The Makeover

Jane continued to stare at her reflection in the mirror. It was becoming an obsession, but she was too young to realize that, or to understand just how unhealthy worrying about appearances could be. She looked at her face, but instead of pretty green eyes and bright, warm smile, she saw a frumpy nose and thin lips. Instead of gorgeous, shiny brown hair, she saw straight, tangled tresses. Rather than pert, perky breasts, she saw small mounds with freakishly large nipples - too long and too wide and much too red. She didn't see a trim, curvy waist with the blossoming sensual voluptuous hips, she saw a wide load and large ass. She thought her legs fat and flabby, not sleek, and smooth.

Jane looked at herself in the mirror and loathed the image. She was fourteen, which is an awkward time for any child, but she was only a few days into summer, the summer between her last year of junior high and her first year of high school. She wanted so desperately to be a cheerleader, but she could never make the team at her old school. Up until the end, they had teased and taunted her. Those girls were so pretty and athletic, and she was so frumpy and gross. No wonder she couldn't make the team!

But, soon she would be in high school - a brand new school with a new team. New classmates she could impress, ones who knew nothing of her previous failures. She only had a couples months to get in shape for the high school competition, but she knew she could do. She would do it. No matter what it took!

But what would it take? She didn't know the first thing about getting in shape or exercise. Then it hit her - Jane could ask her brother, Alan. He was always working out on his weights downstairs or going running around the block- he'd know what to do! He didn't do cheerleading, but he was on the school's track team and surely getting fit for track would be the same.

Just as she thought it, she heard him in the hall, walking by her room to his own. She could tell it was him by the sound of his steps - not fast or light like their petite mother, and not the heavy clomping of their father. Besides, the master bed room was on the first floor, all the way across the house, and their parents had little reason to come upstairs. Even cleaning the upstairs was left to the two children.

Without even hesitating a moment, Jane opened her door and called out to Alan. When he turned, her was shocked to see his sister standing there naked before him, but she didn't even pause a moment. "Al, I need your help. I need to get in shape for cheerleading. Will you help me work out? Can I work out with you?"

Alan blinked a few times, trying to keep his eyes locked on her face, but he a difficult time of that. Not that he hadn't seen a naked girl before, but it was not an ever day occurrence, especially not to have one in the flesh there before him. He knew he shouldn't be gawking at his sister like that, but he couldn't help it. A healthy dose of hormone-driven teenage lust was rippling through his body. "What?" he stammered when he realized she asked him something and he had never even heard the words.

"Will you help me get in shape?"

That was actually a welcome question - it gave him an opening to actually appraise her body. His eyes traveled slowly down her form, drinking in all there was to see. He made sure not to stare too long at her breasts or her mound of fuzzy hair just between her legs, but to drink it all in as part of an act. With a great deal of effort, he focused back on her eyes. "What's wrong with you now?"

That was actually a surprise - usually Alan teased her continuously about her looks. Jane figured he must have been taking pity on her and was trying to keep from hurting her feelings. He was such a good brother to care for her like that, but that made her even more aware of her horrid appearance. She started to sniff, unable to control the emotions welling up inside of her.

"I'm . . . I'm too fat and ugly to get on the cheerleading squat," she said with a sob, slowly stumbling towards him.

Being a couple years older, Alan was a bit taller than his sister, and when she embraced him, her head only came up to his chest. She hugged his abs and buried her face into his pecks and started to cry.

Stunned, Alan let his arms encompass her, trying his best to ignore the naked skin under his hands and the hard nipples poking into his stomach. He hoped Jane wouldn't notice the hardness that was poking back out at her, and she didn't seem to.

"Shhh, shhh," he comforted, like a big brother should. He stroked her hair, trying to calm her, all the while very unbrotherly thoughts rushed through his head. "You beautiful, Jane. She look great! You shouldn't have any problems getting on the team." His words didn't help. She just shook her head and blathered into his body, her words completely lost. At a loss of what else to say or do, Alan acquiesced. "Sure, Jane. I'll do some research and find a work out plan for you or something."

"Really?" she said when she pulled away. Her wide eyes were still dripping, but she wiped a hand across her cheeks to brush away the tears.

