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.
When the ears on the rabbit touched her clit, it sent waves from her toes to the top of her head, this was what she needed more than anything right then. She began moving the toy in and out, not too far each stroke as she needed the sensation against her clit, plus at that depth the rotations of the toy massaged her G-spot. After just a very short time, she felt the signs of a powerful orgasm building, welling up deep within her gut and spreading down her legs, her nipples feeling like they were on fire. The sounds of the rabbit, sloppy from her juices, filled the room along with her scent, and the sound of a woman trying to keep quiet but not being able to. She was nothing but an unintelligible constant moan, with gasps of air as wave upon wave of pure bliss began to overcome her. When she came, she raised up on her hands and elbows from her propped up position. What she had not planned on was the difference in the hotel pillow from her own at home, the hotel pillow squeezed up between her legs, driving the toy even deeper inside her, causing the toy to vibrate harder on her clit and push deeper inside her. She could no longer keep quiet nor did she care to, the orgasm rocking her to her very core. She rode it out for what seemed like an eternity before she laid back down, the toy still going, its movements causing it to slide out of her pussy, its sound, her breathing, and the hotel air conditioner all filling the room with a somehow relaxing tone. She lay there for a while, listening and relaxing for several minutes, before deciding to clean up and get some sleep. She could go over the PowerPoint in the morning.
The next afternoon, Ashley spotted Jimmy going into a classroom at the conference. She had no idea what Azimuth Correction was, but she knew she had to have a way to meet him, a way that he didn't think that she was in control. She needed him to be comfortable, to think he was just extremely lucky, not that he was the prey that he really was, because she was stalking him and would move in for the kill. She had no desire to have an eager sub, she wanted to dominate him whether he wanted it or not.
Ashley slid in and sat behind him in the classroom. Lucky for her, he sat in a middle row but all the way on the end next to a wall. Jimmy hated people walking past him all the time, tripping over his feet when they inevitably came in late. Since he was there early, he pulled out his iPad to check his email. Ashley saw this and began to formulate her plan.
She reached up and put her right hand on his left shoulder, leaned up and began talking to him. She asked him how he liked his iPad and he went off on the usual geek speak about how he liked it but it had its issues, fussing about this and that. All the while, she kept her hand on his shoulder, and as he talked, she began lightly moving her fingers, rubbing him ever so subtly, so that even he didn't realize it. After a few minutes, Ashley decided to jump in. She asked Jimmy if he knew how to transfer E-books from her computer to her phone, and of course he said that he did. This was the opening she was waiting on.
"So, is it really hard to do?" putting a slight emphasis on the word hard.
"No, it is really easy. Doesn't take but just a minute once you have the software installed." He replied.
"I am not sure I know how to install the software, it always asks me about permissions or something." She lied.
"I could do it for you sometime if you like." Jimmy had no clue what he was playing himself into. He was just happy this beautiful woman was talking to him. He was keenly aware that her hand was still on his shoulder, but he was just hoping to get to spend some time with her.
"Could you? Listen, I hate to ask," She lied again. "Is there any way I could get you to come up to my room this afternoon and do it for me? I have a dinner tonight and am headed back tomorrow and really want to read my book while I am waiting in the airport, so I don't have a lot of free time between now and then." She playfully batted her eyes, "I will so owe you dinner at the next conference or the next time I am in Atlanta."
"How do you know I am from Atlanta?" He asked, furrowing his brow.
"It's on your nametag, Jimmy. By the way, I am Ashley. I hate wearing my nametag at these things."
"Well, nice to meet you Ashley." Jimmy had already started having thoughts about going up to the room of this extremely hot woman and had to shift to hide his growing erection. He tried thinking about baseball and whatever else he could, but it wasn't working. He was still concentrating on her hand on his shoulder.
"OK. I am in room 521. I am not going to the next session, so just come on up when it is over and knock on the door. Don't stand me up, OK?"
"Wouldn't dream of it." She finally slid her hand off of his shoulder, dragging it off slowly. Jimmy had trouble concentrating in class, remembering the jerk off session and fantasy about her from the night before, all the while shifting in his seat to conceal his growing discomfort.
Ashley slid out of class a few minutes early so she wouldn't risk talking to him. As she was getting up to leave, she leaned forward and said to him "Remember, 521. See you in a few hours." She then proceeded to go to her room to get everything ready.
