Anything for a Moped?              by: Dawn De Winter

 

Part 6

The characters are fictional, their names and lives a fabrication. The story is not intended for commercial use and is not to be posted at any other site without the author’s permission. It is intended for readers considerably older than its fourteen-year-old hero.

In the first five parts, Kyle finds it more difficult than he expected to keep a deal he made with his mother: That if he wears girls’ clothes for a month that she will buy him a moped (a motor scooter). He’s not quite sure how it happened, but in rapid succession he has lost his friends, convinced his mother that he’s gay and dating a boy named Steve, posed as a lesbian named Demi in order to charm the grandmother of his new girlfriend Joannie, who’d prefer that Kyle wore the panties in the family, and panicked his mother into looking for evidence that he’s a transsexual. At the end of part 5, Kyle has two lives – a public one in which he still tries to look as masculine as possible in his girls’ clothes, and a private one where only he thinks he still looks all-boy.

 

Chapter Seven: Dressing Up is Hard to Do

Her right arm shook uncontrollably. In an attempt to steady it, Barb grasped her right wrist with her left hand. The tremor then passed through both arms into the inner recesses of her body – into her heart, her lungs, her brain, and her soul. Her entire being quaked with emotion.

Inevitably she dropped it: The breast form slipped from her trembling fingers onto the floor. As she saw it lying there quivering, Barb’s legs buckled and she slumped onto Kyle’s bed.

Earlier, she had gone looking for some evidence that Kyle was using a prosthetic breast of some sort. She had never really expected to find it. Indeed, she had assumed, as she started searching Kyle’s room, that she’d find no evidence at all that her son’s interest in cross-dressing went beyond the absolute minimum necessary to gain a moped.

His ‘lingerie’ drawer was therefore the first shocker. She had rummaged through it several times before she’d accept the fact that it contained only two pairs of pink cotton panties. "There should be three," she kept telling herself. "I bought him a pack of three pink panties."

Eventually, she could not avoid the truth: One of the panties was missing; and Kyle must be wearing it. He had, therefore, failed the test she had set for him. She had believed pink to be anathema to her macho son. Apparently it wasn’t. At this very moment he was wearing the most feminine clothes at his disposal. He could have been wearing black, white or gray. His underwear could have had at least the color, if not the cut, of masculinity. Instead, he had chosen the pink panties. They screamed: "I want to look like a woman."

Was it true? Did Kyle want to look like a woman? Was he wearing girls’ jeans only because his mother had not yet bought him a dress?

As an answer, Barb sought to read her son’s mind: "What are you thinking this very moment, Kyle? Are you reveling in your pink panties? Do you wish you had breasts to fill out your bra? What is your real motive for dressing as a girl? A moped, as you claim? Or is it some deep-seated compulsion?"

And then Barb thought of Kyle’s childhood, of all those occasions on which he’d pretended to be Pocahontas, Mulan or Joan of Ark. Had he done it to please Barb? Or had he conned her into thinking that she was in charge? Had Kyle always wanted to be a girl? Or was this some newfound fantasy? Or was there some more innocent, more boyish explanation for his wearing pink?"

She desperately needed to know. Her mind went traveling for a signal from Kyle. "Give me a sign, my beloved son. Some sort of sign. I need to know what you want from me. PLEASE -- so I can help you."

Her right hand soon found the answer. She had been sitting on Kyle’s unmade bed as she anguished over the panties, and her hand had nervously been wandering. After a while, distractedly, it started smoothing his bedding.

With so much disorder in her life it wasn’t surprising that she began to arrange Kyle’s bed. And yet, Barb would always believe that her hand started fluffing Kyle’s pillows because her son had sent her a telepathic message. She was certain for the rest of her life that his mind had told her to look under his spare pillow, so that she could find there the breast forms – the two smoking guns that proved that Kyle was having a shootout with his own masculinity.

She had grabbed one of the forms, and had run for the door as though she were trying to dispose of the ‘evidence,’ but her legs had crumpled before she could make the hallway. She dragged herself back to Kyle’s bed where she now sat weeping.

For an hour she sobbed hysterically. Later she would have been hard-pressed to have told anyone what was going through her mind as the tears erupted. Though no one, not even Kyle, ever asked her what went through her mind during that first hour after she found the tell-tale evidence of her son’s ‘transsexuality,’ Barb would probably have answered: "At first I lamented the death of my son, and then I wept for joy at the birth of my daughter."

This was far from being the last occasion on which Barb tearfully mourned Kyle or welcomed Demi. Over the next few months she frequently wept over the great transition in her family’s life, but Kyle rarely saw those tears, for his mother was a resolute woman. She was not going to weigh him down with a mother’s cares.

And she was not going to waste this vital morning in weeping!

"Shape up, Barb!" she told herself. "Kyle needs your strength. Kyle needs you to shop for him. Kyle needs his mother."

She shouldn’t have said his name three times. That was a mistake. It took another half hour before she could stop crying.

But then, dry-eyed, she hurriedly dressed and rushed off to Macy’s. As she drove, she thought about the cost of the breast forms. Their quality meant they had to be very expensive. How then, she wondered, did Kyle acquire them? Briefly she worried that Kyle somehow had shoplifted them, but she quickly set that apprehension aside, when she realized that no women’s store would allow a fourteen-year-old boy anywhere near such an intimately feminine item. She also dismissed the evanescent fear that Kyle had bought the forms with stolen money, for she knew her son well enough to appreciate that he could never have summoned the courage to buy ‘boobs.’

No, they had to be a gift; and Barb just ‘knew’ who had given her son his very own breasts: Elvira Lancer. Who else could it be? The woman owned a Mercedes, and reportedly had done very well out of her divorce. She must have given Kyle the forms to please her son. Barb was beginning to wonder whether Steve actually was gay, for he seemed to be so enamored with females that he wanted Kyle to become one.

While she didn’t know what to make of Steve, Barb had a definite opinion of Elvira Lancer – namely, that she was a meddling busybody who had no right to put breasts on Kyle.

