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The Deal

Trevor stood there in his tartan boxers, his hands crossing self-consciously over the front of them. Chloe smiled, a bit amazed by how much his body language had changed. He seemed... meeker, that was the word. He had become so much meeker now that he stood in front of her in just his underwear.

"Those'll have to go." She said immediately. "They'll show right through the tights." The blush that formed on his cheeks radiated to his shoulders, to her delight. "Your tights." She added, just to see his blush deepen further.

"What'll I wear instead?" He asked, toes subconsciously clenching on the carpet. He already knew that he would not like the answer.

"These." She held up a pair of white cotton panties with a slight bit of lace around the legs and the waist. His eyes darted away. There was something intimate about seeing the panties in her hands.

"I" He began, unsure of where he was going with it, but feeling that he had to say something. He felt like the silence stretched for a thousand years.

"It's part of the deal, so don't even try to get out of it." She said. He wanted to tell her that he had not even thought of trying to get out of it. "If it makes you feel any better, we won't take any photos. It'll just be you, me, and Courtney." He nodded. "She donated the outfit, so there's really no way to get around it." She walked toward the door. "Since you're about to get naked, I'll give you some privacy. I'll be right outside." His cheeks burned again as she gave him a small wave good-bye.

He took a moment to breathe. Here he was standing in his crush's bedroom in nothing but his boxers. It should have been a dream come true, but that stupid bet had ruined everything. Well, really, it was Courtney, Chloe's eight year old sister that had ruined it all. He had bet her that he could get five paper balls into the wastepaper basket on the other side of the room before she did. If... no, when... when he won, she would have to live him and Courtney alone. He had hardly even listened to Courtney's counter offer before shaking her hand. When she thrown five in a row in, he had been dumbstruck.

"C'mon, Trevor. Let's get ready for our recital." She said. Trevor, still dumbfounded, turned to Chloe to explain. She did and that was how he ended up here, with the outfit on the bed.

"Let's just get this over with." He muttered, Chloe's promise of privacy ringing in his ears. He removed his boxers and deposited them on top of his jeans and t-shirt by the door. He did not even spare a thought about the fact that he was now completely naked in Chloe's bedroom.

A simple pair of cotton panties. He suspected she was taking it easy on him, but an embarrassed squeak escaped his throat as he slipped his feet through the holes before slowly pulling them up. School required him to wear briefs for gym class, but these, these were so much tighter than briefs, seeming to cradle his bottom and subtly shape it. Now that he thought about it, they were indescribably softer too... It was not an entirely unpleasant experience, not that he would admit that to anyone. He sighed and picked up the next item, a matching pink undershirt that he pulled on like an ordinary t-shirt. He had subconsciously turned toward the mirror. Not liking what he saw, he quickly turned back to the bed and picked up the next item, as he was starting to get into the territory he dreaded: tights.

He stared at the thin pink material he held before his eyes, running his fingers over them as he tried to work out how best to get them on. Shrugging his shoulders, he figured it could not be all that different from pants. They seemed so small though. If they were too small, would he get out of it? He remembered Chloe explaining the rules that they played with, where if someone could not complete a dare, they got two dares instead. He shuddered to think of what Courtney would come up with instead.

He felt awkward about sitting on Chloe's bed. It seemed almost like sacred ground, so he sat on the carpeted floor and, taking a couple deep, almost meditative breaths, began to work his feet into the tights, pulling them up his legs bit by bit. The opaque material clung to his legs like a second skin, making him cringe with humiliation as he managed to get his toes into the ends of the legs and the top of the tights around his waist.

Though the panties had been white, the tights concealed their true color completely. Everything he wore appeared to be pink and he knew it would only grow worse as he spied the leotard out of the corner of his eye. He sighed and wistfully eyed his discarded clothes. No. He would go through with this, no matter what it took.

"Just gotta get this over with." He muttered. It was becoming almost a mantra. The carpet felt different through the tights, but he was far more distracted by the feeling of his thighs rubbing together. He gingerly lifted up the leotard, the tutu rustling and crinkling softly. He stood there in panties, a pink undershirt, and tights, but he still trembled as he stared at the leotard. His tremors made the tutu crinkle more. "Just gotta get this over with. Just gotta get this over with." He repeated as he stepped into the leotard, slipping his legs through the holes as he had with the panties and tights. He quietly banished the thoughts that insisted on reviewing the steps he had taken since Chloe had left, the tutu rustling incessantly with every movement as the humiliated boy slipped his arms through the sleeves. The leotard clung to his body with a different sensation than the tights, albeit one just as unfamiliar for the boy.

He groaned as he glanced at the full-length mirror that hung across the room. The combined efforts of the panties, tights, and the leotard shaped his bottom into curvy bubble butt perfection. With the exception of his hair, he looked completely feminine in his ballet outfit. Sighing, he grabbed the ballet slippers and headed for the door, still unfamiliar with the feel of the carpet under his tights-clad feet.