Jimmy, for the next two hours, kept going back and forth, wrestling back and forth between thoughts of her and being professional, they did work for the same company and he worried that if he did something that she may report him to HR and he would get fired. But for Ashley, no such thoughts ever crossed her mind.
She went to her room and carefully set the room up for what she wanted. Because she wanted to reenact her fantasy from last night, she got out the medium vibe she brought with her as well as the rabbit and placed them in the drawer beside the bed, along with the scarves. She looked for a place to tie them to and saw there was none, but remembering how she was tied up one time in a hotel, tied both scarves together and then slid them under the mattress with enough hanging out on either side to be able to tie his wrists up easily about halfway down the bed. She retrieved the conditioner from the bathroom as she had read that this made a great lube, although she had never used it on anyone. She opened her computer up and opened her e-reader up to a story she had saved from Literotica.com about a woman seducing a young man in a hotel room, describing how she rode his thick cock in vivid detail. She left it up on that part and then placed her phone beside the computer, he was supposedly there to fix it. She also decided to leave a prop out, so she got her small bullet vibe out and left it half hidden under a set of panties on the bed, so that he would definitely think he came in after she had just finished masturbating so she could feign embarrassment if needed. After she had the room staged, she waited until about 15 minutes before he was supposed to be there and jumped in the shower. She wanted to be in a towel and dripping wet when he arrived.
Just as she planned, he knocked on her door right as she was toweling off. She wrapped a towel around her and one on her head. She said back through the door, "hold on one minute" and looked over the room one last time to make sure everything was set. She stood on her tiptoes and looked out the peephole and saw him standing there. Her plan was in motion and nothing would stop it now.
She cracked the door open just enough to look through and said to him. "I am sooo sorry, I thought you would be a few more minutes. Here, hold the door open for just a second. I just got out of the shower and need to finish getting ready. Let me run into the bathroom and you can come in. The laptop is on the desk with my cell phone. You can get started while I finish getting dressed." She made sure he had the door in his hand and let go, turning around and going into the bathroom, not closing the door all the way, on purpose of course. She wanted him to see her in that towel.
As Jimmy walked in the room, he noticed the door open to the bathroom. She was facing away from him, her left foot on the tub, bending over drying her hair with another towel, the one wrapped around her riding up so where it barely covered her full, naked lips, which he could see already in his mind's eye. This immediately made him hard again, something he had been fighting off since she put her hand on his shoulder a few hours ago. Ashley could fell him staring, she knew what it was doing to him.
He finally walked into her room. His eyes immediately saw the panties and the vibrator on the bed, which excited him further, imagining her masturbating just before he got there, but dejecting him because he figured she would no longer be horny and he would be out of luck as this would be just another computer repair. He sat down at her computer and immediately saw what was on screen. He began to read it, growing harder as he did. Mindlessly he began rubbing his growing erection through his pants leg, thinking she was still in the bathroom. He had not heard her walk up behind him, wearing only her towel.
She watched him stroke his cock through his trousers. She wanted to reach down and grab it herself right then and there, but she had a plan. As he became more engrossed in the story and began rubbing his cock more, she was getting excited herself. She wanted him to get worked up really well, she wanted him to blow his first load fairly easily so she could enjoy the nice, thick bulge in his pants, she wanted to ride him hard, and he needed to be hard for a nice, long time, not blowing his load before she could enjoy it. She listened to his breathing and watched his stroking and could tell it would not take much now to make him cum, so she made her move.
She reached down and spun his chair around so he was facing her, his hand still on his cock. She was standing there in her towel only, water still gleaming on her naked shoulders, her feet a little wider than shoulder width apart. A look of surprise and fear was on his face, but without thinking, he never stopped rubbing his cock, it felt too good and he was in too much shock to realize he was still rubbing it, although slower. He was eye level with her chest, the towel low on her cleavage coming to about mid-thigh. He did a quick glance, hoping she wouldn't see him for he knew that he was busted and feared the worst. Here he was, getting off in her room, and caught. For an instant, he wanted to reach up and pull her towel off, but he couldn't do it. The look on his face was panic and fear, which was exactly what Ashley wanted to see.
"Just what do you think you are doing?" Ashley demanded, already taking on her Dominant role in the encounter. Jimmy was speechless. "You're still rubbing your dick. Are you shitting me?"