"What gall!" steamed Barb. "She deprived me of an important moment with my son. I should have been the one to buy him the breast forms, so that I could prove that I accepted him whoever he was, whatever he was." She resolved to tell Elvira off at the first opportunity.

Meanwhile Barb had shopping to do. While she had lost the opportunity to demonstrate her support by supplying Kyle with his first female prosthetic, she could still prove she loved him by buying all the clothes, shoes and jewelry that he would need if he really, really wanted to proclaim to the world, "Look at me, I am woman!"

At Macy’s she started in girls’ lingerie, starting with practical cotton goods, for an Iowa winter was looming. Even so, the bras, the panties, and the two nightgowns had as feminine a cut and look as possible. She emphasized pastels, especially pinks, as well as flowered prints. The cotton nightgowns were extremely short with plenty of pink or yellow ribbons and lace to announce their femininity. When wearing them, he would be continually flashing his panties.

Then she moved on to the slinkier lingerie. She was lost in thought, pondering whether black lace was too mature a look for a fourteen-year-old when suddenly she felt a tap on her shoulder. It was, she recognized, the salesgirl who had helped them to outfit Kyle in lingerie the first time.

"Welcome back," chirped Melanie. "You’ve been here before, right? You were with your son, right? What was his name? Ah yes, I remember. It was Kirkdirk, wasn’t it? How could I ever forget that name?"

Barb had forgotten Kyle’s pseudonym, and so she corrected Melanie: "I was here with my son, but his name isn’t anything as preposterous as Kirkdirk. It’s Kyle. He helped me shop for ...," she paused while she struggled to recollect their lies, "... his sister."

"But ma’am, I thought his sister is named Kyla. Kyle? Kyla? That’s cute. They’re twins, right? I remember now that Kyle really enjoyed picking out clothes for his sister. Being a boy, he didn’t want us to know he was having fun in girls’ wear. But he did have fun, didn’t he?" She then winked at Barb.

"She knows," Barb thought. "She’s a lot wiser than I am. She knew from the start that Kyle was buying clothes for himself. She also realized that Kyle probably would have preferred this – and she held up the black lace panties – to the unisex underwear we bought him."

Barb decided she had to talk to someone about Kyle’s cross-dressing. It was a secret too big to keep to herself. It was crushing her. And since Melanie already seemed to understand as much about Kyle’s hidden desires as did his own mother, Barb opened up to her. Haltingly, shyly, Barb said: "The clothes were for Kyle, but you knew that already, didn’t you?"

"Of course, I did, ma’am. May I use your first name so you’ll feel more comfortable talking with me?"

"Yes, by all means. I’m Barb, and you’re Melanie, right? That’s what your name tag says."

"Barb, your son is far from the first boy to be shopping in this department. Granted he’s younger than most, but few teens are lucky enough to have an understanding, compassionate mother."

"Is that what you think I am, Melanie? Understanding, compassionate?"

"Of course, you are, Barb. I remember that you wouldn’t let us tease Kyle. I noticed. I couldn’t help but notice. You love him a lot, don’t you? And you’ll do anything for him, won’t you?"

"Yes," she sighed. "Am I so wrong in helping him become whatever he wants to be, that he needs to be, even something that the world ... scorns?"

"Not at all, Barb. Everyone should have a mother like you. You’re not forcing Kyle to wear girls’ clothes, are you? It’s his choice, right?"

When Barb nodded twice, Melanie said, "Then let’s go shopping. I see that Kyle has reached stage two. I noticed last time that he wanted a unisex look -- in other words, girls’ clothes that, if you didn’t look too closely, might be mistaken for boys’ wear. But, judging from those pretty panties you’re holding, things have changed. He now wants to look as feminine as possible. Is that true?"

"Not yet at school, Melanie. When he goes to school, Kyle still wants to look as masculine as possible in his girls’ clothes. But I think it’s going to be different from now on after school. He’s got a big date tonight, and I just know that he’s going to want to look as pretty as possible."

"Do you think there is any chance that Kyle’s date is going to get a peek at his undergarments?"

Barb thought to herself: "We’re talking about hormone-crazed teenage boys. Can there be any doubt that Steve will be trying to get into Kyle’s panties?" The answer could only be yes, and so Barb affirmed, "Yes, it could happen. This is an important date for Kyle. I want to buy my son something special to wear. What do you recommend?"

"Well, I know from his last visit to the lingerie department that this is what he wants to wear. He couldn’t take his hands off it. I thought he’d leave permanent fingerprints." She then held up a bright pink satin bra-and-panty combination that she said cost only $25. "Why not buy two of them?" she asked, as she assured Barb that Kyle craved a touch of satin.

"Are you sure this is what my son wants?"

"Barb, trust me. I know just what your son really wants. I was watching him carefully when he pretended to want to dress in as drab and as masculine colors as possible. And I can tell you that the more feminine colors, especially pink, turned his crank. His eyes, his hands, even his nerves -- they gave him away."

Was Melanie being entirely honest? Did she truly believe that Kyle wanted to dress in feminine finery? Possibly. But she probably had mixed motives. As Melanie figured it, she couldn’t lose by talking Barb into buying expensive lingerie for her son. It didn’t matter whether Kyle hated it or loved it, wore it, or rejected it, for Barb would score points with her son for caring, and both mother and son would learn the limits, if any, to Kyle’s fetishism.

So long as the clothes never came back to the store, Melanie was a big winner. Her manager would be thrilled to see some of the silk and satin items finally sold. They had been gathering dust now that teenage girls favored the unisex look. And so, Melanie did what salesclerks do: She sold Barb on as many and as expensive outfits as she could.

Barb spent forty-five expensive minutes buying lingerie for Kyle. As Melanie toted up the impressive bill, she confided: "It’s fun to outfit Kyle. Please tell him that if he wants to do his own shopping that I won’t tease him again. I’ll make sure that everything fits his -- how shall I say it? -- his unusual physique."

