The Bet Chapter 2

"Ok, we're here!"

The drivers gruff voice brought Ryan to his senses. What was he doing, cuddling up to Jimmy, resting his head on Jimmy shoulder for the past 10 minutes like some South Town High cheerleader? He jerked his head up suddenly.

Jimmy had been enjoying it too. He enjoyed feeling Ryan next to him, He'd never noticed how feminine some of Ryan's features were until Ryan was in a dress and wig cuddling up to him. But now that he was all done up, resting his head tenderly on his shoulder Ryan was beautiful? Could that be right?

Ryan jerking his head up made Jimmy snap out of it. This was still the kid who had humiliated him at basketball camp this summer, beating him 21-1 in one on one. This was the kid who had mockingly around the locker room in his compression shorts after beating them last year and posted it on snap chat. This was the kid who he had planned on getting revenge on. Was Ryan fucking with him? Was Ryan trying to be a convincing girl to mess with his heart? No of course not. What was he even thinking? He shook his head as if trying to literally shake the idea of it out of his head.

"You ready, Princess?" he asked Ryan, the mocking lilt back in his voice as he left the car.


"Got your purse?" Jimmy teased.

"Got it." Ryan said rolling his eyes as he held it up.

"Alright, lets go purse boy." Jimmy said, putting a hand around Ryans waist, resting it on his hip as they headed towards the school. He needed to approach the issue carefully.

"So before we go in..." Jimmy started but he was cut off.

"Is everyone gonna know its me?" Ryan asked in a small voice.

"A bunch of people will. " Jimmy said slowly "The team will. And some others too. But I was going to go with a real girl too, this girl I know from middle school, really hot, and just kinda have you there on the side for laughs. But she uh... fell through on me. But you actually look like a real girl, so people might just assume you're her." He looked down and Ryan trying to see how he was reacting but Ryan's expression hadn't changed. "Lucky for you really," Jimmy said with a mischeivious smile. "This means you get me all to yourself."

Ryan rolled his eyes.

"You look really bitchy when you roll your eyes." Jimmy hand't meant for it to come out like a dig but he knew it had. Ryan stared at him. "I'm... I'm just saying. The other guys aren't going to be as nice as me, so you should try to to do stuff that's too girly like that..." Ryan was still staring blankly at him "Or you know what, what do I care? Do it."

He glared at Ryan. He still hadn't told him anything.

"So you wanna pretend to be a real girl?" Jimmy asked him. "You look good enough to be one, and this way not everyone will know your that loser from NTHS who lost the bet." Ryan gave him a look and brushed Jimmys hand off his hip.

"You actually do look really pretty." Jimmy offered, apologetically.

What was Jimmy playing at, Ryan thought. What did he want? Was he right? Would it be easier to save face if he pretended to be a girl?

"How will people not know its me? They know I'm with you. Everyone was at that game." He asked.

"Everyone was at that game but that's not what they're thinking about tonight. They're all thinking about themselves, their outfits, trying to hook up. And its like I said" Jimmy explained a little impatiently "It's like I said, I was going to go with a girl that you don't know and they also don't know and you were only going to be there to be made fun of. But she cancelled. This is good for you. You just have to deal with my boys on the team ragging on you, cuz they are looking forward to seeing you in all this, and then just play my girlfriend for the rest of the night. What do you have to lose?"

Ryan continued looking at Jimmy strangely and then smiled.

"This girlfriend you were bringing, she wasn't by any chance, imaginary, was she?"

Fuck, how did he figure that out? Jimmy thought.

"No!" Jimmy said, trying to make it sound absurd. "Look I just need to know if you'll do it." He paused. "I think it might actually be less annoying for you."

Ryan thought for a second. Would it be possible to blend in as a girl? If it was possible would it really be better to blend in as a girl?

He sighed.

"Sure, what have I got to lose I guess."

"Ok, so, if your a girl, and your with me by choice, maybe don't act like my touch is poisonous to you." Jimmy said, slightly relieved.

"Right, sorry" Ryan said, inching closer to Jimmy and allow him to put his arm back around his waist.

"Its fine." Jimmy said stopping outside the door to South Town High. They were already late, a few more minutes wouldn't hurt them.

"And if you're a girl, what's your name?"

Ryan sighed. "Rachel."