"Um, sure. I should be able to find something in on-line or in some magazine about what cheerleads do to get in shape."

Jane squealed in delight. "You're the best brother every!" Then, she suddenly realized she was naked and flushed. "Um, thanks! Ah, I guess I'll talk to you later about it." She broke away from him and rushed into her room, slamming the door in utter embarrassment.

Alan watched her rush off, his eyes lingering upon her round rear as she raced away. He had a raging hard-on that he needed to take care of, and after that, he would have a clearer mind with which to help Jane out with her problem. Yes, that was it, once he jacked off he would be able to focus on getting her a workout plan and not be thinking about her naked body pressed up tight against his.

* * * *

"Are you sure about this?" Jane asked, fixing Alan with a queer look. She was sitting on his bed, looking at a print-out he had found for her about her new work out. Something seemed a bit off, to her, and more-over she was a little down-hearted. She didn't think she would be able to do this work out.

Alan nodded, trying his best to keep from staring. When he told her that he had a work-out plan, Jane had changed into a skimpy little tank-top and itty-bitty shorts to work out in - she looked more like she was wearing a two-piece bathing suit that exercise gear - though a lot of the female runners on the track team wore outfits nearly as skimpy for runs. He had seen Jane in such things before and had never given it a second thought. Now he was having a hard time concentrating on anything but the ample amount of skin she was displaying. And those secret areas she wasn't displaying.

"Sure. I mean, you've heard all those rumors about cheerleaders being sluts, right?"

Jane nodded. That was definitely the stereotype. Dumb slutty bitches - in fact, that was pretty much the rep they had at her school, too. They were popular, boys always gawked at them. How she envied them! It did kind of make sense, in that perpective.

"So, then, it's all part of their workout," Jane concluded.

Alan nodded, suppressing a grin. After jerking off three times in a row, he found the image of his naked sister unshakeable, and as he gripped his still-hard dick in his hands after his third cum, his mind had shifted. After three long wanks fantasizing first just about her naked body, and then about the things he would like to do to it, he started to form a plan. Over the last few hours, he had slowly built it up and then worked to bring it to fruition. Maybe it was risky, but he was no longer concerned about risks, about right or wrong. He knew want he wanted, and by God, he was going to do everything in his power to get it.

Jane looked back down at the sheet in her hand and frowned. "But, who am I going to work out with? I would need to be a cheerleader to find a boy, and I need to find a boy to be a cheerleader. And I need someone who knows how to do these things!" She was starting to get upset - she felt her dreams were becoming unreachable again.

Alan moved over to the bed and sat beside her, giving her a comforting hug. "Look, Jane - I know this may be a little weird and all, but if you really want to do this. Well, I would be willing to help you out if you wanted."

She looked up at him, her eyes wide with love and adoration. "Really? You would do that for me?"

Alan nodded, trying his best to act the part of a self-sacrificing brother. "I know that I'm probably not the person you would want to work-out with, but I just thought I would offer if you - "

"Yes! Oh, yes! Oh thank you, Alan! You the best big brother ever!"

"Have you read the whole thing? The exercise and the diet plan?"

She nodded empathically.

"And the warning?"

She nodded again. "Good cheerleaders practice in secret cause most adults don't like to think about what the cheerleader has to do to keep in shape. So I shouldn't talk about it with anyone, even other cheerleaders. What a cheerleader and her work-out partner do is between them alone."

"Good! Think you can handle that?"

"Sure. Can you?"

Alan grinned at her. "Of course I can."

Jane looked down at the paper. "Some of this looks hard."

"We'll have to work up to it, Jane. Can't do it all at once."

Alan grinned as he looked over her shoulder at the print out. It had taken him a while to write it all up and find the necessary pics, but it seemed like it was going to be worth it. The sheet detailed a workout plan with different positions and movements, each one shown in explicit detail by a variety of different women dressed in cheerleader outfits and being fucked by different men. There were plenty of porn sites dedicated to cheerleaders; Alan had just picked various positions, from the mundane to the extraordinary displays of gymnastics, and created an article for them. He had written out what muscles each position worked and went on for a couple pages about the health and fitness benefits of sex.