Barb gave the salesgirl an exuberant hug, and then went off to look at tops, pants, shoes and dresses. In girls’ outerwear she found Chelsea, another familiar face, at work. Thanks to a call from Melanie, Chelsea already knew that ‘Kirkdirk’ was getting outfitted for a big date.

She and Barb readily agreed that he should have a choice of fashion jeans or dresses -- whichever best suited his mood. For pants, Barb bought black velvet bootlegs; red Spandex, stretch red moleskin flares; and a pair of dark blue Capris with a white tropical border at the leg hem, She thought Kyle might like the Capri pants best because they didn’t have a ‘boyish’ zipper in front.

The tops she kept simple. She decided against blouses, for young teenage girls didn’t seem to be wearing them these days. And so, she selected several striped, acrylic, vee-necked tops with three-quarter length sleeves. One or two of them were short enough, she noted, to give Kyle a chance to show off his navel. Certainly, they were tight enough to show off his breast forms to advantage.

In addition to two plain skirts, she also bought two dresses. She figured that Kyle was, at present, unlikely to wear any dress if it struck him as too ‘feminine,’ and so she adopted ‘masculine’ blue as her fashion motif. One was, therefore, in royal blue cotton batik, with a white hem; and the other, a more formal, square-neck dress in poly-mesh, with silvered floral embroidery. It had an empress waist.

"When he’s wearing that dress on his date with Steve," Barb reflected, "my son will feel like a queen."

Certainly, he’d be feeling half-naked, for the skirts and dresses all revealed a lot of thigh. And if he weren’t careful, he’d be showing off his boyhood when he spread his legs too wide.

Kyle also gained three new pairs of shoes: first, for everyday use, burgundy-colored sneakers in faux snakeskin and padded heels; plus sueded, black Maryjanes, with a t-strap, two-inch heels, and three floral appliques at each toe; and finally, black slip-on shoe boots with red and white floral insets at each toe and outside heel. The heel was the highest yet, by one quarter of an inch. There would be nothing higher, for Barb didn’t want her son to embarrass himself by falling flat on his ankles.

And then the shopping expedition abruptly ended. Her watch demanded that Barb go to work. She had spent so much money on new clothes for Kyle that she couldn’t afford to take the full day off. Indeed, she’d have to find an excuse for paid overtime.

Weighed down by her bags, Barb exited the girls’ department with a bowed head. Hence she did not see Joannie and Virginia as they passed her. Joannie noticed her first. Excitedly, she tugged on Virginia’s sleeve and whispered, "Did you just see Demi’s mother? She’s been shopping in the girls’ department. That’s super! That means that Demi is going to have some great new outfits!"

"That’s nice, dear."

"Gran, we don’t have much time, do we?"

"No, Joannie, I do think we should have gotten an earlier start on the day. But you did insist on going to a pancake house for breakfast. It took so long you’d have thought they had to thresh and grind the buckwheat themselves. And now, I reckon we have only about an hour before we have to head home and get you ready for school."

"I’m not sure we even have that much time, Gran, for I want to make sure that Demi and her friends see my new outfits at lunch, so that there can be maximum buzz."

"What a strange girl," Virginia thought, "first she won’t wear girls’ clothes, and now she wants the whole world to know she’ll be doing it."

It then occurred to Virginia that her granddaughter mainly craved attention. After all, she was an orphan, and one grandmother could not replace two parents. Maybe the girl felt neglected.

"Is it possible," Virginia wondered, "that Joannie has been wearing boys’ clothes to school merely to get noticed? Maybe, she figured it was better to be notorious than to be a nonentity. It’s so easy to get ignored at High School if you’re not limber enough to be a cheerleader, or conniving enough to run for the booster club or student government."

"Are the boxer shorts merely an attention-grabber? And if they’re no more than that, then how genuine is Joannie’s ‘lesbianism’? Heaven knows that she’s shown interest in boys in the past, and as recently as two weeks ago she was talking a fair amount about one of the boys at school."

"Now, what was his name? It starts with a K, doesn’t it? He’s one of the K generation. Let me see: Is it Kirk? No, not Kirk. How about Ken or Kevin? No, too old-fashioned. What about Kyle? That’s got to be it. I’ll have to ask Joannie what became of Kyle. Maybe, I can arrange some sort of date between Kyle and Joannie. But first, I’m going to have to learn his last name."

"Gran, you just agreed we’ve got to rush, and there you are lost in thought. What were you thinking about?" queried Joannie.

"About you, dear. I was thinking about how much I love you, and how I want to do what’s right by you."

Virginia then realized she needed some time for reflection: "I’ve got to think this through. Is Joannie a lesbian? Or is that a façade? Demi’s a lesbian and she’s so much more masculine than Joannie. They’re scarcely the same gender. What’s really going through my daughter’s mind? What is the true nature of Joannie’s relationship with that Demi? I need a few moments to myself to think."

She then told a white lie to Joannie: "There’s something I need at the drugstore. Can you start your shopping while I go pick it up?"

"This is perfect," thought Joannie. "I won’t have to know what Kyle’s mom said to the salesgirls, whether she said she was shopping for Demi, for me, for Kyle, or for his girlfriend Pocahontas. I won’t need a name. I can get the information from the girls before Gran gets back from the drugstore."

Needless to say, she told her grandmother to take her time, that there would be no problem picking out a few clothes in her absence. As they parted, Joannie headed off in a rush to the jeans department. The one item she just knew she had to have was a pair of boot-cut jeans with plaid pockets and a plaid hem -- just like Kyle’s.

As Joannie hunted for the jeans, she encountered Chelsea. They got talking, and it did not take long for Chelsea to admit that cross-dressers did occasionally shop at Macy’s.

"Why," Chelsea confided, "we even get mothers buying for their sissy sons. There was one this morning. Believe it or not: She purchased four skirts and dresses for him. Can you imagine that? What a strange world we live in!"

