A Craigslist orgy

Over the next few weeks Jill pondered and puzzled and tried to figure out the best way to complete her assignment. All the while time ticked away at the semester.

First thing was first, she fucked her boyfriend. Then she promptly broke up with him. She decided not to tell him why. He'd never understand. She bought a little notebook journal and on the first page wrote: "Joel - 1."

She decided she was going to have to become less timid, so that evening she headed to a bar down the street from her apartment to do something she'd never done before. Pick up a guy with the intent of a one night stand.

As it turned out, it wasn't that hard. All it took was a short little white dress that showed off her long shapely legs. All night men came up to her and flirted and offered to buy her drinks and spewed terribly tragic pickup lines. She had her pick and after flirting a while with who she thought was the best looking man with the bar, a well chiseled college boy named Greg, he asked for her phone number. This was her opportunity, she thought. She told herself to be bold.

She leaned in an whispered. "Why put it off? My place is just down the street. Don't you want to get laid tonight?" Greg gave her a look of shock and delight. Even with the leggy dress, men didn't expect her to be quite such a slut.

Drunkenly they tripped down the street toward Jill's building. When they arrived, Greg pressed Jill's back up against the door and kissed her as his hand felt its way under her skirt to her crotch. Jill winced as it moistened. Then after few seconds of fumbling with keys, they burst into the apartment.

Neither of them willing to make it to the bedroom, Jill found the nearest opportunity, the kitchen table. She leaned over it, presenting herself to Greg. Greg lifted up her short skirt and tore down her panties. And Jill let out a deep moan as she felt Greg's hard prick slide inside of her from behind.

That night, moments after Greg left, Jill took out her journal and wrote "Greg - 2" as she couldn't stop smiling. G-d help her, this might be fun.

But she knew that picking up guys in bars would never take her to 500 men, and with January a memory, she had to speed up the process. She still didn't love her original idea of the Craigslist orgy, but it was starting to seem like the only way.

First thing was first, Jill need a location. The student center had an auditorium attached to it that could hold a good number of people. But when she approached the building manager for permission he outright refused.

"Absolutely not. What do you think this is? That behavior is not acceptable." He barked as he sniffled and rubbed his dirty gray beard.

But Jill knew how to get her way. 'Pretend to be a slut. Don't be you.' She thought to herself as she walked up to building manager, uncomfortably close. "I can make it good for you." she said as she placed her hand on his crotch, immediately feeling his dick harden. "And no one has to know."

The building manager answered with his eyes and Jill slid down to her knees, unzipped his pants and pulled out his hard, wrinkled, uncircumcised cock. This would be a first for her. She slipped her lips around it as the old man pushed it into her mouth.

"Building Manager - 3"

That night, alone in her apartment, Jill poured herself a glass of wine for courage and set up a Craigslist listing. She'd talked to Ari earlier in the day and they'd both decided that a month of planning seemed reasonable, although it would lose her all of February as well. Not to mention it would be a bad idea to stipulate men only.

"Massive orgy, March 3rd at the James Blackman auditorium at Miranda College. 3571 Liberal Arts Way. Meet at 10am in the morning. Orgy will last all day."

It seemed clinical and cold. Not the least bit sexy. And to be honest, Jill wasn't sure how sexy she felt about it. The idea was still scary, even though she'd been acting and feeling a little sluttier lately.

And as Jill thought this, she had the desire to continue her slut education. So, already drunk she put on the same short dress that had worked for her before, this time with no panties and stumbled to the bar. As soon as she entered, she noticed one of the men she'd flirted with before in the corner, shooting pool. She pointed at him and he smiled curiously, semi remembering her.

She needed a better reaction than that. So as he looked, she lifted up the front of her skirt, exposing her curly black bush.

That night she didn't get further than a filthy stall in the bar's men's room. But as the man whose name she didn't even know plowed her, she decided to try something. 'Think like a slut' she told herself and soon found herself saying out loud "Yes! Fuck me! I'm a little slut! Fuck your little slut!"

"Man at bar - 4"

That night, the **** wearing off, she felt guilty about it and wondered what she was turning into. But she couldn't help her hand from slipping down into her crotch and fingering herself to sleep as she remembered her voice declaring "I'm a little slut!"

Then a month came and went. The count in Jill's journal was up to 22 and she was proud. Still it wasn't at a rate fast enough to reach her goal, and she was excited that orgy day was upon her.

That morning Jill picked out an outfit for the orgy. Her little white dress had long since been torn apart by a particularly voracious man one night, but she'd replaced it with a frilly little black teddy she'd gotten at a local sex shop. There was really no passing it off as a real dress, and it was apparent to everyone when she walked out in public that she was wearing underwear, but the men's heads turned, and she liked that.

So the teddy it was, along with a pair of black thigh highs, black eyeliner, and ripe red lipstick. She let her long curly black hair fall onto her shoulders naturally. And the night before she'd shaved her bush into a presentable little triangle.

Before heading to the auditorium she stopped at the local mini-mart to get twenty boxes of condoms. She had the money to pay for them, but suspected that she could get them for free if she went down on the clerk. So she went down on the clerk. Some cum washing the back of her tongue would be good preparation for the day ahead.

"Clerk - 23"

And so she arrived at the auditorium and as she entered, heard what sounded like a good crowd of voices behind the door.

She was becoming more bold and sexual every day, but still she had to take a moment to calm herself before opening the door. "Think like a slut. Do what a slut would do." But as she opened the door, something about the crowd surprised her.