Basement recreation room, suburban America, sometime in 1986

The iconic contour-fluted lines of the Coca-Cola bottle spun around and around.

The three teenage boys and one teenage girl watched it eagerly.

All four of the teenagers had not long turned eighteen and would soon be going to separate colleges. They had been friends throughout high school and this would be their last encounter before they left.

They had drunk bourbon and coke from paper cups and Grant Butler had produced a baggie of low-grade weed but they had all partook and were more than a little high.

It was Grant Butler who had suggested they play spin the bottle and they had all pooh-poohed him and told him he was an idiot.

“We stopped playing that game in tenth grade,” William Mitchell laughed drunkenly.

“Anyway it’s not fair. I’m the only girl here,” Christine Baker whined.

They were in the basement of Christine Baker’s parents’ house. The basement had been converted into a rec-room, furnished with street find furniture, carpet remnants and bric-a-brac. There was a battered pool table, a Ping-Pong table and shelves of board games. An old but serviceable console television commanded one corner of the room. A record player and a stack of singles and albums topped a cabinet, inside of which was a cassette player and Christine’s collection of cassette tapes. Two black speaker boxes bookended the cabinet.

The place was a little downtrodden but it was their hangout when they wanted to get away from their parents and Christine parents were away for the weekend and would be returning the next day so they could drive her to Rutgers University where she was enrolled in her freshman year.

“Yeah! We need more girls!” Steven Townsend exclaimed drunkenly.

The other girls and boys that the four teens hung around with were spending their last weekend with their families and couldn’t attend the impromptu farewell party. None of the boys and girls had paired up into serious relationships but they had kissed, groped and fondled each other now and then as they coupled and uncoupled as teenagers were want to do. Steven Townsend claimed that Mary Jürgens had once given him a handjob in his car but Mary denied it but Steve was insistent that she had.

A wicked grin appeared on Christine Baker’s face.

“What if we make another girl?” she said, stifling a hiccup.

“What do you mean?” William Mitchell asked.

“You guys spin the bottle and whoever it lands has to become girl,” Christine giggled.

“Fuck off Christine!” Grant Butler rolled his eyes.

“I don’t think so,” William Mitchell joined in.

“You guys are scaredy-cats. Take on the dare. Whoever the bottle picks I’ll take them upstairs to my bedroom and dress them like a girl,” Christine sounded excited.

“You’re fuckin’ kidding me,” Grant Butler whined, concentrating on rolling another joint.

“Come on! Be game!” Christine implored the boys.

“Hey. Why not? It’ll be fun. We’ve all dressed up for Halloween,” Steven Townsend said levelly.

“I don’t think so,” William Mitchell sighed.

“We’re fuckin’ doin’ it!” Steven Townsend growled.

Steven Townsend was the unelected leader of their group. He wasn’t the most intelligent but he was the biggest and strongest of the group and had been offered a college football scholarship. He also had a car whilst the rest of them had to borrow from their parents, so that kinda made him in charge.

And so the three boys sat, anxiously watching the classic Coca-Cola bottle whirl and twirl, each of them hoping it would point to another when it stopped. Christine Baker watched the bottle spin, her eyes lit up with amusement and mischievousness. Whoever was chosen by the bottle was going to be humiliated and get to know what it felt like to be treated like an object. Christine loved her friends but the boys had all at one time or another come on to her and when she had rejected their advances their relationships had changed and they were more distant with her.

She had discussed this with the other girls and they’d had the same experiences, even Mary Jürgens, who despite her protests, the other girls believed that she had in fact given Steven Townsend a handjob.

This would be a chance for Christine to wreak a little revenge but it was all in fun and she was looking forward to dressing up the unlucky winner.

The bottle slowed down and stopped. It was pointing directly at William Mitchell who blushed and he opened his mouth to argue or complain but Steve Townsend shut him down before could start.

“Don’t fuckin’ whine about it Mitchell. You know the rules. The bottle determined your fate now get your ass upstairs and don’t come down until you’re dressed like a girl,” Steve sneered.

“Come on William it will be fun. Like Steve said, you boys have dressed like girls before at Halloween. Didn’t you go out as a wicked witch with us once?” Christine tried to diffuse the dark mood that was descending on the party.

