by Anya Aurelie
Life of an Escort series
Box set, #1–3 + prequel
(Rough play with alpha males, including group play, MFF threesome, domination)
Prequel: Jenna’s First Job
#1: Jenna’s First Frat Party
#2: Jenna’s New Client
#3: Jenna’s Sex Ed Class
By
Anya Aurelie
Copyright © 2014 by Anya Aurelie
All rights reserved. No part of this publication may be reproduced, distributed, or transmitted in any form or by any means, including photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the publisher, except in the case of brief quotations embodied in critical reviews and certain other noncommercial uses permitted by copyright law.
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Prequel: Jenna’s First Job
(Rough MMF threesome with a stranger)
Jenna was sitting at her favorite bar on the ground floor of a beautiful old hotel, talking to her favorite bartender, Jacob. She was twenty-two years old, had recently graduated from college, and was desperately in need of a job. It had been only a couple of months since graduation, but nothing seemed to be working out and her money was disappearing quickly.
"What all have you tried?" Jacob asked her.
"I've applied for jobs as a waitress, a salesgirl at a clothing store, a barista at a coffee shop, and a few other things," she said. "I majored in anthropology, and believe it or not, there just aren't any anthropology jobs out there. And it doesn't seem like there's much else out there, either." She was definitely getting worried. She knew the recession was making things difficult, but still, she was surprised at how difficult it had been. She was young, she was beautiful, and she had a sexy body. Men tended to find her attractive, and women tended to want to look like her. Didn’t that count for anything in customer service jobs?
"Well, if you're getting desperate, there's always work for you here," Jacob told her.
"Thanks, but I don't know the first thing about mixing drinks,” she said.
"I'm not talking about bartending.”
She was surprised. “Oh,” she said. "What are you talking about, then?"
He looked at her a moment, not saying anything. He seemed to be assessing her. Finally, he said, “There’s always work here as an escort."
“Escort?” she asked, shocked. "You mean like a prostitute?"
"Yes," he said. "It's often like that. But it doesn't always involve sex, and you get to decide when it does and when it doesn't. You'd be totally in control. And," he continued leaning over the bar toward her as though sharing a secret, "between you and me, some of the men we get around here are pretty good looking. And many are very wealthy too."
Jenna was astonished. Sex for money? She'd always been a good girl, and had never considered that she might make money off her body. Could she really bring herself to do that, opening herself up to strange men in strange hotel rooms?
At the same time, though, it was an intriguing prospect. She loved sex, and lately had not been on many dates. The thought of having sex and getting paid for it too was certainly alluring.
"Look," Jacob said, "you don't have to decide right now. Maybe you could even go on a call with one of the other girls who works out of here. See what it's like. There are certain men who enjoy being watched. You wouldn't have to participate."
Slowly, she nodded. There was certainly no harm in going on a call and just watching what happened. She couldn't imagine that she would actually end up doing this, but fantasizing about it, learning about it couldn't hurt.
Jacob told her a few more of the details. He explained that he referred men to the escorts who worked out of the hotel, and then they gave him a cut of their profit. It was a win-win situation. "All you'd have to do is sit here at the bar having some drinks and talking and laughing, and wait,” he said. "You do that already. Why not be working while you're here?"
He went off to service some other customers, and she was left alone with her thoughts. Money had been so tight that this month she wasn't sure she would be able to pay her rent. She hadn't bought new clothes since before her senior year in college. And she could definitely do with some nice meals out, all things she could never afford now, and wouldn't be able to afford very well on a retail or barista salary either.
By the time Jacob came back over to ask her if she wanted something else to drink, she had made up her mind. She would go on a call, just to watch, just to see.
And that's how it all began.
Later that evening, Jacob approached her with a slight grin. "See that woman over there?" he asked.
"Yes," she said. The woman was beautiful, with long, silky hair, an expensive-looking dress, and heels that looked straight out of a New York fashion magazine.
"She is one of our escorts," he said. "She's here only Friday and Saturday nights, and she makes enough in one weekend to pay all her expenses for the month. The rest is just icing on the cake."
"Are you kidding me?" Jenna asked him. Now she was very interested.
"Not kidding at all," he said. "And better yet, she's about to go up to one of the rooms to meet a man. I talked to her about you going with her, and she was down. The man she’s meeting with is a regular client of hers, and he gets off on the idea of being watched. It works out for everyone."
Nervously, Jenna stood up from her barstool and followed Jacob over to the woman. "Elizabeth," he said, "this is Jenna. She’s the one I told you about."
Elizabeth looked up and down, assessing her. She smiled. "Nice to meet you, Jenna," she said. "I think you would do well in this business." Jenna felt flattered.
