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Age when it happend: 22
Where it happened: My mother's office
Langauge: English
Sex: Male
Rating: 5
Category: Straight

I was 22 years old, some straight experiences in my past, but a great desire to experiment with gay sex…
Not daring to go to the local gay club, I asked my straight friends for help: did they know any gay guys who could help me to find my way?
So, I finally was introduced to Larry and Fred two guys who had been together for several years, in what I thought was a classic monogamous relationship. I could not have been farther from the truth…
We quickly became friends, starting to go out together. I was fascinated by their chemistry, I imagined all sorts of sexual situations with the two of them. I was a virgin (in regards to male-to-male sex, at least…) but I was pretty wild, at least in my fantasies. Who did I prefer? Blondish, ligthly skinned Fred, with his rather athletic physique, or bearded, somber Larry, whose skin smelled of pipe tobacco (an enchanting, erotic taste)?
Fate decided for me, since Fred had to leave town for 2 weeks to attend a seminar, and a chance encounter with Larry let to a “friendly” night out on the hills.
We were supposed to have dinner, chat a bit, gossip about Fred— nothing sinful!
Then, as the evening progressed, as we kept drinking wine and chatting about all sort of things, my eyes in his eyes… I finally realized that there was more to this “perfect couple” than I thought.
Basically, Fred had been having affairs on the side from day one, all of which were discussed inside the relationship, approved of beforehand by Larry and quietely accepted. Larry on the other hand did not have any sort of affair, since he was the sort of quiet, solitary, reserved man who does not usually indulge in this sort of things…
When we got out on the hills for a walk, my courage mounted and I embraced Larry planting a big, sensuous kiss on his bearded lips. Inebriated by that feeling— the first male mouth I tasted – I kept kissing with extreme urgency, as my large, circuncised cock became rock hard in my boxers, pressing against Larry’s crotch. We wanted each other, and we started to feel each other’s sexes, asses, chests. For the first time, I could fully feel the joy of holding a man’s cock in my hand, of squeezing his arse, of feeling his tongue dart inside my mouth, quick and skilled. I was feverish, as horny as hell, and even if we were in an open space, covered only by the night’s darkness, I could have had sex right there. Larry suggested we go somewhere private. The only close place we could go was inside my mother’s office. She has a small consulting private practice downtown, in an office for which I had a set of spare keys.
At around midnight, we sneaked into the office, and immediately plunged on the large couch in the lobby. I undressed Larry in a second, almost tearing his clothes off. I just kept his shorts, under which is penis was hard and big. I slowly took the shorts away, exposing an attractive 15cm cock, uncircumsised, under which 2 small, perfectly round balls were suspended. I started to lick his cock, which totally oozed precum, finally taking it all in my mouth. I could feel Larry’s expertise, as he jerked me off with his hands, feeling my big balls and also starting to feel my asshole. “Turn around” he said. I got on top of him, his cock in my mouth, as he positioned himself to rim my arse. The sensation was just too much. His cock, his hands, the wet urge around my arse… I wanted to come, I wanted more. “Let me screw you” said Larry “I want to be the first guy that will make you feel like a real man”. I stopped my blowjob, and started to laugh. The whole situation was funny, exciting, romantic, hot… a powerful mixture. “No, Larry, I do not feel ready yet” I lied. In reality, I had already decided that I wanted Fred to be the first guy to screw me. Larry had explained how well endowed his partner was, and how much he liked me. I was totally turned on at the prospect of losing my verginity in two installments, with these lovely guys. Larry had to be the first guy I screwed…while Fred could have my arse at a later date.
I started to finger his arsehole, which was hot and open after years of pounding from Fred. “I’m very open” explained Larry “I take it up my arse all the time, you know… I really like it.” I continued to finger his hole… one.. two… three fingers. “Screw me, fuck me, right now” begged Larry, as he put his legs on my shoulders, directing my cock towards his pulsating anus. A bit of spit, and my cock plunged inside Larry in a single stroke. It was too much.. Being inside this man,, stroking his cock, looking at his eyes full of abandon… It was just too much, just too much… I fucked his arse for 3-4 seconds, just a handful of deep strokes, and I came inside him…three powerful jets of sperm hitting his prostate gland. As I mixed my sweat with his, my saliva with his, he also came in my hands, the cum hitting the back of the couch…

That was the first time I ever fucked a man, a really incredible experience. I DID lose my own anal virginity with Fred as planned, a few days afterwards, but that’s another story.

NOTE: this is a completely true story. We did have unprotected sex, as I was a total virgin and Larry has been testing regularly. Of course, it was risky anyway, and in retrospect we should have used a condom. But… losing one’s virginity is never a rational affair.

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