“Yeah but I was twelve and it was a fucking black smock, a homemade pointy hat and a straw broom and my face was painted green; I looked pathetic,” William countered.

“Just do it. You took on the dare. We all did. It could have been any one of us,” Grant Butler chimed in having finished rolling his fatty.

He fired it up and passed it to William Mitchell first who took a huge toke and passed it on. The intoxicating smoke mingled with the alcohol he had imbibed and the marijuana that he had smoked earlier created a calmness that descended over him. What the fuck? It was just a harmless prank and he would get to spend some time with Christine Baker alone in her bedroom.

William got to his feet a little groggily and Christine stood with him, accidently flashing her pretty pink panties which all the boys saw because that’s how they were conditioned.

“Come on Will,” Christine took William by the hand and led him to the staircase.

He liked holding Christine’s hand and he followed her willingly, drawing in her perfume which was something oriental and exotic, his eyes on her pert bottom and long legs, her A-line pleated skirt flapping around her thighs as she walked.

“See you when you get back Wendy,” Steve called out.

“Who’s Wendy,” Will asked, his mind confused by booze and drugs.

“I think that’s you honey. Will is going to become Wendy,” Christine giggled and squeezed his hand and led him upstairs.

William chuckled to himself and followed Christine dutifully, catching a nice eyeful of pink panty as she led the way up the stairs. He’d had a crush on Christine as long as he could remember but then again he had crush on most of the girls in their circle of friends.

She led him up a second flight of stairs to her bedroom.

As soon as he entered Christine’s bedroom Will was swept away by the exotic smells created by the miasma of perfumes, powders, lotions and cosmetics. The wall opposite her twin bed, perfectly made with a pink stain comforter over the bedding and a small arrangement of fluffy toys on the pillows, was taken up by a huge armoire, the doors of which were open revealing an extensive wardrobe of clothes.

Next to the lace curtained window overlooking the tree-lined suburban streets and manicured lawns, was a two-door, four-drawer mahogany vanity unit with a large, lighted mirror. Perfectly aligned in rows were Christine’s cosmetics.

Will had to admit he was impressed. His sister’s bedroom mostly looked like a bomb had gone off scattering her clothing, her makeup and all of her possessions around the room and her bed was seldom made. Not that Will went into his sister’s bedroom very often and he had never been in another girl’s bedroom ever.

Just standing there taking in the feminine opulence was an experience in itself.

“Come on silly, don’t just stand there,” Christine led him to the door to her ensuite bathroom.

“Go in there and strip. There’s a nightie hanging on the back of the door. Put that on. I have lady-shavers and foam under the sink, shave that bum-fluff off your face,” Christine said in a commanding tone.

“I don’t think so princess,” Will baulked.

“The JD and grass had given him courage that he seldom possessed.

Christine took a step forward, put her hands on her hips and loomed over him.

Christine Baker stood five-feet seven inches in her stocking feet; her heels gave her a couple more inches. William Mitchell at five-five, slim-framed with his courage leaving him hastily was no match. He felt intimidated by Christine. He was in her bedroom and about to wear her clothes and Steve Townsend had put her in charge, or so it seemed.

“What am I going to wear under my nightie?” Will surrendered and retreated.

He was hardly aware that he referred to the garment as my nightie.

Christine leaned in until her face an inch away from Will’s.

“You’ll wear nothing Wendy. I’m going to dress you when you come out,” she whispered but her tone was menacing.

William flinched when Christine referred to him as Wendy but it was her attitude that frightened him. This silly game had already gotten out of hand. He had things to do. He was leaving for college soon and his life seemed to be going into a spiral over which he had no control.

“And I’m going to make you look pretty and you can be my girlfriend,” Christine’s demeanour suddenly changed and she smiled at him beatifically.

She kissed the tip of his nose and then softly kissed the side of his mouth and William Mitchell was doomed. He was standing in Christine Baker’s bedroom and was about to get naked in her presence and she had just kissed him. They had kissed before when they were kids playing spin the bottle but now she was a young woman and she had kissed him willingly not because the bottle had decided that she had to. Her bedroom smelled nice and it was ‘girly’ and somehow sexy and Christine smelled nice too and there was no doubt that she was sexy.