Jimmy smiled. "Good girl!" He said giving Ryans hip a little pat. Ryan let out a involuntary giggle. "Let;s go."

Ryan's heart was beating out of his chest as his heels clicked down the cold hard floor of South Town High. Was there some kind of joke planned or was he just going to have to deal with the South Town basketball team acting like a bunch of Josh's for a few hours? Would he actually be able to pass as a girl? And why did Jimmy want him to?

"Wiggle your hips a little more when you walk" Jimmy said out of nowhere.

Ryan tried it and found that focusing on something other than his nervousness, even something as stupid as wiggling his hips in a non over the top way, calmed him down a bit. Finally they got to the gymnasium, the very place where Ryan had gotten into this mess. Jimmy opened the door and held it for him.

"Ladies first." He said with a grin and Ryan tentatively walked through into the dance feeling Jimmy walking in behind him and returning his hand to around his waist resting it on his hip as he started to lead him across the room and Ryan instantly realized he was wearing one of the skimpiest dresses in the whole room.

At first it wasn't so bad but then he started hearing the whispers as he walked towards a group of upperclassmen.

"Who's she?"

"She's hot!"

"Is that Ryan Jones?"

"No way!"

"He looks like a real girl"

"Call her she! Call her she!"

"She even walks like a girl."

"Can't be him, dude, thats a girl."

"They look kinda similar."

"Does she have boobs?"

"He looks so comfortable in heels!"

"She loves it. She's practiced this at home"

Ryan tried to block out the whispers that seemed to be coming from all around. A particularly strange couple whispers from what sounded like freshmen boys behind him who clearly thought he was a girl, drove him closer into Jimmy's chest.

"Dude, I can see her panty lines!"

"She's got legs for days!"

"Looks at that booty!"

Blushing heavily Ryan was almost glad when they made it across the room where three of Jimmy's friends were hanging out because it meant the end of the stares and whispers even if it meant the start of whatever the South Town High basketball team had in store for him.

"BOYS! How we doing?!?" Jimmy asked with energy.

"Ok" his friend Eric, the teams center, responded. "The girls literally all just went to the bathroom."

Eric was a very tall, muscular boy, with very red hair. He was handsome but still looked like someone who had lost a lot of weight in a short period of time. Last time Ryan had seen Eric, Eric had snarled "stop whining bitch" as Ryan had complained to the ref about the blatant foul that Eric had just committed as he went up for a layup.

"Have you guys met my date?" Jimmy said with a smirk. "She's lovely."

Mike, a skinny athletic black kid who's game Ryan had always admired, gave Ryan a strange look. Kevin, an aggressive but jacked kid who had little basketball skill but was great on defense looked confused. Eric, however smiled, cruely.

"We haven't" Eric said smiling more broadly. "But she looks lovely."

"Well" Jimmy said, returning the smile and feeling all his sympathy for Ryan vanish now that he was in the presence of his friends again, "feel free to introduce yourself, babe."

Ryan felt his heart beating out of his chest. Did Jimmy want him to pretend to be a girl now? He tried to breath easily and spoke in a voice much higher than his normal voice.

"Hi, I'm Rachel!" He let out a nervous giggle. "I'm Jimmy's girlfriend. It's nice to meet you guys."

All four boys burst out laughing.

"As pretty and feminine as you are, RACHEL" Jimmy said wrapping an arm around Ryan through his laughter, "they know its you, Ryan."

"I never would have guessed if Jimmy hadn't sent me the snaps!" Kevin laughed, as tears ran down his face. "You look so much like a girl!"

"Snaps?" Ryan said confused.

"I may have took a few snaps chats of my girl on her big day while we were in the car. You just looked so beautiful. I couldn't resist." Jimmy explained, still laughing. "You do look beautiful."

"Seriously" Eric said, still laughing. "If I didn't know this was the cocky son of a bitch who cried after we beat him, I'd be hitting on her. Maybe I'll still take a little ass grab." he said, reaching towards Ryan's butt.

"Oh my god! Stop!" Ryan gasped, alarmed, hitting Eric's hands out of the way with his manicured fingers and instantly realizing his reaction made it worse. "I mean.." Ryan said trying to lower his voice. "Don't be gay."

"Don't be homophobic" Jimmy said sharply at Ryan.

