This is a print version of story My Favorite Night As A Bartender. by the_bartender from

My Favorite Night As A Bartender.

My Favorite Night As A Bartender.
Now, If you’ve read my stories or seen any of my videos, you know I had a LOT of fun as a bartender back in the early 90’s. I had the opportunity to fuck a bunch of college girls and 2 milfs during a 2 ½ year period of time. There were a lot of girls. There were a lot of nights. There was a lot of fucking. But there were 3 nights that defined my time as a bartender. The moment a Milf named Laura started to suck my dick the morning after I had had sex with April, The first time I got a girl on tape, and this moment… The single best night I had as a bartender, and the night Anal became my main focus.

Now she wasn’t the hottest girl I fucked, maybe only a 5 out of 10, but Mandy holds a place in my heart for the best sexual encounter I ever had. If you’ve read my story about Mandy, then some of this is old news, but for a moment try and relive this night with me:
I’d been fucking this shy girl Mandy, a college softmore or junior for a little over a month. As I said she was nothing special, just a place to lay some pipe and then move on as she was really reserved in bed. I mean really. She never touched my cock, never made a sound even when she came, and until me, had never even had sex in any position other than the missionary position with the lights off. To be honest about it I was really board fucking her and was ready to stop answering her calls. This was early on in my bartending days, and pussy wasn’t yet falling off of every tree, so I was using her as a cum dumpster/ booty call, but the booty wasn’t really much good. Don’t get me wrong, I still came every time but it was just boring and she was kinda bothersome to put up with.
I mean sure it was fun to break her in, fucking her silly in a bunch of different positions, but that only lasts a few times, and then add to that , Mandy was shy, average, and after about a week had decided we were boyfriend and girlfriend.
At the time I had decided to play along with that as it meant I could fuck her when I wanted to. But In less than a month it became a serious pain in the ass. She was always calling, always wanted to know when we were going to hang out again, and super suspicious. Not that she was wrong to be suspicious as I was fucking other girls.

I had had enough. I was still fucking two other girls who were a lot more fun, and decided to start blowing her off. I decided to have her over for one last fuck, and then stage a fight to get rid of her or at least get her to go away for a while.
Well, she comes over and she asks when she's going to get to move in! Guys, I didn't want to run her off altogether as I was hoping to keep fucking her from time to time. But what the fuck? I thought about it for a moment trying to figure out if it was even worth it to keep her around as backup, and after a bit decided to see if I could get more out of her instead of just “dumping her” right then and there.
So, I put on the best show I could, I told her that I liked her, but she wasn’t fulfilling me sexually and it was frustrating. The look on her face was utter confusion as In her world we had had more sex in more ways than all of her previous “boyfriends” combined.

Now at this point in my life I’d had sex with about 8 to 10 girls, and only fucked 3 of them in the ass, and only 1 of them regularly, So anal was kinda still a rare thing in my life. Blow jobs on the other had were common in early life and as a bartender, and the fact that Mandy refused to do either was bullshit. So I sat there and tried to explain what I expected out of a “girlfriend”. I really just wanted some head from her, but tossed in the anal as a bonus. I had figured this was a lost cause anyway and was ready to toss her out if she didn’t give up something extra.
So , still acting as a “boyfriend” who has needs, I told her that no live in girlfriend is going to be a one hole girl. She didn't get it at all. Still giving me a somewhat vacant look, so I explained the whole Blowjob/Anal thing, and said everyone else that I had dated gave it all up, but since she was so sweet, and I "really liked her" if she really wanted to get serious with me, and to live with me she'd have to do at least one of them. I just couldn't see myself with someone that didn't do more than just plain old sex.
This is the moment that changed me. This is the single moment that made me a bartending freak.
Mandy said nothing, but after a moment sat down. I thought she was going to flip out and leave, but after what felt like a full minute she tells me “I just can’t imagine putting a dick in my mouth, but if you want me to have anal sex, I will”
I shit you not, can you fucking believe it? Who would chose an Ass pounding over a little cumshot in the mouth??? I was fucking stunned! Every time I had fucked a girl’s ass prior to this, It had taken a LOT of drinking and a lot of trying to get it done. But not Mandy. She was like “OK, Fuck My Ass… Boyfriend.” This girl really started the whole Anal thing going for me. From this moment of my life on, it was Ass fucking all the way.

As she was already at the apartment when we had this conversation, I had her in bed in less then 2 minutes.

I couldn't even contain myself. Not more than 10 minutes ago I was done with this chick, and now I wanted her worse than anything. I didn’t beat around the bush and watch TV with her or talk about anything after that statement. All I said was “Ok, let’s do it.” I stood up, she stood up, and I grabbed her hand and walked her down the hall into my bedroom. I really thought I was just going to call her bluff and maybe and up with some head before dumping her, but she wasn’t bluffing.
I had her clothes off, and mine, in another minute all the while explaining that it might hurt a little. Her average body and b cup tits suddenly looked great, and as I put her on the bed in the ass up doggy style position, I realized this was going to be fucking awesome. I sat there for a moment and soacked it all in. I grabbed her thighs and spread her knees apart so she was in the perfect spot, and told her to hang on.
Guys, I tried to spit in my hand to lube up my cock a bit, but I was so stunned, by the turn of events I could hardly get any spit. What little came out of my mouth missed my hand and landed on her ass cheek. It sat their glistening as I tried to work up some more, but it was hopeless. So, I took one finger, and tried to scoop it up, that was all I could get, and it barely got the tip of my dick wet, I remember swirling my finger tip around the tip of my cock trying to get it wet enough to go in. It was useless, but I was fucking going for it! I took one hand and grabbed my shaft, and the other to hold her ass in place, and pushed.... and pushed. I know I should have fucked her pussy a bit to get things wet, but NO FUCKING WAY. I was going strait to that ass. The lack of lube might have made it hard to break her ass open, but it gave way to me insanely rock hard cock. Although I told her relax, her ass felt as tight as a virgin ass should be.