Joannie claimed to be intrigued: "What sort of dresses would a mother buy for her son?"

Soon enough all the clothes that Barb had bought that morning from Chelsea were on display. They agreed that Barb had good taste. Chelsea then exclaimed, "If I were younger, I wouldn’t mind that batik-print dress myself."

"Nor would I," Joannie enthused, as she thought about going out on a date with Demi in identical outfits. Could she ever get Kyle into a dress? "Just watch me," she answered to herself. And then, to Chelsea, she said, "I want that dress. In fact, I want to buy everything that lady bought for her son."

"You want to dress like a transvestite boy?" Chelsea asked dubiously. Yet, looking more closely at Joannie, she realized it was a stupid question. "My god," Chelsea told herself, "this girl is dressed in boys’ clothes. She’s even wearing boxer shorts. She must be a lesbian. This beats everything. I never thought I’d be selling the exact same clothes to a bull dyke and to a sissy queer. I guess it’s true what they say: All extremes eventually meet at a common point. A messed-up girl and a screwed-up boy -- I guess they would want to wear the same things!"

Once Chelsea decided that she approved of Joannie’s dressing like a girl, she threw herself into the project of duplicating Kyle’s wardrobe. She was even willing to call up his earlier purchases on her computer terminal, so that Joannie could buy his ‘drabwear,’ including his khakis and plaid jeans.

Saying that Chelsea should put the clothes to one side until she could come back with her grandmother’s credit card, Joannie headed off to girls’ shoes and lingerie. By the time, she reached both, Chelsea had been on the phone to Melanie, who eagerly helped Joannie to replicate Kyle’s lingerie collection.

Melanie didn’t buy Joannie’s story. She judged it ludicrous. To Melanie it was obvious that this girl had to be Kyle’s big date. She was surprised, for she had inferred from Barb’s comments that Kyle was gay. Perhaps Kyle’s mother had never met the girl; perhaps they had only waved at each other from a distance. In that case, given the way this girl dressed, Barb may have mistaken her for a boy.

Melanie chuckled: "Wow, will Barb ever be surprised when Kyle knocks up his ‘boyfriend’! When that happens, I wonder which one of them will wear the dress at the shotgun wedding? I guess it will be both of them, since this girl seems to want to dress just like Kyle. These kids are weird enough to be on the Jerry Springer show."

Yes they were, weren’t they? That afternoon Melanie was too ‘sick’ to work, as she went home to call the Jerry Springer, Sally Jesse Raphael, Rickie Lake, Montel Williams, Rosie O’Donnell and Vera Smuttee shows to pitch the idea of a show on teenage boys who dressed exactly like their girlfriends. The sundry producers were, as she expected, exceedingly interested -- that is, until they found out that she was representing a fourteen-year-old boy.

"That was too young, there’d be too many legal complications," all but one of them said. The lone exception, Ima Wilde, said that there might be a place for Kyle and his girlfriend on the low-rated Vera Smuttee show, but only if one or both of the teens was prepared to have a sex change.

"I tell you what," said Ima. "We can promise you a finder’s fee of $1000 if the teens are so keen on looking alike that the boy is willing to get breast implants. You tell him that we’re ready to pay for the entire procedure provided that he and his girlfriend agree to appear on the show twice, once dressed as boys, and the second time dressed as girls. You tell this Kyle that we’ll pay him extra if he bares his chest on the first show, and lets us see a lot of cleavage on the second. It goes without saying that the girl will have to show our viewers enough décolletage to convince the audience that she’s for real."

"Can you set this up?" Ima asked. "There’s a thousand dollars for you if you can."

"Can I? You bet I can. I guarantee their appearance."

As she got off the phone, Melanie had a huge smile as she thought of the $1000 and of the fame she’d get for arranging for Kyle to become the first teenage boy in America to get his new tits on a national TV program.

"One or both of them will be back again to shop. And when they do, Plan A will go into action. Kyle, honey, I pledge that you’ll soon not only have the best bust line of any school boy in Iowa, but you’ll be the most famous teenager in the country."

How was Melanie going to persuade him to change his sex? She wasn’t yet sure herself how she’d manage it, but she was going to work on a plan. Where there was a will, there had to be a way. Besides, the boy was obviously a transsexual and simple charity required her to help him to acquire a body worthy of the girls’ clothes he was rapidly accumulating.

Even as Melanie hatched her plot to bring Kyle and Joannie closer -- so close, in fact, that they’d be wearing the same bra cup, Virginia was trying to think of ways to break them apart. She’d decided earlier that day at Starbucks, where she’d gone after leaving Joannie to shop for herself, that she had a duty to end their affair.

After all, why should she allow a lesbian to date her daughter, when Demi’s own mother wouldn’t permit them to be together under her own roof! Joannie had said that Barb James was totally opposed to her daughter dating another girl. This news Virginia had found profoundly unsettling, for Barb was the most tolerant person she had ever met.

She remembered the first time she had ever seen Barb James. It had been at a public meeting, and Barb couldn’t have been a day older than eleven years old. But she bravely came to the microphone to appeal for a compromise in the town’s acrimonious dispute over whether public buildings could have Christmas crèches with the baby Jesus in the manger surrounded by his mother and a host of special invitees.

Barb had suggested that every religion could have a place in the manger scene: "The Wise Men could, you know, carry signs saying they were Jewish, Muslim and Hindu. And the shepherds could be, you know, Buddhist, Confucian, Shinto, and whatever you want. And feminists could be satisfied, you know, by the Virgin Mary having a label sewn onto her robe saying she’s a Wiccan."

The speech was unforgettable, if only because of the ensuing riot. As Virginia dodged flying chairs, she realized she’d never forget little Barb James. And since then, Barb had never let her down -- until now. As an adult, Barb had fought for the right of Shriners to march through Arab-American neighborhoods, for the right of Catholic women to wear priestly dresses, and for the absolute right of free speech, even for those who talked during film-showings. Barb had even sought a court order to require the zoo to release its caged animals on their own recognizance.

