A One Night Stand With Ann From The Bar

Ann, The One Night Stand.


First, let me be upfront about this. Ann was a bitch. I knew Ann from campus and from my freshman year in the dorms. I tried to fuck Ann all freshman year, but like I said, Ann was a bitch.



Ok, now that that’s out of the way, this is the story of how I finally ended up fucking Ann.


She started coming into the bar at the end of junior year. I noticed her right away as I had tried to fuck her for most of my freshman year, before I had become a bartender. She was hot, had a really tight body with hardly a flaw on it. Great tits = Check! Long legs= Check! Nice face=Check, and so on.
To be honest she was way out of my league, but that didn’t stop me from trying. I got shot down hard back then, but as a bartender right in the middle of a great run, things were different. So in she comes with some friends, and the second I realized who she was, I decide right then and there I was going to fuck her. I didn’t care how long it took, but I was going to do it.
Most of the time I was just trolling for ANY pussy that I could catch, usually waiting until someone showed a little interest before going fully after them, but not Ann. I made it a point to say hi right away and set her and her friends up with free drinks for a lot of the night. They didn’t sit at the bar, so it was hard to talk to them, but the free drinks insured they would be back.

3 nights later they were, and wouldn’t you know it? They were really nice to me… I mean why not? I was giving them freebees all night and being super kind asking her how things had been making all sorts of shit up about my last 2 years. One of the waitresses noticed how much time I had spent running back and forth and thought gave me some shit so I had to hang back for the rest of that night.
This shit went on for most of the summer. It was an eternity for me as I was used to fucking girls after a week or two at most, but Ann had a boyfriend and sometimes the little prick even came in with her. But being the nice guy that I was I even gave him a free drink from time to time. I had time, and I was still fucking half of Fairfax anyway so I wasn’t desperate.

Finally as the senior year was about to start, she came in with just 2 other girls. After chatting a bit I determined that her boyfriend had gone home for the last two weeks of summer break and that if there ever was a moment, it had to be now, as she was ripe for the fucking. It was time to pour on the drinks and the “charm”. The first thing I had done over the last two months is make damn sure her friends liked me more than her boyfriend, pretending that I cared about whatever they were talking about and keeping them wet with free booze had worked pretty well to that end. I pretty much could have fucked any of them, but I had waited for my moment with Ann. At this point I was “Trusted” and that was needed so when I peeled her off from them on this night, they wouldn’t protest. Secondly I had convinced Ann that I also had a girlfriend and that she was also home for the summer. So she wouldn’t see me as a trying to get in her pants.
Hey! It was almost true. I had been fucking a lot of “girlfriends”, But they weren’t home for the summer, they were in and out of my bedroom almost every night!

So as the night went on, I kept them topped off with booze, not too much as to make them want to pass out and go home, but just right to keep them partying. Finally at around midnight the girls started talking about heading home. I decided to make my play. I asked Ann if she wanted to hang out with me till close and then I could give her a ride home, or maybe come over for a bit. She looked at her friends and they just smiled. They knew what I meant, and she should have, but I’m not sure she did.

So fast forward till 2AM its closing and I’ve got a tipsy Ann in my car and we are headed back to my place. All she is talking about is missing her boyfriend and I’m her shoulder to cry on. We get to my place and my roommate is on the couch, as always. So I use it as an excuse to head to my room. I stop and get a few beers out of the fridge and off we go.

Now the thing about my room is that it’s not set up to “hang out” it’s set up to sleep and fuck. There is a chair at a small desk, but I keep it an utter mess to deter using it. She is a few steps ahead of me and is already looking for a spot to sit. I just look at her and tell her to hop on the bed and we’ll watch some TV really quickly like there is no motive to it.

So after a brief pause, her half-awake brain responds ”ok” and she’s in bed! I’m thinking I’m more than half way there. So we sit for at least an hour talking about whatever, and drinking beer and she tells me she’s sleepy. I give her a hug and I remember this so well, It was like a highschool move. I just moved in all sweet like and gave her a little kiss on the lips. Bang, she melts and next thing I now were making out. Little by little over some very light “we shouldn’t” and “I have a boyfriend” type protests that I also emulate by talking about how much I miss my “girlfriend” I manage to peel off her clothes. Dear god she had a fine body. I had waited almost 4 fucking years to see it and it was worth it.

It takes another 10 minutes of playing, but I’ve got both of us naked and I am ready to start fucking her. She hits me with the “do you have protection” shit and I dig out my dusty rubbers. If you’ve seen my work, you know I don’t wear rubbers, but I put one on so she won’t stop the fun.