"Wow!" Eric laughed, trying to seem unphased. "Did you see his nails? They're pink! So pretty!"

"You really do look like a girl, dude." Mike said chuckling.

Kevin laughed.

"And that 'hi, I'm Rachel' thing was hilarious!" Kevin added still laughing. "And that little giggle! And look at you with your purse! This look is perfect for you Ryan."

"Uh thanks?" Ryan said, unsure how to react.

"You should see her house" Jimmy said obnoxiously. "Her Mom heard about the bet and renovated her room! Now she's got a sweet little girly bed room with barbies and Bieber posters. The perfect room for Mommy's little princess! She even did her own make up"

Ryan could feel himself blushing and feel his face falling.

"That's adorable" Eric said mockingly. Then catching notice of Ryan's face he smiled. "Awwww. You're making her sad."

Jimmy put his arm back around his "girlfriend" for the night causing Ryan's head to move onto his shoulder.

"It's cute how she puts her head on your shoulder like that" Mike said with a quiet smile.

"No, I'm not, I didn't..." Ryan sputtered but Eric interrupted her.

"Does Rachel need a hug from her BOYFRIEND?"

Jimmy rolled his eyes and gave Eric a smile.

"Girls! They're all so sensitive! Such low self esteem!" he laughed as he gave Ryan a hug, moving his hand down to Ryan's butt to give it a little grab.

"Stoppppp" Ryan whined. "You made my panties get all bunched."

"Panties?" Mike said with a confused grin.

"You should have seen her when I first got there!" Jimmy said confidently. "She was in nothing but her bra and panties!"

All four boys howled in laughter yet again as Ryan blushed, hoping Jimmy would lead him away soon.

"You know, I love crushing you on the court..." Kevin said, again through tears of laughter. "...but from the sounds of it I might never get to do it again because by this time next year you'll be the star of the North Town High Girls varsity team!"

"Girls VARSITY?!?" Eric laughed.

"You're right" Kevin howled. "She'd probably be on girls JV!"

Ryan shifted awkwardly as the boys laughed and adjusted his bra.

"Why don't I get some food?" he asked suddenly, trying to get away from the guys and he turned toward the food table at the other end of the gym.

Ryan wasn't hungry. In fact he was feeling a little sick but he didn't want to go to the bathroom. He couldn't go into the boys bathroom like this and he did not want to use the girls room.

"Are you ok?"

Ryan looked around. A short, slightly chubby, mousy haired girl was looking at him with concerned eyes.

"Yeah, I'm fine." He managed in the same high voice he used when talking to Jimmy's friends.

"Well you look confused. Are you looking for something?" The girl asked kindly.

"Yeah, just some water."

"I can get you some. Its right over here." she said gesturing towards a table with drinks on it. "You don't go here, do you?"

"No" Ryan said pouring a cup. "No, I don't."

"Well who are you here with?" the girl asked pleasantly.

"Uh Jimmy Montford" Ryan replied blusing.

"Ooooo. He's really cute! He's in my English class." the girl gushed. "Are you his girlfriend?"

"Yeah" Ryan said after a slight pause. "He's so sweet. I wasn't gonna come but he really wanted me too."

"Well I'm glad you did!" the girl said sweetly. "You look amazing. I'm Shelby, whats your name?"

"Rachel" Ryan said trying to smile.

"Damn" Mike said, staring at Ryan as he talked to Shelby across the room. "That shit is crazy. Dude legit looks like a
chick. Even moves like one. It's kind of sad honestly. He has literally no trace of manliness. He's a pretty good ball player too. Like that's a waste of a dick. It's sad."

Kevin chuckled "I guess but its more hilarious that it turns out North Town Highs basketball prodigy is a complete sissy."

"Dude's more bangable than Shelby Peters honestly" Eric said with a grin. "You thinking of tapping that Montford?"

Jimmy rolled his eyes again.

"Ew. That's a dude under all that. Don't be gross. I only brought her, I mean him, because that cocky dickface needed to be taken down a peg." he said watching Ryan and Shelby.

"Sure, my guy" Kevin said grinning.

"I wouldn't have!" Jimmy said, slightly annoyed. "You think I'm gay?"

"No" Kevin said still grinning. "But your rep with the girls did take a hit after you dumped Grace."

"Grace!" Jimmy thought. "Why did she have to make it all so complicated?"

