Sex I shouldn’t have had [mf] [pic] | 2016

My roommate Derek is dating this girl, Jane. Jane is this really good-looking brunette. She’s pretty tall, about five feet seven inches, straight dark hair that goes down to just below her shoulders. Great big tits. Great ass. She doesn’t have a cheerleader’s body but she’s got all the right curves in the right places and I think she looks really good. And so does Derek.

Derek and Jane fight all the time. She’s always at our place so I witness a lot of their fights. They fight about everything, big and small. Who’s turn it is to do the dishes. How he only ever says she looks good when she asks him to and he never says it on his own. How he keeps looking at other girls (not to excuse what I did but he hasn’t exactly been faithful all the time)

One Friday night I come home at about two in the morning and the lights are still on but Derek is nowhere to be found. Jane is alone in the living room and she’s obviously been crying. She’s sitting there on the couch wearing only a pink oversized t-shirt. She’s just staring at the wall and her eyes are red and puffy.

One thing I forgot to mention about Jane: she sure isn’t shy. She’s always walking around the apartment wearing nothing but that big pink t-shirt and panties. Usually white. Always lacy, at least judging from what I can see peeking out from under her shirt. She likes the attention it gets her. Derek will sometimes tell her to cover up but he sure enjoys seeing me ogle his girlfriend. It’s this little unspoken ribbing between him and me: “Check out how hot my girlfriend is, bro. That’s right. She’s mine and you can’t have her.” Yeah bro, that’s what you think...

So on that Friday night I wasn’t surprised to find her on the couch wearing that t-shirt. I was surprised though to see her crying like that, and I was really surprised that Derek wasn’t there. I ask her where he’s gone to and she tells me he’s gone. She says they had this huge fight and he wanted to kick her out but she wouldn’t go so he slammed the door and left. He’s probably at a friend’s place somewhere crashing on his couch for the night.

I sit down on the couch next to her and I try to come up with something that will make her feel better. “You guys fight all the time but you always make up. He’ll come back and you two will work it out.” She tells me that no, this time it’s really, really bad and they’re definitely over. She has already packed her stuff and she’s taking it all back to her place first thing tomorrow morning. She starts to cry a little bit again and not sure what else to do I put my arm around her shoulders to try to comfort her.

We sat there on that couch a long, long time. We talked about her and Derek, about their problems, about all their fights and other things like that. I talked a bit too but mostly I just let her get everything that was bothering her off her chest. And all the while she’s leaning against me wearing only that t-shirt. And she’s got no pants on and one of those two great tits is right there pressing against the side of my chest…

And this is the part where I start acting like a jerk. You don’t come on to a girl who’s been crying over her boyfriend. And you don’t come on to your roommate’s girl, even if said roommate is a real dick to her sometimes. But I’ve got this girl who’s almost naked sitting right against me. This girl whose ass I’ve seen so often scamper around the apartment covered only by those little lacy white panties. This isn’t the first time I’ve sat on that couch with her. We’ve squeezed next to each other on that couch more than once to watch a movie with a few friends. And all those times I had to restrain myself not to put a hand around her shoulders or on her thigh. She was Derek’s girl, not mine. He’s the one who got to put his arm around her, not me. But now Derek’s gone. And not to excuse what follows but she had me really convinced that they really were over. This sure didn’t sound like one of their regular fights. At that moment in my head that was it, they were over. And I wasn’t going to ever see her again. I liked the girl but I wasn’t going to go after her and try to date her after she and Derek broke up. That would just be too pathetic. So this is the last time I’m ever going to see this girl. We have this night on this couch and then tomorrow morning she’ll pack up and leave and that’ll be that. I’ve got her pressed against me and we’ve been talking for a solid hour now and my hand is rubbing her back up and down but it’s getting less and less about comforting her and more and more about just feeling her while I still can.

And I’m pretty sure she feels the mood change too and she adjusts her position and she leans into me a bit more and she puts her hand on my upper thigh. And I rub her back a bit more but after five minutes of that I’m hard as a rock and there’s no mistaking what that bulge in my pants is. And her hand is right there less than a couple of inches away from it.

I figure fuck it, I’m making a move. I’m not ever going to see this girl again so if she says no then fine but I’m not going to spend weeks after this wondering what if? My hand reaches under her hair to caress her neck. My other hand goes all the way over to rest on her bare thigh. I’m half-turned toward her and her hand is now touching my cock over my jeans. I don’t rush into it but I don’t take it slow either. I just give her enough time to say no if that’s really what she’s gonna say and then I move her dark brown hair out of the way and I kiss her neck.

She turns her head back and to the side a bit to expose more of her neck. I keep kissing and my hand moves up from her thigh to her boob, grazing her panties on the way. She takes her hand off my cock, lifts up her arm and puts her hand on my shoulder, clearing the space between us and giving me a great view of that nice rack of hers. We’re now facing each other and my hands move to her boobs and her thighs while I keep kissing her neck.

From then on it’s just sex. And I’m not really comfortable writing about throbbing cocks or dripping pussies so I’ll stick to the basics. First I ripped her panties off. I leaned into her so she had to lean back against the side of the couch a bit and I grabbed her ankles and I pulled her legs up on the couch so she was lying down completely. This is your standard three cushion couch: I’m sitting on one end, she’s got her head on the other and her ass is in the middle. I’m still holding on to her ankles and I raise them up so her legs are straight up and I reach down under her and pull her panties all the way off. So technically I didn’t rip them off but I pull hard and fast so it kind of felt like it.