The diet plan consisted of regular doses of protein in the form of cum. Several pictures accompanied the diet plan showing cheerleaders with mouths full and faces and bodies plastered with the stuff. The article said that not only was the protein great for muscle development, it added to fat loss, and when rubbed on like lotion, promoted fabulous, health skin and hair.

Hours of work and preparation, all to dup his littler sister into willingly fucking him. Alan was rather proud of himself.

"So, um - when do we start?" Jane asked, blushing.

Alan looked at the clock. "It's almost dinner time. How about after dinner? You read through your workout a few times and after dinner you can get your first protein supplement. And we can work out some details from there."

Jane nodded, glad to have time to read through the pages once more. She didn't want to appear to be a complete novice with her brother, so she thought it she could try to familiarize herself with some of the positions and moves, then maybe he would see she had actual potential and working out with her would not be a waste of his time.

* * * *

Alan sighed as Jane's mouth engulfed his hard cock. He had never had a blow job before - his last girlfriend had only go so far as to jerk him off once - and it was as wonderful and every porno ever made it out to be. He imagined that with an experienced woman, it would be even better, but right now, just the feel of hot, moist flesh around his shaft was exquisite.

Jane licked and sucked, treating his cock like a fat lollipop, unsure exactly how to entice the sperm from his balls. Having only seen pictures of women with their mouths stuffed, it was hard for her to know exactly what she needed to be doing. All she knew was, after some time of this, some thick white stuff would shoot from Alan's cock and she should try to get it in her mouth and on her body. The women in the pictures seemed to really enjoy it - the taste and the feel of it on their skin - so she was eager to try it herself.

Alan let her go at her own pace for a while, just enjoying the feeling of his first blow job. But he was aching to cum, and despite the amazing pleasure he was receiving, he knew that he was not going to finish soon like this. He had seen enough porn movies to know about blow jobs, to know Jane needed to bob her head up and down and fuck his cock with her face. So, taking measures into his own hands, so to speak, Alan rested his hands on the sides of Jane's head and started to force her face up and down on his cock.

Jane was surprised by her brother's actions, but her let him do as he pleased. He was her instructor, and the article had said to trust her instructor and do whatever he said, because he knew best. Wanting to do everything in the article so that she could be the every best cheerleader ever, she went with it.

As his passion mounted, Alan was unaware of how fast he was fucking himself with her face or how hard he was pumping Jane's mouth on his cock. The heat, the wetness, the delight of the flesh caressing his shaft - it was all so blindingly spectatular he just thrust her face faster and faster on his cock. He felt her gag once, then twice, the feeling of her throat constricting and shaking as his cock thrust into the very depths of his mouth was a shear delight.

And then, suddenly, when he hit her gag reflect again, a thick warm mess engulfed his cock and splattered against his thighs. He kept going, a thrill of pleasure passing through him as another explosion of heat and wetness slathered his groin. It tingled pleasantly, like hundreds of little fingers caressing his cock and balls. But when he heard his sister gasping and sobbing, he looked down and the truth hit him.

She had vomited up all over his cock and his legs. He pulled away, momentarily disgusted. She looked up at him, her eyes watering, puke leaking from her lips, dripping from her chin. Her face held sorrow and despair, though, for some reason, Alan couldn't held but think she looked even sexier then before - even as the thick goop dripped from her face onto her naked tits. And even out of her mouth, his cock was slowly surging on towards climax. He felt like if he just stood there and watched her, watched the vomit drip on her body from her mouth and his cock, if he let the bile continue to tickle and tantalize his tool, he would surely shoot a huge blast of cum all over her face.

His disgust gone, dissolved completely by lust of the sick perversion of her vomiting on him, he looked down at her with the mad desire to shove his dick back down into her throat and make her vomit on him again and again, until her naked body was coated with the stuff and then he would fill her emptied belly with his seed.

"I'm sorry," she mumbled. "Maybe I was never meant to be a cheerleader." Jane was on the verge of crying again.

