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A High School Bet

(Part 1 from 5)

*** This story was originally posted in three parts on Literotica five years ago. I have just discovered this site and I have therefore decided to resurrect it for a new audience here. It contains lesbian sex and male to female crossdressing. Do not read this story if you are offended or not turned on by this. ***

Part One - A High School Bet

Jesse and Jessie Sinclair were two of the most popular kids in school. Twin brother and sister both the sexy brother and sister were tall and thin with shoulder length blond curls and bright blue eyes. Unbeknown to the rest of the school they were also two of the kinkiest people in the whole town.

One day Jessie lay, lounging, on a sofa at their house, bored. Her 32 E tits were just about held in by a tight pink top which cut away to reveal her awesome cleavage. She was wearing a very short pleated skirt which covered very little of her gorgeous long silky legs as she draped them lazily over the arm of the sofa.

"I'm bored with school these days," she was saying in her sexy voice, "We need to make it more interesting."

"What do you mean?" replied Jesse from where he sat on a chair opposite her.

"I mean we should have some fun, a bet."

"On what?"

A wicked grin spread over Jessie's luscious pink lips, "You know Lizzie Nichols?"

"Yeah, little quiet girl, dark hair?"

"My sources tell me little Lizzie's still a virgin," Jessie continued to grin sexily.

"So?" Jesse still didn't get her point.

"So, I propose we bet on which of us will be first to take little Lizzie's virginity?"

Jesse now finally cottoned on and his own good looking face spread in a similarly wicked grin: "You're on, what shall we bet?"

His twin sister smiled even more and said, "Simple, whoever wins can have the other perform whatever forfeit they want."

Jesse was deeply pleased with this. He didn't suspect Lizzie Nichols of harbouring any lesbian tendencies and felt he could easily triumph in this bet and then, and at this he had to stop himself rubbing his hands with glee, he could get Jessie to do whatever he wanted. To Jessie he just said: "Deal."


Lizzie Nichols was quiet and shy. She tried generally to go unnoticed by people and it normally worked. Although had she been more confident and popular Lizzie could definitely be described as attractive as it was she was mostly ignored. She was small and thin with reasonable sized breasts, she knew plenty of girls who stuffed their bras to get attention but Lizzie would do anything to avoid it and kept her 32 C tits covered by big sweatshirts. She had short-ish dark hair and dark brown eyes and her face was very soft and innocent. Lizzie had been out with a couple of guys before and certainly hoped to have sex someday, but, as Jessie had found out, she was still a virgin. Despite her good looks her shyness kept her back when looking for guys. She deeply wished she could be more like Jessie Sinclair who had been her friend when they were kids and now was popular and outgoing.

She never talked to Jessie really any more which is why she was shocked to look up from her reveries whilst taking books from her locker to see Jessie standing there smiling at her as Lizzie closed the locker. Jessie leant nonchalantly against the next locker smiling. Her perfect white teeth standing out against her tanned face. It was summer and Jessie was wearing very little, a red midriff bearing boob tube covered her popular breasts and beneath that she wore a short denim skirt which showed off her long sexy legs. Her blue eyes sparkled. Lizzie looked at her with a hint of envy, seeing how sexy her former friend was.

"What do you want?" said Lizzie, slightly suspicious.

Jessie's face was disarmingly friendly as she smiled at Lizzie, "I was just thinking how we never seem to talk or hang out anymore Lizzie. What happened to our friendship?"

"We haven't really been friends since grade school. You've got all your parties and popular friends now."

Jessie's face softened, looking hurt, "Please don't be bitter Lizzie. I know we haven't got on as well as we might lately but I'm trying to make it up to you. Look, I'm sorry and if you'll accept my apology we can start over again. Please?"

Lizzie looked into her former friend's deep blue eyes and beautiful face and knew she didn't have it in her to be bitter at Jessie, "OK," she said.

The sparkle returned to Jessie's eyes and her brilliant smile lit up her attractive face again. "Thankyou Lizzie, I knew I could count on you. That's what I like about you, you're so forgiving. How about we go for a burger after school and catch up."

Lizzie looked a little sceptical for a moment before finally saying, "Alright, see you at the fountain at four."

"I'll be there," smiled Jessie before hurrying off down the corridor, her sandals clicking on the tiles and her hips swaying in the little skirt that showed off her pert ass.

Lizzie watched her leave and then turned away to walk to her class, a huge grin for once on her own face. As she turned to walk off, her head again in the clouds, Lizzie almost bumped straight into Jesse Sinclair, Jessie's twin brother. Lizzie tried not to smile again at the weird situation that had her meet the two siblings, one right after the other. She looked up at tall Jesse, into his bright blue eyes, the twin of Jessie's but not so sparkling.

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"Sorry," Lizzie said looking down and hoping to continue on her way with nothing more.

