"Ryan! Your date is here!"

The sound of his Mom's voice woke Ryan Jones up. Ryan rolled off his bed and hit the floor. He looked around his room panicked. He had fallen asleep and was no where near ready. Leaning against his bed, he sighed as a look around his room reminded him of the undesirable situation he was in almost as much as the next voice he heard.

"Yo Ryan! I'm here! You ready?"

The voice belonged to Jimmy Montford and Ryan could still hear it echoing in his ears "see you at the dance, wear something pretty" from a few weeks ago, when he'd played his way into this mess. Jimmy went to South Town High School, the rival of Ryan's North Town High School.

"One sec!" Ryan yelled back. A mixture of anger and dread in his voice. After all, it was Jimmy's fault he was here, in his room, now pink and girly, getting ready to attend the South Town High Winter dance as a girl.

Ryan caught a glimpse of himself in the mirror in his room, his expression glum, his short blonde hair unchanged, his skinny frame sporting a pink bra and pair of panties. He looked down sadly at the lingerie he was currently sporting. This all could have been avoided had he not fallen into Jimmy's trap. But here he was, a boy in a bra and panties.

Ryan was one of the best basketball players North Town High had ever seen. He made varsity and a freshmen and although he didn't play much, he learned a lot and was a huge part of the team his Sophomore year. Word started to spread about the Sophomore who was torching every team he faced. Ryan made a habit of going into the crazy crowds that North High found at away gyms, and silencing them as Ryan averaged a cool 34.4 points a game with 8.9 assists and 6.5 rebounds to boot. He loved hearing the silence as they left the once raucous gym. He loved seeing the people who had been yelling and screaming insults at him stunned at what he'd done on the court. This was what he had trained for. All those hours in the gym were paying off. Then came the South Town game. Ryan never liked to pay attention to any of the trash talk in the Facebook event pages before the games but he knew it existed. The day before the South Town he was pulled aside in the hall by his best friend Trevor Doherty.

"Ry, did you see the Facebook page."

"No, why?"

"Dude, there's some brutal stuff on there. I don't know if i should even show you or not."

"Just show me dude, I've seen it all before what's the worst it could be?"

Trevor handed Ryan his phone to show Ryan a bizarrely personal paragraph of insults.

NTHS thinks your boy Ryan Jones is nice but Ryan ain't shit! Little Ry Ry has never played anyone like us. Wait till he meets our boy Jimmy Montford, the real best Sophomore in the conference. You guys are gonna have to carry Ryan off the court in tears when Jimmys done with that little girly boy, whining about fouls like he always does. You better tell Ryan to wear waterproof make up cuz we're gonna make him cry tomorrow. Underneath it was a crudely created meme featuring a shirtless picture of Jimmy Montford flexing and a picture of Ryan wearing one of his sisters training bras from a Youtube video she had made him do for her YouTube channel when he was 12.

Ryan was shocked. He was speechless. What a stupid, desperate but very personal attack. Jimmy and Ryan had known each other for years but never particularly liked each other. Since they were little, they had always attended the same basketball camps, played in the same playgrounds and rec leagues and were almost always been the two best players which generated a natural rivalry. Ryan didn't like Jimmy's confident trash talking style, while Jimmy thought Ryan was a goody two shoes and a whiney bitch who complained about calls too much. They both thought the other one was the cockiest kid on the planet. Ryan knew even though Jimmy was a few inches taller than him that he was the better player and he knew everyone else (including Jimmy) knew it too. He remembered how at a basketball camp this summer he had gotten sick of Jimmy's trash talk and challenged him to one on one and promptly beaten him 21-1. Ryan let him score once out of pity. Maybe this was Jimmy's attempt at revenge? Ryan remembered the speechlessness washing over him. And then the rage. Hadn't Jimmy learned not to talk shit about him?

we'll see who's a big man on the court tomorrow night Montford he commented angrily and then stormed away from Trevor.

When Ryan got home Jimmy had responded.

Hey bitch boy! nice to hear from you. u think your a big man with your little response. why don't we make it interesting. how bout a bet..

Ryan couldn't believe it. North Town High hadn't lost all season thanks to his incredible season. He wondered what kind of bet Jimmy had in mind.

