Kyle is a reckless teenager, despite early panty-training. When he asks for a moped, his mother decides he has to change his behavior before he kills himself on it. She proposes a deal: He gets the moped if he agrees to wear girls' clothes for a month, clothes that he can choose for himself. It seems like bet he cannot lose, but Kyle's life soon begins to spin completely out of control.

Anything for a Moped? – Part 1 By: Dawn De Winter
Chapter One: The Deal

He was at it again. But this time he had unexpected company. His mother wasn’t supposed to be at home. She was supposed to be out. The house should have been empty. It was usually empty, for Kyle was a single child, and half an orphan, his father having died in a car crash three months after his birth.

Kyle thought he had the freedom of the house, the freedom to lie on the living room sofa with the lingerie pages spread open from the Sunday supplement.

As always, the sight of those teen models in their panties and bras had brought down his pants and his boxers. Half naked, he lay on the sofa stroking his hardness. His eyes were shut, his mind light years away in a fantasyland of satin, lace and willing women.

A cough brought him back to reality. Without even taking the time to open his eyes — or possibly he was hoping that the intruder could see no more than he -- Kyle pulled up his pants and boxers with a frantic tug.
Only when he had covered his drooping shaft did he dare to open his eyes. Now that he could no longer see his erection, he could desperately hope that no one ever had.

Who was there? His mother! What could be worse for a fourteen-year-old? His mother had seen him almost naked jerking off! He could have died on the spot had his body not been so tingly with sexual vitality.

Barb spoke first: "Kyle, the lingerie advertisements are there to inform me, not to amuse you. Why don’t you put them away now?"

She had let him off lightly. The oblique reference was her style. Nothing more would have been said had Kyle let the subject drop. But embarrassment loosened his tongue. He blurted out that he too had been seeking information.

Had he stopped there, Barb would have assumed that he meant that he, a young teen, was simply trying to figure out the mechanics of the bra, so that one day he would be able to extricate his girlfriend from one. But Kyle did not stop while ahead. He blundered onward.

"I was doing research on gender," he loftily said.

"On gender? How so?"

"Well, we have a social science teacher who said last Thursday that we now live in a unisexual world thanks to feminism. According to Mr. Barnes, feminists are mostly lesbians, and so they naturally want women to be as much like men as possible."

"I can’t believe Mr. Barnes said anything like that," interrupted Barb. "I know he’s close to retirement age, but I am sure he wouldn’t say anything that foolish."

"Yes, he did too say it," rebutted Kyle. "And why shouldn’t he? Isn’t it true that most feminists are dykes? And don’t dykes really want to be men? That’s true, isn’t it?"

"I can’t believe you’re repeating such garbage to me, Kyle, or using that sort of language. I taught you to be a lot wiser than to believe that homosexuals want to be the other sex. Some homosexuals may want that, but they are far from a majority. You know full well that homosexuals are different from transsexuals, who in turn are different from transvestites and cross-dressers. It’s a complex world, Kyle, and I will not have you stereotype people. I can’t believe that you’ve forgotten all that I have taught you on this subject. What about the books you read last year? And now some teacher tells you bunk and you believe him?"

Her remarks were calmer than her thoughts, which were in turmoil. Barb was a feminist and a political liberal. She even liked to think of herself as politically correct, a label she wore as a badge of honor. She had tried to raise Kyle as a feminist and had done her best to combat gender stereotyping.

As a baby, he had worn both pink and blue so that he would get to know how adults reacted to both sexes. However, as a toddler, he had worn only boys’ clothes, for she wanted no teasing, no humiliation.

Yet she had deferred his first haircut hair to the last possible moment. By then he had grown to take pride in its luxuriance. Until about a year ago, he had kept it unusually long and well conditioned. A cooperative hairstylist had even agreed with her that his hair should be cut in a unisex fashion. That is, lots of the local girls had a similar cut, but no one would have said he had a girl’s hairdo -- so long as he dressed as a boy.

Unisex, not humiliation — that had been Barb’s goal. Thus, she made no attempt to put Kyle into dresses, even when the opportunity arose. One such missed opportunity came on his eighth Halloween when Kyle had asked to go trick or treating dressed as a witch.

