Jessie Sinclair was the hottest, most popular girl in school and Simon Gellar, like lots of the other guys in school, had a huge crush on her. Simon was small, about 5'8", and kind of good looking to women who liked his hairless, boyish looks. He had short dark hair and grey eyes and was generally passed over by most people at school who basically didn't notice him. He didn't mind most people not noticing him but he was desperate to get Jessie Sinclair not only to notice him but also to agree to go out with him. So far, he hadn't had much luck.
Like most other guys in school, Karl Walker too had massive crush on Jessie Sinclair. Unlike Simon, Karl was quite popular, the star of the River Falls High School basketball team where he played alongside Jessie's twin brother Jesse and her ex Brock. Karl was almost six foot tall but, despite his athleticism, slender and quite slight with the sort of long haired androgynous good looks that some women love. Unfortunately for Karl, Jessie Sinclair didn't seem to be one of those women, in fact, although Karl knew her twin brother pretty well, he had absolutely no idea what kind of guy Jessie went for as she seemed to have dated all kinds of popular guys. It wasn't that Karl didn't get plenty of attention from the girls, it was just that he wasn't getting any attention at all from Jessie who he'd had a crush on since the fourth grade. Karl and Jessie were now seniors in High School and he knew that if he didn't make his move right now then she'd be gone to college before he ever got the chance to hook up with her.
Now one thing Simon and Karl didn't know about their goddess was that not only was Jessie Sinclair popular, gorgeous and funny but she was the school's bitchiest, nastiest student and also the kinkiest. Jessie got her kicks out of setting up kinky situations for her own pleasure and often for the embarrassment of others and it was that same wicked sense of humour that attracted both Simon and Karl to her that enabled her to come up with such wicked plans. On the day that Simon and Karl both plucked up the courage to ask Jessie out, Jessie hadn't had any sex or kinky situations for a week, which was a long time for her and she was just dying to find somebody to involve in one of her wicked schemes. Unwittingly Simon and Karl walked straight into her trap.
It was Karl who found and asked her first. Jessie was head cheerleader which meant she was there to lead the cheers at River Falls Storm's basketball match that afternoon. Karl, dressed in the green vest and shorts with white trim that the River Falls Storm players wore, was named MVP and scored 35 points as River Falls stormed to victory. Karl might have been imagining it but he felt Jessie was particularly vocal in her cheers that day. She looked hotter than ever in her skimpy cheerleader outfit, her massive breasts barely contained by the green and white top with the letters RFHS picked out in white letters right across her breasts as if to draw attention to them as they bounced up and down in time with her. Meanwhile her stylish blonde curls were flicked back elegantly from her face and the tiny green pleated skirt lifted so far as to almost reveal her panties every time her long legs had to give a kick. Karl probably could have scored even more points that day if he hadn't been so distracted by the cheerleaders.
After the game, Karl jogged over to where Jessie was standing laughing with fellow cheerleaders Sarah Green and Lucy Watts, he was slightly out of breath but none the less attractive for it with little beads of sweat on his forehead and his long dark hair tied back by a white headband. He smiled at the girls and, as he talked to Jessie, he thought he saw out of the corner of his eye how Lucy was pouting her lips and arching her body so her breasts stuck out more and running her hands along her bare legs as if to try and get his attention. But Karl had eyes only for Jessie who he now tried to persuade to go out with him.
"I don't know if you're seeing anyone at the moment Jess," he said, running his fingers through his long hair nervously, "But, you know, I really like you and I think it would be great for us to go out some time."
Jessie gave a white smile so perfectly sweet that it had to be sarcastic and said in a voice just as sweet, "I'm sorry Karl but I'm not sure about that. I'll get back to you if I change my mind."
Karl flushed red with embarrassment, annoyed that his teammates had to see his humiliation, and even Lucy stopped trying to catch his eye. As he walked away he heard the cheerleaders giggling amongst themselves and he felt himself flush red again.
Simon was next, not more than a few minutes later, and if he'd known about Karl's recent rejection maybe he wouldn't even have tried his luck but he'd been psyching himself up for months and today was the day to do it. As Jessie left the gym after the basketball match, still dressed in her sexy, skimpy green and white cheerleader uniform. Lucy and Sarah had gone on ahead to the girl's locker room and so Jessie was left alone with Simon who stood there nervously as the much taller Jessie towered above him so he found himself almost at eye level with her breasts.