Your on

Montford responded in less than 30 seconds.

if we win tomorrow, I take you to the south high winter dance, AS A GIRL WEARING A DRESS. if we lose I'll go with you to yours.

Ryan was surprised. This wasn't the kind of bet he expected. He didn't even want Jimmy Montford to go with him to the winter dance. He was hoping one of the hot senior girls would be interested in him after the season he was having. But he couldn't back down on Facebook with everyone reading it. So he responded Your on

And then Ryan got to South Town High. They had printed giant posters of him in the training bra, drawn on make up, made massive signs taunting him. When he stepped on the court they went crazy. Ryan had never played in conditions this hostile before so he tried to focus in and play the best game of his life. He played the worst. He only scored 3 points had 12 turnovers and when he fouled out late in the 4th quarter with North High down 19 the building exploded with cheers as he let out a scream of frustration. Soon chants of "you can't do that" transitioned into a chant of "bye bye princess" which rained down upon him for a solid minute before transitioning into "Ryan has a vagina." A devastated Ryan sat at the end of the bench with a towel over his head, hiding his tears. In the hand shake lines Montford pulled him close for a second and whispered into his ear "see you at the dance, wear something pretty."

"What's taking you so long!? Jeez you really are a girl!" Jimmy Montfords voice brought Ryan back to the present. He was standing in his room, wearing a bra and panties, 30 minutes away from being seen in a glittery fancy dress by a room full of people who angrily chanted insults at him. The door opened and Jimmy Montford barged in, wearing a dapper black tux, and almost immediately burst out laughing.

"OH MY GOD GET OUT!" Ryan screamed instinctively putting his hands over his chest before, feeling overly feminine, putting them down by his sides thinking this was the better of the two options even if it meant Jimmy seeing him in his bra.

"WOW! Just wow! Look at you all pretty in your panties! But why aren't you dressed? We need to leave! Now! And why is your room all girly? Found your true self, have you Ry?" Jimmy laughed a full haughty laugh. Jimmy was a fairly, but not overly tall boy. He was muscular and proud of his body and, unlike Ryan, could grow the odd facial hair which he shaved about every few weeks. He had spikey brown hair that was gelled up and a confident gait in his posture.

Ryan didn't want to explain to Jimmy about how, upon hearing about Ryan's bet from his older sister, his Mom had lectured him for 2 hours about the sexist nature of the bet and saying that she "wouldn't have this out of her son" had decided to renovated Ryan's typical teenage boy room into a girly pink nightmare, replacing his LeBron James posters with Justin Bieber and One Direction posters, his bed and sheets with the ones his sister Jennifer used when she was about 8, at the height of her princess phase, and painting his whole room pink. She even made him dress as a girl "to practice" on the weekends. They were the three worst weekends of Ryan's life.

"My mom chang..."

"Forget about it! Why aren't you in your dress? Unless..." he smirked "this is what your planning to wear?"

"No, I have a dress" Ryan said, without much conviction.

"What's this?" Jimmy said, picking up an old barbie that Ryan's mom had put in his "new" room to give it some character. She had provided Ryan with a lot of Jennifer's old toys and possessions in addition to buying Ryan a few new ones even though Ryan was 16 and completely uninterested. "You've got a little barbie doll?"

"No its my..."

"Does she have a name" Jimmy sneered.

"Um, Princess Ryan" Ryan said quietly wondering why he didn't lie. His sister had named it after him when he was little.

"Ok! I thought you were only doing this because you lost the bet but based on your room, your dolly, and how you look in a bra and panties you'll probably have fun tonight" Jimmy said mockingly.

Ryan felt a surge of anger. "Shut up, this is all your fault!"

"My fault?" Jimmy laughed. "I'm not the one who lost the bet. Now put your dress on so we can go. We're late!"

"Ok! Leave so I can change!" Ryan said annoyed.

"Oh I get it" Jimmy laughed. "A little embarrassed to change in front of a real boy? Although I'm already seeing you in your underwear. Nothing to be embarrassed about. You look like a lovely young lady!" He said giving Ryan a douchey smile.

Ryan blushed. "Can you just leave?"

"Oh I get it. Someone wants to wear fancy panties for me." Jimmy leered. "Don't want me to see your vajajay, Ry?"