While Barb had briefly fantasized about putting Kyle into a witch’s mini-skirt and with teaching him how to apply his own witch’s make-up, including the blood-red lipstick and black eyeshade, she had finally vetoed his going out in public in a witch’s dress because of her Wicca friends. She knew what a real witch looked like — and it was nothing like a Halloween hag.

So what he worn instead? Why, a darling Peter Pan outfit. It resembled all the other Halloween outfits Barb encouraged or permitted: it required tights. If there was one thing Kyle was used to wearing by the age of twelve, it was tights. He had worn them as Batman’s Robin, as Super Boy, as Spiderman, as a Three Musketeer, and as Robin Hood. Kyle was always a superhero in tights.

It tickled Barb’s fancy to channel his boyish enthusiasm for comic book heroes into nonchalance toward at least one item of girls’ clothing — namely tights. He even knew that his tights came from the girls’ department; but could care less, Barb was glad to see, because they enabled him to be a macho superhero, at least in his own mind.
She got a kick out of seeing him run around in green, black, white and red tights, and for about a month each year they’d engage in mock sword fights in the kitchen or challenge each other to an archery contest in the backyard — or at least they did until Kyle became strong enough to project his arrows into Mr. Mitchell’s yard, one time scoring a perfect bulls-eye on the towering sunflower under which their elderly neighbor was bent over gardening. So comfortable and macho did Kyle feel in tights, that he even wore them as "long johns" on cold winter days. At least, he did until his thirteenth year.

The tights were the only "girls’ clothes" that young Kyle knowingly wore. But they were far from the only girls’ clothes he did wear. In dressing her son, Barb had tried to get him to wear at least one item of girls’ wear. As she hadn’t wanted to embarrass him, she had found unisex items like socks, tee shirts and sweaters.

Though purchased in the girls’ department, the clothes were neutral enough in color and design that Kyle never realized he was cross-dressing. If anyone else did, they never admitted it to either Kyle or Barb. They contented themselves with raised eyebrows, a suppressed giggle, or a covert sneer.

Until Kyle was nine, the boy had unwittingly worn girls’ panties most of the time. Why panties? Because Barb believed that clothes made the boy. If his outfit were a mix of genders, so too would be his personality, or so she hoped. She endowed the panties with almost mystical significance: they would make the boy a more sensitive, more caring male -- even if he didn’t know he was wearing anything unusual. Or so Barb hoped.

To avoid a confrontation with her son, Barb deliberately purchased plain cotton panties, with a minimum of trim or special stitching. Some had solid colors — sometimes a vivid green or red, sometimes a pastel blue or yellow. Many were white, and four were pink, thanks to Kyle’s botched first attempt to help his mother out with her laundering.

He hadn’t known about separating the whites from the colors. As he agreed, "Money doesn’t grow on trees," Kyle manfully wore the pink underpants from time to time — in other words, when the rest of his panties were dirty and piled up in the corner of his bedroom. To be candid, the pink underwear did bother him; every time he had to put on his pink-dyed briefs he openly cursed his folly in making his "boys’ underwear" look … like panties.

Barb also dressed Kyle in print panties — that is, in prints that Barb believed would appeal to the little boy. As Kyle loved animals, he had, as a little boy, liked wearing panties with teddy bears, Dalmatians, or kittens frolicking on them. Several of his panties had a Disney theme, for Barb had made a ritual out of their movie nights: for all animated features, they’d start the evening by going to his favorite burger restaurant, then they’d see the film, and the evening would end with a theme gift: a pair of print underpants and, whenever available, the matching undershirt — or should we say, the matching cami?

While Aladdin and the dinosaurs were definitely boys’ wear, Pocahontas, Mulan, the Littlest Mermaid and the Lion King were definitely adorning girls’ panties. When Kyle was seven or eight, he loved to race around the house clothed only in his underwear, pretending as he did, that he was the superhero whose face and form clung to his bottom or his nipples. More often than not the superhero was female, simply because Kyle’s underwear drawer contained more girls’ panties than boys’ briefs.

Kyle found that his mother seemed to lose track of the time whenever he played at being Mulan or Pocahontas, and he’d sometimes wear their underwear — and nothing else -- in a conscious bid to stay up late. His mother had never believed that little boys should stay up past midnight; that was a teenage perk, she said. But Kyle did finally break through that temporal barrier when he was nine.

