Jane had been Ryan’s roommate for a few months, the two working at the same large state agency together. Ryan was thirty years old, fit, attractive and had an incredibly sexy and kinky girlfriend named Stacey. Jane, was twenty nine years old, about 5’5, with shoulder length black hair, a slight tan all year round and an athletic body that she took good care of going to the gym five days a week. Before Ryan had gotten to know Jane the first thin he noticed about her was her extremely gorgeous tits, in his estimation D cups which might be fake because of the way they defied gravity.
She also had an extremely sexy walk, her hips moving side to side, giving her ass a captivating wiggle.
Jane and Ryan were good friends and although there often had been a sexual tension between them that was all they’d ever be despite the two of them occasionally winding up in some intimate and sexual situations together: seeing each other scantily clad around the apartment, hearing each other having sex or masturbating in the next room, talking about what they liked sexually or wanted to do.
One night Friday night, while Ryan was relaxing on the couch watching TV, Jane came home. It was late and she was obviously drunk, having gone out with a large group of her girlfriends. As soon as she came in she went to the bathroom. When she came out she hadn’t buttoned up her jeans and he could see several inches of her black and green panties as she crashed on the couch next to him putting her head in his lap saying that she was going to feel like shit in the morning. He wasted no time making fun of her running his hands through her soft hair to make her feel better. Minutes later she was passed out cold. Not wanting to disturb her right away he sat back and made himself comfortable. Looking down her body her he noticed that her jeans had slid down due to not being buttoned up and he had an amazing view of her tanned, gorgeous ass. Her black and green panties turned out to be a thong, slipping down between the cheeks of her ass, not covering much at all. He told himself he should but how could he resist?
He slowly began stroking her ass, looking for a sign that she was waking up, but she didn’t. As he stroked her ass, enjoying the feeling and the sight of her in her thong, jeans pushed down he felt his cock jump, getting extremely hard. His cock got so hard that he wondered if Jane might feel his erection because her face was in his lap but his cock was directly touching her. The more he stroked her ass, running his fingertips over the design of her lower back tattoo the more he could tell she was completely passed out. He didn’t want to get caught because she would probably tell his girlfriend and force him to move out, but he was so turned on he decided to push his luck. He wiggled her jeans down her ass, deciding that if she woke up he could remind her that she’d gone to the bathroom and not buttoned up her jeans. Now he had a full view of her ass, pushed up in the air slightly, the thin material of her thong covering her pussy. He gently ran his fingertips over the material, feeling her pussy just on the other side, slightly moist. She didn’t stir at all so he decided to tease his cock through his pants, and eventually pull his cock out, rubbing and teasing the head, alternating between looking at her full, luscious lips and her gorgeous ass. He would have given anything to be able to smack her ass hard and slip his fingers into her pussy but knew the key to prolonging his fun was not getting too carried away.
Just then, her cell phone, which was in her purse near the front door, began to ring. He knew she would probably wake up so he quickly put his cock away and pulled her jeans back up over her ass. She started muttering, moving around.
“Your phone is ringing,” Ryan told her.
“I don’t care, I want to sleep,” she mumbled.
She wiggled around, reposition herself her hand coming into contact with his hard cock pushing against his pants.
“Do you have a hard on?” she giggled.
There was no way he could deny it so he said he did and before he could stammer out an apology she started running her hand up and down the length of his cock through his pants drunkenly mumbling how good it felt. He couldn’t believe his luck, she was too drunk to mind. Naturally his hand returned to her ass, stroking it again wondering what she’d say to this. Not only did she not protest but also she made this little moan-giggling sound as she continued to tease his cock.
“Did I catch you watching porn?” she asked.
He decided to lie and say yes that she had to see how she’d react. He almost couldn’t believe his ears when she told him not to let her interrupt him and that he should finish. Seeing as her face would be no more than four or five inches away from his cock he made sure she really meant the offer and she said yes. With one hand he guided his cock out and began stroking and teasing it with one hand, the other stroking her ass. From time to time she opened her eyes commenting on how “lovely” his cock looked as he slowly stroked it over her face. His other hand pulled her jeans down over her ass again, half expecting her to protest but she didn’t and soon he was teasing her pussy through her thong.
“I like watching a guy stroke his cock,” she said as she teased his balls with her hand, wiggling her ass back and forth as he felt her pussy getting wet.