Ryan shifted awkwardly "Can you just go?! Please!" Reluctantly and unenthusiasticly adding "so I can get all pretty for you."

"That's the spirit!" Jimmy said with a grin.

Sadly Ryan wondered over to his closet and took out the dress that he'd bought with his Mom. The dress store had been an excruciating experience with his Mom making him try on at least 10 dresses in a store full of hot girls his age. When he came out of the dressing room to show his Mom each dress all the girls and Moms in the shop stopped and stared as if they were all personally invested in what the lone teenage boy trying on dresses was ultimately going to choose. A particularly embarrassing moment was when he emerged from the dressing room in a particularly tight and short, form fitting red dress, a pretty girl around his age who was in the dressing room next to his came up to him and told him he "looked sexy" was "very brave" and was "just as much a girl as the rest of us" and then told him that he hadn't zipped up the back and did it for him. Not knowing what to say Ryan gave her a glum thank you.

Ryan, knowing he can't sulk in his room forever, stepped into the dress they'd eventually settled on, a tight, bright pink, strapless dress, that had a flouncy skirt around the waist that went to about his mid thigh. He zipped himself up, grabbed his shoes, and with a sad sigh, headed to the bathroom to do his make up.

He was able to finish it off pretty quickly. His mom and sister had excitedly taught him how to apply lipstick, foundation, eye shadow, and eye liner and had already done his nails a bright shade of pink earlier in the day (to match his dress.) He hated to admit it but he really did look like a girl when he was all made up. Is it a good thing or bad thing that everyone who doesn't know me is going to think I'm a real girl, he thought.

He added a little blush and carefully placed the long blonde wig, matching his own hair color, on his head. He looked in the mirror and a teenage girl looked back at him. With that, he slipped his pedicured feet into the 4 inch heels his mom had bought him and went down stairs. "Here goes nothing" he thought.

"WOW! You look INCREDIBLE!" Jimmy marveled. "Like actually stunning! Are you sure your not a real girl?"

"Fuck you!" Ryan said quietly. As they walked through the kitchen he noticed that with the heels he was only an inch or 2 shorter than Jimmy. "Let's just go before my family sees me."

But the damage had already been done.

"Is that Ryan?!?" came the voice of his younger brother Josh, who was sitting in the living room with his Mom. Ryan tried to keep going but his Mom called out "have him home by 1 Jimmy!"

"HER!" Josh corrected as he howled with laughter. "Have HER home by 1."

Ryan tried to leave quickly but as the headed for the door to wait for the car outside, Josh followed them.

"Wow Ryan! You look like a real girl! I can't believe my big brother is such a little fairy. Or should I say big sister!" he said with an devious smile as they crossed the threshold out the door.

"Its so cold! I don't have a jacket." Ryan complained.

"Take mine" Jimmy said with a smirk.

"Uchh no, I'm not wearing your jacket like a..."

"Girl?" Jimmy offered. "That's fine, just don't be such a little diva about not having a jacket then. Should have known, your a diva on the court and off."

"You should have heard her whining to Mom last night!" Josh laughed and put on a high pitched voice. "Its not fair, I'm not a girl."

"Shut up you little shit" Ryan shot at him.

Jimmy laughed but said nothing as Josh continued.

"Then Mom said 'whats wrong with being a girl?' and Ryan got all quiet and was like 'nothing I'm just not one' and Mom was like 'if your not a girl then why are you wearing a bra little missy?' and then she asked Ryan why his lipstick was smudged and then Ryan..."

"SHUT THE FUCK UP!" Ryan yelled furious at his brother for enjoying his humiliation so thoroughly.

Josh smiled broadly.

"OK! Calm down! Are you on your period or something? Your lipstick looks great by the way."

Jimmy smiled and put a well toned arm around Ryan's skinny bare shoulder.

"Be nice to Rachel. She lost but she's worked real hard to get all pretty for me tonight and I appreciate that. By the way, Rachel, you smell lovely. Perfume?"

"No" Ryan said, humiliated.

"Well then you naturally smell like a pretty girl" Jimmy said with a smile.

Ryan had never felt more humiliated in his life as Josh choked with laughter behind him and was slightly relieved when he saw the a limo pull up.

"Only the best for you, Princess" Jimmy said with a dickish smile.