He and his mother had been watching a video she’d rented about Joan of Ark, the medieval French heroine. Kyle had gotten so excited by the battle scenes that he insisted that he be able to dress just like Joan.

They stopped watching the video long enough to dress him in his Halloween tights, in one of his mother’s peasant blouses, her Gucci belt, and her patent leather shoes (because of their outsized buckle). His unisex hairstyle already looked like Joan’s boyish cut, and so needed a few brush strokes to be pronounced "perfect for a French knight." As he was already wearing his Pocahontas panties and cami, Kyle had not a single item of male clothing -- unless you counted the aluminum foil that Barb wrapped around his torso as Joan’s body armor.

Even the "armor" didn’t look masculine, for Barb applied several extra layers of the foil to the boy’s pectorals, saying as she did that the armor wouldn’t otherwise look like Joan of Ark’s. She didn’t make the breasts too perky or prominent, but he clearly had a "rack" when viewed from the side. Thus attired, and thrusting a wooden sword skyward in a militant pose, Kyle beamed as Barb took several photographs, including some profiles.

The pictures with a side view she kept for herself; Kyle could see them when there was no risk of his panicking over the first photos of his bust line. Those taken head on she gave to Kyle, who thought them a hoot; for half a year they had pride of place on his bedroom bulletin board.

The photos taken, they watched the Maid of Orleans go into battle several times, for Kyle insisted on seeing it the video twice through that night. He thus got to stay up to one a.m. — an achievement that he thought of as a significant milestone in his coming-of-age.

After midnight, Barb, bored by the movie’s second run, silently studied "Joan of Ark," her macho son. She noted that the parts he liked best were the battle scenes and the burning of Joan at the stake.

She wondered why he wanted to watch the movie twice. Barb, reflecting on his decision that morning to wear his "I want to stay up late" Pocahontas panties, concluded that Kyle was simply determined to breach the midnight barrier, and that he would have found some way or another to do it. Still, it was interesting that he chose to close a chapter in his boyhood by opening a new one in his "girlhood."

For the first time Kyle had actually consciously dressed as a female — and as a female heroine, to boot. Barb was thrilled by Kyle’s androgyny. She now believed he was going to grow up into a man who’d admire strong women and possibly marry one.

If all went as she hoped, Kyle would always see himself as male, but would be able to share everything with his wife — cooking, childcare, lingerie, and make-up. There would be no artificial gender barriers in her son’s home. Or that was the plan at least.

The plan went awry. Kyle had never again dressed as a female, and as his tastes in clothing "matured," he had gradually refused to wear girls’ underclothes. He still didn’t realize that his mother had put him into panties; indeed, the suspicion never surfaced. Rather he decided that only a sissy wore — in succession -- underpants with teddy bears or cartoon lions on them, next any sort of undershirt, then any underpants without a y-front, and finally, any sort of brief. He had begun to rebel against his mother’s taste in underwear when he was ten, and by the time he was thirteen he wore only boxer shorts.

The boxer rebellion had by the age of fourteen produced a teenage boy whom his mother still admired, yet found profoundly disappointing. What did she admire? His great sense of adventure. Kyle was willing to try anything at least once. And he laughed at danger. Indeed, it seemed that the fatherless boy was constantly trying to prove that he was no mommy’s boy, that he’d accept any dare and take any risk.

There seemed to be no sport too extreme for Kyle, who loved to rock climb, snowboard and ski — on snow, water, on soapy water in a hallway. At school his favorite sport was platform diving because it involved the most risk, especially for a boy who always insisted on being the first to try a twist or a flip, even though most of his friends had more natural ability at diving.

Kyle had also been inseparable from his skateboard since he received it on his twelfth birthday, and he liked to weave his way through traffic on his way to the skateboard park where he always seemed about to launch himself into free falling space.

Barb had to admire Kyle’s raw courage, but she disapproved of the risks he took. She thought him foolhardy at times, and she sometimes wondered whether he’d survive his teen years. He had had several accidents, and in three short years had broken a collarbone, a leg, and an arm. Barb simply didn’t buy his excuse that he was, each time, simply unlucky. She saw a pattern of recklessness, and wondered if she somehow were to blame for it.

