I met Kim right during the middle of my run as a bartender. I was in full stride by that time, fucking everything I could, anytime I could and that was very fucking often.

To be honest I don't really remember much about Kim herself, other than that she was a college student, and lived on campus. She showed up at the bar one night with some friends and I managed to convince her to call me. Anyway, as I was in my prime, I was already fucking 3 or 4 other girls at the time. I know that the waitress April was about a month in, Laura the Milf was on call about anytime I wanted, and Heather, another college student was also in the picture for a week or so somewhere in the time we were together. The fact that I actually found the time to fuck Kim was impressive in itself!

Anyway, Kim was a short little thing, with a somewhat rare at the time belly button ring, and reddish hair. To match her hair was a pale white skin that I remember turned me on for some reason. Her other asset? Her 4 foot something average body, was offset by a massive set of somewhat floppy tits.
Needless to say, I fucked her that first night, and added her to the list of regulars. This meant that I was sometimes fucking her the same day as another girl, but I managed to pull it off. Time went on, and there are some pretty funny side stories involving her and the other girls that you can read about in my other work, but, I continued to fuck Kim on and off for about 2 or 3 weeks, and had pretty much done what I wanted to do with her up to this point. She was actually pretty fun in bed. She’d do pussy to mouth without pause, something I really liked, and had been a great add to the stable of regular fucks I was amassing.

Still, there was that one thing… I’d done pretty much everything, but I just had to try and plow that ass.
So, one night after a long shift at the bar, and many drinks with her after we closed, I took her home determined to make her a 3-hole girl.
My roommate Larry was well aware of my plans, and like most nights, he was ready with camera cords running to the VCR in the main room to tape it all. While we taped literally 100’s of nights, this is certainly in the top 20 of all time, and if you’ve ever seen the footage, I’m sure you’ll agree. The night Kim lost her anal virginity is epic in every way.
Once we got back to my place, Larry was in his usual spot on the couch. He like to camp there to help move the girls down into the bedroom faster, and on this night like so many others it worked perfectly. I made a motion towards him, and in a hushed voice asked her to follow me.
Once in my bedroom, I wasted no time at all. A few quick kisses as I pealed her out of her cloths and quickly positioned her on the bed. I learned early on was that once a woman came, they were usually more likely to just go along with whatever I wanted to try, so I went to town eating her out till she came. Once the rapid pulses of her orgasm slowed, I quickly moved up and entered her, moving her about from position to position, fucking her this way and that way. 10 minutes in, I was already starting to feel the urge to cum so I stopped long enough to recover and plot my next move.
I turned her over, and put her in the doggy style position. I had found it to be the easiest position for first time ass fucking. I'd put their head very close to the wall (or later my head board), that way they were pretty locked into position. If they had too much room, as I’d try and enter, they move up and forward making it hard to get in.

If you’ve ever seen the video of this night, you already know, but the night played out like this…

I had her in a good spot, she never would have known it, but her head was tucked into the headboard, her ass was up high, and I was pretty much boxing her in from the rear. If I had opted for the “Slip and bang” she would have had my cock balls deep in her before she’d had a chance to think. But I went with the “Let’s try and see approach”.
Slowly I entered her from behind and started to fuck her pussy again. Her cunt was still fairly slippery with the juice from her orgasm still lining it’s walls. I worked myself up to that moment when your balls begin to throb with a hot load in them and stopped, pulling out abruptly. She wiggled a little as it happened, and as I let the urge to cum drop off, I found myself looking down at her perfect tight little ass, quickly deciding to try fingering her. Although she squirmed a bit as I slowly slipped my finger from her wet cunt into her very tight ass, she was mostly silent. After just a moment or two, I decided to go for it. I pulled out my finger, and lining up my rock-hard cock, I took the plunge.
She gasped while trying to buck forward, but finding nowhere to move, she instead reached back and grabbed my leg hard. Her fingers dug deeply into my skin, but still stayed mostly silent as my cock hit bottom.

I paused only for a moment and I remember asking her if she’d ever tried “This” before. She said no, and my cock grew harder as I realized that I had just added another anal cherry to my list. I waited just another breath or two, but didn’t ask me to pull out, so I took this as a go ahead and started to fuck her no longer virgin ass.