Grace was one of the hottest girls in school and Jimmy's ex girlfriend, who he had dumped rather cruelly, after thinking she was cheating on him. Grace in turn had essentially turned all the girls in school against Jimmy making it almost impossible for him to get a good looking girl to agree to go to the dance with him. Jimmy knew this which is why he made the bet with Ryan, trying to humiliate his on court rival and make it clear to his classmates he was taking to whole dance as a joke in the process. But after making the bet he thought people might think he was gay so he tried to get a hot girl from another school, ones who Grace couldn't bad mouth him to, to come with him. However, every girl shot him down when he mentioned that there would be another "girl" (Ryan) on the date. Even with his good looks and charm, Jimmy couldn't sell any girl he knew on going to the dance with him AND Ryan in a dress solely for the purpose of humiliating him. And he'd rather just go with Ryan as a joke than go with some ugly girl. Obviously. But when he saw what a good looking girl Ryan made he saw an chance to kill two bird with one stone. He could show Ryan what a little bitch he was compared to him AND have Grace seething with jealousy wondering who that pretty little blonde thing he was with was.

"I literally just wanted to stick it to Ryan" Jimmy lied. "That's all. Him thinking he's king of the league and all that, it had to stop."

"I think its a great idea." Eric said supportively. "That cocky asshole thought we was gonna run over us. Now, he's talking about his nails with one of the ugliest girls in our school."

Jimmy looked over. Shelby and Ryan were looking at each others fingers the way that girls do when talking about nail polish while a few of his other teammates, Dennis, James and Jeff, who had clearly found out Ryan's true identity giggled. He turned away from him. What a loser! How was he ever concerned that that guy might be a better player than him.


A little shriek pierced the air.

"What was that?" Jimmy asked, brought back to his sense.

"I think that was your girl" said Kevin smiling.

"No, that was a real girl. It sounded like a real girl." Jimmy said.

"Oh yeah?" Kevin asked pointing over Jimmy's shoulder.

Jimmy turned. Ryan was lying on the ground, his purse feet away from him.

"Yeah, you better go check on her." Kevin said with a slight sneer.

Jimmy rushed over to where a concerned Shelby was leaning over Ryan.

"What happened? Are you alright babe?" he threw the last word in trying to be convincingly concerned.

"It was terrible!" Shelby gasped. "She was just standing there not doing anything, and then some seniors grabbed her purse and started throwing it around and when she started chasing after it her high heel broke. She hit the ground really hard!"

"Which seniors?" Jimmy asked knowing the answer.

"Basically all the seniors on the basketball team. Dennis Stores, James Parker, Jeff Rollins." Shelby responded. "They were behind us, laughing at her for some reason, and then they just rushed her!"

Jimmy looked at Ryan. He had a slight cut on his leg and a mark on his face but other than that seemed fine.

"Are you ok babe?" Jimmy asked again as the heavy breathing Ryan hadn't answered him the first time.

"Fine" Ryan said though looking upset.

"Why don't we get you fixed up? Can you stand up?" Jimmy said, giving Ryan what he hoped seemed like a tender pat on the cheek. Trying to be kind he added "I'm sure you can make yourself up and look even prettier."

"Give me a sec" Ryan said quietly. He could feel blood on his leg and he knew it would be hard to walk with his heel broken. He noticed there was a crowd gathering.

"How bout I help you out?" Jimmy said also noticing the sudden crowd knowing that his best chance at passing Ryan off as a real girl would be out the window if everyone gathered around him on the ground and looked at him at once.

He put his hands under Ryan's back and scooped Ryan into his arms. Startled, Ryan put his arms around Jimmy's neck.

"You didn't have to do that" Ryan whispered so no one else could here.

"Oh but I did!" Jimmy whispered back, still aware of the many people staring at him and the "girl" in his arms. "I couldn't leave my girl on the ground there. Besides, way more people would have figured out who you were the longer you were down there. Now most of them think your some sweet girl who had a rough night who I'm helping out. Besides, you're so light!"

Ryan heard more whispers.

"Wow, couple goals right there!" a bratty girls voice said.

"Awww, look at how she's clinging to him!" another girl said.

"Dude I can totally see her panties!" a boy exclaimed.