Now as an adult, I can’t fucking believe I never caught anything or got anyone pregnant, but at this phase in my life I’m an asshole, so I use the “proven” method of putting the condom on so she can see it in all its glory, and then climbing on top of her and with one hand, I grasp my cock at the tip and pull down hard. Pow! The condom breaks right off and ends up at the base of my dick. She has no idea, and I’m ready to fuck her.
In I go and I’m as slow as possible in the beginning, fucking her like I would have freshman year. But as you know my cock did most of the thinking back then and its not too long before I’m fucking her like a rabbit! She’s into it for a while but as the clock ticks towards 4am she’s starting to fade a bit. But not me. I want more of her, and I know this is all I’m going to get with her so I start moving her around. I flip over and get her on top despite some complaining and take the time to let her fuck me for a bit while I admire her sweet body and great rack. As she slows down, I realize it’s time to turn her over, and when I push her off she notices the broken rubber! Oh my, I had no idea! Well, no worries I have another and I make the show of taking the old one off and putting the new one on before flipping her over and getting her into doggy position.

With a quick thrust of the hand, POP goes the new rubber and its tattered remains lay at the base of my cock. I slide my dick back in and start to fuck her from behind. I fucked her this way for a long while, building up to an orgasm and then letting it subside. After the 4 or 5 times of this happening I decide our night is almost at an end As I can’t keep from cumming forever. But no anal….

No anal…. I am knee deep in my anal quest, and here is a piece of ass I’m only going to see once…
I ponder the moment for a while as I stroke in and out of her pussy. Finally I decided to go for it. I decided to get in her ass with the slip and bang “mistake”. I knew there was no way I could get her to let me fuck her ass all the way, but if I was lucky and timed it right I could pop it in and cum in it in the same stoke.

Timing was everything here guys. I continued to fuck her while slowly moving both her and myself into position. First pushing against her with harder strokes so she would shimmy up the bed until her head was at the wall, giving her no place to pull away to. Then increasing my strokes so that my cock would come out of her pussy from time to time just enough to hit the lips and then plunge back in.
As I felt my urge to cum start to climb again I slipped it all the way out as an “accident” giving me a moment to wipe a large pile of spit I had wiped from my mouth on my cock to get it lubed up, and to adjust my position with one leg up and one leg down. The perfect placement for an “accident”.
I deposited a large bit of the spit from the tip of my dick right at her butthole as I positioned my cock near her pussy, and then back in it went as and I started to fuck her pussy for the last time. Long strokes with power behind them, that increased as the tightness in my balls increased as well. This went on for maybe two minutes until It was time to cum. It was a perfectly executed “slip and bang” I was holding on for dear life trying not to cum as I pulled out “just a bit too far” letting my cock pop up a bit too much till it hit the tip of a well-placed finger on making sure that it wouldn’t pop up too far… And then…

Bang! I hit her ass at 100 miles per hour as the first load of jizz sprayed out of my cock. She tried to pull forward, but she could only move her head to the side since the wall blocked her escape. I fell forward onto her as she let out a yelp, still deep in her ass while both cumming and asking her in a startled voice “what’s wrong?”
I of course knew what was wrong, but needed at least another 5 seconds to finish cumming and pullout, so I stalled with that question. She tried twisting her body to the side again mostly blocked by the wall , but I flopped down on her farther as I finished pumping her ass full of cum. She screamed out “Wrong hole!”. And as I had finished unloading into her ass, I acted even more startled and pulled out.

I acted so sorry and told her it was a mistake, then without missing a beat, I acted like I had had a change of heart, and that we never should have had sex in the first place. She went with that as well saying what a mistake it had been to come over while begging my not to ever say anything to her boyfriend or friends about it. I agreed, acting the same way and asking that she never say anything about it to my “girlfriend”. With that the moment was over. (She never knew that I came in her ass.)
I apologized a hundred times about the “accident” ,with her saying it was ok, and we both got dressed.

I had her back at her place right as the sun started to rise. It had been a long night, but I had to see if my roommate had taped it.

When I got back to the house. There was my roommate, and there was the tape. Although I hadn’t slept in 40 hours or so, we watched it twice that morning, and must have rewinded and rewatched the ending two dozen times. Over the next two months I had every friend, and even some of their friends over to watch it. It was an instant classic. The guys loved how I was able to cum in her ass without her ever having a clue. They all knew the rubber trick as I think one of them had told me about it freshman year, but the “Slip and bang” method of Ass fucking was usually hit or miss. And then to top it off with me cumming in her? It was great. On video you could totally tell I was cumming, as you can see me make a few extra thrusts as I’m in her ass and my face in the “oh ya” look, plus when I pulled my cock out it was still dribbling jizz. But she never had a clue. She was caught up in the shock of the moment and then right after with the thought of regret that I placed in her head. She never noticed the broken rubber or my cock dripping cum.

Sadly less than a month later, just 3 short months after it happened, it was gone. Larry taped over it by accident. To be honest I think he was more tore up about it than me, but it was gone, and now only my memory of the night remains.

Of course that was the only night I fucked Ann, and after that, she hardly came around the bar anymore. However her friends still did from time to time and I ended up fucking one of them too, But that’s another story.