Jimmy was a little nervous as he checked into his hotel. This was the first time he had ever been allowed to go to an overnight conference for work, most of the time they don't let engineers out of their offices, much less to go to a conference. Sure, he had traveled for work before, but before it had always been classes with other engineers and people like him, he had never been allowed to go to the dealer conference. But a few weeks back, Jimmy found a bunch of porn on his boss's work computer and he knew he had an opportunity. Jimmy exchanged an all-expenses paid trip to the dealer conference (the only way his boss could hide it) for erasing the files (he didn't, he kept a copy for himself) and not telling anyone. So here he was, checking in to his hotel in Miami on the company dime.
Jimmy was an average kind of guy, your regular engineer/computer kind of guy. He was 26 years old, about 5'10", medium build with dark hair and not much of a tan. One thing that did separate Jimmy out was his striking green eyes, they were almost so green that people would have asked him if they were contacts if it weren't for the tinted glasses he wore while working at his computer. He really didn't need them to see, but he got so used to wearing them while working that he just kept them on most of the time.
After he checked into the hotel, before he went upstairs, he saw the registration booth for his conference. He decided to go ahead and check in to see if they had any info on where to eat for the night and find out what time he needed to be downstairs in the morning. Although he didn't have to go to any of the classes, he figured he might as well, he didn't know anyone else in Miami and figured he might meet a few people in class to hang out with for the week. As he was walking up to the booth, he caught his first glimpse of Ashley.
Ashley was a marketing rep for his company for the west coast, someone that wouldn't have anything to do with James in the normal course of business, but today they were at the same place at the same time. Ashley was 34, about 5'4", nice hourglass shape with firm tits and a nice curve to her hips, brunette shoulder length hair, and a radiant smile.
Ashley saw him walking up to the booth and noticed him right away. She had always had a thing for the nerdy guys, especially those who were actually kind of cute but just didn't realize it. Before he even made it up to the booth, she already decided that he was going to get fucked, whether he wanted it or not.
See, Ashley had a wild streak in her. Her last boyfriend had introduced her into the world of B&D, and she took to it immediately. She liked being a sub sometimes, it was nice relinquishing control for a while and doing whatever she was told, but with her small stature, she really liked being in control of a guy twice her size. Whips and chains were too stereotypical, she preferred tying a guy up and "exploring" his sexuality at her pleasure, making him cum in ways he didn't want to, like a vibrator up his ass while she jerked him off from behind or making him suck on a dildo and give it head while she blew him, not letting him cum until she believed he had made the fake dick in his mouth cum. She really didn't care about watching two guys together or anything, but it made her last boyfriend uncomfortable but he did it because she made him, she was in control, and that really got her off.
But now, 4 years later, Ashley was married to a different man, one who did not share her, let's say, enthusiasm, for anything other than missionary and very rarely, her on top. Since she parted with her last boyfriend, she hadn't had what she considered good sex in quite a while. Granted, Mark was a great guy and treated her well, she loved him dearly, but he hadn't really fucked her yet in her opinion. "Hell, he doesn't even like doggy style" Ashley remembered saying to herself while packing to come to the convention, already convincing herself she was going to have fun. She packed while Mark was away at work so he wouldn't see what all was going in her suitcase. Small bullet vibe, check. Medium size vibe that was her favorite for a little ass play, check. Rabbit, just in case, check. "50 shades of Gray" well, that was going in her carry-on bag so she would have something to read on plane. She also packed a few long scarves, just in case.
Back to the convention, as Jimmy approached the booth he was already nervous about talking to Ashley. He liked looking at girls like her online, petite, curvy, with a cute smile which hid a fantastic orgasm face, showing how hard they were really cumming. Jimmy had a bit of a voyeuristic side to him, when he watched porn and when he masturbated it was usually watching a girl masturbate or watching a girl get fucked by some non-descript guy, he just liked seeing the girl cum hard. He never really pictured himself in the guy's shoes, he just never fantasized about anything other than jerking off while seeing this. Now, here Ashley was, looking just like the girls he really liked watching, standing there in the flesh smiling at him. He couldn't help but feeling a stir in his pants which quickly turned into his cock starting to swell uncomfortably against his slacks. He hoped she wouldn't notice.
She did.
As Jimmy was approaching, Ashley was already checking him out and wondering if she could corrupt him, and while checking him out, she noticed a sudden change in his stride. She saw that his package was starting to push out on his trousers and that he looked a little embarrassed as he was walking up to her. "Oh, I am so going to fuck him. Little boy, you have no idea what you are in for" she said to herself.
When Jimmy made it up to the table, he couldn't concentrate and find his nametag, he just kept looking at Ashley. She noticed is trouble and asked his name. "Ji-Jimmy" he stuttered.