Had he somehow known or understood that she had been trying to feminize him? Is that why he had become so cock-of-the-walk? Or had his boxer rebellion been the inevitable, logical assertion of puberty by a boy who had no father to guide him into manhood more safely? As she observed what Kyle had become by age fourteen, Barb rued not having asked for a Big Brother to help her son adjust to puberty before he had himself turned it into a game of survivor.

If things didn’t change, Barb feared for her son’s life. He seemed determined to go higher and faster until he broke more than his leg. For the past two months he had been pleading with her for a moped, a motorized bike that fourteen-year-olds could drive on Iowa’s public roads, including the city streets of their native Des Moines. After that, he’d want a motorcycle, Barb knew. He’d keep upping the bet on his life, until he crashed into a wall doing 100 miles an hour.

Of course, a moped couldn’t go more than thirty miles per hour, and it in theory it had to stick close to the curb; but Barb knew that Kyle would somehow find a way to get into danger — for example, by running red lights and by weaving between cars at full speed to execute a left turn.

"Execute?" Why had she thought of that dreadful word? Actually, Kyle had just used it, and by doing so had brought her back from her reverie to their real time argument. "Execution" is what he thought should be done to all sorts of people these days. He had become so terribly judgmental — just like the average teen. So who was it that should be executed this time?

Why it was Calvin Klein, according to Kyle.

Her son didn’t care how many women Klein dated, he must be a fag, for didn’t he design men’s underwear that flaunted their sexuality and women’s underwear that obscured theirs? Kyle was back on the warpath about girls’ underwear, still trying, in effect, to deny that he could possibly have been masturbating over the underwear ads in the Sunday newspaper when his mother had interrupted his "reading."

"So let me understand. Your basic point, Kyle, is that gay and lesbian fashion designers have tricked women into wearing men’s clothes?"

"Yup," he vigorously nodded. "Girls these days go around looking just like guys. It’s one big homo plot."

"Kyle, don’t use that sort of language. One more bigoted remark out of you, young man, and you’ll have to go to your room."

Then, before he had an opportunity to exile himself, Barb set her trap. "You’re simply wrong in any case. Even if girls are now wearing gray cotton underwear and blue jeans, they are, I assure you, definitely wearing girls’ clothes. Are you saying that girls’ clothes are so masculine these days that a boy could wear them and that no one, not even his friends, would know he was dressed like a girl?"

"He wouldn’t be dressed like a girl. That’s the point," Kyle objected. "That boy could find all sorts of boys’ clothes in any girls’ store. There’d be sweatshirts or sweaters, blue jeans, sports socks and sneakers. All boys’ stuff. A boy could easily do all his shopping in the girls’ department and no one would know he was doing it. And that’s the problem. Girls these days are un-sexed."

"Let me get this straight, Kyle, if such screwy thinking could be considered ‘straight.’ You’re telling me that a boy — you, for example, could find several different outfits — say, four or five outfits — that you could wear to school, and no one would suspect that you’re dressing like a girl?"

"You don’t get it. I would be dressing like a boy. No one would know I had bought the clothes in the girls’ department of the stores."

It was time to spring the trap. "That being the case, Kyle, I assume you would not object to an experiment."

"What experiment?" he warily asked.

"This experiment — that you wear girls’ clothes every day for one month, including to school. You’d get to pick the clothes. They can be as masculine-looking as you want, as you can find, as long as you find them in the girls’ department of Macy’s."

Kyle’s mouth gaped open. He couldn’t figure out his mother. Sometimes she was really strange. "Jeez, adults!" he sighed. "Why would I agree to wearing girls’ clothes for a month? Why would I bother? Sure, I could get away with it. It’d be no big deal. But what’s in it for me?"

"A moped, the best Des Moines has on offer," Barb quietly replied.

"A moped? You’re saying if I dress in girls’ clothes for a month I get a moped? And what if I don’t want to do that? Are you saying I don’t get the moped if I don’t dress up like a dumb girl?"

Barb, her arms folded across her breasts, nodded, "Yes, Kyle, no dress-up, no moped."

"But why?" he whined.

"Because," Barb said, "I don’t like your attitude of late. It’s sexist. I think your disdain for the way we women dress is just the tip of the iceberg. If you don’t change your ways, young man, you’re going to end up being either a crummy husband or dead, or both. This foolish conversation sums up the problem. You’re so old-fashioned in your thinking about women that you won’t even allow their clothes to evolve. Well, Kyle, it’s like this: if lesbians have conned girls and women into wearing men’s clothes, then you shouldn’t have any problem wearing the clothes yourself. And if you do it for one month, you get a moped at the end of the month."