Try as she might to support Trevor, Chloe could not help but giggle as the bashful teen emerged from her bedroom. She quickly covered her mouth and mumbled an apology.

"I can't believe it fits you. Perfectly." She said. Trevor's face showed just what he thought of that. "Oh, come on." She said. "Might as well try to enjoy it. You've come this far. Me and Courtney won't tell anyone." She noticed the slippers in his hand. "Sit down on the floor. I'll help you get your slippers on." She could not help but giggle again as Trevor sat down.

"What's so funny?" He asked, staring up at her from the floor. Normally, he would have enjoyed the view, but not like this. She took the slippers from him and began to put them on him as she explained.

"Oh, nothing. It's just, that was the most ungraceful I've ever seen anyone in a tutu be."

"Shuddup." Trevor muttered.

"The leotard, at least, isn't new."

"What?"

"Didn't you tell me that your mom signed you up for dance classes when you were like five?" Trevor stared at her, trying to ignore the sensation of the ribbons of the ballet slippers being tied around his ankles and calves.

"That was gymnastics"

"Oh, right." Chloe barely restrained herself from adding that they were basically the same thing on the sissy scale.

"And I just wore shorts and a t-shirt, not" He gestured wildly up and down his body. "Not like this." He took her hand and she helped him stand. "So, what's this recital thing that Courtney was talking about?" Chloe led him back toward the living room, explaining along the way. Trevor followed, a bit annoyed by how the tutu around his waist refused to stay still, crinkling with each and every step.

"It's really nothing to worry about. She'll just make you do a lesson or two." Before she could elaborate further, they came to the living room. Courtney's eyes were as wide as dinner plates and her face made it seem as if it was Christmas and her birthday at the same time. "Remember, Courtney. You promised no pics!" Courtney nodded, the reminder only dampening her mood slightly.

Trevor turned from the still grinning eight year old to investigate the origin of some light music he heard to his left. His eyes fell upon the brightly colored main menu of some DVD on the television screen. It proudly decreed Madame Martin's Ballet School along the top and beneath stood three little girls around Courtney's age, each in a pink tutu and tights very similar to the outfit that Trevor himself wore.

"Here's the deal!" Courtney said with obvious delight. Trevor turned back to look at her. Since she had been forbidden to take pictures, she seemed determined to prevent herself from blinking so that she could remember as much about the teenager in a crinkly tutu before her as she possibly could. "You're going to do the first two lessons of Madame Martin. It's for little girls, so you shouldn't have any problems. Once you're done, you can change. Okay?"

"Sure." Trevor replied with a shrug. Misjudging the reason for his apprehension, Chloe smiled at him.

"They start out slow. You'll do fine." She playfully patted the bashful boy's tutu, making it rustle.

"Ready?" Courtney asked gleefully. Trevor nodded. He did not trust his voice not to crack if he tried speaking. She hit play on the remote and Trevor's lesson began.

The moment that Madame Martin came onto screen, Trevor gritted his teeth. He could tell from the smile on her face that her voice would be treacly and sweet.

"Hello there!" She said breezily. "I'm so happy you're able to join the other students for class today. Are you ready to become a ballerina?"

"Well, are you?" Courtney asked, barely able to stop giggling.

"Yeah." Trevor mumbled.

Just as Chloe had said, the lesson began easily enough with some exercises to warm up. Holding his arms out, Trevor first extended his right leg in front of him so that only his toes touched the ground, then all the way to the side, and then to the back. Courtney paused it immediately.

"Get your leg out straight, Trevor." She said. Trevor complied. "Much better. From the top!" To his horror, she restarted the lesson from the beginning. It took five more tries for him to make it through the initial leg exercises and Courtney made him answer Madame Martin every time her introduction played over. Learning what happened when he messed up, Trevor paid close attention to foot positions, ignoring the snickers of Courtney and Chloe as he did his very best ballet.

"Last of all, we're going to learn how to do a plié." Madame Martin said. She very gracefully demonstrated and Trevor knew immediately that he would never be able to do it correctly on the first try. Finding the pink plastic bar to his right, he did his best plié, nodding to himself as Courtney stopped the lesson and sent it back to the beginning.

It took more tries than he cared to admit, but he finally reached the end of the lesson. He turned around, red-faced, and looked at the two delighted girls on the couch. Only then did he realize that the deal had been for two lessons, not just one. He would be here all night!

"On to lesson two?" Trevor begrudgingly asked. Courtney looked as if she was more than happy to oblige, but Chloe intervened.

"Courtney, don't you think Trevor's done enough?"

"Yeah, fine." Courtney allowed. "Sure wish we could have taken pictures of the ballerina though." She rubbed her arm after Chloe smacked it.

"Tell Trevor he can go change, Courtney."

"You can go" before she even finished saying it, Trevor charged out of the room, tutu bouncing and crinkling as he dashed up the stairs. The girls watched him go before pulling out their phones to compare the pictures and videos that they had each taken of the bashful boy ballerina. One thing was for certain. Trevor would be back in a tutu for the other nine lessons and soon.