A High School Bet

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Eyl 6, 2023 // By:analsex // No Comment

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Jesse and Jessie Sinclair were two of the most popular kids in their senior year at high school. Twin brother and sister both were eighteen, 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. “Thank you 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.

“Sorry,” şişli eskort 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,” çapa eskort 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.

Impressed with the effect the bra had on her breasts Lizzie decided to buy it and Jessie continued to take her round fashionable clothes stores until Lizzie had quite a full sexy wardrobe. All the time Lizzie felt so comfortable and entertained in Jessie’s company. She had no idea why Jessie had suddenly decided to be friends with her but she was very glad she did.


The next day Lizzie shocked people at school and drew many admiring glances from guys when she turned up in her new sexy clothes. Her 32 C tits now stood proudly out in a push-up bra and she wore a black halter-neck top that showed off her cleavage. Beneath this she wore a knee length denim skirt and heels that made her short frame slightly taller. To top this off sh had styled her hair in a new sexy way and now wore pink lipgloss and some understated make-up. As she walked to class Lizzie felt many eyes on her sexy body and surprisingly she didn’t feel embarassed. Jessie was right, her sexy clothes had made her feel more confident and as she walked now she gave a sexy sway of her hips as she’d seen Jessie do and this encouraged even more open mouthed staring from guys she’d thought were out of her league before.

Just before she came to class Lizzie ran into Jesse again.

“Hey Lizzie,” he said, “You look great.” Lizzie felt herself blush under her make-up, “listen, I’m sorry for the other day, I just don’t feel you should let my sister push you around. Anyway, I’d still love to have that date some time.”

Happy that her sexy new look was already paying off Lizzie agreed to go to a movie with Jesse the next Tuesday, that gave her six days to get Jessie’s advice and guidance on how she should behave. She walked into class with a grin on her face, feeling a lot happier and more confident than ever before.

“You know, you should smile more often,” Jessie had said, “It really makes you look good.”


Over the next week Lizzie spent all her time with Jessie and her friends, it was fun and entertaining and Lizzie felt on top of the world. Jessie’s friends were quite nice and fun, but it was Jessie herself with whom Lizzie felt really great. She was beginning to feel Jessie liked her a lot too as Jessie would spend more and more time with her than with her other friends.

Lizzie didn’t want to admit it, even to herself, but she began to wonder whether her attraction to Jessie was more than just friendship. Sometimes, accidently, Jessie would brush her hand or her breasts against Lizzie’s skin and Lizzie would again feel that electric tingle of arousal. She found herself when nobody was looking just getting lost, staring at her friend’s cleavage and her beautiful face and long legs.

Over the week Jessie continued to give Lizzie helpful advice, not just on dating her twin but on guys in general and Lizzie was forever grateful for this as much as her attractive friends entertaining sense of humour. One day, it was the Monday of the week of Lizzie’s date they were talking about this and Jessie said.

“Do you mind if I ask you a personal question?” Lizzie shook her head, she felt totally comfortable and trusting towards Jessie, “You’re still a virgin aren’t you?”

“How did you know?” said Lizzie.

“I just notice these sorts of things. Don’t worry, I’m your friend, I won’t tell anyone. It’s just that you’ve got to realise Jesse is obssessed with sex and he might only want to date you to get into your panties. Just remember you don’t have to do anything you don’t want.”

“Thanks,” said Lizzie.


“I want to call off the bet,” Jessie was saying, voice raised in argument with her twin.

It was seven in the evening of the Tuesday of Jesse’s date with Lizzie. Jessie and her twin were arguing over their bet.

“You can’t just call it off, you’ve agreed to it. You know I’m gonna win, little Lizzie doesn’t stand a chance tonight and you’ve just helped me with all your efforts to make her sexy.”

“I don’t want to be involved in this any more.”

“Why not? Just because I’ll win, don’t worry I’ve got plenty of forfeit ideas for you,” Jesse grinned wickedly.

“It’s not right,” Jessie was saying, “I don’t think we should corrupt her. Lizzie’s a sweet innocent girl and I want no part in it.”

Jesse etiler escort burst out laughing, “I can’t believe it, you’ve actually fallen for her. Well this will make it interesting when I fuck her till she passes out. You know you can’t pull out of a bet now, you’ve given your word.”

Jessie looked at the floor, head bowed, knowing Jesse was right. Jesse grinned wickedly.

“Tonight your delicate little beloved will be corrupted for ever.”