"Hi Sam, what do you want?" said Jessie, slightly irritably, to Simon's ever waning confidence.
He coughed to clear his throat, "It's Simon," he paused nervously, "I was just wondering, er, I know this sounds weird, but, er, would you like to go out with me some time?"
Jessie was about to laugh out loud at this suggestion, this was even more ridiculous than Karl, at least he was sort of a jock, but this guy. .! Then she thought for a moment, then she smiled, but not the mock sweet smile she'd given to Karl, this was a wicked smile to match the wicked plan she was hatching.
"Maybe Simon, I might just do that," she grinned as Simon felt his heart leap with joy, "How would you feel about a threesome?"
Simon would have given anything to get with Jessie but the thought of another guy being involved disgusted him, another girl, however . . .
"What, with another girl?"
Jessie gave an even bigger grin, "With a really pretty girl. How would you feel about dressing up then?"
By this point Simon was really turned on by the idea of getting together with Jessie and one of her sexy girlfriends that he was ready to agree to anything and so just nodded eagerly.
"Great," Jessie smiled, "My house at eight on Friday, my parents are out of town and we can get up to whatever we want," she winked.
Karl was a little surprised, later that afternoon, to find Jessie standing by his locker. She wasn't just standing either, she was leaning against it in such a gorgeous way as to enhance her curvy figure. Changed from her cheerleader's unifrom she looked no less hot in tight hipsters and a purple bra top that revealed a lot of her smooth skin. She smiled seductively at him.
"I've changed my mind Karl," she purred as Karl became excited just at the thought of it, "But only on the condition that: a) you're willing to dress up," here she winked seductively as if to suggest this wasn't so much a condition as something that he'd really like, "and b) you're willing to share me in a threesome with another girl."
Things just got better and better and Karl jumped at the chance not only to agree to Jessie but to agree without question to her conditions. She had a way with people that could seduce them to do far worse things than that and Karl agreed readily.
"OK, see you at my house at 8:15 on Friday," she winked as she walked off, when she was out of earshot, Jessie let out a hysterical laugh at how well her plan was working out.
At eight that Friday evening Simon arrived at the door of the Sinclair house, standing nervously on the doorstep. Simon had been on a reasonable number of dates since he'd been at River Falls High School but tonight he was going to be with his dream woman, not only that but she had promised him sex. As a result, Simon stood nervously waiting on the doorstep having rung the doorbell to the large Sinclair house. He was dressed in his best dark slacks and a cream coloured shirt that he thought made him look good, even though Jessie had promised dressing up, he decided he needed to dress quite well to make an impression.
Finally, as Simon was nervously thinking maybe this wasn't such a good idea and was about to leave, Jessie came to the door. Gorgeous as ever, she was dressed, despite the quite cold weather, in a denim mini-skirt and a blue bra-top. Any doubts about whether he wanted to be here faded away totally when Simon saw Jessie dressed like that. He could almost feel himself drooling as, dumbstruck, he allowed his dream girl to lead him into the house.
Sarah Green, one of Jessie's fellow cheerleaders sat on the sofa, dressed in a knee length black skirt and a pale yellow halterneck that showed off the curve of her breasts. Simon could feel his cock already beginning to spring to attention at the sort of a possible threesome with these two gorgeous cheerleaders. Sarah was lounging on the sofa idly, but she looked up when Jessie escorted Simon in.
"I think you know Sarah, Simon," she said smiling, "Sarah, this is Simon, the guy I told you about."
"Oh," said Sarah, getting up and winking, "You're the dress-up guy."
"Remember you agreed to dress up for me," Jessie said, "Well, Sarah's going to help you get ready. I'll leave you in her capable hands."
Sarah took Simon by the hand and lead him from the living room up the stairs and into a bedroom. Simon could feel his cock grow hard and a wet patch of pre-cum grow on his pants as at the touch and closeness of the beautiful blonde cheerleader. In the bedroom the clothes Jessie wanted Simon to dress in were laid out on the bed and Simon's eyes widened in surprise when he saw them.
