Undoubtedly, many of us have found ourselves hanging out with an ex- in the hopes of just enjoying some not-together-any-more- so let’s just fuck…this is one such story. It has been forever burned in my memory, as one of my worst sexual experiences EVER. It is a story of sex with a once familiar girl, who became a stranger one fateful night...

So “Jane” and I had been together for over a year when I decided that she may not be “the one” (ok, so I knew after a week or two- but I was living in a very unfavorable area for meeting women). So we broke up in my normal fashion:  no notice, no indications, and no regrets to the times we had. Jane was a petite hairdresser, whose pastimes were drinking, smoking, fishing, and don’t you know- fucking.  Jane was the type that gave you an angry-aggressive game face, when she wanted to really get down.  She liked to be roughed up, fucked everywhere, you get the idea.  She just had a nasty mind about her.

Our last evening together…

6pm. It’s been a long day at work.  I call Jane to see what’s on the schedule for tonight, we had been getting together once a week or two, after we stopped seeing each other officially, for sex and drinks. I had work the next day- really EARLY- so I told her I would see her in a few hours to make it an early night. She sounded like she was already ahead of me with the drinks over the phone (mental note: don’t bring more than a 6pack when Jane sounds loaded.)

8:30pm. I head out to her house, stopping by the gas station to pickup necessities only- a 6 pack. These are for me, Jane always has plenty of alcohol on hand. That’s how she rolls.

9:15pm. I arrive at her condo. The windows are open, nice breeze, candles, she is on the rear porch with cigarette lit, beer in hand. Her place overlooks a nice lake, so we usually hang out in the back. The scene is WAY too romantic for our purpose, but I am already here, and I might as well make the best of it.  I am constantly steering our conversations away from making her think there is even a chance in hell of us getting back together, but unfortunately, without that hope in her mind, I probably wouldn’t be here this evening.

10:45pm. I have had my fill of beer, and I start making conversation to get things rolling; I have to wake up early, so I tell her we should go to bed. She convinces me to have a few more beers.  I was already tired, and really didn’t want to drink to begin with- (fucking alcoholic- that’s why we aren’t seeing each other Jane!).  The conversation has gone to hell. She is talking about herself “ being ruled by the moon." WOW! Some other crazy shit followed in our conversation, that would just give you a headache to listen to. I know she is drunk, but holy shit (you should really keep these ideas in your head Jane, drink up!)

About 11:30pm. She is finally ready to get her freak on.  At this point, and regardless of my time investment in the evening- it’s now or else I’m out of here in my head. I’m tired, a little drunk, and have lost some of my ambition, but I’m still here.  I lock the rear door, and we take off most of our clothes to get comfortable. She is wearing those white, tight-ass, spandex-like short-shorts that aren’t really made for exercise.  She starts blowing me in the living room, where I am standing, with the rest of a warm beer in hand. I don’t know what it is, but for some reason, after you have graduated to no-strings stage, with an ex, the sex seems almost better than ever. This girl is a freak, but this has to be one of the best blow jobs she has ever given me. A little drunk, but a nice little pick me up. We fool around a bit on the couch, and it feels like it is getting late.

After midnight. We move to the bedroom, I tell her I want to fuck her from behind. She leaves her little shorts on, and I pull them to the side so we can get down to business. I pull her hair a little, as was our custom, and she is on it tonight, talking smack, made only for the ears of porn stars.  We get humping for a little while, and I am thinking this is not going to happen for either of us; we’re both more wasted than I realized. Jane is really feeling it tonight, and suggests we try something new. She tells me to fuck her in the ass…that was never on the table when we were together, hmmm...very bad girl Jane.  I am not really into ass fucking, but let us not waste the opportunities the good lord allows us.  

Who-Gives-a-fuck o’clock.  Before our endeavor, I decide to swig a little more warm beer, and she lights a cigarette (yes, in the house, and next to the bed, lovely!). I must tell you, I fucking hate people smoking in houses, in general, and not sure I have ever felt more dirty than having thought of what happened next. She rests the half-smoked cigarette in an ash tray on the night table, and she proceeds to go down on me again, so we can give this a good effort. I make my attempt, as I push up against her. I feel like I am trying to stick a square peg in a round hole. I am pushing so hard, I think my dick might snap in half, and I tell her I don’t think this is going to work. We try for what seemed like several minutes, now with lube. As I mentioned, I am not too much of the ass-fucker, so the thought of me starting with fingers or whatever you ass-fuckers do in preparation, is out of the question.

She keeps encouraging me, and I am starting to think too much about what she is thiniking about at this moment. She has to be a-lot-fucked-in-the-head to be enjoying any of this. As I press harder, and finally get a little bit inside her, she starts getting down with that pornstar mouth of hers. After I am a few inches in, I think, progress, this is good. Almost immediately, she reaches for the cigarette. I think I’m going to barf.  I smell disgusting cigarette, I am almost painfully forcing myself into this girl, and she is starting to drag on the cigarette. I now want to crawl inside a hole (for lack of better words), and hide, but I feel obligated to keep going because of the efforts thus far. With each partial thrust, I am almost sure if it is possible to break your dick, I might be driving myself to the ER tonight. The cigarette smoke is filling her small bedroom. I HATE cigarettes. At this moment, I have an out of body realization, that this must be what it feels like to fuck a hooker.  As she keeps turing her head back to look at us, she still has the cigarette in her lips. To avoid pulling out, I help her reach her pack to light up another smoke, after the last one finishes. That’s as far as I can go, so hopefully you get the picture.

All of my fantasies of fucking a girl in the ass have been shattered by this experience. I felt like a used male prostitute that was getting paid with crack rock when we were done.