Posts Tagged ‘first’

Roy Takes My Cherry

Monday, December 31st, 2007

Bi guys get their first anal.

I remember the first time I ever thought of being of receiving anal. It was 1973 and I was laying in bed with my girlfriend at the time. We had just had sex and I asked her about having anal sex. She laughed and asked me how I would feel about having someone shove a big cock up my ass. I told her that I didn’t think that anyone would be interested in fucking my ass and she blurted out that Roy probably would.
Roy was Karen’s brother, 18 years old and what would best be described as a nerd. In the days of long hair and beards Roy looked like he had just stepped out of a 1950’s farm calendar. As much as I knew him quite well I had never considered him as a potential sex partner. As the weeks went by each time we met I began to wonder about him and about being fucked. The more I wondered the more I wanted to try it.

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Prison Sex

Monday, December 24th, 2007

His first gay experience.

As I lay there on the bunk, the world a distant thing, I felt the sting of tears in my eyes as I stared at the wall beside me.
Sometimes, when it was quiet, like now, and dark, I could still see it before me: the court room, the judge with his wig staring down at me with hatred in his eyes, the guards glaring at me and placing a hand near their batons, the crowd’s eyes all on me, and in each one the anger was painfully clear to me.
I had wanted to scream out: “I didn’t do it! This is all a mistake!” But it hadn’t come out. I already knew my fate was sealed. And I had gotten so used to people believing me guilty that I had forgotten whether I was or not.

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Playing With Leonard

Saturday, December 22nd, 2007

First timer ignores his conscience.

-The voice in my head kept telling me to walk away; you have a family, it said, -if word of this gets out…. Geez, that fucking voice.
There was a pair of pantiehose, still in their wrapper, on the coffee table between us.
“-Having second thoughts?” Leonard said, “Here, let me get you another drink.”
I put my hand over my glass when he reached for it. Stupid, it was good brandy too, but I didn’t like what he was implying, as if I’d only go through with it if I was drunk. He was rich, a suave, sophisticated looking fucker in a white shirt and dark trousers.
I shook my head, “No. I’m okay.” I said.
He was smiling as he reached for my glass and his smile faded a little as he took his hand back. Now he looked a little uncertain, until I reached for the hose. My heart was beating like a bastard and I noticed him looking at me in a different way. He looked pleased, but there was also something else in his eyes, something that gave me butterflies because I’d never had that look from another guy before. I thought I knew what it was; it was lust.
I held open the top of the pantiehose and Leonard trickled the oil inside. It was cold and thick. Some of it went over my pubic hair and hung there, creamy and glistening, like a rich man’s exotic semen. The rest of it found its way to my cock. I felt it trickling slowly down to my balls. It turned the front of the hose dark where it touched it.

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Our First Meeting

Sunday, December 16th, 2007

He’s treated like a lady for a weekend.

One day, while in a gay chat room on the Internet I met Roger. He actually contacted me after he visited my home page.
After having cyber sex that first night, we began exchanging pictures and e-mails. Within about two weeks, we began having phone sex on a regular basis. We shared the same curiosities, fantasies and went in the same direction during our chat room and phone sessions.
One day, Roger announced that he was coming to town and would really like to meet me. I didn’t know what to do. I told him on the phone that I was nervous and that I had never met with someone from the Internet, nor had I ever had sex with a man.
He assured me that we would not rush things. Roger had never had sex with a man either, but we were continuing this non-touching relationship and this would be the first and probably the last chance to meet for a long time.
I thought about the possibilities of meeting with him and actually trying out our fantasies. The idea got me hot and I couldn’t really think of a reason not to.
On our next phone session, I told Roger that I was indeed ready to meet and we made our preliminary plans.

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