"No! No, you are doing very well! That's all part of it," he said, trying to recover the moment. "You know cheerleaders need to be thin, right? You've heard of people throwing up after they each in order to stay thin, right? Well, cheerleaders do that too! They puke out what they ate and then take their protein supplement to get the nutrients back."

Jane wiped her eyes and considered this. "It didn't say that in my workout plan."

"They didn't mention it there. I read it on a few other pages. I didn't include that because - um, well, I thought you might be grossed out by the idea. So, I decided to do it without telling you - I thought if you did it the first time, it might not be such a big deal and you would be okay to do it afterwards. Sorry, I guess I should have told you."

She was grinning again, pleased that he had tried to look out for her like that, glad that was going to do whatever she needed in order for her to be a cheerleader. "It's okay. I thought I was doing it wrong. If that's how you do it . . ." She let the words trail off as she leaned back in and took his bile coated member back into her mouth. It tasted terrible, of course, but Jane took it all and shoved it deep down her throat and held it there.
She dry heaved a few times, but never pulled back a bit, then she her vomit exploded from her lips, spewing out all over Alan's cock, spraying across both of their bodies. After that, she fucked her mouth on his fast, plunging her face up and down on his cock faster and harder then he had, letting her lips slide all the way forward to the base of his cock. And there, when he head of his dick jabbed at the back of her throat, she would gag again. Sometimes she puked, other times it was nothing more than a dry heave, but she continued time and again, listening to Alan's mounting moans of delight, until finally he told her he was about to cum.

She drew back off his cock and held it in her hands, sliding her fingers along the slime covered shaft as was directed in her article. She jerked him, the hot puke being a wonderful lube against his skin, and she waited, her mouth open, for his cum.

He grunted once and then his cum sprayed, falling across her face in thick splatters. She managed to catch a shot in her mouth, and she swallowed it down, feeling no small amount of pride at the successful completion of her first workout task. Globs and globs shot out, raining down on her face and chest, mingling with the globs of puke that covered her body. She continued to jerk him until the cum stopped, and then, following the instructions laid out in her guide, she took his fouled dick back in her mouth and sucked the remaining drops from his cock, sucking down the remaining puke in the process and swallowing it all down together,

When his dick went soft and nothing more seemed to be forth coming, Jane pulled back and looked up at her brother. "How did I do?"

He was still panting heavily from his explosive orgasm, but he looked down at her nodding. "Excellent! Very well! So far, you're a natural!"

She beamed at the compliment. She wasn't really sure if she had liked it or not, but the fact that it was a step closer towards being a cheerleader and that she had been good at it made it such a thrilling and wonderful experience. She knew she would be glad to do it again.

"What now?"

"Now," Alan started, looking at the mess on his body and on his floor - he knew they would have to clean it up - then an idea hit him. "It is customary for the cheerleader to clean up the mess since her partner was so good to help her out with it."

She smiled and nodded. It seemed only fair, since Alan was only doing this to help her bcause she had asked him to, that it should be her responsibility. She stood to get a wash cloth to clean him off with, but he put a hand on her head to keep her from rising. "What you are supposed to do is lick and suck me clean," he said, as if letting her in on a secret she should have know about cheerleader ettiqute. "Then you lick the floor as clean as you can. After that, you wash yourself and the floor up with a cloth. You don't want to loose everything you ate for dinner, just part of it."

Jane nodded, seeing the wisdom in that. She lowered her mouth to her brother's pelvis and began to lick and suck away the vomit that coated his skin. As she did so, lapping away every bit of it, Alan murmured through his pleasure, "I'm sorry, Jane. I was supposed to shave off my hair to make this easier on you. I didn't have time. Next time."

Jane gave a little nod. She was amazed at how much her brother loved her, that he would be willing to shave off his pubic hair for her. After all, teenagers waited so long in order to grow their pubic hair, it would be such a loss of him to cut it all off for her! Maybe she should do that herself, that way he wouldn't be the only shaven one. Jane decided that that was the right thing to do - most of the cheerleaders in the article seemed to be shaven, or at least very trim. Maybe that's why, in support of their training partners.