And if a woman with this record could not tolerate having her daughter date another girl, then why should Virginia? Why indeed? It especially galled Virginia that Barb might think she was protecting Demi if she kept the two girls apart.

"Demi? What a laugh," Virginia thought, "that girl is as gay as Dame Edna. She’s quite clearly the hunter, and Joannie the hunted. I doubt very much that Joannie is in fact a lesbian. She’s merely confused." If that were the case, then Virginia had a duty to kill this romance with Demi before it became too serious and changed the course of Joannie’s life.

Certainly their affair had to end before it climaxed. Judging from the hints that Joannie had been heavily dropping since summer camp, her granddaughter had fooled around sexually with Demi as well as Monique, the French girl. Even so, the three of them apparently had been too callow to know either that they should, or could, bring each other to orgasm. In that sense, Joannie was still a virgin. Possibly she had never truly soared, even in solo flight.

Had Demi ever experienced an orgasm? Virginia wasn’t sure. The girl was too homely to have had many dates with either sex. And yet, Demi struck Virginia as the type who’d ‘put out’ on her first date. Given enough practise, it was likely that Demi had learned, if only by trial and error, that she had an ‘O’ spot. Certainly, the girl’s hands had once or twice wandered -- or so Virginia had noticed -- towards her own crotch, as though she were a teenage boy bent on playing pocket pool. It seemed unlikely that Demi had never had an orgasm.

By the time she had finished her coffee, Virginia had come close to deciding that she would do her utmost to keep Demi away from her granddaughter. She wanted Joannie to date boys first. Let one of them give Joannie her first orgasm -- before the butch lesbian did.

"Why not that Kyle she talked about?" mused Virginia. "Better Kyle than Demi."

Virginia’s resentment against Demi increased fourfold when, having returned to Macy’s, she saw the size of the bill she was being asked to pay so that Joannie could dress ‘just like Demi’. Virginia decided that she could no more afford this affair financially than could Joannie handle it emotionally.

Virginia decided, even so, to pay for the several shopping bags of clothes that Joannie had selected, so that her granddaughter would not suspect that Virginia was now intent on scuttling the relationship with Demi.

Joannie must never know, of course, that Virginia had sabotaged Demi’s chances. Accordingly, Virginia spent the rest of the afternoon alternately cooking a chicken for Joannie’s date with Demi, and hatching a scheme to cook Demi’s goose.

Joannie was meanwhile enjoying the turmoil at Hoover High. She had predicted to Kyle that her attending school in girls’ clothes would unleash considerably more gossip than had his cross-dressing, and was she ever right! And she was right despite the fact that Kyle’s clothes had finally sparked speculation in some quarters as to whether he was, in fact, dressing like a girl.

The plaid jeans had been his undoing, despite his best efforts to hide their telltale hem in stylish cowboy boots that he’d borrowed from his mother. He’d endeavored to hide the plaid lining of his front pockets by keeping his hands in them, and despite some dirty looks from his English teacher, who suspected Kyle -- with some cause -- of playing with himself during Cynthia Parker’s recitation of the balcony scene from Romeo and Juliet, Kyle had managed to keep the plaid a secret until lunchtime.

Lunch had started off well, as two more students had joined Kyle, Steve and Tim at their table. He was beginning to feel popular again, and as the five joked around, Kyle had forgotten his plaid predicament. As he waved around his hands, demonstrating the jump shot that Michael Jordan had taken to win Chicago its last NBA championship, Amana Bormann happened to notice the plaid.

It was unfortunate for Kyle that Amana had a keen eye for fashion, for she not only resented any boy who wore her favorite jeans, but she was also romantically interested in Tristin, the boy who had replaced Kyle in the black-shirt gang. As Tristin so far had been more interested in hanging out with boys than in dating girls, Amana figured she’d finally get his attention by teasing him with the news that Kyle James, a one-time associate of his new crowd, was a sissy who cross-dressed.

All but one of the gang scoffed at her news. Only Jason took her seriously, and he was, to her surprise, utterly hostile to Kyle. Until then, she’d thought him Kyle’s best friend. Yet Jason now announced that he was going to ‘beat the living crap’ out of Kyle as soon as school let out for the day. In the meantime, he glared in Kyle’s direction, all the while muttering about betrayal and humiliation. Amana even thought she heard him say, "What are they going to say about me?"

That comment got her wondering. It also got her gossiping: In minutes, word surged around the cafeteria that Kyle and Jason had been lovers. The news overshadowed the speculation as to whether Kyle was wearing girls’ clothes, for the ninth grade found it more fascinating to speculate about who was taking his clothes off, than who was putting them on. When the gossip reached Jason, he had one more reason ‘to pound the pansy to a pulp’.

Just as gossip reached a fevered pitch as to whether Kyle was gay and going out with one of the male students – ‘with Jason’ some said; ‘with Steve’ said others – Joannie threw everyone for a loop. She made it clear to the entire cafeteria that she had her hooks into Kyle.

Everyone saw or heard Joannie make her grand entrance into the school cafeteria. She had heralded her arrival by casually knocking two food trays onto the floor. As they clattered, heads rose to witness Joannie stomping down the aisle towards Kyle and his friends. Her walk was even more exaggeratedly male than usual, and the first impulse of the student flock was to cluck sympathetically about the sad case of the "girl who wants to be a boy."

But then, suddenly, the ninth-grade boys became silent, as their lower jaw sagged. Their mouth agape, their tongue feverishly moistening their lips, they watched in amazement as Joannie’s ample breasts passed near their tables. Even some of the senior students became slack-jawed in stupefaction. Could it be? Could Joannie, hitherto, the girl with the flattest chest in the ninth grade have overnight become buxom?

Males fell to chattering: The question on every lip was, "Are they real?"

