I worked at the Gay Disco for two years before I left to go back to school (sadly I made more money bartending 4 nights a week than I did for the first six years after graduate school) - I had some incredibly hot sex in those two years, including getting caught in the storage room bent over a beer keg getting pounded by some smoking hot guy, my first forays to the bathhouse, and a wild weekend out of town with two other bartenders. More on those stories later...this post is about Trip, an incredibly hot Corporal in the Army stationed at a nearby base.
Trip had these piercing blue eyes, a fresh-out-of-bootcamp body, an impish grin, and that military style haircut that still drives me wild. More than 15 years later I still get butterflies thinking about him. Trip started coming into the bar because he was friends with one of our barbacks, well actually they were in AA together. I only mention it because I had to ply him with my charm and tight jeans, rather than the usual free drinks. Keep in mind it was incredibly risky for him, in those days the Army CID would send undercover agents into gay bars looking for men to arrest simply for being gay, don't-ask-don't-tell did not come along for another couple of years.
Whenever Trip came into the bar he would always sit and talk with me until the crowd arrived and I was too busy to talk much. Everytime we made eye contact, he would grin and give me the most devilish look. I had to have him. Finally, we had some all-day saturday event that had all of 10 or 20 people, suffice to say a bored bar staff is usually a fairly drunk bar staff, and I finally had the courage to make a move, we were out on the patio talking and there was a lull in our conversation, I grabbed him by the back of his head and kissed him, that kind of forceful, passionate kiss that says, "my cock will be in your mouth later." I got up from my chair, grabbed his hand and pulled him towards the back of the patio. There was a seclued spot, where we could have some more privacy. We kissed for what seemed like hours and I finally couldn't stand it anymore and reached down to feel his extremely hard, and very fat cock. He let me get a good feel for its size before he pushed my hand away and whispered "later." At this point I realized I was supposed to be behind the bar, and while the owners were always lenient, especially if someone was getting laid out of the deal, well actually it was more like "you better be getting some good dick" they were all whores as well, anyway...it was three torturous hours before I finally got to leave. Thankfully it was only a block to my apartment, we started pulling each others clothes off during the ride up in the elevator.
We were naked by the time we walked from the front door to my bed. He had a killer body, with both of his arms covered in tattoos. I was in hog heaven. His dick curved straight up, about 7-7.5" and was hard enough to pound nails. We layed down on the bed and grabbed each other's dicks. Mine is your average white-boy penis, nice but not big by any means, around 6.5 to 7 depending on its mood and maybe slightly less than average in width (see the picture above). I find with a cock that curves up, it's easier to deep throat lying down, so we flopped onto my bed I began licking him all over. I started by sucking on his nipples, which was driving him wild. I quickly started licking his cock up and down and then finally took the head of his cock in my mouth, this is when I discovered he had an oddly shaped cock, the head was not very big, maybe a little bigger than mine, but it was incredibly thick at the base, it took me a while to figure out how to best work with it but a good cocksucker like myself will try his best and I did get it down fairly quickly. He threw me over and attacked my cock with his mouth, gobbling it up and had me on the edge of blowing within a few minutes. That night he fucked me a little but I just couldnt seem to get used to it, it got so much bigger the more he put it in - oh dont worry, I eventually figured out how to take it, more on that in a minute.
We immediately started dating, and a few nights later he asked if I would fuck him. I said I would try, but I hadn't really done it much (really, at all at this point). I put on a condom (we had been having safe-sex thus far) and as soon as I pressed my dick against his hole, I lost my hardon, after 30 very frustrating minutes we gave up, both incredibly frustrated. Trip was not giving up however, he really wanted me to fuck him, so we a couple more times, until one night, on his back with his legs in the air I hear "try it without the rubber." I said "are you sure?" YES was the answer, so I lubed up my cock, lined it up with his incredibly hot, smooth hole, and slipped the head in! Fuck his hole felt good! He groaned, and pushed his ass up, begging me to fuck him, so I slammed my entire cock in, balls deep in one stroke. The shocked look on his face quickly became that devilish grin I fell for and I knew I was going to love topping his ass.
It took me a few strokes to figure out how deep to go, how far I could pull back without coming out of his hole. He was in hog heaven, and urging me to fuck him harder, I knew I wasnt going to last long, and after about 5 minutes I yanked my cock out and blew a huge load that landed partially on his face, but mostly went past his head, immediately his cock started gushing out a huge load of cum.
From that moment on it was bareback sex all the time. We would spend hours flip fucking - as soon as whoever was topping was close to cumming we would switch positions. Of course, a few times I didnt pull out in time, and this is when I learned how to cum quietly and just keep fucking, Trip sometimes didnt notice - it takes a lot of conentration but if I'm going to cum too quickly I will keep fucking and the trobbing of my orgasm isnt noticed because they're too busy feeling it slide in and out of their fuckhole.
We were together about 4 months, during which we fucked non-stop. Tben one day he just disappeared. Literally, I couldnt figure out what happened until several months later he called to apologize - this started a fairly lengthy stint of refusing to even consider a relationship. My friends were there for my emotional needs, other men were just there for sex.