"No, I'm sorry I startled you Lizzie," replied Jesse, "I was sort of looking for you actually."

Lizzie just looked back at him with a confused expression. Jesse began to run his fingers through his long blond curls and looked slightly embarassed.

"You're not going to make this easy for me are you?" he said, "OK, here goes. I've been quite attracted to you for a long time but have been too shy to just come out and speak to you so I've had to admire you from afar."

"YOU were too shy to ask ME out?" said Lizzie, incredulously.

"A lot of people think I'm like this cool, confident guy," Jesse was saying, looking bashful, "But when it comes to asking out a girl I really like I'm just as nervy as the rest of them."

Lizzie continued to look at him, faintly disbelieving, as he attractively but nervously tossed his hair away from his eyes.

"So about we go out after school today?" said Jesse.

Lizzie couldn't believe it one of the most popular hunks in school was asking HER out. Then she remembered she'd agreed to hang out with Jessie after school.

"This is really weird," she said, "But your sister's already asked to hang out after school and I can't go back on my promise."

Jesse's attractive face darkened and he frowned, "I wouldn't trust anything my sister wants you to do."

With that he turned and strode angrily away down the corridor.

"Another time then?" called Lizzie after him before muttering to herself, "another time then?"

For a few moments she thought on the bizzare coincidence that had her talking to both twins immediately after each other. Was Jessie really not to be trusted? Was she trying to break up any potential relationship with her twin? Or was it Jesse she couldn't trust? Was he really trying to stop her friendship with Jessie? Lizzie shook her head to banish these thoughts. She was a trusting person and didn't want to think badly of either of them.


That day after school Lizzie met Jessie and they went to the diner near the school to have burgers and a chat. Lizzie couldn't remember a time when she'd had so much fun and laughed as much. She and Jessie actually had a lot in common and Jessie had a wicked sense of humour. Sometimes Lizzie felt her friend could become a little too insulting about other people but she still found herself laughing at almost everything she said. When Jessie laughed she tossed back her luxuriant blonde curls and showed off her perfect white teeth in a way that made Lizzie quite envious. Throughout the meal in fact Lizzie couldn't help but stare with admiration at Jessie's impressive, large breasts.

At one point Lizzie decided to bring up the subject of her odd meeting with Jesse earlier that day. She felt totally at ease and comfortable in Jessie's company that there was no question about trusting her. So she told Jessie about the whole meeting.

"And he said not to trust anything you wanted," she concluded.

"That's odd," said Jessie, her beautiful smiling face for a moment confused, "I don't think I've done anything to offend him. Tell you what, I'll go home tonight and ask him about it."

There was a pause for a few minutes in which both girls just sat eating their burgers before Jessie said: "So, you've been asked out by one of the most popular guys in school, what do you think?"

"To be honest, after he stormed off I don't know if we'll ever go out. Anyway I'd be really nervous, I'm not good with guys."

"What you need to do is not be so shy. You need confidence and the first thing is to look confident. You're an attractive girl, I wouldn't hide everything you've got under baggy sweatshirts and jeans. If you want guys to like you you're gonna have to show off your assets."

"I'm not sure I'm really up to that," Lizzie replied.

"Don't worry I'll help. Tomorrow, after school, we'll go shopping for a new sexy wardrobe."

So Lizzie went home that night happier than she'd been in a long time at the fun she'd had with Jessie that afternoon. She smiled to herself at the prospect of spending more time with her the next day. Jessie was gorgeous, funny and popular and Lizzie admired her and hoped that by spending time together she could be more like her.


The next day Lizzie met Jessie after school again and Jessie whisked her off to the nearest shopping mall. That day Jessie had introduced Lizzie to all her popular sexy friends from the cheerleading squad and talked about how great Lizzie was. From then all the cheerleaders and popular girls would say hi to Lizzie and make conversation with her and so Lizzie seemed to everyone at school to be more popular.

That afternoon Jessie was still thoroughly amusing and entertaining and again Lizzie hardly remembered when she'd laughed so much, but she was also very helpful in finding Lizzie a new sexy and attention grabbing wardrobe.

"First thing is," Jessie was saying, "that you've got gorgeous breasts if you don't mind me saying. You can't hide them away, you've got to show them off, it's the best way to get a guy's attention. Just look at how much attention I get from guys just because of these."

As a result of this Jessie took Lizzie first to an underwear store where she showed Lizzie push-up bras and how they could enhance her tits. Jessie came into the fitting room with Lizzie as she tried the bra on which Lizzie didn't dare comment on. As her friend brushed her hand across Lizzie's smooth skin helping to fasten the bra Lizzie felt a tingle of pleasure run through her body and her exposed nipples get hard. Fortunately she felt Jessie hadn't noticed anything.

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