Along with her navy-blue pleated little A-line skirt she was wearing a pink V-necked angora sweater that fitted her curves and showed off her perky teenage breasts to perfection. Her legs were sheathed in flesh-toned sheer pantyhose and she was shod in black chunky heeled Mary Jane pumps.

Will stood there looking at her taking in her beauty. She was a redhead, her hair cut in flippy waves with bangs that sometimes fell into her eyes. She wasn’t conventionally pretty, her mouth was little too big and her nose was crooked but she wore plenty of makeup and knew how to use it to good effect. Her style was very eighties forward and Will thought she looked just like Molly Ringwald who was currently starring in Pretty In Pink.

“Go!” Christine pointed at her bathroom door and Will retreated to her bathroom.

He did as he was told and nervously stripped, hanging his clothes on the back of the door having taken down the nightie which turned out to be a sheer black negligée that tickled his knees. He held the silky garment against his face before he put it on, feeling the gossamer fabric on his cheek and inhaling Christine’s scent. He had become slightly tumescent and had briefly considered masturbating to relive himself.

A quick peek into Christine’s laundry basket revealed a tangle of sheer pantyhose, transparent nylon hipster panties and satin full-cut drawers. He would never admit to anyone, not even under torture, but William sometimes stole his mother’s and sister’s panties and nylons from the laundry hamper and masturbated with them.

He shook his head and came to his senses and did as he had been told and quickly shaved the fluff off his chin and cheeks. He came out the bedroom feeling quite silly staring at the floor, barefoot and naked except for the chemise, unable to look up at Christine Baker.

“Your figure is nearly as good as mine. You just don’t have any tits,” Christine smiled at him as he approached her.

Will didn’t have the frame for football or baseball or the bulk for wrestling or hockey. He played tennis and volleyball and enjoyed cross-country running and cycling. The other guys teased him about his slim frame and slight build and he had once opened his gym locker and found a tennis dress instead of his tennis shorts and polo. Steve had pranked him and the other boys had laughed along.

“Just as well because otherwise none of my clothes will fit you,” Christine pushed him down into the chair facing the vanity mirror.

“You’re not really going to really make me look like a girl, are you?” Will smiled nervously.

Christine just smiled at him.

“Shut up and turn to face me,” Christine spun William around on the swivel chair and went to work on his face.

The smell, feel and taste of the cosmetics was foreign to Will but it was also exotic. He felt her putting foundation, finishing powder and rouge on his face and eyeliner, eyeshadow and mascara on his eyes and finally lipstick on his lips.

“Bite down on this,” Christine put a tissue between his lips and he bit down and was surprised to see a lipstick kiss on the tissue.

“That will set the lipstick. It’s long-lasting so it won’t come off when you kiss,” Christine said rather seriously and put a coat of gloss sealer over lipstick.

“No one’s kissing me,” Will said trying not to sound too sulky.

“When they see what I’ve done to you Steve and Grant won’t be able to keep their hands off you,” Christine chided.

“Shut up!” this time Will did sound like a petulant child.

Christine brushed out and teased William’s shoulder length blonde hair. His mullet transformed into very feminine layered shag with bangs. She painstakingly painted his fingernails bright red.

“Can I see?” William asked.

“Not until I’ve finished with you,” here put these on.

She handed him a pair of sheer-to-the-waist glossy tan pantyhose.

“I’ll turn around while you put them on. Step into them one foot at a time and pull them up to your knees, then pull them all the way up around your waist and smooth out the wrinkles,” Christine said and turned her back as promised.

Will’s legs were practically hairless. The few fine blonde hairs he had were shaved for cycling.

He rolled up the pantyhose and put his toes in each of the footlets and pulled them up to his knees as he had been told, then he stood and pulled them up around his waist. What Christine had not told him was how wonderful the nylons felt on his flesh. He masturbated into his mother and sister’s pantyhose often but he’d never put them on and now he knew what he was missing out on.

They felt silky and caressed his skin like featherlight kisses. He was becoming a little tumescent and to make it worse Christine turned around and peeked. He’d had to open the chemise to pull up the pantyhose and she caught him smoothing out the wrinkles.

“Perfect except for one thing,” Christine giggled and flicked the bulge in his crotch with a finger.

