pretending you were a
girl. How did you deal with outsiders? Didn't you feel
creepy letting them think you were a girl named Jennifer?"
There weren't that many people who saw me dressed as
Jennifer. I made sure of that. At my insistence, Jennifer
bought her entire wardrobe at a single store, and we got
takeout for our lunch that day. It was the only time
Jennifer left the lake. Only a few people ever saw me
dressed as a girl."
"Was any of them a boy? Was there another boy your age at
the lake? I bet there was. There always is. And once boys
get old enough, they always find the good-looking (she
winked) girls at the next cottage over. I think they scout
for females when they're boating."
Josh blushed yet again.
"He's cute when he blushes," Denise thought.
"There was one teenage boy who was about our age," Josh
began. Kerry lived in the next cottage and hung around us
because he was, he said, bored out of his tree."
"I bet. He wanted to get into your panties."
"No, he didn't. Not at the start. He just wanted some
friends his own age. However, that did change after a
while."
"Yup, his hormones kicked in, and so he decided to go
beaver-hunting," chuckled Denise.
"He got a crush on me."
"Doesn't everyone? Both sexes?"
Was she joking? He wasn't sure. If he was going to have sex
with her tonight, he figured he had to convince her that he
was as normal a heterosexual male as she was ever going to
meet.
Denise suddenly asked: "You kissed him, didn't you. I can't
believe it. You tell me how straight you are, but you
kissed another boy during the very week you first got
intimate with a girl!"
"I didn't kiss him. He kissed me. But this time I saw him
coming, and I had my teeth clenched when he dove for the
kiss. So he never got his tongue inside my mouth, although
he sure tried. He kissed like a puppy. I had slobber all
over my chin."
"Well, that doesn't sound very romantic."
"I can assure you it definitely wasn't. But how could it be
romantic? With a boy? Never! Why won't you believe me that
I like GIRLS? I'm straight!"
"But you're a guy who also likes to dress up like a girl,
right? It's cool. You can tell the truth. You don't have to
lie to me. I can see ... (she looked down at his groin)
that you like girls ... too."
He became a bit more upright. "Denise, you've got it all
wrong. I don't like to wear girl's clothes. My mom, and
Mike, and Bart, and Cynthia and her two moms - they made me
wear 'em. They gave me no choice."
"Was there anyone else who made ... (her voice rose
ironically) ... you wear girl's clothes before you lost
your cherry to Bart?
"No one, I swear there was no one else. You've now heard
every secret from my youth."
"No I haven't. You haven't told me about your first time
with a girl. You have had sex with a girl, right? You're
not a virgin, are you, that way at least?"
"I'm not a virgin!" he said heatedly.
"Then I must know about her. That's what I'm playing for -
the full story of the first time you had intercourse with a
woman. You, dear Josh, will be playing for my panties. If I
lose, you'll get to see me, as I see you, naked."
The word made him even more vertical.
The thought of seeing her take off her panties must have
distracted him: Josh lost yet again. By his own admission,
he made a foolish discard. "I was thinking about how
beautiful you'll be naked instead of thinking about my
hand. Foolish of me, huh? I'm not very good at cards."
"But are you good at love, Josh? Now it's time for the
biggest secret of all. Since you bet and lost, you have to
tell me about the first girl you had intercourse with.
We'll start with her name and whether I know her. Does she
go to Harvard Square?"
"No, I knew her only during my last year at high school. I
can't imagine you know her. Cindy was her name. Ah, do you
really want to know this story? You might not like it.
Maybe it's time we changed games. I lost; you won. That was
the luck of the draw."
"Hold on there. Let me guess. You're wearing a dress when,
or just before you had sex with your first woman. That's
it, isn't it? That's what you're afraid to tell me. It's
time to'fess up, Josh. What was your name this time?"
"Jessica," he answered gloomily.
"Ah, hah! I knew it. I'm no fool. Well, Jessica, how come
you were in girl's clothes the first time you had sex with
one? I'm dying to hear the story. I just know it's going to
be a doozie!"
She was mocking him! "It's not fair," Josh thought. "Not
once did I want to dress up like a girl. I just have bad
luck. I meet weird people."
To Denise he said, "Any guy would have put on that
cheerleader's outfit to get into Cindy's pussy. Sorry,
that's a bit crude, isn't it?"
"I'll say! And what's so special about Cindy?"
"She's almost as beautiful as you are." Denise noticed the
'almost' and smiled; he'd recouped some lost ground. He
plunged onward: "Cindy was the best looking girl in my high
school. Blond, short and green-eyed -- she looked like a
young Drew Barrymore. She turned me on so much that my
knees crumpled when I was around her, which is my only
excuse for dropping her during one of our practices."
"How could you? Was she hurt badly?"
"It was only a twisted ankle. But it meant that she
couldn't walk home after practice, like she usually did.
Because it was my fault she hurt her ankle, I had to stay
with her until her mother arrived."
"And that's when you and Cindy first realized you were made
for each other?"
"It was more than that. That's the evening we made each
other, because her mother had a car accident while she was
en route to pick Cindy up. No one got hurt, but the left
rear wheel of her mom's car was badly bent, and by the time
she came for Cindy in a taxi, Cindy wasn't a virgin
anymore."
"How long were you alone with Cindy? You must be a fast
operator." Or he was then. He didn't seem to moving very
fast tonight, Denise grumbled to herself.