Meanwhile, the ninth-grade girls had fallen silent, as they puzzled over Joannie’s new look. It was less masculine than usual, they agreed, and might even -- incredibly -- include an item or two of girls’ clothing.

It was, however, when she sat down heavily, and somehow noisily, beside Kyle that the tongues of Hoover’s girls began wagging: "They’re dressed alike! And they’re wearing the same jeans! They’re obviously a couple. But if that’s true, are they both straight? Didn’t Joannie say she’s a lesbian? Didn’t we just hear that Kyle is dating Jason? Or was it Steve he’s dating?"

Well, if he had ever been dating boys, he apparently wasn’t doing it any longer, as Joannie made abundantly clear, for she ostentatiously put her arm around Kyle’s shoulders. She then beamed triumphantly to the room: "This boy is mine."

Steve looked dismayed.

The buzz then switched to the meaning of plaid. A boy and a girl were wearing the very same jeans. One of them was cross-dressing. That was the logical conclusion. But which ? Joannie or Kyle?

The consensus was not unanimous, for a few of the guys believed Jason’s story, now going the rounds, that Kyle had been in drag for days; but nine out of ten Hooverites believed that Joannie was the cross-dresser, as before. Apparently she and Kyle had agreed to wear the same boys’ clothes to announce they were going steady.

How cute! How drole! In fact, so convinced was Hoover High that Joannie was still dressing like a boy, that any girl who admitted to owning plaid-hemmed jeans was being ridiculed for having been conned into buying something that must have started off as winter wear for effete Scottish males.

"What’s next?" they were asked, "Will you be buying a man’s kilt and calling it a skirt?"

Not everyone took the joshing in good humor, least of all Jason. He tried to convince the black-shirt gang, indeed anyone who’d listen, that they should strip Kyle of his outer clothes and leave him in the girls’ locker room wearing only his underwear. "If you do that," Jason promised, "you’ll find out that Kyle’s a sissy wearing a bra and panties."

Temporarily, it seemed that Jason would be able to assemble his posse. However, Derek broke the mood by saying that it was up to Jason to settle his own accounts – if he were man enough. "We’ll watch you whup Kyle, but we’re not going to help. You can beat up a sissy by yourself, can’t you, Jason?"

"Sure," said Jason. He expected, as before, an easy victory. And this time he’d get his trophy: Kyle’s bra. If all went according to plan, Jason would wrest the bra from Kyle’s prostrate body, and then, by waving it about in the air, establish his own veracity and Kyle’s duplicity.

By publicly humiliating the cross-dressing boy, Jason would dispel the foul rumors about his own sexuality. Then everyone would know that Jason despised, rather than loved, Kyle; and that it hadn’t been Joannie, a girl, who had come between the erstwhile friends, but rather Kyle’s freakish perversions.

Kyle realized he had no choice but to fight Jason, and he came to the schoolyard ready to rumble. He had the backing of his newfound friends, including Steve, Tim and Joannie. They were numerous enough to persuade the black shirts that no one would interfere in the fight. It would be up to Kyle and Jason to prove which one of them was the better man.

Kyle held out his arms in front, motioning towards Jason to begin grappling. Jason was only too pleased to wrestle, for close-in fighting would him to tear off the sissy’s bra. Jason extended his arms and grabbed Kyle. Jason looked smug. Kyle looked terrified.

Briefly they danced, and then Kyle, absolutely without warning, kneed Jason viciously in the groin. Jason crumpled to the ground, a shocked grimace replacing his smug grin. As he lay writhing on the ground, Kyle kicked him hard in the butt. "Take that, creep. What goes around comes around, you stupid jerk."

Heads nodded, and Derek spoke for all: "It’s true. Jason was the first to fight dirty. He did it to Kyle the last time. Jason got what was coming to him."

There was, therefore, no thought of avenging the stricken boy. Any notion of stripping Kyle of his clothes and dignity had vanished as he stood glowering, his fists clenched, and his body tensed for battle.

Kyle was safe. No one was going to mess with him today. His friends were duly impressed; and Joannie was downright awestruck: "Super cool. My boyfriend’s got to be the toughest dude in the whole world to wear a bra."

When he saw that he controlled the field of battle, Kyle relaxed. He signaled to Joannie that should leave (before the black shirts changed their mind), and they headed off in a quick step. After a couple of blocks, however, they stopped to catch their breath.

Joannie then grabbed Kyle, pulled him to her, and gave him a big wet kiss. "You were fantastic, Kyle James," she gushed. "You’re all man even in a bra and panties. I just know you could whip everyone of those boys even if you were wearing a dress, even a blue batik dress."

Kyle looked at her quizzically: "How come you mentioned a blue dress? Why blue? And why does it have to come from a boutique?"

"Because I know you own two blue dresses, silly. I saw your mother buying them for you this morning."

This was not news that Kyle wanted to hear. Their moment of pastoral tenderness gave way to a storm of wrath: "What’s come over her?" he thundered. "My mother is crazy! All you women are crazy!"

The sparks flew, as he demanded that Joannie affirm that she knew full well that Kyle never had, and never would, want to wear either a skirt or a dress.

She answered with lightning speed: "Of course, I know that. But your mother does care for you. She thinks you want a dress. She paid a lot of money for it. You’ll make her cry if you throw a tantrum when she shows you the two dresses she’s bought you. You don’t want your mother to cry, do you, Kyle?"

"Of course not. She’s everything to me. She’s the only family I’ve got."

"Do you love her enough to wear a dress when it’s just the two of you at home, when there’s no one else about, when there’s no one else to see you?"

When Joannie put it that way, Kyle had no choice but to affirm: "I’ll wear the damn dress once, just once, if that’s the only way to stop her from bawling."

Joannie kissed him again, as she purred, "Kyle, you’re the sweetest boy in the whole world. I know you’re going to keep your promise. You’ll wear that dress if she asks you to. Right?"

Glumly, Kyle nodded. Then he said: "I’d much rather wear pants, even these sissy jeans with the plaid hem and pockets." Then he looked down to confirm that she was wearing the exact same jeans. Kyle asked, "Did you get those today? What else did you get?"