Alan's cock was rock hard by the time Jane was done cleaning him, and then he watched Jane smear his cum and vomit all over her body as part of her workout to make her skin healthy and clean. And then she got on all fours and lapped her puke up off his floor - that was incredible! He felt like he was going to cum just watching the lewd display.

The poor girl was gagging through it all from the vile taste and horrible feeling of eating her own spew, but like a troopers, she worked diligently through it all. It was so fucking hot, he felt like he was going to explode. Before she could go get a cloth to clean the floor, Alan told her not to worry about it yet, that they would clean it later. He needed to fuck her so bad he couldn't wait for the clean-up.

He set her down on the bed, lust driving his body so completely he never even considered the mess this might make of his sheets. He climbed on top of her, his large frame dwarfing her naked body under him. He had no real experience with sex, only what he had seen in movies or read in stories, but between than and the primal urgings of his hormone-drive body, it was enough. He lined up his cock head with her tight, young cunt, and slid his tool up and down across her slit, slicking his member up with her juices. Her pussy was hot on his sensitive flesh, and very wet - though, he supposed that could have been from some of the vomit that had not been cleaned up, not that it mattered to him one way or the other.

"This may hurt," he whispered to her, wanting her to be fully aware of what would happen. "But it should start to feel good soon after."

Jane nodded, her eyes full of worry, but trust as well. Her brother was being so wonderful to her helping her reach her goals, she would take any pain it took without complaint so that he knew just how much it meant to her.

He slid his cock forward, piercing her opening. His cock head bunted against something holding his out, barring his passage. He pulled back a little and thrust with more strength, punching through her hymen and filling her young sex with his member. Jane winced under him, but made no noise. He didn't move at all, letting her body grow accustomed to the feel of a cock inside of it. And he let his own body cool from the experience. He had just taken his younger sister's virginity, but he gave up his own at the same time.

Her eyes peered up from under him, and he looked down at her beautiful, innocent face. At first, she was smiling through the discomfort, putting on a strong face for him to see. He stroked her hair and whispered soothingly to her, and in a few moments, her smile was no longer a mask, but genuine. She shifted under him and Alan felt her pussy tighten momentarily around his shaft. They both sighed with pleasure, and then, looking into each others eyes, both giggled a bit at having shuddered and moaned in unison when Jane had flexed her pussy muscles.

"The workout says I should keep constricting and releasing to strengthen my, um, trans-something," Jane said softly as her body clenched up tight on Alan's cock for a second then released. It was a decent squeeze, but she couldn't hold it.

"Transverse-abdomen," Alan stated. He didn't know if that would really work to strengthen his sister's core, but from the pleasure he was receiving from it, he was glad he had put that in there. "Don't do too much at first, you'll ware yourself out."

Jane nodded and slowed her squeezes down, taking a longer pause between them. Both of them moaned whenever she clenched up, and after a few moments, Jane grinned at her brother. "This is more fun then I thought it would be. I thought it was going to be a lot of work."

Alan smiled back at her. "It will be, but it is fun. Are you ready to go on?"

Jane nodded.

Alan began slowly, pulling back over the length of a minute and sliding back in just as slow. Jane was hissing as he did so, a little bit of pain, but Alan could also hear a lot of pleasure in the sound. He drew back again, and pushed in once more, keeping the same slow pace to warm her up to the act and get her loosened up a bit. Her hiss slowly turned into a purr, and with that signal, Alan slowly picked up the pace.

Jane wrapped her legs around Alan's waist, trying for the life of her to remember all of the techniques she had read about, but she couldn't concentrate, couldn't think. The sweeping jolts of pleasure from having Alan's cock thrusting in and out of her was over-loading her ability to recall. She arched her back and began to thrust her hips back against him, working in unison with his own pumping body. She didn't know if that was right, but it felt right; it felt spectacular!

The feeling in her was growing, if that was the right word - swelling, almost, and each thrust of him inside of her was better than the last. But, somehow, it felt like it was growing towards something, building up inside of her like water at a dam, water that would soon make the dam burst in a flood.