"Fast enough. I had two hours to work with. Even so, Cindy
and I would never have had sex if it weren't for the games
we played. That's what we were doing - playing games. Even
the sex was a game. It wasn't like making love. I haven't
done that yet, but I hope to soon," Josh said it so quietly
that Denise wasn't quite sure he'd actually been talking
romantically.
"What do you mean playing games?"
"We were playing turnabout. I know, I know - it's something
five-year-olds might play, but Cindy was in a really
strange mood. Cheerleading was everything to her, and she
was worrying about whether her ankle would hold up in the
future. Was she washed up at eighteen? That's what she was
wondering. That sort of anxiety can put a girl's head in a
strange place."
"What do you mean?"
"She started talking about how much she loved her uniform.
She still had it on. The way she was going on and on about
her pride in the uniform you would have thought she was a
U.S. Marine. So I cracked a joke about my own."
"Do you remember it?"
"Not exactly. I think I said I now took mine off only when
I showered. Something like that. My comment was stupid,
considering how important the cheerleading squad was to
her. And she was hurt, and it was my fault. I immediately
felt like a schmuck for making fun of her."
"Was she angry?"
"Maybe. Because she said that I couldn't possibly feel the
same pride in my cheerleading uniform as she did because
mine wasn't the real thing. A real cheerleading uniform,
she said, had a red skirt and matching red panties. I
couldn't believe what she said next."
"You're not going to tell me that she suggested you put on
her cheerleading skirt?"
"Not just her skirt, her whole damn outfit. Of course, I
said no. There was no way I was going to be caught dead in
a girl's cheerleader's uniform, never mind alive in one
while waiting for her mother or the school custodian to
show up at any moment."
"But she was persuasive, right?"
"You have to understand that I was desperate to see Cindy's
body."
"I know - you were a horny teenager."
"You're darn right. I was your normal teenage boy who'd do
anything to get a pretty girl out of her underwear, even
... (he smiled) if I had to wear it myself. Well, that was
the deal: I could see Cindy with her clothes off if - and
this was a big if - if I was willing to put on her cotton
sports bra and matching red panties, her black letter
sweater, her red skirt, black socks and red sneakers. That
was an easy deal to accept."
"I bet. You weren't giving up much."
"Yes, I was. I was taking a big chance. If the custodian or
her mother had showed up, my reputation was shot. But I
definitely knew I had made the right decision when she
asked me to steady her - with my hands around her tiny
waist! -- while she stood to apply my lipstick and makeup,
and to comb out my hair. She even gave me her hair band to
wear. I still have it in my trophy drawer!"
"And then what happened?"
"Cindy said I had to do the school cheer while I was
wearing a real cheerleader's outfit. So I did. And do you
know something? She was right. As I was jumping up and
down, my skirt following my every move, I realized that
cheerleading is a special art. The skirt is what makes it
an art. It accentuates and complements every move a
cheerleader makes. I could understand why Cindy was proud
of her uniform and why my uniform - the one with the slacks
and carefully hidden briefs - left me cold."
"How did all this get you into bed with Cindy? I realize
she was already sitting there in the buff, but how did you
change her lesson in cross-dressing into one in sex
education?"
"I was doing a headstand when I noticed that she was
masturbating. She didn't realize I could see what was going
on when I was upside down. Of course, I could. So I smartly
said, 'I can do that for you. I can give you pleasure,' and
then I walked on my hands - can you believe it? - over to
her and started working on her with my tongue."
"It wasn't just pussy licking, was it? You did screw her?"
"Yes, about two dozen times over the next three weeks. All
I had to do was put on her cheerleading outfit, and she was
so hot for sex that I couldn't have fought her off, not
that I wanted to."
"You're telling me you were wearing Cindy's cheerleading
outfit almost every day for three weeks?"
"Hers or the one her older sister had worn when she
attended our high school."
"Josh, it sounds like the perfect set-up for you. I bet you
got another pet name. What was it this time?"
He answered as softly as possible, but she was sure he
said, "Candy. She called me Candy because I was so ...
sweet."
"Candy, why aren't you two still twirling around in short
skirts together? What went wrong?"
"I wish you wouldn't call me Candy. We're talking about
high school. That was a long time ago. I'd much rather be
called Josh or, if you like, stud'." This time they both
laughed at his little joke. Then he admitted, "I was the
one who ended the relationship. She was trying to turn me
into a girl."
"What do you mean? Didn't she do that the first time she
got you to put on the cheerleading costume?"
"No, that was play-acting. After all, we're talking about
my wearing a costume, just as you said. But Cindy started
pressuring me to dress like a woman all the time. She
actually claimed that's what I really wanted."
"You didn't?"
"No, I've never wanted to dress like a girl. Really! I'm
serious. Every time I dressed in drag it was because
someone else wanted me to. Anyway, Cindy pressured me into
going out with her one evening dressed as a woman. She took
a lot of time getting me ready for what she called "Candy's
debut in Boston society." And she did a good job too.
Everyone accepted me as a girl, and I do mean everyone."
"Which means that guys were hitting on you all night?"
"Right, and Cindy was egging them on. I decided I no longer
liked her. I was tired of her games. That evening she
seduced me one last time, and then it was over. She told me
to keep Candy's clothes, but I gave them away to The
Goodwill. So that's the entire story of the girl who took
my virginity."
"I thought Bart took your vir