“Hey!” Will flinched.

“Tuck it under your crotch and the pantyhose will keep it in place I bet,” Christine laughed.

“Turn around then,” Will said sulkily and she did.

Will managed to awkwardly tuck his penis along his perineum and squeeze his scrotum there too.

“Put these on to help keep that thing tucked away,” Christine handed him a pair full-cut satin panties.

He stepped into them and pulled them up. Christine had not warned him how wonderful the satin panties would feel against his silky pantyhose either. It was doubly amazing and when he pulled them up snugly he was glad his penis was tucked away because it was becoming uncomfortably tumescent. No wonder girls liked frilly, satiny, lacy things against their bodies he thought.

Christine put him in the matching bra and stuffed the cups with balled-up pantyhose and then she put him in a little black velvet miniskirt and purple satin blouse. He had small feet and just managed to squeeze into a pair of Christine’s black open-toe pumps.

She clipped earrings to his earlobes and put a matching choker around his neck and bangles on his wrists spraying him liberally with perfume.

“Now you can look,” Christine turned Will around to face the mirror.

William Mitchell was stunned. Looking back at him was a slim-figured, very pretty, blonde teenage girl with long shapely legs and tousled blonde hair.

“I don’t believe it’s me,” Will whispered.

“It is you Wendy,” Christine laughed and spanked his ass.

“Those two idiots downstairs think I’m going to bring down some clown-faced Halloween gargoyle woman but wait until they get a load of you,” Christine said, obviously proud of her work.

“They won’t really kiss me though, will they?” Wendy said absentmindedly staring at herself in the mirror.

She would certainly kiss the girl in the mirror. She looked like a Wendy and smelled like a Wendy and she even felt like a Wendy, she thought to herself as she smoothed her skirt down her thigh. In his mind, William had become Wendy.

“Careful walking down the stairs,” Christine led him out of her bedroom and down the two flights of stairs to the basement playroom.

“Cover your eyes and don’t open them until I tell you,” Christine called ahead to Steve and Grant and led Wendy into the centre of the room

“Ok you can look now,” she chuckled gleefully.

Steven Townsend and Grant Butler were both astounded and stood there slack jawed staring at Wendy with both awe and bewilderment.

“Jesus! You look like a girl!” Grant stammered.

“No you don’t! You look like a beautiful girl!” Steven corrected him.

Christine brought out her Polaroid One-Step SX-70 instant film camera that she’d been given for her birthday and took a few shots of Wendy who got into the spirit of it and posed. Wendy had expected to be ribbed by the other two boys but when they stood staring at her and making flattering comments she couldn’t help but feel less trepidatious and more comfortable in her skin.

“You tart!” Grant chided Wendy playfully and lit up another joint which they passed around until it was a tiny roach.

The smoke mellowed them out and Christine put ice in four cups and filled them with JD and Coke and set them down on the floor around the Coke bottle.

“Ok. We have two boys and two girls now so let’s play!” she said excitedly sitting down and crossing her legs.

Christine was correct. Steven and Grant had expected William to return looking like a ‘man in a dress’ with clown-like makeup, clomping around in ‘Minnie Mouse’ high heels.

But Wendy was stunning, and taking Christine’s advice to take shorter steps, point her toes slightly inwards and land on the balls of her feet first, she actually glided across the floor sensually and swayed her hips seductively.

“You’re not serious about playing spin the bottle? I thought that once you’d humiliated me, dressing me up this way and teasing me, the gig would be up?” Wendy said.

“We’re playing! Sit the fuck down Wendy!” Steve barked.

Wendy complied, sitting down awkwardly, both Steve and Grant ogling her legs and sneaking a panty-peek as she struggled to sit cross-legged with any hint of decorum.

“I’m going first,” Steve declared and spun the bottle on the floor.

It stopped spinning between Grant and Christine. They were sitting boy-girl-boy-girl but there were spaces between them.

“Everyone move in closer otherwise we’ll never get the bottle to point to anyone,” Steve sighed.

“And I’m taking another turn,” he declared as they scooched in closer.

“I like your perfume Wendy,” Grant whispered into Wendy’s ear and she blushed.

The bottle stopped spinning pointing at Grant Butler and Steven Townsend reluctantly shook his hand according to the rules they played by.