Once it was in, I stopped at about 1/2 way, and let it sit there for a moment, asking her if she was ok. Like a trooper, she just said "Its Ok". I knew she was lying, but I couldn't hold back. From that moment on, a tiger could have been chewing on my leg and I wouldn’t have been able to stop. My cock was rock hard, and it was ready to play.
I started fucking her ass. 1/2 way in at first as I could feel her body tense up in my hands with every stroke. But then after less then a minute I couldn’t hold back. I felt the need to really fuck her. I pushed my cock in until it hit a turn inside her and then pushed past it. She jumped back a little, and it made me even crazier. I started to ram my cock in and out of her ass like it was the last day of my life. Fucking her at a speed and pace that only a young man can sustain. I jack hammered away at her ass slamming myself in as deep as I could and then I'd back it all the way out a few inches then slam it back in until it was "balls deep". It would miss the hole at times when fucking at that pace, either popping up or slamming into her vagina. I didn’t care, I was going full throttle. She never said a word or made a sound, but with every stroke I could feel her body that was clasped between my hands on her hips tense up and then release, tense up, and release as I pounded her virgin ass time after time. This went on for at least 10 minutes until the first time I had to stop.
I was lost in the moment. The building could have come down, but I wouldn’t have noticed. I was SO focused on watching my dick slam in and out of her ass, and I savored that moment too. For every time I felt as I was going to cum, I’d ram my cock in as deep as I could go and stop. Letting the throbbing in my balls and shaft subside before starting the process again. It took over 20 minutes before I began to feel her loosen up. The writhing in my hands started to settle out, and she just began to take it like a champ. I knew it was finally time to cum. If it was even possible, I managed to fuck her even faster, the bed shaking rapidly as I built up for the final time.

Now Mandy wasn't on any birth control, so I always had to pull out when I fucked her. But not this time. As the throbbing in my balls and the tightness of my cock reached critical mass, I rammed myself as deep as I could and blew a hefty load right in her ass pumping load after load of hot jizz deep in her. It felt as though I had built up a gallon of cum while fucking her, and it was one of the best orgasms I ever had.

That was it. The Moment had passed, My brain returned to normal when I was finished. I pushed off of her, and asked her if she wanted to shower. She could hardly speak, but was as nice as someone that just got a hundred dollar tip. She hobbled to the bath room with me and we showered, with me telling her how great it was, and how I couldn't wait to do it again! She just stood there stunned, looking at the shower floor.
When we were done, we crawled back into bed, and passed out. The next morning I woke up with a hard-on, and a smile on my face. All I could think about was her Ass.

Hell maybe she was right to choose Anal over Blowjobs.... I never remembered the blowjob from last night as greatest, only that I came. But this...This was nice. I remember every ass I fuck, and every time I fucked it. the way the girls responded the feel of it, the tightness, the heat. Mostly I remember the start of it. Like opening a can of beer, the first plunge. That was it.

I woke her up, and after some sweet talk, I was back in that ass for a quickie. She just laid there on her side as I stuck it in her pussy to get it wet, and then switched to her ass for a little side fucking till I came, and when I cam it was deep in her ass again. After a few minutes of sweet talk, she got dressed, and Then it was off to class for her, with a load of cum in her ass, and a nap for me.

Now Guys, I never let her move in, but I delayed "dumping" her for at least 90 days, Mandy had given me a reason to be her “boyfriend” Her virgin ass! I don’t know how she put up with it. I never took her out, never did much of anything, She’d just come over after work or school and after some very brief small talk or some TV time, I’d look at her and say “you ready?” She took it like a champ too. Never complained, never stopped me. I would sometimes go straight to it, never even telling her I was about to fuck her ass, just sliding it In and fucking it start to finish, but most times, since she let me, I'd fuck her pussy, then switch to ass, then back to pussy, and then finish off in her ass. She must have hated to be on the rag as I would always end up having a LOT of free time when she was on the rag, using it as an excuse to fuck her ass daily skipping her pussy altogether . It was great. And I always cam in her ass.

So that was it, the most memorable night of my bartending career. The night a girl who was 60 seconds away from being dumped became the best fuck of my life. After plowing her Ass that night and every time afterwards I was a changed man. Anal was something to have with every girl I slept with. I still had to dump mandy, but I held on for 3 months, putting up with her boyfriend girlfriend shit, and letting her sleep over way too many times. I tried to keep her around as some side pussy , but she told me she wasn’t that kind of girl…

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1 year ago
very good
3 years ago