"But why do I have to wear girls’ clothes to get a moped? Why? Why?"

"Because," Barb explained, "I think you might become less sexist if you live one month of your life in girls’ clothes, and because I hope that if you become less sexist, then the moped might not kill you. It’s your life we’re talking about saving."

Kyle thought for a moment. He picked up the newspaper and closely scrutinized the lingerie advertisements. Barb patiently waited. Then Kyle spoke: "Okay, I’ll do it, but I have conditions."

"And what might they be, young man?"

"First, that no one else ever knows about this deal. Second, that I choose the clothes, but you actually buy them. And I definitely don’t try anything on in the store. Third, I get to wear pants everyday. No sissy skirts or dresses. And fourth, I choose the moped. It will cost you."

"Agreed. But I too have conditions. First, as I’m not going to have my son wear the same clothes to school day after day, and so you’ll have to agree to our buying at least five different outfits for you. And they can’t all be blue denim."

"How about khaki or black denim?"

"No problem, Kyle. You can even get two pairs of blue jeans if you want, provided they’re different brands. You’ll also need some leather shoes. Not every day can be sneaker day. I have a second condition: I expect you to wear a bra every day."

"A bra?!" Kyle almost shouted. "Whatever for? Why do you want me to wear a bra? That is girls’ clothes, definitely."

"Precisely. I want you to wear the bra so that you’ll never forget, no matter how masculine looking your clothes are, that you are indeed dressed in girls’ clothes. No bra, no deal."

"But everyone will see the bra. Jeez, some guy will be flicking my bra strap!"

"No, they won’t see it, Kyle, because you’ll be wearing a sweatshirt or sweater, something bulky. Only you and I will know about the bra. Besides, pick up the newspaper and you’ll see a type of bra there that will scarcely show. Look. It’s called a sports bra," she said as she pointed to the newspaper ads.

Kyle examined the sports bras carefully, and he decided that they weren’t much different from a sleeveless tee shirt. They seemed designed to hide rather than to reveal a woman’s breasts. The "Cooper Sport" bra seemed especially safe for a boy to wear. "Cooper," he sneered, "I bet it’s another one of those lesbo-homo designers. Yeh, they make bras for boys, not for girls." That image made him giggle.

Giggling, he extended his hand. Kyle and Barb shook on it. They agreed that he would play hooky the next day so that they could have more privacy as they shopped for him in the girls’ department at Macy’s.

As soon as they got home from the store, the experiment would start. One month later Kyle would be allowed to switch back to his boys’ clothes — "if you still want to wear them" Barb joshed — and they’d go shopping for the flashiest, fastest moped the town had on offer.

That night both Kyle and Barb were too excited to sleep. Barb kept asking herself, "Do clothes really make the boy? Was I ever right about that? Why did all those panties and tights not have more effect on the boy? Why is he so sexist and macho? Is it because he never knew he was wearing girls’ clothes?

This time he would know that he was cross-dressing. The bra would constantly remind him, even if the lack of space at his crotch did not. What the boy knew could help him. Girls’ clothes might feminize Kyle enough to save his life, even if he spent the entire month boasting of how masculine he still looked.

As for Kyle, the fourteen-year-old was too sexually excited to sleep. Several times his right hand slipped into his boxers, as his left hand pinched his nipples. Several times he came in great spurts, as he fantasized, over and over, about mounting his moped.

As he mounted it, buck-naked, the moped changed into a raven-haired girl, into the lingerie model who had so aroused and distracted him earlier that day that he had been caught masturbating by his own mother. Confusingly, he came each time prematurely — just as he was unhooking her bra, and not as he hoped, deep inside the raven-haired vixen.

His dreams, half-recalled, were even more perplexing — in them he would cover his nakedness with the panty and bra that he’d taken from the model. He would then roar off into battle. This dream would end with Kyle triumphant, one foot on the chest of a fallen soldier, dressed in chain-mail and — now this was odd — boxer shorts. Kyle had his sword raised high over his head, as the soldiers chanted, "All hail, Joan of Ark."