Paying Their Way Ch. 01

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Jessie & Lizzie must find creative ways to pay for college.
2.3k words
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Part 1 of the 2 part series

Updated 10/26/2022
Created 10/06/2004
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This is the first part of a new story featuring the characters Jessie and Lizzie which I am writing due to all the good feedback I got for the previous one "A High School Bet", so I would like to thank everybody who has been generous enough to give their comments and support, it means a lot to me.

*

Lizzie Nichols was on her hands and knees, a six inch cock thrusting hard in and out of her mouth while behind her her tiny skirt was pulled up and another cock was thrust inside her tight ass. Lizzie looked across to her right to see her friend Jessie Sinclair lying on her back with her long smooth legs spread wide open and another guy inside her, thrusting his cock hard in and out of her cunt. Lizzie was dressed sluttily in a red boob tube, black leather ankle boots, a tight black leather skirt that had been pulled up around her waist and red lace panties which now hung around her knees, meanwhile her friend was completely naked, except her long legs were covered by slutty thigh high leather boots with six inch heels.

Lizzie tried not to concentrate on the pain in her ass as it was stretched out by the large guy behind her. He was not very attractive, a muscular, lumbering guy with a shaved head and squashed facial features. He was kind of a man's man and liked to take control of the situation, his hands on Lizzie's hips controlling the depth that he fucked her ass. Trying to ignore the pain that was almost causing tears to run down her face, Lizzie tried to concentrate on the firm, throbbing cock in her mouth which she ran her tongue around while it thrust in and out of her face. The guy owning the cock was a slightly better physical prospect than the guy behind her, tall, skinny and wearing glasses, at least he was a little more gentle with her.

In a way, Lizzie was relieved to feel the cock in her mouth twitch and blow it's load into her mouth. She knew she was expected to swallow the warm salty cum, something she didn't relish, so she gulped down a couple of mouthfuls, but the guy kept cumming and Lizzie didn't have the ability to keep swallowing. She had to let him pull out his cock and continue to cum across her heavily made up face and into her hair. At the same time the big guy behind her grabbed her by her long black hair, pulling her head back, and came, filling the condom stretched over his unimpressive cock. For show, Lizzie thought it was best if it seemed like she came too, so she did her inexperienced best to fake an orgasm, crying out and shaking her body. Fortunately these didn't look like the sort of guys who'd be that aware what a real girl's orgasm was like anyway. Looking across the room, Lizzie could see her friend making a much better job of faking hers. As she lay back on the floor with a cock in her pussy, her head was thrown back, her body convulsing and she let out a number of loud screams that could have fooled anyone who didn't know Jessie as well as Lizzie did.

Finally the guys withdrew from Lizzie and Jessie and put their clothes back on, not really looking at each other at all. They walked quietly and shyly out of the room and, as they went, left a large pile of twenty dollar bills on the table by the door. Getting up from her place, lying on her back on the floor, Jessie sauntered over to the table and counted and straightened the money. She smiled down at Lizzie, who, face stained with cum, slutty make-up smudged and ass sore, had collapsed onto the floor. Jessie looked gorgeously sexy dressed in just the slutty thigh high boots. Her tall, slender figure, unbelievably enormous, beautiful breasts and long golden curls made her look like some gorgeous porn star as she swayed back across the room to put the money in a drawer.

As Jessie sat back on the couch and removed the slutty boots, Lizzie went into the bathroom and got cleaned up. Stripping off her own slutty clothing, she stepped into the shower and let the warm, soothing water wash away the cum and make-up on her face and wash away all memory of this evening's activities. Wrapping herself in a towel, feeling now more clean and pure, Lizzie wandered into the bedroom that she shared with Jessie. Jessie was now dressed in a pink lace babydoll nightie that clung to her large breasts and showed off her long legs. She walked over to the now much cleanier and more relaxed Lizzie, swaying her wide hips and ass, and placed a little kiss on Lizzie's lips.

Jessie took Lizzie's towel and let it fall to the floor as she began kissing Lizzie's neck and down towards her firm round tits. But here Lizzie took Jessie's head and pulled it from her chest. Smiling at Jessie she said:

"Do you mind if we don't tonight? I'm really not in the mood."

Jessie looked a little disappointed but smiled her perfect white smile back at Lizzie, reassuringly.

"That's ok honey, we don't need to do anything you don't want."

She kissed Lizzie gently on the lips again and climbed into the king size double bed that they shared in their small apartment. Lizzie finished drying herself off and put on her own sensual nightclothes, a cream coloured silk slip that she loved the feel of, before climbing in beside her gorgeous lover. Jessie opened her arms and Lizzie curled up, cocooned inside her girlfriend's embrace. She felt safe and secure here, pressed against the body of the woman she loved, wrapped in her arms she felt that she could forget this whole evening ever happened.

***

To explain how Lizzie and Jessie found themselves in the situation of selling their luscious bodies to make a living it is necessary to look back at the girls' background. They'd met at River Falls High School, in a small Californian town, where Jessie was the popular head cheerleader. However, when the girls showed up at the senior prom together as a couple they met with shock and judgemental anger from the rest of the school. Soon the news was all round the small town, a town where everybody knew everybody's business. Jessie and Lizzie's parents had both decided to throw the girls out when they left for college a few months later and refused to give them any support.

As a result the girls had ended up at college together in far away Boston where their disapproving parents could be well rid of them. Jessie had found them a small, sparsely furnished apartment that would be fairly cheap for them to afford. Their total lack of any money meant that for the first few months of college they had desperately tried to work a number of jobs to raise the money, but so much work, both day and night, had damaged their school work and by the time Jessie's twin came to stay at Christmas both girls were in danger of failing their college courses and being forced to drop out. They were desperately in need of a quicker way to make money so they could concentrate on their schoolwork and their relationship. Although they'd managed to stay together through thick and thin since graduating from River Falls, these money problems were putting a strain on Jessie and Lizzie's relationship and the increasingly stressed Lizzie did not always give in to Jessie's forceful sex drive any more.

