Gary's Choice

“It’s a given that a Fire Island houseboy is going to be a hot young blond piece of ass who gives great head and can take a rough fuck. Timothy, however, was beyond category. You certainly know that. It was his masculinity, intensity and sensitivity that made him so special. His luminous blue eyes that locked with mine as he was sucking my cock or when I was fucking him on his back made the sex so vivid” said Hunter to me in his deep voice. We were in his cool Chelsea apartment having drinks. His email invitation was a surprise.

Hunter was 48, medium height with graying short dark hair and a beard. He was quite worked out as serious biceps and a broad chest were displayed in his black T-shirt. Tight jeans showcased his trim solid lower body. He was a well-known gay writer whom I had seen interviewed on television.

“Last summer, I was at a good friend’s Pines house for the weekend. Martin always gets the best boys and as I said, Timothy was exceptional. Besides Martin and me, there were three other friends. We’re all in the hot daddy category. Mature, masculine accomplished, hung, in great shape and into young. It was a wild weekend with clubbing and bringing guys back to the house. Between light drug use and Viagra we were all horned up around the clock.”

“Timothy totally satisfied everyone constantly. Whether one on one or in groups he was awesome taking dick. I became fascinated and intrigued by him and got to know him during downtimes. I wanted to learn how he got to be in this position, and he told me everything. Such a fucking turn on!”

“We’ve kept in touch and I’ve seen him a few times professionally and personally. I’m writing a novel about him. It’s an incredible story. An upper middle-class white straight teenager is not only is coerced into prostitution by his family but has sex with them, including his father!” I was silent. Hunter then handed me a box. Inside was a microcassette recorder and several tapes.

“I’ve been interviewing him. These are copies of our conversations that I’ve arranged for narrative effect. He’s so articulate in expressing his observations and detailing his transformation. I wanted you to hear them for several reasons. Mainly, if you disagree with any of his statements, you can tell me. Also, the two of you don’t communicate and I thought you’d like to hear what Timothy has gone through and how feels about it in his own words. Hey, I’m not judgmental about your actions and I’m not sentimental about Timothy. He’s hardcore by circumstances and I’ve taken advantage of that. It’s just the way it is and the whole story would make for a great book. I’ve been working on it, but I teach full-time at Princeton, and so it won’t come out until next year at the earliest. In the meantime, you have these and if you have any issues, reach out…”

I drove home numb with that box on the passenger seat. After getting in, I went to my study, poured a whiskey and pressed play. I listened to Timothy’s serene boyish voice:

I’m grateful that Hank was the first man to fuck me. He was right about everything. I will always remember him. His kindness and steadiness got me through accepting what I was going to be.

After that first night when I sucked dick for the first time, the next four days were a blur of giving so many blowjobs. Dimitri took me all over to hotels and apartments. All kinds of guys. I got good at it. I grew to like the attention. I got used to swallowing cum. I didn’t think about whether I “liked it.” I did it. Ok! Honestly, I did find myself liking it. I got hard doing it. I got used to the taste and the smell. It became exciting. After only being aware of just my own dick, it was a whole new world getting up close with so many so fast. Did I “turn gay?” I don’t know. I was aware that some dicks turned me on more than others, but I did them all. Giving hand jobs was just as striking. Stroking another guy’s hard dick was strange at first. With some guys it was impersonal and with others there was more of a brief connection. It depended on the client.

One afternoon soon after, Dimitri told me that my was ass had been sold and I would be fucked the next night and that I would have prepare. Stuff I I didn’t know about. It was all so painful and humiliating.

I wasn’t to eat anything. He gave me something to drink that made me shit a lot. He took me to a salon in Brighton Beach. I got naked in a room and a woman came in. I saw myself blushing in a mirror and I was hard. I had to lay on my back on a table. She waxed my chest, dick and balls. It hurt so much. Then I had to get on the table on all fours. She waxed my ass. “Now, your pussy is clean and pretty for your first man” she laughed. The next day, I had more blowjobs to give. Then I was told to take a shower. Dimitri was with me and told me to bend over. He put this long metal nozzle in my ass that sprayed my insides. “Boy ass must be perfect for client.”  

We went to a fancy hotel. Hank introduced himself. He was old but looked good and was very friendly and as normal as could be considering the situation. Hank totally got me into understanding my body and the pleasure that was possible from being with men. When he was through sucking and rimming me, I was horned up but still afraid about what was going to happen, especially because Hank had such a big thick dick. I knew he was going to fuck me, and I just wanted it to be over with.

Of course the pain and shame was tremendous. I cried. I wasn’t gay, I hadn’t been dreaming of this! The stabbing feeling of Hank’s dick going in my ass and stretching me open was too much, I thought I’d be messed up. The pounding away at me was horrible. Then, after awhile it began to feel good. That was the hardest thing to accept. Growing up thinking this was bad, that this is the worst thing a man could allow himself to have done, and then finding out that the pleasure from it is incredible. My dick was never so hard before, I never came with such force. Hank was a great lover and he got me used to giving up my ass to guys.

I quickly had to realize that not everyone was going to be as concerned or respectful to me as Hank was. Dimitri having me sit on him and ride him was a taste of the roughness I would soon get used to. To be clear, it wasn’t like anyone was holding a gun on me. I had reasons for doing it of my own free will.  

Right, you want to know about my father and how I became a whore.