At a quarter past eight the doorbell rang again. On the doorstep, Karl Walker stood waiting as nervously as Simon had some fifteen minutes earlier. Like Simon, he had made an effort with his appearance, and felt slightly more confident about the evening ahead with his dream woman. Confidence that was only damaged slightly by the arrival of Jessie opening the door to let him in, looking sexier than ever. Jessie took him by the hand and led him upstairs towards an empty bedroom.
"Remember you promised to dress up?" Jessie said, and Karl nodded eagerly, keen to play a part in Jessie's sex games to be able to get into his dream girl's panties, "Claire will help you out," Jessie continued as Karl saw Jessie's fellow cheerleader Claire Lancaster sitting on the bed in the room.
This made Karl quite excited, although a little skinny and flat chested, Claire was a tall, slender, blonde cheerleader and Karl felt his cock tugging at his pants at the thought of Claire dressing him up and then getting involved in a threesome with her and Jessie. Karl didn't know how it had happened, but his dreams and fantasies were suddenly coming true and he felt keen to exploit it. However, when Jessie left him with Claire and he walked into the bedroom, Karl was shocked to see the clothes that Jessie wanted him to dress up in laid out on the bed.
Laid out on the bed in front of Simon was a red lingerie set with a bra, panties, stockings and garter, and a red dress with a short skirt and low-cut neckline. Simon looked confused for a moment and then realised that this sexy ensemble was probably what Sarah would be wearing. He turned to Sarah and smiled.
"What will I be wearing then?" Simon said.
Sarah smiled back pleasantly and said in a voice that was equally pleasant although with a harder, patronising edge to it, "That's your outfit there on the bed."
Simon gulped and began to panic, what had he gotten himself into? At that moment Jessie swayed into the room.
"Ah, I see you've found your outfit, what do you think?" she purred sexily.
Simon began to stutter and panic, "I. . . I'm sorry Jessie, but this really isn't what I wanted to do."
Jessie smiled and spoke in a calm, soothing, coaxing voice that Simon desperately wanted to respond to, "Come on, Simon, you never know, you might like it. Besides, it's the only way you'll ever get what you want," she winked as if to indicate that meant herself, "and nobody but Sarah and me will ever know anyway."
Jessie's gentle coaxing calmed Simon down as he began to realise she was right. There's nothing that he wanted more than to get into Jessie's panties and he began to realise that if that meant also wearing them then maybe that would be ok with him. Simon realised that he'd basically have done anything for Jessie right then so after a pause to consider he said:
"OK, I'll do it."
Jessie smiled re-assuringly, "Great, don't worry, Sarah will help you to become the perfect woman, I'll leave you with her."
Jessie left and closed the door behind her leaving Simon alone in the room with just Sarah and the lingerie. Sarah smiled at him.
"Now, let's get you undressed first," she said.
Shyly and reluctantly, Simon stripped from his pants and shirt. Although he often desired to strip off in front of a beautiful girl in his fantasies, Simon wasn't entirely comfortable with his small, slight, hairless body. However Sarah smiled reassuringly at him, assuring him that his small body could be far more convincingly feminine. Although his body was virtually hairless, Sarah told Simon to have a shower in the adjoining en-suite bathroom, cleaning his body and shaving it totally clean and smooth. Although he'd always felt hairless, Simon now took pleasure in how silky smooth he had become.
After drying himself off, Simon wrapped himself in a towel and rejoined Sarah in the bedroom. Sarah ran her hand up his smooth, clean shaven legs and nodded her approval. Simon felt his cock twitch in anticipation at Sarah's light touch on his legs. Dropping the towel, Simon slipped into the dark red satin panties that felt so sensual on his ass and cock, while Sarah helped him into the matching dark red bra that she filled with two large silicone falsies. Dressed in the underwear with his skin smooth and hairless, Simon felt more feminine already. He didn't want to admit it but the sensual satin underwear was beginning to make him a little aroused.
Meanwhile Karl was also shocked at the outfit laid out for him in the other bedroom. There was a black lace basque and a long black dress that was slit right up the side. Like Simon, Karl was suddenly a little unsure about this. He looked over at Jessie who had come back in and was standing next to him, she nodded to him re-assuringly.
"You know Karl," she purred, "It might be fun, haven't you ever wondered what it would be like to be a girl. Besides only me and Claire will know and it'll get you to enjoy my threesome."