She waited a few seconds, spotted his nametag and waited for him to reach for it. As he reached for it, she made sure to reach at the same time and touch his hand, which sent sparks of excitement through both of them. They exchanged a few glances and smiles, then Jimmy left and headed to his room.
Jimmy couldn't believe how hot she was, and he was turned on as he could be. He had to get into his room and jerk off as quickly as he could. He made it into his room and turned his laptop on, but before his computer had even finished booting, he had already grabbed some conditioner from the hotel bathroom and began to stroke himself thinking about Ashley. He imagined her, riding a guy, bouncing up and down, her firm little tits bouncing each time she did, her hands taking turns pulling at her nipples, playing with her clit, and holding herself up as she was riding him to a fantastic orgasm. Then it hit Jimmy, she was riding him in his mind. He could see her shaved pussy vulgarly sliding up and down his thick cock, watching her hand playing with her clit as she rode him. He could see her face, that wonderful, "fucking face," the one that women get when they are truly getting fucked on their way to a huge orgasm. He didn't think about jerking off to her, he wanted to fuck her, and in his mind, right then he was. He could see her face change and was ready for her to cum. As he was imagining her cumming, showing him that beautiful O-Face, he squeezed his cock tighter with his right hand, pumping it tighter as he pumped his dick up and down, he felt that unmistakable feeling welling up inside of him. He pumped harder and faster with his right hand while he reached under his balls with his left, pressing with two fingers on his taint which put extra pressure on his prostate. That extra pressure on his prostate pushed him over the edge, Jimmy came so hard that his back arched, his ass rising up off the bed. Ropes of cum shot out, one actually landing as far up as on his cheek, before he relaxed enough to lie back down and catch his breath. He realized that he hadn't even logged into his computer before he got carried away which caused him to laugh. He cleaned himself up and began to unpack his clothes before dinner.
After setting up his computer in the hotel room and mindlessly playing online for a few hours, Jimmy decided to just go down to the restaurant in the hotel for dinner that night. He was hoping he would catch "her" down there at dinner, at that point he didn't even know her name. He kicked himself for not asking, but he figured he may as well not know her name, that way she stayed a fantasy and not a real person he had to deal with. He had been reliving the fantasy in his mind all night, trying to shake it, but it kept creeping back in. He shook his head and said out loud, "Fuck it, I am going down there. I'm hungry."
Jimmy went downstairs to the restaurant and ordered his meal, sat in a corner booth by himself, eating his hamburger and looking for "her" but never did see her. He went back upstairs, jerked off again thinking about her, and went to sleep.
What Jimmy had not known was that Ashley was downstairs at dinner earlier. She had been watching to see if he would come down to eat, but he had not. Realizing she had work to do before the next day's classes, she retired early to her room and got out her laptop. She started off well, reviewing her presentation for the next day, but 4 hours on the plane reading "50 Shades of Gray" coupled with meeting Jimmy earlier in the day distracted her to the point she no longer cared about the PowerPoint show. She started drifting off in her thoughts, not paying attention to the fact that she had lightly began rubbing the backs of her fingers across her breasts. She drifted further into her thoughts, remembering what if felt like to tie someone up, the control, the power it gave her. She remembered how wet it made her, helplessly toying with them, making them cum while they had no control over it. She began to picture Jimmy, how she was going to tie him up, tease him, make him want to cum so badly that he begged her to let him, then mercilessly make him feel so uncomfortable that he almost doesn't want to cum, the first time at least. As she thought about the look of confusion on his face, she slipped her fingers inside her panties, noticing for the first time how wet she had become as she slowly and easily parted her slit.
She stood up and removed her clothes unceremoniously as she was walking to her suitcase. She opened the lid and pulled her clothes to the side and looked mischievously at the toys that she brought with her. She already knew what she had in mind for poor Jimmy, but it would be worth it to him later. After she dominated him and made him cum the first time, she would ride him like a rodeo stallion and give him a fucking he would never forget. But for now, she pulled out her Rabbit for some of her own self pleasure.
She walked over to her bed and pulled the covers back, propping the pillows up behind her back and putting one long-ways under her lower back and ass so she had an easy reach and so it got her in the optimum position. She turned the Rabbit on and smiled as it started gyrating and moving. She licked it a few times like the head of a cock then moved it down to her nipples, dragging it slowly across first the right then the left. This sent jolts of electricity to her already aching clit which made her stomach jump with anticipation. Not wasting any more time, she slid the toy down her stomach and slid it across her clit and her outer lips. She began rubbing it lengthwise up and down, between her lips and across the hood, its vibrations causing her clit to feel like it was going to explode she wanted to cum so badly. She pulled the toy back one time, turning on all of its features at once, she needed to cum now. As the toy rotated and the beads spun, she slid it inside her without needing any additional lube, her pussy so ready it almost pulled it inside of her.
