This is the story of my first and only time, best as I remember it. The names have been changed.
Michael was the former fiancée of a girl I once dated, Jill. Michael and Jill had broken off their engagement when he admitted his sexuality to her, and himself (on the other hand, Jill and I broke up because she was a screaming harpy). Although they say that there's no way to tell from the outside, Michael seemed perfectly obvious to me, in his mannerisms. Maybe now that he was 'out', or at least more comfortable with his sexuality, he wasn't afraid to show it. He was around 5'8", naturally blonde, had a ruddy complexion and a developed physique - not "cut" but it was obvious that he had a very physical job. Light construction, I think I was.
Michael and I were at a get-together that our mutual former girlfriend had thrown. As the party wound down to the wee hours, Michael and I were the only ones left there. Jill had gone to bed and one of her friends crashed on the couch. This was a chance I had waited for. I had fantasized about being with a man since I was a teen. I had had several girlfriends and loved having sex with them, yada yada yada, same old story. Reality loves a cliché I suppose.
Michael said he had to get home; I said, "Hey, you wanna get some breakfast or something"?
"Well maybe, but I'm broke."
"I'll buy, I really don't feel like going to sleep yet." We walked outside to our cars, and I asked David if he was seeing anybody. He said no, it had been a month since he had been with anyone. With my heart pounding, I asked, "Would you like to come home with me?"
"Sure," he said blankly, as if the sudden turn of luck wiped his mind otherwise blank. I had not given any previous indication to him that I might be interested in men, so he asked, "Are you sure?"
"Yes," I said, breathless and hoping that momentum would carry this through, if nothing else would.
I drove us to my basement apartment, in downtown. I remember being so nervous about this, that I asked him to hold my hand during the ride. We arrived, and quietly slipped in the door. It's 3 or 4 in the morning and the last thing I wanted was to have any of the neighbors waking up to find me bringing a man home. I didn't turn on any lights; the streetlamp through the blinds made it just light enough in my one-roomer. He was already taking off his shirt when I came up and kissed him, one arm snaking around his back and one hand rubbing the front of his jeans. I wouldn't normally be so direct, and certainly I wanted this experience to last, but nervous energy propelled me forward.
We moved around to sit on the side of the bed, still kissing, and I reached for David's belt. I was fumbling so badly that he just stood up and undid it himself, followed by his jeans. He then took off his underwear, leaving himself naked in front of me. There was no turning back now. I got up and undressed. I sat back down next to him on the bed, kissing him and fondling his cock.