Faced with all these arguments Karl decided he didn't really have anything to lose by dressing as a girl, he had to admit he was curious and at that point he would have readily done even more if it got him his dream girl. So Karl, under Claire's direction, stripped and showered, shaving his body totally hairless, and came back into the room, concealing his modesty with a towel. Despite his athleticism, Karl had been with very few women, he was embarrassed to be naked infront of them because of the size of his cock. However Claire re-assured him that in this case it was good as he could conceal his true identity far easier.
"It's not much of a cock," she admitted, "but it'll make an excellent clit."
Meanwhile, Sarah had now attached Simon's garter and slid the dark red silk stockings sensually up Simon's smooth legs, Simon was now truly getting into it and he was now beginning to struggle to hide his arousal at the sexy underwear and Sarah's fingers running over his body as he lifted his arms and she slipped the little dark red dress over his head so that it fell around him. Although looking down, Simon could mostly see the outline of a sexy woman, there was an unsightly bulge at the front of the dress and Simon could feel the panties slightly stained and wet by a small patch of pre-cum. Sarah noticed this too and shook her head.
"We can't have that," she said, reaching down and grabbing his cock through the material of his dress and panties.
Simon felt like his cock was about to explode as Sarah ducked under his dress and pulled his panties down to his stocking clad knees. Sarah took Simon's whole cock in her mouth and quickly and efficiently sucked him off. It wasn't long before Simon felt his knees buckle and his cock twitch and shoot his wad into Sarah's mouth. Sarah efficiently swallowed all his cum so as not to stain his outfit and, without comment, took Simon over to the make-up table, not allowing him to see his reflection just yet. Simon, however was delighted by the joy of Sarah's blowjob and found himself almost as pleased that, as he sat down, he could smooth the skirt of his dress in a perfectly feminine way with no tell-tale bulge.
Meanwhile, Karl was now dressed in the black lace basque which was, like Simon's, filled with silicone falsies, and the long black dress, the slit up the side ran all the way up his long legs, which, now shaved, looked perfectly smooth, sexy and feminine. He now sat down on the bed as Claire applied heavy make-up to enhance the femininity of his androgynous features while at the same time she styled his long, dark hair into sexy dark curls that framed perfectly his well made-up face. When Claire had finally finished and he was allowed to see his reflection in the full length mirror, Karl was unsure if there even was a mirror, staring back at him, completely unrecognisable as the River Falls basketball star, was a tall, slender, sexy girl with dark curls and a black dress slit up the side to reveal her long legs. Claire took him by the hand again and led him back down to the living room, this time much slower as Karl was now learning to walk in the three inch heels of his black stiletto sandals.
"Now, there's just a couple more things," Claire told him as he sat down on the sofa, remembering to cross his legs in a feminine way, causing the dress to fall away and reveal the full length of his smooth long legs up to his hips, "I've got to leave now. Jessie will be in here in a few minutes with the other girl. The other girl doesn't know you're not a guy so you have to play along and be a girl called Chloe, OK?" This surprised Karl a little as he'd assumed the threesome was going to be with Claire and Jessie, however by now he wasn't particularly bothered about being with another girl instead, "Good luck," Claire leant over and kissed his cheek so as not to stain the dark lipstick on his lips and left the room.
As Jessie lead Simon down the stairs he was equally surprised to find out that Sarah was not going to be the other girl. However he now felt confident and happy, dressed as a girl. His outfit had been topped off with pointy red heels and a blonde Marilyn Monroe wig with slutty scarlet lipstick and heavy blush.
"Remember, the other girl doesn't know that your not one too," Jessie was telling him, "So you'll have to play along as a girl called Sally."
Coming into the living room, Simon was introduced to the other girl, Chloe, every bit as stunning as Sarah, and all his worries went away, knowing it was going to be a great evening.
Simon sat down beside Chloe and Jessie left the living room to bring them drinks. Chloe smiled nervously at him, she'd probably never done anything like this either. Simon smiled back re-assuringly at her. Attempting to speak in a high, feminine voice, Simon tried to re-assure Chloe, he placed his hand, given a scarlet manicure to look more feminine, on her knee. Her legs were crossed protectively, but this just allowed the slit up the side of her black dress to open and show off this long leg that Simon liked the touch of.