The driver got out of the car. He was slightly overweight and very tall, at least 6'3 and slightly intimidating.

"Car for Jimmy Montford?" He asked.

"That's me!" Jimmy said. "Lets go Rachel."

"Alright Rachel, have fun but don't let Jimmy screw up your lipstick when you kiss. And don't let Jimmy get past 3rd base." Josh said with a wink.

Ryan said nothing and sulked into the car.

"Bye kid" Jimmy said to Josh. "Don't worry, I'll show your "sister" a night she'll never forget."

"So..." Jimmy said as he got into the car. "Your Mom calls you little Missy?"

Ryan glared at him, then turned to looked out the window as the car started moving.

Jimmy started to feel a bit awkward, a little sympathetic. Sure, Ryan was a cocky prick who thought he was God's gift to the game of basketball but being alone in the back of the car with him as he pouted was a little sad. Here he was, his crazy revenge plan finally working with the kid he hated more than anything looking exactly like a basic white girl and he was feeling bad for the kid he'd hated for years? How could this be? Should he apologize? No, he can't do that. Should he make more jokes? No that would just make things worse and there would be plenty of time to make jokes at the dance. Should he just treat him like a normal girl? Worth a shot I guess. He looked over at Ryan, the picture of femininity, with his legs crossed perfectly, looking sadly out the window. The dress showed a good deal of leg and with the way Ryan was seated he could see all the way up his leg.

"Your legs look really great.. in that dress" Jimmy said somewhat awkwardly.

"What?" Ryan turned suddenly.

"Your legs. You, you have good legs." Jimmy repeated wondering if he was making a mistake.

"Oh, uh thanks" Ryan said, blushing.

Jimmy smiled at his reaction.

"Did you shave them?" he asked.

"Oh yeah a little. I don't really have hairy legs but my mom made me shave everywhere. Legs, armpits, even my uh yeah, legs and armpits."

Jimmy looked at Ryan's armpits. Sure enough, where there was usually a small tuft of armpit hair that was only visible in his jersey when he shot, Ryan's armpits were completely, femininely smooth.

"Well you look great." Jimmy said, trying to make his odd glance at Ryan's armpit go unnoticed.

"Oh no!" Ryan said suddenly.

"What's wrong?" Jimmy asked.

Ryan took a deep breath. "Don't make fun of me but I left my purse at home. I was so focused on trying to get out without Josh seeing us, I left it in the living room."

"Do you need it?" Jimmy asked smiling broadly.

"It has my phone, my keys, everything."

"Fine, lets go back." he tapped on the barrier behind the drivers head and the driver rolled down the window. "Um she forgot her purse, could you take us back?"

"Of course" the driver grunted in a slight accent. "Typical girl. Let me guess, it has all her make up in it?"

Jimmy smiled as he saw Ryan blush. It was funny again.

"Yeah probably." He laughed.

"You are very pretty girl" the driver continued looking at Ryan through the rear view mirror, "you no need wear so much make up."

"Oh thanks" Ryan said in a small voice as Jimmy laughed.

"Hey, girls are gonna be girls. My girl needs her purse. What am I gonna do?" Jimmy chuckled.

The driver laughed.

"Do you know what a good boyfriend you have?" he said to Ryan.

"Yeah, he's great." Ryan said with embarrassment.

"Make sure you appreciate him" the driver continued. "Give him a little kiss now. Just so he knows you appreciate him. The men are always under appreciated but look at the effort he goes to make sure you have your purse."

Ryan gave Jimmy a tentative look and saw him barely containing his laughter.

"Go on" the driver coaxed. "he deserves it."

Finally Ryan leaned over and gave Jimmy a soft peck on the cheek.

"Awww. Thanks babe." Jimmy said genially, giving Ryan a little pat on his hairless leg.

When they got back to Ryan's house rushed into the living room.

"Back already Sweety?" his mom asked.

"No" Ryan said with a blush, "I... I forgot my purse."

"Forgot your purse!" Josh howled in laughter from the couch wear he was watching TV.

His mom walked into the room. "Its on the table sweety. I put some... why is your lipstick smudged? Have you... have you been kissing?"

Josh, sat up straight on the couch and turned around. Ryan gave a blush for the ages.

"I... I... I just..." he stammered.