Elizabeth led her up the beautiful old elevator in the hotel to the eighth floor. Although Jenna loved the hotel and visited the bar there often, she had never been into the main hotel area, had never seen the rooms. This was a treat. She loved the old style of the architecture and decoration. It looked very posh and expensive.
In front of her, Elizabeth knocked on the door. A man about 40 years old answered, wearing an expensive-looking business suit. He was not the type of client Jenna would have imagined would hire an escort. He looked like he could quite easily find free sex on his own.
“This is Jenna," Elizabeth said to the man, who did not introduce himself back. “She’s thinking about becoming an escort, and wants to learn what I do. Do you mind if she watches us today?"
The men look her up and down lasciviously. "Oh, that is perfectly alright with me." He seemed to like what he saw, his eyes roaming over her large breasts, her shapely hips, her round ass.
"Thank you," Jenna said quietly. Nervously, she sat down in the corner on an ornate chair. Elizabeth sat beside the man on the bed.
"So how have you been?” she asked him.
"Missing you," he said, beginning to stroke her shoulder and arm with his strong-looking hand.
Elizabeth touched his arm in return. "I missed you too," she said.
But the caressing didn't last long. Soon, the man grabbed Elizabeth's hair, shoving her face down into his lap. He was still fully clothed, but the message was clear: you are mine. Jenna felt a tingle of excitement go through her body. Elizabeth was beautiful, and Jenna was excited to watch her get fucked. On top of that, she loved strong, dominant me
n, and this man clearly was one.
Recognizing that they were now at stage two of their interaction, Elizabeth began stroking her own body, teasing him by squeezing her breasts, running her hands up and down her stomach, and resting one palm between her legs, as though covering up her sex.
The man seemed to like what he saw. "Here, let me do that for you,” he said. He roughly grabbed one breast in his hand, squeezing it. She moaned. Jenna almost moaned too, as though she could feel her own breast being squeezed at the same time.
The man commanded, “Take that dress off." Elizabeth complied. Jenna watched her as she wiggled out of the tight, elegant dress, and it slid to the floor. Elizabeth’s body was perfect. Her stomach was smooth, her breasts were perfectly shaped, and Jenna found herself wanting to grab them herself.
No, she reminded herself. You're just watching. Not participating. The man grabbed Elizabeth's breasts again, her bra still on. He roughly pulled one bra cup to the side, exposing her beautiful breast and hard nipple. His mouth was on it instantly, licking and sucking it. Elizabeth threw her head back in apparent pleasure, and the man was encouraged. He seemed to get even more excited. Jenna could see his hard erection bulging through his expensive pants. She wondered what his cock looked like.
Soon Elizabeth’s bra was on the floor, and the man roughly pulled her panties down. Stand right there," he commanded. She stood still as a statue. He shoved his fingers between the folds of her pussy, furtively rubbing and pushing into her.
“You’re so wet," he moaned.
"You turn me on so much," she said. She looked at Jenna, and Jenna started in surprise. She had been getting so into the scene in front of her that she had almost forgotten she was sitting right here, where they could see her. "Jenna," Elizabeth said with a coy smile. "How are you liking this so far?"
The man looked at her too. "I'm liking her being here so far," he said. "Watch this," he said directly to Jenna.
He seemed to be showing off. He shoved Elizabeth back on the bed, completely naked to his fully clothed, and again dove into her waiting wet pussy with his fingers. He stretched her wide open, showing her to Jenna. She looked at the folds of pink pussy, noticing that they glinted in the light. Elizabeth was clearly very wet.
"Now your turn," Elizabeth said. She grabbed the man's pants and started to undo his top button. "Oh no you don't," he said. "I'll give you my cock when I'm ready. I want to make you beg for it first."
Elizabeth smiled. "I want it," she said. "I want it so bad. I want you to give it to me. I want you to fill my cunt with it."
Jenna’s nipples were hard as rocks watching and hearing this interaction, and she almost longed to touch herself too. "Beg for it," the man commanded again.
“Please,” Elizabeth begged, "please give me your cock. I am such a dirty whore, and I need cock to live."
And then he smiled down at her. Without saying a word, he unfastened his belt, unzipped his pants, and let them fall to the ground as he pulled out the biggest dick Jenna had ever seen. It looked like something out of porn, it was so wide and long.
In that moment, she was so jealous of Elizabeth. She too needed her cunt filled up with his cock, the same way that Elizabeth had begged him to do to her. As Elizabeth got on her hands and knees on the bed and begin licking and stroking his cock while he stood beside her, shirt still on, Jenna began to rub her clit through her panties, reaching underneath the skirt of her dress to feel the heat coming off of her. Neither Elizabeth nor the man had noticed her doing it yet, and it gave her pleasure to think that she was watching them while now providing a mini show of her own as well, unnoticed.