"I got all the same clothes as you, Kyle. I saw your mother shopping at Macy’s and I had Melanie and Chelsea, the salesgirls, find me exactly the same clothes as your mom bought for you."

He pondered the implications of what she’d just said. He then asked: "Are you saying that you bought some dresses, that you now own a blue boutique dress, just like me?"

"Yes, isn’t that great, Kyle? When Demi comes to my house, we’ll look like twins. Isn’t that cool?"

"You’re not hinting that I should wear the dress tonight, are you? Because there is no way in the world that I’ll do that. If my mother insists, I’ll wear a dress around the house. But outside it? No way! Not even in the back alley. If someone saw me in a dress, I’d have to leave town -- in a big hurry."

"I don’t want you to wear a dress tonight, Kyle, because I’m definitely not ready to wear one myself. But I do think I’m ready to wear the black pants I bought today. I will wear them, if you wear yours. Is it a deal?"

Black? That didn’t sound so bad. How feminine could they be? And, in the dark of the alley, who’d even notice them? Kyle agreed to wear his new black pants, as well as a complementary striped top. However, he specified that he wouldn’t be coming over until the sheen of the pants faded into the lengthening shadows of twilight.

They parted. Joannie blew Kyle a kiss. He caught it with his right hand, and then released it like a prayer skyward. He skipped homeward.

Half an hour after his arrival, Barb came staggering through the doorway. Joannie had been right about the shopping expedition. He had never seen so many bags. His mother had bought enough to outfit a harem. And were they all for him?

"Cripes," Kyle gulped. His mouth began working like a guppy’s in a dirty fishbowl. Suddenly, and desperately, he needed a drink -- of water. He began to wonder what those black pants looked like. Had he been tricked? However, the fear soon fled, for he fully realized that black pants would be much easier to explain away than a blue dress. He hoped he’d never have to wear it. After all, blue didn’t really go with his complexion.

To Barb’s surprise, Kyle was keen to see the pants she’d bought him. He went rummaging through the bags, casting bras, stockings, slips, and panties about, as he looked for them. And then, when he’d found the black velvet pants, and to his immense relief, found no sissy flowers or teddy bears on their back pocket or legs, he insisted on trying them on -- right there in the middle of the living room.

Barb had her earlier suspicions confirmed as he flashed his pink cotton panties as he changed trousers.

He actually seemed to like the fact that they had no back pockets, as he attempted to twist around sufficiently to see his right hand caress his buttocks. As he preened, Barb noticed that some of his postures and hand motions were quite ‘feminine’.

"Deliberately? Subconsciously? Accidentally?" She wondered. She was dumbfounded by his apparent eagerness to wear black velvet: "It’s not yet a skirt or a dress," Barb thought, "But I never thought I’d again see Kyle actually want to wear girls’ pants. I thought those days were long behind us, a passing pleasure of his childhood."

Keen surprised her again by excitedly asking to see the tops she’d bought him, and to her amazement he delighted in one with three-quarter length sleeves and an especially audacious plunge to its vee neck. All that Kyle noticed was its color complementarity with the pants he planned to wear on his big date with Joannie. But Barb noticed that he was wearing a white sports bra, and that even after he’d put on the top that she could tell that her son had not an ounce of fat on his lower abdomen, and an ‘out’ belly button.

"Do you really want to wear that top on your date, Kyle? Don’t you think it’s a bit revealing?" As she spoke, Barb reflected that she never thought she’d be worried about her son going out on a date looking ‘too easy’.

Mentally Barb slapped herself: "What are you worrying about? Kyle may be signally that he’s a rather ‘loose girl’ by wearing that top with that bottom, but he’s not in any danger of getting pregnant." Then she thought of AIDS -- boys could get that, couldn’t they? -- and later, before he left for his date, she slipped two condoms into the leather bag he was taking with him on his date.

Kyle thought the top would do. After all, it didn’t reveal his bra or its straps. As for showing off his navel, many of the guys were cutting off the bottoms of tee shirts that had shrunk in the wash (perhaps during the first time they’d been coerced into doing their own laundry), and wearing them almost like sports bras as they played sports. He’d thought it a super look -- very macho -- and saw nothing wrong with showing off his navel to Joannie.

To Joannie, mind you, but not to Steve. If Joannie got ideas about Kyle’s sexual availability, that was all right with him. However, he’d feel uncomfortable if Steve were to have a chance to stare at his navel, and so Kyle made a mental note not to wear this top, or any others like it, in front of Steve. After all, it was one thing to invite a girl to marvel at his taut, narrow waist, it was quite another to have a gay boy ‘ogle’ him.

Yet Kyle then surprised himself with this wayward thought: "I’ll have to be careful where and when I wear this outfit, for it won’t be just Steve who will be eating me up with their eyes, it will be all the boys."

This thought perturbed him: "Jeez, why did I say ‘all the boys’? I meant all the gay boys, right? Didn’t I? Could any regular guy find me a turn-on in girls’ clothes? What a bogus idea!"

Kyle realized that some part of him -- in his own mind, an infinitesimally small part -- considered cross-dressing to be a high-risk adventure. To go out in public looking like a girl hot for action would, he recognized, be as risky as hurtling through rush-hour traffic on a moped.

"It would be an adrenalin rush," he realized. "But it will never happen. Never. For if I crash and burn on my moped, maybe I end up in the hospital with a broken leg, but I’ll still have a reputation for being a regular dude, and my friends will drop by with video games to play. But if I were to flirt with a hetero guy, and if he got a hard for me, then when he found out the truth about my real sex, he’d be so mad that he’d round up a gang who’d break both my legs. And I probably couldn’t get into hospital because none of doctors would be willing to help a sissy queer in a bloody blue dress. Then there’d be no hospital, no reputation, no friends, no video games!"