Jimmy, suddenly aware he was, immediately stopped. He was hoping that his hard-on would subside, but Ashley looking at it made it worse. "I'm sorry, I, uh..."
"Just wanted to jerk off in my room? Really?" Ashley scolded him. Jimmy's head dropped. There was silence for a moment while Jimmy worried about how he had just ruined his life.
"Fine" she huffed, "but I am the one in control here. Got it asshole?"
Jimmy looked up at her even more confused than he was scared. "You are going to get off, but on my terms. But you so much as think about saying anything other than "Yes, ma'am" to me and I'll have your ass. Remember, you came in my room jerking your dick." Ashley was getting more and more tuned on. She almost broke he act when she felt a drip of her own juices run down the inside of her right leg. This was really turning her on, she longed to do this for years and now it was happening.
"Stand up and strip, nothing on at all." Jimmy quickly stripped his clothes. As he slid his boxers down, his cock sprang free. Ashley couldn't help but stare. It was fairly average in length, about 6 ½ inches, but the base was thick and the shaft was curved up and the head even larger than the shaft. She remembered having a dildo shaped like that and she immediately remembered how hard it made her cum, that large, bulbous head rubbing her G-spot. But as excited as she was, she had to stay in control.
As Jimmy stood there, his dick bouncing to his heartbeat, Ashley walked around the side of the bed. She tossed three pillows down to the foot of the bed. She walked back over to Jimmy and looked at him. Not knowing that his glasses weren't prescription, she took them off, telling him that he didn't need to see what he was doing, he was going to do exactly as she said. When she asked him if he understood, he only nodded his head. Ashley took her bare hand and slapped his ass hard, leaving a red handprint that was visible almost immediately. Jimmy jumped and almost put his hand back there. Ashley grabbed his hand and slapped him on the ass again, this time on the other cheek. "Answer me when I ask you a question! Do you understand?"
"Yes Ma'am."
Ashley walked in front of Jimmy, standing directly in front of him, so close Jimmy could feel her towel brush against his cock lightly. "Do you want to see these tits?" She asked.
Jimmy closed his eyes briefly and said yes as he then looked down at her. He wanted to reach out and touch her, but he was afraid to.
"Do you want to lick my pussy, you fucking pervert?"
"Yes." It was barely audible. A drop of pre-cum was forming on the tip of his dick.
"I might let you, depending on if you cum for me AND I like what I see. But don't do exactly what I say, and you will experience pain like you have never known." She reached down with her left hand and wrapped it roughly around his cock. "This will do" she said.
She turned around and positioned the three pillows on the end of the bed, stacked at the end of the bed. She walked around behind Jimmy and shoved him forward. He almost fell on the bed but caught himself with his hands on the mattress. Ashley walked around to the side of the bed and grabbed his left wrist and quickly grabbed the scarf already tucked under the mattress. She quickly pulled his wrist out from under him, causing him to flop forward on the bed, bent over at the waist with his feet on the floor, the pillows under his stomach. She crawled across the bed in front of him, the towel coming loose and falling off her naked body. She looked at him and told him that if he kept looking at her, that he would never cum in that room, which caused him to look away. She then tied his other wrist down on the other side of the bed.
She crawled off the bed and walked around behind him. She had a wonderful view of him. He was laid out, his chest on the bed with his arms tied straight out to his sides, his head laid on the mattress. The three pillows were under his stomach at the end of the bed, his pelvis unsupported, but his dick trapped underneath his stomach. His legs were bent kind of funny, so she kicked each of his feet out about twice his shoulder width, which had his ass up in the air nicely and exposed his puckered hole to her. She reached up under him from between his legs and raised him up slightly and pulled his dick out, so it was pointing straight down now, throbbing even more than before.
"IS this what the fuck you had in mind?" She slapped his ass again. Before he could answer, she slapped it again and said "I can't hear you!" Her juices were running down both legs she was getting so hot.
"No ma'am!" he said back this time. He was frightened and turned on at the same time. His ass cheeks hurt and he didn't know what she was going to do to him.
"Look at that little, puckered hole. I bet you have dreamed of fucking some girl there before, haven't you?" before she let him reply, she took her index finger and tapped at its entrance a few times. His hole puckered and his hips bucked, first away from her, then back towards her.
