*** 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
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
"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."
A wicked grin spread over Jessie's luscious pink lips, "You know Lizzie
"Yeah, little quiet girl, dark hair?"
"My sources tell me little Lizzie's still a virgin," Jessie continued to grin
"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
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
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
"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.
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.
"Sorry," Lizzie said looking down and hoping to continue on her way with nothing
"No, I'm sorry I startled you Lizzie," replied Jesse, "I was sort of looking for
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
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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