My First Time Masturbating With a Guy

Well, this is my second and maybe last story I'll post. I'll probably post more stories.

Just a little info here, nothing to revealing but I'm gay and chubby, about 250 pounds now, but around 225 when the story takes place. My friend was probably, at most, 285 pounds himself. I happen to be attracted to chubby guys.

So one day, when I was 16, me and a friend were all alone at my house. I had been wanting to do something with him for so long, and little did I know that that day we would finally do something.

Matt never knew that I'm gay. In fact, he always assumed I was straight and I never got the chance to tell him I am gay.

We were talking about sex while he was on my computer, playing Diablo. Eventually, I was so hard that I decided to just jerk off in front of him.

'I'm bored,' I said.

'Watch tv,' Matt said. As if I needed permission, lol!

'Nah, I think I'll jerk off!'

At that, Matt laughed out loud. Soon though, he turned his head to look at me and all he immediately saw what I was doing. And boy, was I enjoying myself! His mouth fell open a little as he exclaimed, 'What do you think you're doing?'

'What's it look like I'm doing!?' I said sarcastically.

All he did was shake his head at first, but then he kept turning his head and watching me stroke my penis then looking back at the game. I could tell he was a bit interested, so I decided to go for it.

'Why don't you jerk off too? This is great!'

So he turned off his game, and his right hand went down to his shorts. I couldn't tell what he was doing at first, because his thigh was pretty much covering his cock from the point of view that I saw, so I asked him. At the time, I just didn't think he'd actually do it right away.

'I'm jerking off,' he said.

I asked him to turn in his chair so I could see. With that, he turned and I saw his cock and sack hanging out of his left pant leg of his shorts (Which reminds me of my first masturbation which is up on this site). As we jerked off in front of each other, he asked me why I was so quiet. He said he liked to moan while he jerked off, it turned him on.

Eventually I came and then he came. From that moment on, every weekend for almost a year we were jerk off buds.

Four or Six months after that moment, we were both watching a recorded tape of VH-1's pop-up video. The subject was masturbation songs. Once Billy Idol's 'Dancing With Myself' video came on, I whipped my cock out and began jerking it off.

Matt always found it incredible that I could always jerk off when something reminded me of it, so he whipped his cock out too. This was the day I decided to go for some more action than normal.

I told Matt that I'd jerk him off if he jerked me off. Really, if he had said no I'd have offered to jerk him off only, and only to see what it 'felt like'. He immediately let go of his cock and said, 'Only if you do me first.'

I was extremely ecstatic. I went over to him and jerked him off for what seemed like an hour. He had such a hard cock, so leathery and sweaty. When he came, I spent a while rubbing his cum on his cock.

And when he jerked me off, I was holding onto the side of my chair so hard, and moaning too. I was grateful my parents weren;t home. He kept telling me how hard I was, and I was really hard when he touched me. After about ten minutes, I came all over his hands. He was astounded at the amount of cum, and told me he had never seen me cum that much before.

Eventually, we drifted apart, not having anything to do with being jerk-off buds but other petty teenage stuff that drove us a part. I'll always have fond memories of my jerk off bud though, and our time together.