With her panties off I spread her legs and I get my first look at her shaved pussy. I’ve been hard for a while already so I’m in no mood for any more foreplay so I take my shirt off, I unbutton my pants and I slide right in. We fuck like that for a while and I try to keep kissing her neck and caress her boobs but it’s hard to keep my balance on that narrow couch so pretty soon we get up and we go to my bed.

We fucked for a long time. I wasn’t drunk but I’d been drinking and it always takes me forever to come when I’ve had a few drinks. I checked my phone when we got in bed and the clock read a bit past three thirty. When we finished it was well past four in the morning. We fucked that whole time. Other than the occasional pause to change position I was banging away that whole entire time.

We started in doggy and that’s when I snapped that pic I promised in the title. Click here to check out that great ass of hers. (By the way I don’t know what the policy is for posting pictures other than that it seems to be encouraged in the sidebar. She knows I took the pic and she’s fine with it since it’s pretty much completely anonymous but she doesn’t know I’m writing this story. If this goes against the rules just let me know and I’ll take it out) We were both enjoying that and she was moaning with each of my thrusts but after a while, when it was clear I wasn’t going to come anytime soon, she wanted to come so she got on top and rode me. We had our clothes off at that point and her great big tits were bouncing up and down. She leaned backwards and arched her back and reached a hand between her legs while she kept her balance with her other one on my leg. She rode me fast and hard and her ass was bouncing up and down and then she was moaning and shaking all over. That was her first orgasm of the night and quite frankly the only one I noticed. It was a great one though, at least from where I was standing. She told me after that she came a second time later on but that other orgasm must have been less intense because really I completely missed that one. The first one though there was no way not to see that. Her thighs were shivering so much the whole bed was shaking.

As I said we fucked a long time and we went through a lot of positions. After cowgirl we did missionary and then doggy again. During doggy she got lower and lower until she was just lying on her stomach so we fucked like that for a while. I was just pounding away harder and faster. I could feel myself getting more and more turned on and excited but because of the alcohol I just couldn’t come. On one hand that was frustrating but on the other if it meant that the night didn’t have to end right away then I figured I might as well make the most of it and enjoy the build-up. Around that time though she complained about it chafing a little so I reached for the lube I keep in my nightstand. Not to brag but I’m a bit of a lube expert. I haven’t tried them all but I’ve tried an awful lot and I’ve long ago stopped using cheap lube like that KY shit. What I keep in my nightstand is only the best stuff. I grabbed a bottle and I poured some over my cock and rubbed it all over before reaching between her legs and sliding a slick finger inside her.

After that we fucked some more in that position. My fingers were wet and sticky with the lube so I wiped them over her ass. She moaned a bit and she clenched around my cock so I figured she must like that. The lube was great for her but my cock was sliding in and out so easily now it took a bit of the intensity out of it so I was happy for the additional pressure. I grabbed more lube and rubbed it over her ass, this time reaching her asshole.

When I touched her asshole her pussy clenched really tightly around my cock. I didn’t know if she was into anal or not but I was going to find out. We’d been banging a good thirty minutes and all that time I’d been getting closer and closer and by then I had this frantic need to come. The way her pussy tightened every time I touched her ass and the thought of me sliding inside had me a good part of the way there.

My fingers were so slippery I fumbled with the bottle of lube. I poured a bit more right on her asshole and gently pressed in with my index finger. Her pussy stayed tight around my cock as my finger went in all the way. I could feel it pressing against my cock and that started to really get me going. I took my finger out, pulled my cock out of her pussy and pressed it against her ass. I waited a second to make sure she was okay with it. She breathed in and pushed her ass up. At that point everything was so covered in lube my cock slid right in. The first couple of strokes I took slow but then I was banging away like I’d banged at her pussy moments before. She started moaning again and reached a hand between her legs. Her ass got tight, tight, tight around my cock and finally that’s all I needed. Finally I released what must have been just the hugest load right in her ass. Again and again I felt it gush out, six, seven, eight times. Finally I collapsed over her, my cock still in her while she kept rubbing her clit. We stayed like that a while with me resting on top of her and my cock still hard in her ass while she tried to spark one last orgasm out of herself.

That was our night together. We fell asleep almost instantly after that with the bed a mess around us. The next morning she was up bright and early and as she’d promised she took her stuff with her and left in a cab. I figured that was the last I’d see of her.

Derek came home around noon when I was still asleep. He didn’t notice that I’d had sex that night or at least he didn’t say anything about it. For a few days afterwards nothing much happened. But then, in the middle of the following week, Derek announced that he and Jane had made up and they were back together. A couple of days after that Jane was back in our apartment like nothing happened.

She didn’t tell Derek about us and I sure as hell won’t. I figure nothing good can come of that. But now I see Jane once again walking around in that big t-shirt and panties and it’s starting to drive me nuts. It’s hard not to remember what that ass looks like without those panties on. But I won’t try to fuck her again. I know that would be crossing the line. From the way she acts around me I suspect she still thinks about that night sometimes too but she says that her and Derek are back together now and that makes her happy.