It was very late at night. My now ex-wife - “the bitch” - was upstairs fast asleep. I sat at the computer as I had for so many nights, for so many years, flirting, chatting and cyber-fantasizing with other men online. Men much like myself, pretending to be women in one room, the women our wives never were, or in another room, men who would never be again in this age of AIDS. Lately though, my curiosity had been getting the better of me. I had experimented many years ago, enjoying having my cock sucked or my ass eaten in a bookstore not far from where I lived. (Ironically, there is now a JiffyLube on the same spot!) But, I was too repressed to go any further. Now, night after night, I flirted with guys online, leading them and myself on toward a tryst only to back out at the last moment. Then lubing up my ass with my own fingers and drilling myself with a trusty, thick, hard, fake cock. Yea, teasing myself night after night, only to satisfy myself with a dildo. This night was different though. I had had to much to drink, I was too horny, too curious, angry, frustrated ... you name it. I wanted to be fucked.
A few nights earlier, I had met a guy online and hooked up in a nearby field engaging in mutual oral sex. That was a first for me. In my previous encounters 20 years before, I had only been the recipient. That evening, I willingly knelt in the shadows of a soccer field and sucked my first cock. It was a strange sensation. The shaft so hard and throbbing and the head so soft and spongy. I reveled in running my tongue over the head and into the slit, sucking hard on his length until he pulled away and sprayed his cum on the damp grass. This night, I sat and stroked my cock as I teased back and forth with J online, telling him of my exploits of a few nights past and boasting of what I would do if we should get together.
Suddenly, the desire began to overwhelm me. Why not? Why shouldn’t I experience my fantasy? Why not try it and no longer be curious? I was tired of lubing my own ass for a fake cock. Whether it was my own “itch” or the ouzo talking, I don’t know, but I found myself in my car, driving to this stranger’s apartment, stopping only to pick up condoms and lube along the way.
Before I allowed myself to think about what was going on, I had knocked on the door of his apartment. The door was opened by a cute 20-something guy in t-shirt and briefs. I admired his basket, his handsome face and his charm and stepped across the threshold of losing my anal virginity.
J was still online with a friend when I arrived, so I sat for a while as he finished his chat. I became impatient with waiting and went to kneel next to his chair so I could stroke his cock while he said his goodbyes. Not soon enough for me, he logged off and turned his attention to me. “Ready for your massage?” he asked.
“And whatever happens, too!” I responded.
J spread a sheet for me on the floor and got his lotion as I got undressed. “Here we go, finally” I thought to myself as I stripped naked and lay down on my stomach for him. J gave me a beautiful massage, working out my tension and apprehensions. I loved the feel of his hands as he caressed my ass, teasing me without touching my hole, my balls or my cock. After an eternity of enjoying his hands stroking my flesh, he asked me to turn over. He kissed me gently as his fingers found my nipples and tugged at them. His hands roamed over my front, as firmly and seductively as they had my back. My cock was rock hard and leaking pre-cum like mad. His hands finally found my cock and balls and I moaned deeply in response. Before I could recover his mouth covered my cock and I almost shouted. It was so hot and delicious getting sucked by J. I was so relaxed and excited at the same time that I was about to shoot. I stopped him. “I want to cum the other way,” I said, pulling my cock out of his mouth (reluctantly) and rolling over on my stomach.