Jimmy had never had anyone touch his asshole other than a doctor before, and this was much better. He didn't know what was coming next, but he wasn't sure he was going to like it. He always believed that if a guy liked something in his ass that meant he was gay, and he was scared of what this meant, but all he knew was at the moment it felt good.
Ashley walked around to the side of the bed and retrieved her medium vibe and walked back to Jimmy. She retrieved the bottle of conditioner from earlier and squirted some on her left hand. She smeared it out and then grabbed his cock and started giving him a hand job. Immediately Jimmy responded relaxing his body which caused his feet to slide a little further apart on the floor. Ashley tugged on his cock a few more times and then smeared some of the conditioner on the vibe. She turned it on high and put the entrance of Jimmy's ass. He instinctively bucked his hips forward, so she tugged on his cock again, causing him to relax his ass. When she saw his muscles relax, she slid the tip of the vibe in his ass, then slid the rest in without issue, the conditioner allowing it to slide in without issue.
She immediately found his prostate with the end of the vice and put pressure on it. Jimmy jumped then moaned immediately, she knew he was close to cumming. She was holding the vibe in her right hand, so she stopped stroking his cock with her left and kind of crawled her naked body up onto his left side, her face right next to his head which was buried in the mattress. She kept sliding the vibe in and out of his ass with her right hand, making sure to pause while she pressed on his prostate each thrust.
"Have you ever been fucked in the ass before, little boy?" she asked as she pressed the vibe on his prostate and held it there.
"No..." he whimpered. He was full of thoughts. He loved how this felt, sending jolts of electricity through his body every time it vibrated on his prostate. He loved how wonderful it felt as it slid so smoothly in and out of his tight little hole. He felt so ready to cum, even without her touching his cock. He was humping the air, his ass going back eagerly each time to meet the vibe and then going forward pressing his cock against the side of the bed, trying to cum, each time she pulled it out. He loved the feel of her breast pressed against his side, but he was so torn. He was getting fucked in the ass and it felt wonderful.
"Do you like getting fucked in the ass, you little slut?" she sped up how fast she was fucking him.
"Yesssss...." It was almost just a hiss.
With that, she left the vibrator in his ass, pressed up against his prostate, and crawled off the bed. She got up and got her rabbit out the walked back to the left side of the bed. She told him to look at her and he did. Jimmy got his first view of her naked body, and it was just like he imagined. Her tits were dotted by small, dark nipples. She had an amazingly curved figure, and her shaved pussy was right in front of him, her lips swollen and parted with lust.
She took the rabbit and put it in his mouth. "If you want to cum, you are going to cum while getting fucked in the ass and sucking this like it was a cock. You don't get to cum thinking about me, not yet at least. So you have a choice, cum while getting fucked in the ass and sucking a dick and then if you are lucky and I like what I see, I will let you lick my pussy. Or, you could not cum and just know that you came in my room to jerk off and I fucked you in the ass instead. Your choice."
Jimmy wanted to cum so badly, but he was torn. Could he get off while he pretended to suck a cock while getting fucked in the ass? Fortunately for him, Ashley made this decision for him, as she wanted to get off, too. She had walked around behind him and gotten on the floor between his legs so he could no longer see or touch her. She took the vibe again in her right hand and reached for his prick with her left. Pre-cum was dripping off the end, she knew he was close. She looked up over his shoulder and saw the dildo in his mouth but he was not sucking. She stroked his cock a few times with her left hand while fucking him in the ass with the vibe in her right, pausing in his prostate longer and longer each time.
"I don't see you sucking" she said. With that, she rubbed the head of his cock exclusively and held the vibe on his prostate. He started sucking immediately. She continued her manipulations, telling he was getting close to cumming. She could see his body getting ready to draw up and explode when she said to him "you came up here to jerk off to me, but now you are getting fucked in the ass while sucking a cock, you little slut. Tell me you want to cum, tell me you want to cum because you are getting fucked in the ass, TELL ME!"
He dropped the vibe out of his mouth. "Please let me cum, please..."
"Say it!"
"Fuck me, Fuck me, FUCK ME!" She sped up her hands and fucked him faster with the vibe, short strokes keeping pressure on his prostate.