"And as a bonus" Jimmy said with a smile "this is probably the most humiliating thing possible for you. I mean, me carrying you out, all girled up and fussy while freshmen try to catch a glimpse of your panties. That's better than I could have possibly hoped for." He leaned on the door and headed into the hallway toward the bathroom, with Ryan still in his arms.

"I hate you" Ryan said, his teeth clenched.

"I'm sure people got some precious pics of you just now" Jimmy chided.

"I really hate you" Ryan said, teeth still clenched.

"And sorry about my friends by the way." Jimmy said sounding sincre. "I had no idea they were gonna do something like that."

He genuinely was surprised. He thought Dennis, James, and Jeff would have told him if they were planning on doing something like that but he couldn't have stopped it even if he wanted too. Sure, he was the best player on the team but the seniors were gonna do what they wanted to do. He had actually got a lot of cred with the seniors after the bet, almost all of whom were annoyed with the hype around the league surrounding Ryan.

Jimmy set Ryan down in front of the doors to the bathroom and something occurred to him.

"Hey Ryan?" he asked.

"Yeah?" Ryan responded as he smoothed his dress.

"Did you enjoy that? Being carried by me?"

Ryan was flustered.

"What? No! Of course not! Why?"

Jimmy smiled.

"It's just you never asked me to put you down. Not even when we were in the hallway."

Ryan blushed.

"You just held on, like a good little girl."

Ryan blushed even more and looked down.

"Shut up."

Jimmy smiled.

"Anyway, why don't you get yourself fixed up."

Ryan looked at the bathroom doors and looked back.

"Um, which one should I use." he asked Jimmy uncertainly.

"Really?" Jimmy asked with a smirk. "What are you wearing?"

Ryan looked down.

"A dress" he said meekly, smoothing out his dress again. "I just thought..."

"Rachel," Jimmy interrupted. "You are currently wearing a sexy pink dress and a sleek blonde wig, are showing more
leg than any girl here, had to be carried here because you broke your high heel, and are going into the bathroom to fix your make up! You're even standing like a girl now!"

Ryan looked down and noticed that he was standing with his butt jutted out to the side slightly. He straightened up quickly. Jimmy smiled at the sweet moment of insecurity. He moved closer.

"But that's ok!" Jimmy continued, once again feeling sympathy for his rival and placing a large hand on Ryan's small manicured one. "I like you this way! But don't act like you don't know which bathroom to use." He looked Ryan in the eyes, Jimmys deep brown ones finding Ryan's sharp blue. "I'll meet you out there when your done."

Ryan smiled slightly.

"Uh thanks?"

Jimmy returned the smile as Ryan headed toward to girls bathroom.

Once inside Ryan looked at himself in the mirror.

How could that teenage girl in the mirror be him?

He took a few deep breaths like he did at the free throw line. Ok. It was gonna be fine. He'd just fix up his make up
and go back out there. It wouldn't be that bad. Jimmy was kind of sweet. He thought.

No he wasn't! What was he thinking! Jimmy was a dick! He thought angry with himself for even thinking otherwise.

But was kind of cute.

NO HE WASN'T! he reminded himself. What was wrong with him?

Deep breaths, he reminded himself.

He reached for his purse. Where was it? Suddenly he pictured it, lying on the ground as Jimmy carried him away. He started freaking out again.

That purse had everything. His phone. His keys. His wallet. His makeup. I never thought I'd think that, he thought. And the only way to get it was to go back out there like this. He couldn't even text anyone. Should he call Jimmy and see if he'd bring it to him. But he didn't have his phone! Should he try to find Jimmy out there and have him bring it to him. What if he couldn't find Jimmy quickly? What if they couldn't find his purse at all? It was his sisters new purse and she was just lending it to him for the night! WHAT WAS HE GOING TO DO?!?

Ryan dropped to the floor, feeling the tears pouring from his eyes and started crying. He cried hard. He cried out his feelings over the last three hours, over the last three weeks. He cried out his embarrassment about the pretty girl at the dress store zipping up his dress for him, and his embarrassment of Jimmy finding him in his panties earlier that day. He cried out his anger at himself for playing his worst game of the season at the worst time, and his anger at his brother for enjoying his embarrassment so much. He cried out any other sound that was in that bathroom.

Suddenly the door to one of the stalls opened and he turned around.

"Oh. My. God! Are you ok?" came a voice.

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