“Do you like the way I’m touching you?” he asked and she moaned that she did. This made him push her thong aside and start alternating between rubbing her clit and slipping a finger in and out of her pussy, feeling his fingers getting wetter. He leaned over to admire the view, seeing that her thong and pussy were glistening with her juices. Without saying a word she began licking his balls and then his shaft and soon he guided his cock in her mouth. He watched her instinctively begin sucking and pumping him between her lips, sitting up slightly which made her jeans fall down around her knees. The faster he played with her pussy, the faster and harder she sucked him, moaning around his cock. Soon, without warning her hips and ass began wiggling and she began moaning out, taking his cock out of her mouth only long enough to say she was cumming. After her orgasm subsided she began stroking his cock, licking all over it.
“Cum on my face?” she whispered, still obviously drunk.
“You want me to cum all over your face?” he asked making sure he hadn’t caught part of her request.
She moaned that she loved to be cum on. As he fucked her mouth, pulling her smooth dark hair out of her face so he could get the perfect view of his cock exploding all over beautiful face he smacked her ass hard. She responded by moaning and wiggling even more, his hand gripping and pulling on her thong to the point it was about to rip.
“Oh god yeah, I’m coming,” he yelled out as she slid his cock out of her mouth, pumping his creamy cum all over face from her chin to her eyebrows, her lips getting the most of his load.
Afterwards she smiled a wide drunk smile, giggled and told him “that was a lot of fun and went off to the bathroom.” When she came out she was only in her bra and panties, her clothes all over the floor. He could also tell she had whipped the cum off of her face just as she slipped into her bedroom and crashed into bed passing out for good.
The next morning he wondered if things would be awkward between them but to his surprise she seemed pretty chipper and didn’t act weird at all. After a while he began to suspect she might not remember too much of what happened and so he decided to fish for details.
“I know my friends dropped me off but I don’t remember anything else after that, I hope I wasn’t too obnoxious last night?”
Ryan said that she’d banged around the place last night making a lot of noise, leaving her clothes around but that was it. That’s when she said admitted that if she drank past a certain point she could never remember anything. Ryan had almost wanted her to remember and enjoyed it, increasing the chances that something like that might happen again but he also knew he was playing with fire and he should thank his lucky stars.
He thought about what had happened off and on, remembering how hot it was, wishing it would happen again but months went on and the only times she drank that much again his girlfriend was either over there, or Jane seemed more coherent than she had been and he decided against risking it.
That is until about six months after that night, he was in the kitchen cooking when she came home from bar hopping three sheets to the wind. Once again she stormed in and sat on the couch, this time unbuttoning her shirt and slipping it off. As he talked to her he couldn’t help but admire her beautifully toned, large breasts somewhat visible through her bra. She stumbled into the kitchen and actually began making herself another drink. Ryan wondered if this could be the night. As she mixed the drink his eyes made their way up and down her body. She had on a black skirt that ended just below her knees and a pair of black, high boots. He felt his cock jump inside his pants as he remembered the night where she sucked him, making him cum all over her face.
After she finished her drink she unzipped her skirt but didn’t take it off, sitting down at the table rambling on about completely random things, her speech totally slurred. Just then the phone rang and Jane got up and answered it. It was Ryan’s girlfriend who was out of town for the weekend. When she handed the phone over to him she looked down at his crotch and he knew that she could tell he was hard. They starred at each other for a minute and while he made small talk with his girlfriend wondering where this was going. Then he turned back to the food he was cooking remembering that he was talking to his girlfriend after all and shouldn’t risk getting caught. That’s when Jane reached around and began teasing his cock, pressing her body against him. He just kept talking, playing along, knowing that if he showed too much excitement she would probably stop. Then she undid his pants and took his hard cock out, teasing it, running her hands all over his body.