The man groaned as Elizabeth licked up and down his shaft, and Jenna could almost feel his cock on her own tongue, so engrossed was she in their interaction. He grabbed her hair by the back of her head and pulled her further on to his cock. She gagged on the massive beast in her mouth, and Jenna rubbed her clit harder.
"Suck it," the man demanded.
Elizabeth's naked ass was up in the air, and she was totally controlled by his hand in her hair. He held her there for another few moments, then roughly shoved her off him.
He turned her over onto her back on the bed, and climbed up between her legs. Bending down, he lapped at her pussy, and she moaned in pleasure. “That feels so good," she said. She ground her cunt up into his face. He inserted a couple of fingers inside of her, and she moaned again. "Fuck me with those fingers and that hot tongue,” she said.
Jenna was almost ready to jump up and do it herself.
It was at that moment that they noticed her rubbing herself. She was still rubbing the outside of her underwear, but she had her legs splayed open to them, and they looked at her approvingly as she flicked her clit through the silky fabric of her panties.
They didn't say anything, just smiled, and she knew that this was acceptable, encouraged even. She peeled back her panties with her finger, revealing just a bit of her wet snatch, and began stroking directly on her own skin as they watched. She surprised herself with how wet she was. This was so much fun, she couldn't believe she had never considered escorting earlier. Why had she been hesitant again?
Soon, her finger was soaked, and she brought it up to her mouth and licked the juices off seductively, staring at them both as they stared back at her, the man's face still buried deep in Elizabeth's pussy.
The man took his shirt off then, and was no longer an important businessman, he was just a horny client who couldn't wait to get balls deep in dripping wet cunt.
Straddling Elizabeth on the bed, he impaled her with his cock, shoving it in all at once and making her moan with pleasure again. Jenna was amazed at how far in he was able to go with that massive dick. She saw Elizabeth's pussy stretch to accommodate him, saw his cock glisten as he pushed it in and out of her, instantly wet with her juices. He grabbed her bouncing tits as he fucked her, then with one hand grabbed both of her wrists and pinned them over her head. She was totally in his control.
The man looked back and forth between Jenna and Elizabeth as he thrusted in and out, and she could tell that he got off on having her watching and touching herself to his movements. Jenna began squeezing her own tits with her other hand, and then shoved the front of her dress and her bra down to squeeze her bare tits and nipples. He watched as she did so, taking in every movement. She wanted so badly to join their encounter, but was trying to hold off until Elizabeth invited her. She wasn't sure what escort etiquette was, but she had a feeling it didn't involve joining an encounter uninvited. But one thing was sure: she wanted to do more than just watch.
After a few minutes of fucking, the man pulled out of Elizabeth, and Jenna saw her stretched-open pussy, pounded raw. As she continued to lay on her back, he climbed up her body and shoved his cock into her mouth from above, fucking her face with his huge cock.
Jenna was close to orgasm watching them, but she forced herself to hold off. She wanted to make it build until she exploded with pleasure, ideally all over his cock or in Elizabeth's mouth.
Finally, the man said to Jenna, “Would you like to join in? You look like you could use a good fucking."
Elizabeth smiled at her. "If you want to, you're welcome," she said. "I wouldn't mind fucking you myself. "
Jenna was nervous, but also excited out of her mind. She removed her finger from her dripping pussy, let go of her breast, and stood up. Her dress was disheveled, and she ripped it off over her head, exposing her silky underwear and matching bra. Both sets of eyes roamed over her body, taking her all in. She had huge, perfectly round breasts, and she loved having them squeezed and licked. Her underwear was soaked through. She approached the bed.
The man smiled slightly at her. "I'm so excited I get to take your escorting virginity," he said. He snapped her bra clasp open, letting her breasts bounce free, then grabbed them in his fists right away.
Elizabeth had turned over onto her stomach to watch, and she reached out now too, fondling Jenna's tits alongside the man. Jenna allow
ed the man take control. He stood up beside her, towering over her. She hadn't noticed how tall he was before, but now that he was trying to be intimidating, it worked. Her clit tingled in anticipation. He grabbed the top of her panties in both hands, but rather than pulling them down over her legs, he suddenly ripped them in two, leaving her standing there naked in the middle of the room. The force and unexpectedness of his action shocked her, but it also sent waves of excitement through her. She almost couldn't wait. She felt her inner thighs starting to drip with her own moisture.