Christine spun next and the bottle landed on Grant again. They stood up and kissed closemouthed, Grant trying to extend the kiss as long as possible. Steve and Wendy still sitting on the floor could see Grant’s burgeoning erection and Steve sniggered while Wendy blushed.

“My turn,” Grant was happy to be having his turn having just kissed Christine Baker.

This time it landed on Wendy and everyone froze. It was crunch time. Were they really going to make William Mitchell dressed as Wendy kiss a boy? Wendy looked from face to face and saw lechery on Grant’s face, resentment on Steve’s and expectation on Christine’s.

“Come on Wendy, you agreed to this,” Christine niggled her.

“Not really, Christine. I was sort of forced into it,” Wendy said defensively.

“Fucking kiss her you tool!” Steve barked at Grant and the room went silent.

Grant stood up and when Wendy struggled to stand in her heels he helped her to her feet. She tottered on her feet and fell awkwardly against him and Grant took the initiative and leaned into Wendy and kissed her.

The kiss was clumsy. He held Wendy by her forearms, their bodies hardly touching, Grant’s lips puckered stiffly. Wendy pursed her lips in response. At first she felt silly and embarrassed, then Grant put an arm around her and pulled Wendy a little closer and suddenly Wendy felt quite comfortable ... more than that she felt coveted, someone wanted her. The kiss, although chaste, became pleasurable. She closed her eyes and let Grant kiss her softly for the prescribed one minute.

“Ok; time!” Steven called out, the jealousy evident in his voice.

Wendy and Grant disengaged ungainly and Grant pulled out his shirttails and Christine smiled when she saw him trying to hide an erection.

Steve was getting pissed because he hadn’t got to kiss a girl yet and when Christine spun and it landed on him he was happy. He took more that the prescribed minute kissing Christine, trying vainly to force his tongue into her mouth while he squeezed her butt. He made no attempt to disguise the erection digging into her belly.

Christine was flattered that Steve became aroused kissing her but she struggled to keep his hands off her ass and his tongue out of her mouth. She was used to struggling with boys who tried to take liberties with her and she gave as good as she got.

“Ok, enough!” she finally broke free of him.

“One of you others are supposed to time us!” she whined petulantly.

The truth was that both Grant and Wendy were getting off a little watching Christine and Steve go at it.

The circle reformed on the floor and they took a quick break for everyone to have a drink. The four teens were well on the way to being intoxicated and still high from Grant’s stash of ditch weed.

Steve spun the bottle and the iconic contour-fluted lines of the Coca-Cola bottle spun around and around.

The two teenage boys, one genuine girl and one crossdressed girl watched it eagerly.

It landed firmly and squarely on Wendy and she gasped.

She looked at Steve and saw the look of lechery on his face and she swallowed.

“I invoke the closet rule!” Wendy stammered dryly.

The other three looked at each other inquisitively.

‘The closet rule’ had been introduced into the game when they were young teens and the girls in particular were embarrassed to kiss a boy in front of the others. The rule allowed the couple to go into the closet and kiss in the dark whilst one of the others timed them and knocked on the door when the minute was up.

“Fuck that,” Steve grumbled.

“It’s allowed,” Christine snapped back.

Wendy was hoping that by invoking the closet rule she would be able to fight off Steve and keep him at arm’s length if he tried to feel her up like he had just done to Christine. It would be harder for him to find her in the dark closet with the light off and she only had to endure one minute.

Steve turned to Grant who nodded meekly.

“Christine’s right Steve; it’s allowed,” Grant couldn’t meet Steve’s gaze.

“Ok. In that case I’m changing the game to seven minutes in heaven,” Steve sniggered.

“Hey! You can’t change the game halfway through!” Wendy protested.

“And who is going to stop me?” Steve got to his feet and towered over Wendy and held out his hand.

“Ok Steve, I think this has gone far enough,” Christine said sharply.

“I’ll decide when it has gone far enough. Come on Wendy,” Steve reached down and Wendy meekly took his hand.

“You time it Grant and I want my full seven minutes,” he called over his shoulder as he led Wendy to the closet.

Steve opened the door and pushed Wendy inside and slammed the door closed.