"Suck that cock now!" With that, he dropped his head back to the mattress and sucked the dildo back in his mouth and sucked it with everything he had. His mind raced, he was sucking the cock as hard as he could while getting fucked in the ass and jerked off at the same time. He didn't think about it long because without warning, He came in a huge way, like he had never cum before, ropes of cum shooting out on the floor below him. His ass clenched around the vibe with each spasm of his orgasm, sending a new sensation to his brain with each passing second. His body shook so violently, but Ashley stayed with him, continuing to fuck him and stroke his cock until he begged her to stop because it was too much.
Watching such an orgasm had her turned on beyond belief and she needed to cum herself, now. She knew that he wouldn't be ready to fuck her for a little bit, so she knew what to do to pass the time so to speak. While he was still whimpering, she made sure the vibe was still firmly in his ass as this would help get him hard again quicker. Jimmy groaned and drew up a little bit when she checked it and she slapped him on the ass and admonished him.
"You had better leave that in there, you little slut. Do you hear me?"
"Yes ma'am." He groaned again. The vibrations in his ass, still buzzing his prostate had subsided enough that they were no longer so intense that they were unpleasant and he could feel the blood returning to his cock, amazed that he may be getting another erection so quickly. But while he was concentrating on the feeling and himself, he hadn't noticed Ashley get up from behind him and walk around to the side of the bed.
Ashley had planned perfectly where to put the scarves to tie Jimmy's hands up, not only did it leave his ass in the air for her, his head was in the perfect spot for her body. She reached out and grabbed his hair and picked his head up, his chest still on the mattress. "Did you like that little boy? I know you did. You little sluts are all the same. But you are only allowed to cum when I tell you to, got it?" He nodded his head yes.
"Since you were such a good little slut and came for me when I told you to, I'm gonna let you make me cum. But since you decided to barge in my room and start jerking off, you are going to do it my way. Understand?"
"Yes ma'am." He felt a new surge in his cock at this thought.
"Good." She slapped his ass again. When he jumped, he made a little yelp. Before he could make any more sounds, she slapped his ass again. "No, you don't get to cry. This is for me. If I want to slap your ass I will, but you don't get to say a word. Got it?" With that she slapped his other ass cheek, Jimmy knew better than to do anything but nod his head.
"That's my little pervert." Ashley climbed up on the bed above Jimmy. She opened her legs up wide in front of him and slid down towards his head. She reached down and lifted his head again by his hair so he was looking directly at her pussy. She put her legs over his shoulders and slid right up to his face. This was the first up close look at her pussy that Jimmy had gotten, and he studied it as best as he could.
Her outer lips were completely swollen and engorged, giving way to her inner lips. Her clit was peeking out slightly from under its hood and she was completely covered in her own juices, glistening in the light of the room. Jimmy knew from the videos that he had seen online that she was extremely horny and it wouldn't be long before she came if he did it right. He thought back to all of the videos he had seen of guys and girls licking pussy and remembered one he particularly liked because the girl came so hard. He just hoped he could do the same things since he couldn't use his hands and he had to hold his head up the whole time. Before he could think much more about it, Ashley had slid down the bed and shoved her pussy in his face and had moved her hand from holding his hair to holding the back of his head, pulling it against her hungrily waiting snatch.
Jimmy went to town on her, not wasting time teasing her as all. He dove in, licking with broad, wide strokes on her clit with the flat part of his tongue, first applying heavy pressure then lightly flicking the tip of his tongue rapidly back and forth on the exposed tip of her clit. Ashley, not expecting him to drive her so crazy so quickly, arched her back up, and had to release her hand hold on the back of his head to use both elbows to hold her up, raising her pelvis up to meet his hungry mouth, pushing his head back, his body captive and not able to raise up. When she lowered her pelvis back down briefly he moved from licking her clit to fucking her with his tongue, sticking it in as far as he could, his nose rubbing on her nub. This caused Ashley to raise up to meet his face again, this time keeping her ass raised up off the bed, her hips fucking his face. He continued this for just a minute or so as Ashley was quickly approaching her orgasm. Her nipples needed attention, so Ashley laid back on her back and put her feet up on Jimmy's shoulders, rubbing her tits with both hands. Putting her feet so high up on Jimmy's shoulder opened her up to him, so he was able to tongue fuck her a little deeper. She was nearing orgasm, her hips bucking up and fucking his face, roughly grabbing her nipples. She could feel that all too familiar feeling starting in her stomach, radiating out from her body's core. Her stomach muscles are the first to tighten up, seizing so tight that they start to quiver a few seconds before her orgasm actually hits.