He laughed and walked out of the house on his way to pick Lizzie up, leaving Jessie despondent.


Lizzie arrived at the door in a little pink baby t-shirt, tightly showing off her curves and revealing her belly button and a knee length skirt. Her dark hair was again teased into a sexy style and she wore more shiny pink lipgloss. Jesse had to admit that his sister had taste Lizzie was both sexy and innocent. He smiled to himself thinking soon he’d strip her off that innocence.

The movie was not that great but Lizzie did enjoy Jesse’s company although sometimes she felt him getting a little too close for comfort. He had put his arm round her which she enjoyed she felt safe and happy, but she wasn’t so sure when he put his hand on her bare knee and began to stroke her thigh. She moved his hand away, it made her feel uncomfortable. Although Jessie had her hand on Lizzie’s thigh a lot for some reason Lizzie felt far more comfortable with Jessie than she ever did with her twin. At one point Jesse leaned over to kiss her but Lizzie pulled away.

Despite these moments Lizzie had fun on her date and generally enjoyed Jesse’s company, although not such hilarious fun as his twin Jesse still entertained her and made her laugh and Lizzie didn’t think twice when he invited her in and sat her on the couch.

Jesse handed Lizzie a drink and she took it but before she could drink any he leant over to kiss her. This time Lizzie didn’t resist and she felt happy as Jesse placed his lips on hers and forced his tongue into her mouth. Lost in the joy of the kiss Lizzie didn’t immediately notice that Jesse’s hand had pushed up the little pink t-shirt and was feeling her breast. The other hand was running under her skirt, inside her thighs towards her panties.

Realising this Lizzie pushed him away. For a second a look of anger passed over Jesse’s attractive face and Lizzie was reminded of his reaction when he had first asked her out and she’d told him about Jessie.

“I’m sorry,” she said, “I’m just not ready for that yet.”

Lizzie thought he would sit back, understanding, but at the back of her mind she remembered what Jessie said, “he might only want to date you to get into your panties.” At that moment she felt herself pinned down on the couch by one of Jesse’s strong arms.

“I’m afraid you don’t get to choose here,” he said, unbuttoning his jeans with his other hand to release his erect cock.

He began to push up her skirt again with a triumphant leer on his face. Lizzie felt scared and shocked by what was happening but again Jessie’s words came to her, “you don’t have to do anything you don’t want to.” This gave her strength and she brought her knee up into his groin. As Jesse rolled back in pain she slapped him and ran, straightening her skirt as she went, tears welling up in her dark eyes and mascara running across her cheeks.

As she ran from the house Lizzie ran straight into Jessie who was just coming up the drive. Jessie was dressed in a tiny pair of denim cut-offs that showed the full length of her tanned smooth legs and a pale yellow blouse with some off the buttons undone to reveal her cleavage. Lizzie looked through the tears into Jessie’s deep blue eyes.

“What’s wrong? What’s happened?” Jessie said, instantly concerned at the sight of Lizzie in tears.

Through the tears Lizzie managed to get out the story of how Jesse had tried to force himself on her.

“You were right about him,” Lizzie sobbed.

“I didn’t want to be,” said Jessie.

She opened her arms and allowed her friend to fall into them as Jessie hugged her affectionately. A wet patch appeared on her blouse as Lizzie’s tears continued to flow as she pressed herself against Jessie’s ample bosom.

“You shouldn’t be alone tonight,” Jessie was saying as Lizzie pressed against her curvaceous body, “Come inside, I’ll look after you.”

Lizzie smiled at her friend through her tears, relieved that she knew she could trust and care for Jessie, as she followed her into the house. Avoiding Jesse, Jessie led Lizzie up to her bedroom and they sat on the bed together. Jessie continued to hug her friend as Lizzie continued to cry.

“It’s OK,” Jessie continually re-assured her as she began to plant kisses over her friend’s face.

Lizzie looked up from her tears into Jessie’s beautiful blue eyes. For what seemed like ages but was actually just a few seconds they stared into each other’s eyes. Then, slowly, Jessie took Lizzie’s head in her hands, and gently planted a kiss on her inviting shiny pink lips. Instinctively Lizzie opened her mouth and took in Jessie’s tongue, caressing it with her own and closing her eyes, savouring the kiss. The feel of her friend’s fine breasts pressed against hers was causing a feeling of arousal to run through Lizzie’s body and she felt her nipples becoming erect.

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