As a young man in the early days of the internet I discovered a small handful of adult personal sites. Most of these were all but worthless in providing an outlet for a horny 21 year old like myself but one provided me with a few partners that helped me satisfy my growing curiosity about man to man sex.

The details of the profile I had put up escape me now but basically it said that I was new to gay sex and wanted to try being fucked. If you’ve been on the internet for any time at all you can imagine that such a profile from a decent looking 21 year old virgin got its share of replies. After filtering through the creeps, the guys that couldn’t host (I was still living with my parents), and the ones that were just too aggressive I started messaging with a guy I’ll call Jeff.

Jeff was 34, about 6 foot, maybe 230 pounds, had a bit of belly, short brown hair, and a beautiful 7” cut cock. We exchanged messages for a week or so before he asked if I’d like to meet. I was incredibly nervous but agreed. He was living with roommates at the time so we arranged to meet the next night at his office, he was running a company so had access and knew we’d have the place to ourselves.

Finding the building was easy enough, and it was only about a 20 minute drive from where I was living. I parked the car and he was waiting for me at the door as I walked up. We went into the small nondescript building and into a decent sized office in the back corner. It was sparsely furnished, a desk, chair, a few filing cabinets and shelves. He had made a space in the middle of the floor and spread out a blanket, a bottle of lube and condoms sitting next to it. I stood there a bit awkwardly until he spoke up.

“Are you ready?”

“Sure. What should I do?”

He started to unbuckle and drop his pants as he said “Get down on your knees.”

I slowly got down on the floor and was suddenly face to face with his semi hard cock. This wasn’t my first blowjob so I knew what to do and began to take him into my mouth. I worked his cock in and out, tonguing the head and the underside of the shaft. I sucked on him for maybe five minutes before he pulled away.

“Why don’t you get undressed.” It wasn’t really a question.

“Okay.”

Jeff took off the shirt he was still wearing while I removed my own clothes and set them on a nearby chair.

“Get down on the blanket and lay on your stomach.”

Once in the prone position where I would lose my virginity I felt Jeff’s hands on my ass. At first it felt almost like a massage but quickly turned into more of a groping. One hand left my flesh and suddenly there was a cold sensation in my crack.

“Lube is important, it’ll help me go in easier, you’re going to be tight.”

I stayed silent as his fingers found my hole, teasing it at first, then applying a little pressure. I gasped as the tip of his first finger penetrated me. I’d never had anything up there, this was all new. He pushed and withdrew a few times, slowly working deeper.

“Ready for another?”

I nodded in response.

The second finger really stretched me out but the full feeling brought with it a sense of contentment. The third finger let me know I needed the real thing so I started pushing my ass out at him, thrusting back to meet his fingers.

“Someone’s getting horny.”

“Yes.”

“You want me to fuck you?”

“Yes. I want you to fuck me.”

“Good boy.”

With that he threw one leg over mine and straddled my thighs, pinning me down. Leaning forward he put his hands by my shoulders and rubbed his hardness between my cheeks.

“You’re going to feel so good,” he said “I can’t wait to fuck your virgin hole.”

“Yes. Fuck me, I need to feel you inside me.”

Supporting his weight on one hand he reached the other down to guide his cock into me. He penetrated me slowly at first, letting me get used to it. An inch, then two, then three, then all seven inches of rock hard man cock buried in my no longer virgin ass. His trusting was slow, deliberate, like he wanted me to feel it.

I don’t know how long he fucked me, it could have been 5 minutes or 45 minutes, all I know is that while my cock stayed limp the whole time I had never felt as horny as I did while he was inside me. All good things come to an end though and I heard him say the magic words.

“Fuck. I’m going to come soon.”

“Uh. Fuck, do it.”

“Do you want me to come inside you?

“Whatever you want. I don’t care.”

Several short, hard thrusts followed and I felt it. His cum shooting inside me.

“Sorry about that, I sort of got caught up in the moment.”

“That’s okay.”

“I should have put a condom on but I got a bit caught up. I’m clean, just so you know.”

“Yeah, me too.”

“Cool. That was hot though, you’ve got a really great ass, super tight.”

“Thanks. It was good for me too.”

“Well, if you’re interested and we can make it work, I’d be up for doing it again sometime. Here’s my email, we can skip that site this way.”

“Yeah, that’s probably easier. I’ll let you know.”

After that I dressed, went home,cleaned myself up as best I could and went to bed. I did end up emailing him and we did end up fucking a few more times. Once at a place he was housesitting and once at his spot while his roommates were gone for a weekend. Eventually we lost touch, I think he may have moved out of state. While he was the fist man to fuck my ass, he certainly wasn’t the last.