This happened over 15 years ago, when I, and my friends, were 24-25, and still single. It was completely unexpected from my point of view. It was the first of several experiences I had with some of my friends.
The three of us had been out bar hopping the night before, and had all slept at my studio apartment, me in my bed, my friend B on the couch, and our friend N. on the futon.
Sunday morning, we all wake up, B heads into my shower.
'Don't use all the hot water, jerking off in there,' N. says.
'And be sure to use the conditioner for lube...the shampoo stings,' I said.
'Thanks, I'll keep that in mind,' B. said.
This kind of banter was typical for us. I didn't care if he jerked off in my shower, I did it all the time. What guy didn't?
'I hate getting soap in my dick,' N. says.
'Me too,' I said.
'You do it in the shower alot?'
'Yeah,' I said.
'Me too,' N. said.
'Good way to start the day,' I said.
He didn't say anything for a couple of minutes. From the bathroom, the shower had started. Then I heard that tell-tale sound of hand on skin, and the futon frame creak. There was a divider down half my room, so I couldn't actually see the futon, and N. coldn't see my bed.
'Are you doing what I think you're oing?'
'Yeah.' I was a little surprised, but it didn't bother me. I usually masturbated when I got up. There just wasn't anyone else around when I did it.
'I've got some lube if you want it,' I said.
I rolled out of bed and got the little bottle of liquid lube I used and walked over to the edge of the divider, and just walked around the edge. N. was laying on his back, nude, slowly stroking himself. I'd never seen him nude before, certainly had never seen him, or any other adult guy masturbating. (I'd done it with a couple friends as a kid, but that's different.)
N. sat up and I handed him the lube and we looked at each other. It was a pretty odd moment. I'd gotten an erection by this time in my boxers which was just about at N.'s eye level.
'Here, give me your hand,' I said.
He held up his cupped hands and I squired some lube in them and he lay back down and slathered his penis. I went back around to my bed and took down my shorts and lay down to do the same thing when N. came around the divider toward me.
'You want to do it to each other, or just by yourself?' he asked.
N. had told me, and B., one time when we'd all been talking about our sex lives that he'd fooled around with a couple of friends when he was about 14-15. More than just jerking each other off...sort of masturbating on each other..between the butt cheeks, between the legs, stuff like that. Nothing really 'gay' he'd said (that would have been actual anal or oral sex). I think B. had thought it was pretty gay. I'd just thought N. was really horny. I might have done the same thing when I was a teenager, but I wasn't attracted to any guys, so I never looked for it and the opportunity had never presented itself.
But, now it had. I wasn't attracted to N.-looking at him standing there with his erection wasn't a turn on like looking at a nude woman, but I was curious, and I was horny and I had the chance, so I said 'OK.'
N. sat down on the edge of the bed and just reached over and took hold of my erection and started to pump me. I'd thought he was going to get on top of me and hump me or something but he didn't. His hand felt good and I watched him for a minute or so then just lay back an closed my eyes. He stroked me for a little while and I remembered B. in the shower.
'S-t, we'd better hurry.'
He shifted around a little bit, took the base of my penis in his left hand gave it a firm squeeze then started pumping me furiously with his right. This was faster and harder than I did it, and I started to squirm, but N. pushed my hips down with his left hand and kept at it, and his technique had its intended effect. It wasn't the most pleasurable handjob I'd ever had, it almost hurt...but it was still fun. I watched his hand flying up and down my penis, and he quiclky got me off. I came on myself and his hands, and he kept pumping until after I'd stopped squirting and told him to stop.
He told me to roll over on my stomach and I felt him squirt some of the lube between my cheeks.
'Don't put it in my ass,' I was suddenly a little scared that he was actually going to have sex with me. He didn't say anything, but when he got on top of me, he just pressed his penis lengthwise down between my cheeks and after settling into what must have been a comfortable position for him (not so comfortable for me, as he had all his weight on me) he started to slide back and forth. He hooked his arms around my chest and pressed my thighs between his and basically rode me for a few minutes before speeding up and then I felt him cumming on my lower back. He gave a few gentle thrusts as he finished then climbed off.
I could still hear the shower and wondered if B. was jerking himself off. N. and I had both gotten off in less than ten minutes, and we managed to wipe ourselves up and get our boxers back on before B. finally came out of the shower.