And she was right. Her first orgasm ripped through her body, making her cry out in joy as her flesh quaked and shivered beneath Alan. Her joyous out-burst was quickly silenced by Alan's mouth on her own, kissing her as her ecstasy continued. His tongue licked at her lips, then dove into her mouth, seeking her own, and she answered in kind, doing her best to navigate unknown waters by imitation. It was wonderful to be kissing him in this moment of complete and over-whelming pleasure, and as their tongues and lips played hotly against each other's, Jane trembled with delight, her climax reaching new heights in this intimacy. She wrapped her arms around his neck and pulled her body from the mattress with her arms and legs. Hanging from him, she swayed, ramming her body hard against his. She didn't know if this was part of her workout or not, but she didn't care. It made her feel absolutely fabulous, and at this moment, her pleasure out-weighed all, even her workout.

Alan had been trying to hold back, but it was no use. Even after three wanks and a blow job, he could not last any longer once his sister began to thrust herself with such passion against his body. He groaned and spurted, dosing her violated pussy with shot after shot of his cum.

He rolled off of her, panting, and she laid beside him, equally out of breath. Neither spoke for some time, just stayed there, naked, enjoying the afterglow and the feel of their bodies so close together.

"Wow!" Jane murmured. I hadn't thought it would be so good! And still so tiring."

Alan just nodded.

"Was it good for you too?"

He grinned. "Yes, Jane, it was incredible."

"So, you'll keep helping me workout then?"

"Of course!"

"Oh, thank you!" She rolled onto him, kissing him again on the lips and wrapping her arms around his body. Her budding breasts pressed hard into his chest, her nipples poking into his flesh. At first it was a quick peck on the lips, but before she withdrew, Jane kissed Alan again, returning the heat and passion they had shared just moments before in the thralls of their orgasms. She knew that something had changed between them, something large and dramatic. She liked it. She liked kissing him like this much more than the sisterly pecks she usually gave him. Being naked with him seemed strange and foreign, and yet right some how. She was glad he returned her kiss in kind, wrapping his arms about her and holding her tight.

They rolled apart after a few minutes, and once more laid on Alan's bed, basking in the pleasure and joy they had found with each other. And then a thought came to Jane. "Shoot! You should have cum in my mouth or on my face or something."

She reached down between her legs and began wiping her cunt with her hands and then licking the cum smears clean. Jane wasn't thinking about pregnancy, just about her diet plan and skin care regime, but Alan was a bit sharper on that front. He realized something would have to be done or else Jane's workout plan was going to keep her from ever being a cheerleader.

After her quick 'meal,' Jane got up. "Well, I'm all tired out. I guess I'll go to bed. Should we get an early start tomorrow? Work out all day as soon as Mom and Dad leave for work?"

Alan grinned. "Sure, Jane. That sounds like a good plan."

"Great!" She leaned over him and kissed him again, then scooped up her cloths and scurried into her own room.

Alan had to clean his floor and change his sheets, but it was worth it after everything that occurred. He kept replaying the evening in his mind, and by the time his cleaning was done, another hard-on was poking through his shorts.

Intrigued by his discovery of gagging blow-jobs - in all his time of looking at porn, he had yet to come across anything like a woman vomiting on the cock she was sucking - he decided he would make an in-depth search of the topic for his viewing pleasure.

And during his quest, he found a whole world of dirty sex he never knew existed. At first, some of it disgusted him, but after a couple hours of slow wanking to his porn searches, he had come to appreciate, even desire some of the filth acts he saw. He was sure the rest would probably grow on him in time, but for now, he had one in particular he really wanted to try. Now all he needed to do was write a fitness article that described the health benefits of such an act, and then he would be set.

He chuckled to himself as he began his work. He never before thought he could have such a pliable fuck-toy. While not a slave, not in the real sense of someone who could be ordered to do anything he wanted, Jane was close because he could dupe her into anything he wanted. Not only that, but she would thank him for the sacrifices he was making on her behalf and love him all the more for it. That was even better then just being able to order someone around. And that fact that she was his younger sister, well, that just made the whole thing even better.

He stayed up another few hours, pulling a late night writing spree he had thought he was done with for three months. But in the morning, Jane would have another diet tip and all the while she would unknowingly be indulging him in a new-found pleasure. Even begging to indulge him his pleasure. It was worth the lack of sleep.