Kyle accordingly dismissed the temptation to see cross-dressing as another high-risk sport like rock climbing, motorcycling, or para-sailing. He put temptation on the back burner.

Having found the red and black, striped top and the velvet pants a remarkably easy sale to make, Barb found Kyle a difficult ‘customer’ when it came to the rest of his proposed wardrobe. The skirts and dresses he could not put down fast enough, consenting to no more than a cursory inspection to see if the dresses fitted his shoulders. As he promised Joannie, he said not a negative word about either the skirts or the dresses. When asked for a direct comment, he ventured that all of them were "It’s okay."

Slips and nylon stockings he also treated like hot coals, dropping them back into their bag, almost as soon as he had recognized their true nature. Tights, on the other hand, he treated with tender respect, his eyes getting a misty, faraway look as he handled them, as though he were reliving fond memories.

Indeed, he decided the tights would come in handy when winter came and the mercury dropped below freezing. By then, the bet would be over, and he wouldn’t be wearing girls’ clothes, of course, but the tights, well hidden by his Levis, would help shield him against the Alberta Clipper as he raced through Des Moines on his moped. It was so important to be snugly dressed in January that he realized he’d even wear the pink tights, if the others were in the wash.

At first, Kyle gave the panties and bras a casual dismissal. But Barb insisted that he couldn’t go out on a big date with a mismatched bra and panty. She therefore had him look carefully at everything she’d bought him. Barb also demanded that that he say something about each, either negative or positive, so that she could get some idea of his taste.

"There’s no point in my buying satin and silk, which are expensive, unless you prefer it," she advised.

Kyle replied with a variety of grunted remarks that Barb learned to decode: "I guess so" was, she decided, more approving than "I suppose", and both were superior to "okay". The highest praise he could offer, it seemed, was "it could be worse."

The secret of the cipher was the length of the sentence, Barb calculated; the more words he used the better he liked the undergarment. With the code broken, it then became possible to tell that Kyle liked bright colors -- even the pinks, if bold enough, but especially the reds -- as well as satiny-soft fabrics. Indeed, he commented as he held up a pink satin panty, "This isn’t as bad as some."

Six words! A gain of fifty percent! The pink satin panties were clearly Kyle’s favorite, just as Melanie foresaw. The salesgirl seemed to be able to read Kyle like a TG story, and Barb resolved to rely more heavily on Melanie in future for advice as to what Kyle should wear.

Why stop at clothes suggestions? Henceforth, she’d rely on Melanie for basic advice on whether Barb should respond to Kyle’s feminization with the brakes or the accelerator. There weren’t too many people you’d ask whether they approved of a teenager changing his gender. But Melanie, wise beyond her years, seemed like someone whose opinion Barb could trust.

It didn’t take much effort to coax Kyle into wearing the pink satin underwear for his big date. However, the black slip-on shoe boots with red and white flowers on the toes took a major sales job. Yet Kyle’s resistance eventually cracked.

He ‘bought’ three of her arguments: first, that these weren’t the first women’s shoes he’d be putting on, since he had that very day worn his mother’s cowboy boots to school; second, that the shoes weren’t going to make him look any more feminine than did the rest of his outfit; and third, that the shoes went perfectly with both his top and his velvet pants.

Ninety minutes later Kyle was ready for his date. It was definitely with Joannie, even if his mother thought it was with Steve. And for Joannie he was dressed as femininely as possible. He wanted to provide a feminine ideal to inspire her to feminize as well. Thus he had spent most of the intervening time doing his make-up and combing out his hair. This evening there would be no hairspray to de-feminize his look.

Nor would a sweatshirt hide his striped, vee-neck top. And it in turn would do a poor job of concealing his bra strap in back. As the pink satin bra had been lightly padded (as were most of his new bras), Kyle looked a bit like a pre-teen girl in her training bra. His bra forms would, of course, change his shape dramatically. They’d give him a very mature look, but not one he was yet ready for his mother to see.

As he had lots to carry -- a small bottle of perfume, a tube of lipstick, a make-up compact, paper tissues, a hairbrush, a can of hairspray and his breast forms -- Kyle had little choice but to accept the leather shoulder bag from his mother as a "special present for his first date," even though he scorned it as a ‘purse.’

"It’s a pity," Barb mused, "that he doesn’t know that I found the breast prosthetics. But how I could tell him? He’d know that I was snooping." Yet Barb considered it stupid that he was going to have to sneak into the alley before he could put on his breasts. "He’ll probably show up at the Lancers with his breasts inserted upside down. He’ll look like a hapless slob. That will be a real pity. I want Kyle to look as pretty as possible when he’s going out as Demi. He shouldn’t look like a slovenly tart."

Slovenly we can understand, but why ‘tart’? It would seem that the bare midriff rankled. Barb would have preferred a more lady-like look for her son.

But did he look like a girl? Yes, a homely girl, to be sure, but definitely a girl, as everyone who subsequently viewed the video footage she took that night, readily agreed. Kyle, in high spirits, hadn’t even objected when she asked him to "pretend he was a girl" for the camera. Instead, he had camped it up like a small-town transvestite.

As Kyle left the house, Barb called out, "Give my regards to Mrs. Lancer!"

Kyle was non-plussed: "Mrs. Lancer? Steve’s mom? Jeez, my mother just won’t listen. She must think I’m going to Steve’s for dinner." He thought of turning around to yell out a correction, to tell her he wouldn’t be seeing either of the Lancers, but decided not to bother. After all, he had better things to do in life than straighten out his mother.

As Barb saw Kyle head down the back alley for parts unknown, it struck her hard in the gut that her son was, for the first time, leaving the house looking definitely, indisputably, and remarkably like a girl. She cried for almost an hour after he left. Then, dry-eyed, a smile occasionally on her lips, she watched the video she’d just taken, over and over again, of her daughter’s first date.

  

To be continued in Part 7 (which will be, yes, finally, about Kyle’s dates with Joannie and Steve)

 

 

© 2001
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