"It's ok sweety." his mother said sweetly. "Its perfectly normal..."

"FOR A GIRL!" Josh interrupted. "IT'S PERFECTLY NORMAL FOR A GIRL!"

"Here Ryan, let me fix your make up" his mom said ignoring Josh but smiling slightly and taking out the extra make up she had stashed in Ryan's purse and started applying.

"Hurry up Mom, he's waiting in the car" Ryan pressured.

"She's gotta get back to her boyfriend" Josh giggled.

"I'm trying to make you look your best, gorgeous." his mom said calmly.

"Ok, we're done!" his mom said a few minutes later.

Ryan looked at himself on his phone.

"Wow. I actually look really pretty."

"The prettiest" Josh gasped, losing his breath with laughter.

"I really gotta go. Thanks Mom, bye" Ryan said, grabbing his purse and heading towards the door.

"Mom?" Josh asked. "Did you ever think you'd hear Ryan squeal 'where's my purse?'"

"No" his mom replied with a smile. "But now it really suits her. I mean him. Don't tell Ryan but I think he got his mothers legs"

Josh laughed.

"He got your pussy too" Josh laughed until his mom gave him a stern look.

Back in the car, Jimmy couldn't believe how long it was taking. He knew the driver was getting impatient.

"Women... right?" he offered but the driver wasn't as friendly this time.

"Text your ditzy girlfriend to come out now. I can't stay here all night!" he scoffed.

"She's right there!" he said as Ryan emerged from his house now holding a small, pale pink purse.

"Sorry" Ryan apologized as he reentered the limo.

"Got your purse?" Jimmy asked.

"Got it" Ryan said with an embarrassed smile.

Jimmy smiled back when he saw Ryan's noticeably different make up.

"Rachel, did you change your make up in there?" he asked pleasantly as the car started moving.

Ryan blushed, predictably. Did he notice the mascara? It felt so weird on Ryan's eyes but his Mom insisted she do it.

"Yeah, I just freshened up a bit" Ryan said.

"You look great." Jimmy said noticing for the first time as Ryan sat down that Ryan had a decent ass. How did he not notice that when he saw her in her panties? HIM. Saw HIM in the panties.

"Thanks" said Ryan, shivering slightly.

"You cold?" Jimmy asked, scooting towards the shivering, purse clutching boy.

"Oh yeah a little, its really cold out." Ryan said, shivering more.

"You sure you don't want my jacket?" Jimmy asked.

"I'm fine" Ryan responded, girlishly putting his purse on the seat next to him and his hand next to his thigh near Jimmy and shivering even more.

"How are you so cold? You were outside for 30 seconds!" Jimmy said with a laugh and then for a reason he couldn't explain he put his hand on Ryan's shivering one.

Ryan looked up at him, his mascara laden eyes wide and confused.

"What.. what are you doing? Your... your... your hands are big... and warm" he said slightly stupidly.

WHAT ARE YOU EVEN SAYING, Ryan thought angrily.

"And your manicured little hands looked a little cold" Jimmy said with a slight smile. "How did you ever play basketball with such dainty little hands?"

Ryan was stunned. "Is he flirting with me?" he thought.

"Relax" Jimmy drawled, putting his hand on Ryan's bare shoulder for a second time. "Um, put your head on my shoulder."

He could see Ryan's confusion in his face.

"Um ok" Ryan said tentatively resting his head on Jimmy's broad should as Jimmy wrapped his arm around Ryan's waist.

As they sat, Ryan fully made up and dressed in an ensemble that would make any teenage girl jealous, Jimmy looking like the typical All American boy, good looking, sharply dressed, and with a pretty girl (or what looked like a pretty girl) on his arm, their minds wondered.

"What is wrong with me? Why would I say ok?" Ryan groaned mentally.

"Why did I start flirting with her? I mean him. Am I actually enjoying this?" Jimmy thought.

"Jimmy actually smells kinda good" Ryan thought as he looked up at Jimmy.

"Is she, I mean he, actually enjoying this?" Jimmy thought as Ryan looked up at him.

"OH MY GOD AM I ACTUALLY ENJOYING THIS?!?" Ryan thought as he rode, legs shaved, make up done, dress, panties, purse, and all, to the winter dance.