The closet was used to store old furniture, unused games and cleaning gear. With Steve and Wendy inside there wasn’t much room.

Steve groped for Wendy in the dark and found her and pulled her to him. He pressed his lips on hers and kissed her, forcing his tongue into her mouth. Wendy was so surprised that she didn’t fight back initially and as she had no sense of orientation in the dark she clung to him to keep her feet.

Steven misread Wendy’s actions as active participation and he kissed her passionately, his hands going to her ass, his fingers pawing at the velvet miniskirt, squeezing her buttocks. Wendy could feel his steely erection pressing into her belly and she was so stunned that she just grasped at him in the dark.

Wendy had half expected Steve to deride her and laugh at her or maybe even beat up on her a little. Steve liked to horse around with William and often wrestled with him to belittle him and keep him in his place. Wendy had not expected to be treated this way.

Was he bullying her ... yes for sure? Was she somehow secretly enjoying it ... possibly?

Wearing the clothes was exciting: the sheer pantyhose clinging to her buttocks and legs, softly caressing her skin whenever she moved, the full-cut satin panties worn over them added a scintilla of decadence that stimulated every nerve in her groin and she had been semi-tumescent ever since she had stepped into them. Then there was the cool soft satin blouse caressing her shoulders, chest and belly and that tight velvet skirt around her waist, buttocks and thighs.

If William could dress a girl any way he wished, she would be wearing exactly what he was wearing now.

Then there was the makeup, perfume, jewellery and high heels. Wearing the makeup was exotic. She could taste her lipstick as Steven kissed her, she could smell her perfume, and those ridiculous heels that kept her tottering just looked so damn good and she felt so sexy wearing them.

Wendy justified putting her arms around Steve as a means of staying on her feet in the dark confines of the closet. Of course he was taking liberties kneading her buttocks but he was keeping her on her feet wasn’t he? Those soft lips pressed on hers and his thick tongue invading her mouth was a liberty, but wasn’t that was part of the game? Wasn’t the whole idea of spin the bottle to kiss the person that the bottle pointed at?

But none of that explained why she felt so excited feeling his hard prodigious rod pressing into her flat belly or why her own cock was uncomfortably erect lying pressed along her perineum or why she felt so feminine and girl-like. It was somehow empowering to be submissive and submit. She wondered if this was how girls felt when boys they liked were pressing their needs on them.

William was used to being the butt of the jokes, the sidekick; the one who always had to run-go-fetch for the bigger boys and for Steven in particular. He was the last one chosen for team sports and games; he was the one that seldom got to kiss the girl. He was the guy who sat with other ‘losers’ behind the other boys and girls in the cinema watching them make out in the gloom.

But Wendy was desired and wanted. She was Christine’s friend and Steve and Grant were jealous of each other when the bottle landed on her. It was empowering and feeling feminine and submissive was not as ghastly and abhorrent as she thought it would be.

In the dark Steve had forgotten all about William Mitchell. William had ceased to exist. He was holding this beautiful sexy young woman in his grasp whom he had deemed to call Wendy and Wendy she was. As their eyesight adjusted to the dark he could see how beautiful she was.

She felt soft. He knew those tits were false but her curves were real, her lips were real, her pretty face was real, her soft buttocks were real and those gorgeous long legs were real. It was all a game. No harm done. But Steve was determined to mine every second of pleasure he could out of Wendy Mitchell.

The booze and the grass had fuelled his desire of that there was no doubt; but it was something else that drove those primal urges. She was just so sexy and fuckable!

She felt so soft and feminine in his arms and she had stopped struggling and become compliant. Had she become more than just passively compliant? Was she actively participating?

Wendy let her mind go blank, driving out all of the doubts, contrivances, fears and speculation and just lived in the moment. She was a beautiful desirable, and yes sexy, young woman and she was in the closet with a hunky jock whom almost every girl at school would drop her panties for.

She draped her arms around Steve’s shoulders and returned the kiss, slipping her tongue into his mouth. She subconsciously kicked her leg back like she had seen girls do when they were kissing and Steve’s hand went to her thigh. He stroked it, evoking twinkling wavelets of pleasure as his fingertips caressed the gossamer nylon. Wendy gasped into his mouth and Steve smiled around the kiss.