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Chapter 3
What's Jill's plan?
Ari comes to town.
Jill went to bed that night nervous. Nervous that she wouldn't find a way to complete her assignment. Nervous that if she did, it would still mean having a lot of sex with strangers.
She knew one thing for sure. The next day she had to tell James. James was a nice enough guy who she'd seen a few times. It wasn't serious enough that she'd call him her "boyfriend" yet, but if she had to do this assignment it would probably count as cheated.
Who knew, she thought, maybe he would want to help. She'd heard that some guys were turned on by the idea of their girl sleeping with other men. Maybe he'd want to watch, or could recruit his friends for the cause.
Just thinking about things like this made Jill feel dirty. Her whole life suddenly felt strange. Still, she hoped James would take the news well.
Two days later she was on the phone with Ari again. "He left me immediately," she said, not terribly broken up about it but still disappointed.
"What a jerk" Ari answered.
"I don't know." Jill was hesitant to judge. "I don't blame him. I mean if your boyfriend told you he had an assignment that would require him to fuck 500 girls, would you stay with him?"
Ari was silent on the other end of the line.
"I'm totally lost" Jill went on, admitting. "I have no idea what to do, and sometimes thinking about it even makes me scared. I need someone to help.... and I kinda need a hug." Jill felt fragile.
"I'm booking a plane ticket right now." Ari said. And although Jill initially resisted, insisting that she wasn't trying to guilt her friend into paying her a visit, she probably was.
A week passed, and all Jill thought about was sex. Too scared to actually have any she'd started looking at a lot of porn and masturbating more than she ever had. It was awkward, even among herself at first, but she told herself it worked as practice of some sort.
And soon it came more easily. That first night, Jill had been a little turned on by the orgy videos she found online. So several nights later she looked them up again, orgies and double-penetrations, and things she figured she'd probably have to do. Fucking one guy at a time just wouldn't get the job done.
One she started rubbing herself to the sight of a dumb porn bimbo moaning with a cock in her ass and one in her pussy, something in her brain changed, like a switch being flipped. Suddenly she found herself thinking about the images a lot, when at school, when at work in the Jewish center teaching kids, feeling terribly guilty about it. But she'd still yet to want to picture herself as the girl in the middle. She was still somewhat afraid to do it.
It was a calming day when Ari arrived. Jill met her best friend at the airport and it was impossible not to smile when she saw her turn a corner and walk in sight. Ari had always been there for Jill and this was no exception. She never judged, even now in the most unusual circumstances.
Ari was a big goof ball who always brought a smile to Jill's face. But she still knew when to be serious and when to be comforting and exactly how to cheer her friend up. Jill cherished nothing more than their friendship. Men came and went, even family had their issues. But Ari and Jill were always a perfect fit.
So immediately they hugged. Ari was a skinny girl, more petite than Jill with b-cup breasts and big doe-eyes. She wasn't lying when she told Jill that she'd recently chopped off all her hair and now sported a pixie-boy do' that actually looked fantastic on her and showed off her long neck and soft jaw. The hug lasted a long time. For Jill it was wonderful to feel Ari's comforting arms around her.
And then Ari the goofball showed up. "There. I hope that was a good hug for you." she said smiling. "Now I can get on my job of being your pimp."
Jill couldn't help but laugh.
"Trust me." Ari went on. "I've got all sorts of good ideas. Remember in high school when you thought Johnny Depp was the sexiest thing ever?"
Jill nodded, slightly embarrassed.
"Okay, so we only find guys named Johnny. Five hundred of them. That way you'll always just be like 'oh Johnny yes' and it'll be great for you" Ari winked.
Jill laughed again.
On the drive home they discussed their actual options, and brought up some of the ideas they'd had that first night on the phone. They included, dressing Jill up provocatively and putting her somewhere filled with a lot of horny men, like a bar, or putting on a show that ended in an orgy. "Like a performance piece" Ari insisted.
"A performance piece?"
"C'mon this is the Pacific Northwest. You hippies out here do things like this all the time, right?"
Jill wasn't sure if that was true. On the phone that night Ari had offered to do this 'performance piece' with her. But Jill decided not to bring that up just now.
Still, some topics had to be broached and that evening Ari insisted they had to get down to work. The two friends had shared a bottle of wine on Ari's insistence, and had spent the last few hours talking about good times past and Jill's anxiety about the assignment.
"Now don't be shy" Ari said. "This is me here with you, not other people. But if I'm going to be your pimp... honestly, I have to know some things."
Jill nodded and swallowed hard.
"How many men have you been with?" Ari asked.
"Seven."
"Ever been with more than one at a time?"
"No."
"Ever fantasized about it?"
"Maybe a little... just recently." Jill was surprisingly not nervous. Ari's presence helped.
And Ari went on. "I assume the seven you're talking about is regular sex. How about oral?"
"Um... four more." Jill felt a little embarrassed, like the number was low and she was a dull girl.
"How about anal?" Ari asked.
"Never." Jill answered.
"Girls?" Ari asked.
"No... I don't think they count for this assignment anyway."
"Black guys?"
"No."
"Any goys even?"
"Um.... two."
"Okay... strip."
Jill didn't quite understand at first. "Wait... what?"
"Strip." Ari repeated "I've gotta see what I'm working with here."
Jill felt a pinch nervous, but remembered this was Ari. This was a friend. And after all... "You've seen me naked before."
"That was a while ago." Ari insisted. "I need to see you now."
'Okay, you can do this' Jill thought. 'It's Ari, don't be nervous' Yet Jill was nervous. She took another sip of her wine and then pulled her sweater off over her head. Her bra was unspectacular, just meant to hold her C-cups in place, not to be particularly sexy. Then she stood up, unbuttoned her jeans slowly, unzipped them and pulled them down. Her panties were also plain, white, and the color of her thick black bush could be seen behind them.
Something about having Ari's eyes on her as she did this felt comforting yet still disconcerting. "Keep going" Ari said.
So Jill reached behind her and unhooked her bra, her nice sized breasts spilling out as the bra fell to the ground. She reached down to her panties and started to tremble just a bit.
And was comforted when Ari stepped toward her and placed her hands on her own. "Here... I'll help... be calm" her best friend said, taking the sides of her panties and pulling them down. Then caressing her flat stomach just a bit with the tips of her fingers.
Jill felt exposed yet comforted, ashamed yet empowered, proud of her body yet scared to be judged. Most of all she felt confused.
"You're very pretty Jilly" Ari said. "Finding people to sleep with you won't be hard at all. We just need to work up your courage."
Jill nodded. Ari was definitely right.
"Now tell me hon" Ari went on. "What plan sounds better to you? Barmaid or performance artist?"
Jill wasn't sure. She tried to think about the upsides of both, but it was hard not to focus on the fact that she was naked. Was that part of Ari's plan? Get her naked first, then make her decide. She felt the cool air of the night plan on her flesh.
"Jilly? Be honest." Ari said. And Jill had to choose.
What plan does Jill prefer?
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A Transformation
From schoolgirls to super sluts
A kinky school assignment changes four grad students from normal girls into wild sex maniacs.
Created on Sep 23, 2012
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