Feeling her stomach begin to tighten, she looked down at Jimmy's face. He is completely engulfed in what he is doing and she doesn't want him to stop. She wants to dominate him at this time, but she is so ready to cum that she is completely at his mercy. She takes both hands and places them on the sides and back of his head, pulling his face in even harder to her pussy as she begins to cum. Her legs wrap around the side of his head, her hands grabbing his hair and pulling him even harder into her. She can feel the stubble on his face rub roughly against her thighs, the pain it brings intensifying her orgasm. She rides his face relentlessly, not caring anything about him at that point in time, she is consumed by the feeling of her orgasm, her juices covering his face, her body spasms working in a ripple she can feel, each one starting from her pelvis, radiating out from there reaching all the way to head and her toes. As the throes of her orgasm begin to subside, she relaxes her grip on Jimmy and lets his raise his head from her pussy. His face is gleaming with her juices.
Without warning she climbs up off the bed and walks around behind Jimmy. He is now completely hard again, his erection bouncing off of the side of the bed, precum starting to drip from his engorged head and the vibrator still buzzing in his ass. She takes her right hand and slaps him on the ass again. She is standing behind him, so he can't see the content look on her face, but she adjusts her voice for him.
"You like watching me cum, little boy?" She slaps his ass again. "You're a good little pussy eater, but did I say you could enjoy that? NO!" Another slap on the ass. By this time, his ass is bright red and each time he gets hit, he jumps as the pain is starting to build. But apparently, his cock likes it, because it is getting harder, now bouncing with each heartbeat.
"You stay right where and do exactly as you are told. You are my bitch and bitches do what they are told." She walked around and untied his left hand. She crawled across the bed and untied his right. She told him to lie down on the bed on his back and not to say a word. Of course, Jimmy did as he was told.
When he laid down on the bed, his erection came into full view. Even Jimmy was surprised at how hard he was and that fact that it was standing straight up, bouncing back and forth. He didn't ever remember being this hard before, especially since he just came a few minutes ago. The vibrator still humming in his ass, now being held in by the pressure on the bed, was sending wonderful vibrations through his whole pelvis. He shifted around a few times trying to get it to press on his prostate again, but could not. But he was happy with the vibrations none the less as they were keeping him harder than he had ever been.
While he was admiring the situation, he did not notice that Ashley had retrieved a candle from her bag and now carried it and a lighter over to the bed. She laid it down beside Jimmy and moved his arms up behind his head. "You don't get to touch me, slut." She said to him.
Ashley crawled over top of him and lined her slit up with his throbbing erection. She slid down easily on his shaft, the large head rubbing her in all the right places as it entered her. She slid all the way down his shaft and stopped there, taking a moment to move her legs into the right place, her knees at his sides. She reached over and grabbed the candle and lighter from off the side of the bed. While doing this, she gave a little wiggle and squeezed his cock with her pussy, just to give him a little buzz, which caused his hips to involuntarily rise to meet her. While he was looking down at her pussy completely engulfing his cock, he couldn't help but remember his fantasy from the night before, with her riding his cock to a mind numbing orgasm. He raised his hips again to start fucking her, but he hadn't been paying attention to the candle.
"Aaahhhhhh... Ouch!" Jimmy said. He started to raise his hands up from behind his head but she quickly stopped him. He put his hands back behind his head and tried to concentrate on fucking her. He began bucking his hips, slowly fucking her and she responded by matching his motions. She still had the lit candle in her right hand and had her left hand on his chest, and every two or three thrusts she would drip wax on his chest. The look of pain and loss of control on Jimmy's face turning her on even more. She did this for two to three minutes before the fucking she was getting, even through the pain, was feeling too good and she knew she needed to cum again. She set the candle down to the side and placed both hands on Jimmy's chest.
"You hold still. You're just a warm dildo right now. Don't you fuck me you little slut, you were the one who just got fucked, do you hear me or do I have to get the candle back out?" Ashley tried to be as domineering as she could, but she was having trouble. The bulbous head of his cock, made even harder and more enticing to her by the pressure being exerted on his prostate by her well placed vibe still in his ass, was mercilessly rubbing on her G-spot. Jimmy could tell he was getting to her, but was afraid to try anything at this time.