Fortunately Jessie's twin had just the solution when staying at the girls' apartment that Christmas. Any thoughts that Jessie's family were deeply distressed and angered by Jessie's lifestyle choice were undermined by this twin. Jessie had actually turned out to be the family's favourite child, even though she'd been disowned, when compared to the wrath of her father against her twin. Her twin had been born her twin brother Jesse Sinclair, however in high school, around the time Jessie and Lizzie had got together, he had discovered a love for women's clothing which soon grew into full blown crossdressing, something the twins' parents were not pleased to discover.

Jessie's father had always been obssessively proud of his all-American twin children, Jessie the popular cheerleader and Jesse the sporting jock, so to discover his son's crossdressing was the worst thing he could possibly imagine. It completely ruined his perfect American family. Calling Jesse a "sissy" and a "fag" he banned his son from ever coming near the Sinclair family home again. The two disowned twins stuck together but without any support from their parents they struggled.

Not long later Jesse, now calling himself Julie, arrived in Hollywood to become a porn star. By the Christmas when she came to stay at Jessie and Lizzie's apartment, Julie had already become something of a success in the world of transsexual porn. Her convincingly feminine good looks and obssessive sex drive were just perfect for the porn world. Now going by the porn star name of Juliet Seaman, to distance herself from her family, Julie was starting to make some quite considerable amounts of money. Unfortunately for Jessie and Lizzie, all the money that Julie was making as a porn star was needed to provide for the surgery to make her increasingly feminine, so Julie wasn't able to help out directly with their financial problems. However, she did make some suggestions.

"Why don't you two work in the sex industry too," she suggested, "It doesn't take many hours work to make far more than both of you make in a whole day on your menial jobs."

"Become a porn star?" Jessie said incredulously, "Round here? I don't think so."

"We wouldn't know where to start, where to go," Lizzie continued.

"You don't have to do porn," Julie said, "You could become escorts."

And so, after Christmas, when all the students were back in college for the new semester, they discovered flyers strategically placed around campus advertising, "Two sexy female escorts; available for men and women," and then a telephone number that just happened to be Jessie's cellphone.

Thus, two weeks later, Lizzie found herself on her hands and knees with a firm, hard cock in her mouth and another up her ass, the small girl feeling totally impaled between the firm beasts. However at the end of the evening, when Jessie counted the money, the girls knew that at least they wouldn't have to keep working all hours for no pay just to keep going.

***

Hannah Monroe was walking back across the campus to her dorm after another unexciting day. It was five o'clock and as it was winter it felt a little chilly and the sky was already darkening towards the evening. Hannah wore a long black coat and a multi-coloured scarf, while her braided blonde hair was tucked under a woolly hat. Still, she could feel a cold breeze across her face as she bowed her head against the cold, held her coat closer around her and quickened her step. The darkening sky promised a frosty night and even the possibility of mid-winter snow, something that would have excited the usually cheerful Hannah in previous years, but now she had a lot on her mind.

Now the cold winter air didn't make her excited about seeing the college campus with a beautiful white covering. It didn't make her think of going out and playing wild games, having snowball fights with her friends as she had done throughout her childhood and even high school. Hannah usually took everything in her stride and felt the happy side in whatever nature threw at her, but today the cold wind chilled right through her and made her feel empty and lost. Normally a happy, bubbly, freespirited woman, Hannah hadn't really felt like she had settled into college in Boston that well. Her family didn't live that far away in Maine, and Hannah often went home for weekends. She hadn't yet made any friends away from home who she felt a real connection with, who would understand her lifestyle and sense of adventure, not to mention her bright and colourful fashion sense.

When she was seventeen, Hannah's best friend Joey had moved away to California with her family and now Hannah could only ever speak to Joey on the phone. In those days Hannah knew she could always talk to Joey and be comforted whenever she felt a bit down, but since moving to Boston she had struggled to make a lot of friends. The girls in her dorm, all coming from wealthy families like hers, were very uptight and dull and didn't take kindly to Hannah's love of free-spirited experimentation, and she didn't think she'd fit in if she joined a sorority. All of this was on Hannah's mind as she trudged across the attractive tree-lined campus towards the red-brick building of her dorm. Hannah was just using her key to unlock the door to her dorm building when she noticed a flyer on red paper stuck to the wall.

"Two Sexy Female Escorts; Available To Men and Women," it read, and there was a number beneath it. For some reason she wasn't entirely sure of at the time, Hannah tore the flyer down, folded it and put it into her bag before unlocking the door and going in. Although she was always keen to try new things, Hannah had never had a sexual experience with another woman before and she wasn't sure how she would feel about that. Back when she was a sophomore in High School, Hannah had felt herself a little turned on to see her friend Joey in just her underwear in the locker room before gym class, however that was the last and only time she'd ever thought about other women that way. Soon after that Joey had moved to California and Hannah hadn't remembered the incident. As she stepped through the door into her dorm building, Hannah completely forgot about the flyer she'd torn down as well. . .

To be continued. . .

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4 Comments
lynnluvr87lynnluvr87almost 12 years ago
Nice

I like the setup here. Clear writing and interesting characters.

AnonymousAnonymousover 17 years ago
Excellent but please continue

Why don't you write the next chapter?

Please don't let Lizzie and Jessie in distress!

AnonymousAnonymousabout 19 years ago
More

Please give us another chapter

AnonymousAnonymousover 19 years ago
I like how human these girls are.

Your background is fabulous. I like the way you make escorts sympathetic while also sexy.

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