First time for everything

I look back on that night and wonder what was going through my mind. What was I thinking? I have to remember though that I was only about 23 years old, fresh out of college, and dumb as a stick. I also have to remember my best friend was the world to me. More than my father, more than my girlfriend, more than my best friend, my he was everything that I wanted to be. I’m not sure he knew that at the time or even if he knows it now, but he truly was the person I wanted to be. And probably because of that, I gave him a lot more latitude than anyone else I had contact with. A lot more freedom to do what he wanted and a lot more freedom to say what he wanted.

That night, we’d been out drinking with our other friends and for whatever reason he and I left early. I guess in hindsight, he’d had planned it that way, but at the time, we were both pretty wasted and I wanted to leave. Though it was only about nine o’clock, he agreed to go with me.

We told everyone else we were headed back to the house, fully expecting them to stay until closing, then headed out for the short walk back to one of the guys’ house.

When we got back, we both took our coats off, throwing them to the floor, and closing the door behind us. It was a little chilly that night, I think.

We both grabbed beers from the fridge and made our way to the couch and the television to watch a movie or whatever was on.

He sat right next to me at one end of the couch, which in and of itself wasn’t very unexpected. We were very close, the very best of friends. Everyone knew we were close and it wouldn’t have seemed strange that we were leg to leg with no one else on the couch or in the other seats in the living room.

He quick got up to close the blinds, saying the street light was bothering him. I was trying to find something on the tv and maybe I heard him click the front door locked, I can’t be sure.

Anyway, he sat down next to me again on my right, I put my right arm around him, and he put his head on my right shoulder. Again, it wasn’t anything strange for us to do this. He and I were pretty close. This wasn’t anything unusual. We’d done this a hundred times.

But this time it was a little different.

About five minutes after he sat down, I watched as he lifted his left arm slightly and rested it on my right thigh. He didn’t say anything; I just figured he thought it was more comfortable. Again, it wasn’t unusual. He’d never done this before, but it didn’t bother me and I didn’t think twice about it.

Whatever the reason, he fingers were now resting on my upper thigh near the pocket, and I’m thinking because I was half-wasted, my penis started to go wild.

Within a few minutes, I was fully erect in my skin-tight jeans. He had to have seen the large lump in the front of my pants.

Sure enough, within another few minutes, his fingers had moved to the top of my jeans and were now on top of my erection.

This was not something he’d done before and it still didn’t bother me. If he wanted to put his hand on my erection and feel me up, I was okay with that. Nonetheless, I was going wild.

He started to rub my pants and I felt my breathing pick up a little. We both continued to watch the movie, I can’t remember what it was, and he continued to rub his hand all over the front of my jeans.

A few minutes later, with his left hand, he’d successfully unbuttoned my jeans. He moved next to my zipper, then pulled the two flaps open.

It was so surreal. I didn’t want to stop him because I disagreed with what he was doing. I didn’t want to stop him because I was afraid of his reaction. I didn’t want to stop him because I was going wild and it still didn’t occur to me that someone else might have a problem with this.

I just sat there and watched as he then relaxed again, resting his fingers on top of my underwear, still rubbing my erection.

After a few more minutes, he moved to pull my jeans down. I needed to arch my back a little to let him pull them down over my penis. I thought he’d just pull them down to my thighs, but he kept pulling them to my knees and I figured he’d stop there, but he kept pulling my jeans all the way down to my ankles. I guess I wasn’t paying attention, because when I looked back at myself, I realized he’d pulled my underwear down with the jeans and my underwear were then at my knees. He continued to pull at my jeans until they were in his hands and being thrown across the room.

He leaned into me and we watched each other intently as he pulled my underwear off and threw them to the jeans.

I relaxed back down on the couch a little scared of what he’d do next.

He sat back down next to me and rested his left hand again on my penis, pumping it slowly. He felt my balls with his fingers, squeezing my testicles a little.

And then he bent over me and rested his head on my stomach and I knew what was next.

I felt his hot, dry lips on the head of my penis as he gently kissed it. His hot sticky tongue was next as he ran it through the opening, slurping it slowly.

I’m not sure why I did what I did next. I just wanted to give him what he was giving me, so I reached between his legs and grabbed a hold of his erection through his jeans.

He’d moved down to fully giving me a blowjob and I unbuttoned his jeans and made my way to holding his erection as he was blowing mine.

I'm not sure it was the first time I’d ever had another boy touch me in this way... not sure because I wasn't sure if my first roommate had made a move on me. It was that I remembered touching another boy this way.

His penis was like mine. The head of his was enormous though. I couldn’t believe how big it was.

I reached down a little further to play with his balls and he pulled slightly on his jeans to pull them down to his thighs. He helped me along by pulling them and his underwear down and kicking them off to where my stuff was.

I could see him in the light from the streets. His pubic hairs covered everything, but I could see some details.

And he was starting to get me going. I couldn’t concentrate on his penis anymore because I was about to explode. I hadn’t realized how quickly he’d gotten me to the point of cumming. With his fingers, he was playing with and squeezing my testicles, as his head bobbed up and down on my erection.

I was hardly breathing and I think we both knew I was close. He must have sensed it because he started going faster and faster until finally, with a huge pelvic thrust, I came with a fury into his waiting mouth, filling it with my sticky goo once, twice, three times, and finally it was over for me.

He pulled back off of me and turned his head to look at me.

I sat there stunned. Not only did I just get a blowjob by another boy, but I'd gone ahead and touched another boy's privates.

I kept my eyes closed. I hoped he didn’t see me. I reached over for my underwear and jeans and quickly pulled them on. And not a moment too soon as a moment later, I heard the other guys in the alley next to the house. I jumped up and quickly made sure nothing looked out of order, then remembered to unlock the door.

About a minute later, the guys started streaming in and spilling out into the living room. A few minutes later, he came back downstairs.


We didn’t talk about that first time for a few years. Looking back on it I always wonder what he was thinking, what was I thinking? I’m not sure I can answer that for him. But for me, it’s a question I ask myself at least once a month.

Whenever I run across an email from him or see a picture of the college days or sometimes when I’m having sex with myself, I might think of him.

Even after all these years, I wonder about what I was thinking. Honestly, I think back on that decision and wonder, wonder, wonder.