She whimpered a bit, and said that it hurt as I began to pick up the pace so I slowed for a moment, asking again if it was ok, and although I could tell she wasn't into it, she said nothing so I kept right on fucking her tightly clenched ass with deep long strokes. She was tight! Her ass was clamping down on my cock with the convince of a vice and it was pure bliss.
I went slow for the first 2 minutes or so, or as slowly as my throbbing cock would allow. The urge to jack hammer her was overwhelming, but I resisted. Instead, I kept a decent pace and listened to her as, little by little, her whimpers became more gasps, and then just heavy breathing as her complaints died down. Sensing I was past the point of her changing her mind, my desire to jack hammer went up.
The thought adding another anal cherry to my list was overpowering. Many times, I didn’t realize it until I was already finished, or sometimes not until weeks later. Here was a rare thing, a virgin ass, a camera rolling, and a guy with a LOT of energy! I plotted a mental course. I wanted to get some good views for the camera, that was clear, but I also wanted to really break her in, and of course cumming in her ass was such a turn on I almost couldn’t wait to do it. I never got to cum in girls pussy’s back then, always having to convince myself to pull out, and other than one accidental creampie I had let loose in April a few weeks prior to this moment, as well and a few random times in the MILF who was “Fixed” I only ever got to come in a girl when in her ass. With Kim, that meant this would be the first time I was able to bust a nut in her, and I suspect I was able to catch the very first time anyone EVER came in her that night as well. As I continued to fuck her as, I realized that I wanted that first load to be truly massive so I made sure to make the night and my time in her ass count. In order to do so, I would have to build up to a cumshot over and over again, and I did.
The original tape from this night was nearly an hour long, and that was from the time Larry hit record right as she came to the time I came, and only 10 minutes or so of that was spent in her pussy, although I slipped back into it for a few strokes every once and a while before realizing it and switching back to her ass. Although the full night is lost, I still have over 30 minutes that incredible night. It’s full of fucking her ass slow and shallow, hard and deep, and from every angle in and out of her ass. Her ass stayed so clenched down that first night it was pure bliss. I built up to an orgasm more times than I can remember, then pulled out giving myself time to recover while I “readjusted” her ass for a new angle.
Down the hall I knew my roommate was recording and watching as the night progressed. Every now and again, I’d hear a muted laugh, or a stomp as something I did to her impressed him. These were things that the girls never registered when they heard them, but after nearly 2 years of filming I had come to know when he was enjoying the show, and tonight he was,
I put her head down flat into the pillow and stood over her, hammering balls deep for a while with my legs bent and my hands on her back to hold her steady. When I popped out, I moved one knee down and went for a 10-minute-long deep stroke marathon. Listening to hear gasps continue to get lighter and lighter as I plowed away. After many attempts to make her gape, I finally succeeded, but only after an epic anal hammering that is insane to watch even now. The entire floor of the apartment shook and the camera wobbled back and forth as I pounded my cock as deep and fast as I could into her for a solid 30 seconds. My balls felt as though they would burst if I went one more stroke, so I stopped. When I pulled out, I was greeted with a nice “Pop”, and looked down in time to see that I finally got that fine tight little ass of hers to gape. I knew my work was done, but I just couldn’t bring myself to cum. This was a virgin ass I was fucking, and I was 100% convinced that she would never let me fuck her again, so I wanted to make sure I got my fill. I spent those last 10 minutes or so slowly using her now relaxed ass to edge to the point of cumming over and over. My whole body was vibrating with pleasure by the time I finally decided It was time to finish up. I was exhausted from all the work.
I pulled out, just long enough for the feeling to pass one last time, and then I plunged back in her completely hands free, and fucked her harder and harder until the feeling inside my balls couldn't take it anymore. After edging with her pussy and ass for nearly an hour, I had saved up what felt like the load of a lifetime, and it was finally time to release. With the moment of no return reached, I jammed my cock in as deep as it would go and blew my load in her. Her tight ass fit like a condom, and as a result, I could feel every drop of my jizz as it pumped out of my dick and into her ass. Stream after stream of cum plowed into her as I pushed deeper and deeper with each spurt. Slowly the moment passed, but I stayed in her ass until my dick started to soften, slowly pumping back and forth until I could stay in no more.

Then it was over. I pulled out, hearing her ass make a squish sound as it tried to snap shut. I took a quick look at it before she moved away and it was certainly no longer virgin. Instead of the tight little button I had slipped a finger in just an hour ago, a quick flash of her ass revealed a swollen, puckered, and slightly gaped ass that was slowly leaking jizz as it moved forward and away out of sight. She flopped over onto the bed, and soon, I lying beside her. I was exhausted, breathing hard from the workout, while she on the other hand had that stunned look on her face that most of the girls would have after a night with the bartender. I asked her how she felt, and she just said "sore".

She spent the night, something that most girls didn’t do. She didn’t shower, or even get up to use the bathroom. She just laid there until she *****. I was actually a bit disappointed as I wanted to have a look at the tape, but soon it was dawn, and it was time to take her home. I strongly felt that I would never hear from her again, but not more than a day or two later she was back in the bedroom for more, and from that point on, her ass was almost always on tap!

When I finally got home sometime after 11am that following day, Larry was already watching the tape for the 3rd or 4th time. Needless to say, he rewound it, and I got to see what went on to be a fan favorite anytime I shared my videos with friends. Well lit, epic action, and a hot body all added up to one great first time with Kim’s anal virginity. Although I’ve edited a lot of her grunts, gasps and whimpers from the videos I’ve released, the sounds she made make it one of the greatest in the collection.

Kim also has the crown for being only one of two girls back then to take it up that ass the same day as another girl. I fucked both her and April in the ass on the same day during the last week we were together. I hung out with April before her shift started and worked her up to fucking her in the ass before she went on to work at 4pm. Since I had the day off, I went out with Kim that night, and while nowhere near as epic as that first night by 11pm that same night after a “Date” I had Kim sprawled out on the bed doing the same. She must have wondered why it took me over an hour to cum, but I was on a roll that week. I fucked every day, and slept very little. I blasted a much smaller load into her, and rushed her back to the dorms. I was fairly burned out with all the girls I was hiding from each other, so It wasn't long after that night that I finally called if off with her. She was pissed!


So that's the story of the night I took Kim’s anal virginity. I have just a few videos of her, but that first anal is priceless! Those that have seen it often want to argue that it wasn’t her first time, but I assure you, it was.


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The bartender, serving up bedroom fun since 1989.