Ashley began rocking up and down on his cock, making sure to rub his head inside her over and over on her g-spot. Every time she rocked forward, she rubbed her clit on his pelvis, giving her extra stimulation. She loved to masturbate, but this was perfect. The warm feeling of his cock inside her, the veins rubbing on her inner walls, the feeling of her lips being spread, the pressure on her clit as she slid back down his veiny shaft, and that wonderful head hitting her g-spot every time, she was lost in the moment. She was concentrating so hard on making sure everything was just right that she hadn't realized how close to her second orgasm of the day that she actually was. It crashed over her by surprise, causing her to collapse forward onto Jimmy's chest, her hips bucking wildly on him, trying to get all the stimulation that she could at any time. Her breathing and voice almost sounded like she was panting and crying, she was just making a long, drawn out "Ahahahahahahahaaaaaa" noise. Her pussy was gripping Jimmy's shaft and bringing him even closer to his second orgasm of the day. He knew he couldn't last much longer and knew he needed to fuck her, not just be her dildo as she had called him, so he took his opportunity. While Ashley was still in the throes of her own orgasm, Jimmy began pounding her like a jackhammer.
Just as Ashley thought she was done, she felt Jimmy really start fucking her good. She rose up off of him with her hands, which repositioned her hips where he could really thrust against her. Jimmy decided to be bold and took his hands out from behind his head and pushes her back. He figured it was now or never if he was going to fuck her, so he did.
His actions caught Ashley totally by surprise and she had to catch herself with her hands behind her hips, which arched her back. Before she knew what had happened, Jimmy had grabbed hold of her hips with his hands and was fucking her as fast as he could, so fast that even though he was below her, she could feel his balls slapping her each time he rose up to her. She let go of her hold on the bed and her hold on dominating him and decided to ride him out, knowing she was close to another orgasm having never really come down off of the last one. She kept her right hand on the mattress and began roughly grabbing her nipples with her left, the pain adding to her excitement. She could feel Jimmy pulling her down with his hands and then feel him slamming into her raising her back up. He kept pounding and pounding on her g-spot every thrust, bringing her closer and closer to orgasm.
Jimmy knew he was getting close and was ready to cum. With every thrust, he could feel the vibe still in his ass, his own muscles doing all they could to hold it in, and every time he came down, the pressure pushing it against his prostate. His stomach hurt he needed to cum so badly into this beautiful woman and he was going to do it now. He pumped his hips hard into her a few more times as he felt his orgasm begin. He arched his back up as far as he could, raising both of them off of the bed as well as forcing his ass to clamp down on the vibe. He pulled her hard down against him, thrusting his cock as deep into her as he could. As the first shot of his orgasm hit, he buckled at the waist, his ass dropping and his stomach crunching, dropping Ashley on top of him as rope after rope exploded out of him, his body bucking in small, rapid movements. The throbbing of his cock inside of Ashley sent her over the edge again, causing her to lean back, almost against his legs, her back arched, her tits pointing up at the ceiling, shaking and bouncing with her own orgasm. They both rode their orgasms out, Ashley wiggling her hips around on him causing him to shudder each time, his throbbing but softening cock still inside her.
She leaned forward , still with him inside her and reached behind her and between his legs. She caressed his balls for a few seconds and then reached below them. Jimmy opened his legs and she grabbed hold of the vibe in his ass, still on the entire time. She gave it a few pumps and spun it around a little bit, feeling his cock jump a little bit but knowing that he would not be ready for another round in the next little bit. Feeling content with her own orgasms, she rocked her hips forward just enough to allow him to raise his hips enough for her to ever so slowly slide the vibe out of his ass. She rubbed it a few times across his asshole, still slick from a mix of conditioner and her own juices. Jimmy's eyes closed and rolled back in his head. When he did this, she leaned down and kissed him one time on the lips, then rose up off of him, his semi-flaccid and cum covered cock sliding out of her. She stood up and walked across the room and into the bathroom. She wet a washcloth and then walked back into the room wearing a bathrobe she had already stored in the bathroom. She handed him the washcloth and smiled as she looked at him one more time, still lying on the bed. She turned and walked back into the bathroom.
"Clean yourself up and let yourself out. Don't worry about the computer, I'll fix it myself." She said and closed the bathroom door.
Jimmy quickly dressed and left the room with a story he would never, ever forget!
