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 considerable editorial assistance, as well as Josie for allowing me to borrow her name. Josie swears she’s never lost at cards.

 

Unlucky at Cards    by: Dawn DeWinter

 

"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 – "Is he?" she wondered – 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’d didn’t. True, she 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 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 the 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 naïve. 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 a bid of $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 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, passé, 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,’ she said, ‘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 an 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 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 girls’ 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 know, 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 virginity?" she teased.

"Not where it matters." Josh pointed proudly to his penis, which was as erect as ever. He had remarkable endurance, Denise decided. She was eager to discover whether he would stay just as hard in bed.

It was time for the last hand. It was time for Denise to lose her panties and for Josh to prove that he was as heterosexual as he claimed. So Denise took advantage of Josh’s brief visit to the bathroom to stack the deck in his favor. When he got back, she told him that she’d already shuffled the cards, so he should just go ahead and deal them. He should have won with a full house. Unaccountably, he lost. So Denise had another opportunity to pry secrets from him.

 

"Josh, was Cindy the only girl with whom you’ve had intercourse? Were there any others? Let me know how many there were, and then I’ll decide whether I want to know their names."

"There was just one. Her name was Samantha and there’s not much to tell about her."

"When did you date her?"

"Most of last year. We lived together for a while," he muttered.

"A while? How long is a while?"

"Six months."

"Josh, did she ever talk you into putting on a dress?"

"She was constantly badgering me to get into drag. I made the mistake of telling her about the cheerleading game with Cindy. The next day she’d bought me the college’s uniform – you know, the one with the flared pink skirt and the bare midriff. And she nagged me day and night until I agreed to wear it around the apartment."

"Soon she had me practicing to be a cheerleader for Harvard Square. She was going to sue the school if they didn’t let me try out for the team. I was getting really upset and about to walk out on her, until the downstairs neighbor called the landlord, and I had an excuse to stop practicing."

"So that was the end of Josh’s cheerleading career?"

"You bet. But Samantha always had some sort of woman’s wear she wanted me to put on. She was constantly buying me dresses and skirts and cut-off slacks – and the lingerie to go underneath. I humored her as much as I could, but I was bound to leave her sooner or later. It really bothered me that she started calling me Josie. I don’t where she got the name from, for I never told her about Mike. Why would I?"

"It that why you broke up with Samantha after six months? Because she called you Josie and insisted you wear women’s clothes?"

"Yeah, that was most of the problem. There was," he said sheepishly, "another reason it didn’t work out. She was also a vegan."

"Well, no wonder you broke up! Guys do like their meat. Did she cook you lentils one time too many?"

"The herbs were the problem," he muttered.

"The herbs? What could be wrong with them?"

"She was cooking with some mighty strange herbs. Have you ever heard of blue cohosh, chaste tree, goats rue, pleurisy root, gotu kola, dong quai, tansy, and mother’s wort? That’s just some of ‘em. I think she was giving me a couple of dozen different herbs a day, and in big quantities."

"She fed you something called chaste tree? And tansy? Those don’t sound like something that would keep a guy ready for action."

 

"Well, they don’t. In fact, when you take them together over several months, like I did, they… GIVE you breasts. They’re herbs that pump you full of estrogen and, if you’re a guy, suppress your testosterone. I might as well have been taking hormones. Same thing."

He’d finally shocked Denise. "You’re not serious? You’re kidding me, right? You don’t have breasts! Those are muscles I see, right?" She couldn’t be sure, since Josh had been keeping his chest in shadows. He’d arranged the candles to keep Denise looking downward – where he had much to offer a woman – rather than upward, where he resembled a woman.

Denise moved closer and peered. "Gosh, it’s true. You do have breasts! Those are mammaries. My god, you’re almost a B cup. Samantha really did a job on you. No wonder you left her! What are you going to do about … your breasts?"

"What can I do about them? They’re here to stay. Do you see yourself making love to a guy with breasts? If you can’t, if it’s too much for you, I’ll understand. If you want to go now, I’ll understand. But I want you to know that you mean a lot to me. I didn’t ask for the breasts and I have no idea why Samantha thought I’d want them. She was delusional, I guess."

"Josh, if they bother you, they could probably be removed by surgery. Have you ever thought of having a radical mastectomy?"

"Surgery? No, I don’t think I could do that. I’m squeamish about blood. I don’t know what to do about … me …the breasts. I’m afraid I’m stuck with them."

"I see. Hmm." She thought over her options. He was, she decided, still the cutest looking boy she’d ever seen. And the herbs hadn’t affected him where it mattered most. So she said, "Josh, I’ve decided there’s no way I am going to leave here until the game is over. It’s not finished until I’ve lost my panties. Do you agree?"

A tear welled up in his right eye, then trickled down his cheek, as he nodded.

"But what can we play for? You don’t have any secrets left to tell me, do you?" She had it figured out. His answer was no surprise: "No." She knew it all, as she suspected.

"You have to wager something, Josh, if you expect me to see me naked.: She pulled her shoulders together and wiggled her them, setting her breasts in motion. "You do want to see me naked, right?"

He nodded eagerly.

 

"Then here’s the bet. It’s the only one that makes any sense. If you win, I’ll take off my panties. I’ll then be stark naked and you can have your way with me."

"Yes," she said when she saw a puzzled look on his face. "If you win, we’ll have sex, and it will be just the way you like it. However, if I win, I get to call the shots. Since the game can’t end until I’m as naked as you are, I will take off my panties no matter who wins this next hand. But if I win, you’ll have to put my panties on, and my bra too. And then we’ll have sex the way I like it."

 

"Do you agree to the bet, Josh? Or should I call you Josie, ‘cause that’s what I’m calling you if you lose this hand and have to wear my bra and panties while we make love."

 

"Then I had better not lose this hand. You’ve been infernally lucky all evening, Denise, but now your luck is going to change. There’s no way you’re going to get me into a push-up, pink satin bra and panties with white lace trim. Prepare to lose."

 

"We’ll see," Denise thought. "It’s time for Josie to show her hand." Denise shuffled the cards like a riverboat gambler. She dealt Josh three aces. Four he might find suspicious. The aces were enough for victory – that is, if he really wanted to win. To herself she dealt three kings.

"Josh, how many cards did you discard? How many do you need?"

"Three please." She chuckled to herself, then dealt him garbage. She drew a deuce for herself.

He lost to her kings with a Queen high.

He smiled bashfully. "All I’ve got is a Queen and four little cards. I was going for a straight. But I didn’t get the three or five I needed. I guess I’m just unlucky at cards."

Denise grinned as she handed over her bra. Relieved, Josh also grinned as he deftly put it on. It was a good fit. Then he said very quietly, "They say that if you’re unlucky at cards, you’ll be lucky in love. I think my losing tonight means that I’m going to be really lucky in love. After all, I’ve found you."

Denise slipped off her panties wordlessly. Neither said a word until he had put them on, and had placed his hand high on her inner thigh. As he leant forward to kiss her, Denise whispered in his ear, "You will be lucky in love, Josie, I’m sure you will, just as soon as Josh stops telling stories about you. Tomorrow morning, Josh and I are going to have a heart-to-heart and …."

She got no further, for their breasts had finally touched. Denise was heart-to-heart with Josie. Would Josh be apologizing one day for the time a girl tricked him into wearing a bra and panties by cheating at cards? Denise decided she didn’t care whether he did. All that mattered tonight was making love to Josie.

 

THE END

 

 

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© 2001 by Dawn DeWinter. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.