“Let me call you back in a bit, ok, I don’t want to burn my food?” Ryan told his girlfriend but Jane whispered for him to keep talking and she led his over to the table where she sat in front of him. With her legs spread wide apart she pushed his hard cock in her mouth, sucking and pumping him between her lips, looking up at him while he talked about everyday things with his girlfriend, seeing that he had to concentrate on not moaning or giving away the fact he was getting his cock sucked. With his one free hand he reached down, playing with her breasts, stroking her nipples while she licked all over his cock, making him rock hard and wet. Again he started to say he was having trouble cooking and talking at the same time but Jane grabbed a piece of paper and pen and wrote out a note that read “You can do whatever you want to me as long as you stay on the phone with your G.F.” He paused for a minute thinking if he could actually pull it off as well as wondering if Jane was for real and she wouldn’t fuck him if he ended his phone call. He knew he had to do it, but how could he talk about everyday things while his over the top hot roommate sucked his cock, spilling out of her bra and skirt?
He knew he could add to this encounter if he could get his girlfriend to have phone sex with him like they often did when one or the other was out of town. After a bit of coaxing she agreed as he wiggled Jane out of her skirt, admiring her body as she stood there in a black thong, her bra and boots. He told his girlfriend he was now in his bedroom and Jane couldn’t hear them as he began dirty talking to her, telling her how he wished he could taste her pussy at that moment while he fingered her. Jane, hearing this slipped her thong off and spread her legs wide apart pulling his hand between her legs, wanting him to play with her pussy. Ryan couldn’t believe how turned on he was playing with Jane’s pussy, seeing and feeling her getting wet while he listened to his girlfriend tease her pussy and tell him how she would love to climb on top of him and have him lick her pussy while she sucked his cock. After a few minutes of dirty talk he could tell his girlfriend was getting really into it, telling him how much she loved feeling his cock fill her up. That’s when Ryan positioned Jane so she was sitting on top of the table, her legs spread wide apart and slipped inside of her dripping wet pussy, pumping slowly and out of her. He was so close to her that she could also hear what his girlfriend was saying which turned her on even more. He kept pumping and thrusting into her, spreading her pussy apart all around his cock while he moaned out that he wished he were fucking his girlfriend. The experience was almost mind-blowing, how erotic the idea of fucking his drunk roommate while he listened to his girlfriend play with her pussy.
“I wish you could bend me over right now and fuck me Ryan,” his girlfriend moaned out.
“Me too,” he said.
With that Jane slid him out of her and bent over the table offering her pussy from behind. He didn’t wait a single second sliding back in her, fucking her deep and hard now, stroking her ass, gripping her hips while he cradled the phone under his neck and chin. Her pussy felt incredible wrapped around his cock, watching her under him, taking every bit of his cock, seeing how badly she wished she could moan out to be fucked harder or how much she liked it. Gripping her ass, pounding into her he spread her ass open, slipping a wet finger into her feeling her spread apart easily which told him she liked her ass being played with and possibly fucked just like his girlfriend.
“You know what I’d really like to do right now?” he asked his girlfriend.
“What? You can do anything to me I’m so horny right now.”
“I wish I could fuck your ass.”
“Oh yeah, it’s been a little while since you did that, I’d love it.”
Although he was telling his girlfriend, he was hoping that Jane would also want her ass fucked. As he fucked her pussy harder and deeper he pushed his finger into her ass also. She then forced him to slide out of her and ran off to her room. When she returned she had a bottle of lube in her hand and she’d taken her bra off, just wearing her calve length black boots only. Once again she bent over, offering her pussy or her ass for him as he rubbed the lube all over his cock. He could hear his girlfriend moaning, rubbing her pussy harder and faster now telling him she wanted him to fuck her ass. Just as she told him that he slipped the swollen head of cock into Jane’s ass, watching her take him slowly. Once she was used to having his cock in her ass he began pumping and pushing into her, deeper and deeper while she rubbed and played with her pussy.
When he heard his girlfriend cumming on the other end of the phone he began pumping into Jane’s ass faster wanting to explode too. He listened to his girlfriend tell him how good it felt to have her ass fucked and how she could feel him spreading her apart. He reached forward and pulled Jane’s hair as his cock began to spasm, exploding deep inside her ass. Just as his orgasm was ending he could feel her ass tighten around his hyper sensitive cock, her body squirming under him. Unknown to Ryan’s girlfriend, Jane was having an intense orgasm of her own. As Ryan talked to his girlfriend Jane took of her boots, smiling from ear to ear and then stumbled into her room and passed out.
The next morning. Severely hung over Jane asked if anything out of the ordinary happened. He told her not really as he admired her in just her silk bathrobe, remembering how good she looked bent over the table, his cock filling her pussy and ass looked.