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Late Night Fun on Sleepovers

Author: Age: 44, 15 then Posted on: 4 comments
5 likes 8184 views Category: Masturbation Male-Male Tags: stroking, male, teen, oral, cum, precum, eighties

I show my friend how to j/o, and it leads to a hot year full of cumming together


When I was 15, I met Paul in my scout troop. We went to different high schools but got along really well and had a lot of fun goofing around on campouts, listening to music, playing in the woods, normal guy stuff I guess. Within a couple of months I knew I wanted him to spend the night at my house. This was pre-internet, but I had a small stash of porn mags hidden in my basement bedroom, and I was hoping to see his cock.

By this time I had been masturbating for quite a number of years, having learned from a neighbor when I was younger. Paul looked like he had a nice cock but it really didn't matter to me, I just wanted to see it. So eventually the big night came, and he spent the night at my house. I had already primed the pump by telling him during a scout meeting that I had some porn that was pretty good and we could check it out on the sleepover. As it turned out he had also scored some decent porn which he brought along. (For those of you who don't remember these days - "bringing it along" meant he had rolled up and folded this magazine so it could be stuffed in his waistband and snuck out of his house, in the car, and to my house!! The pages were creased, folded, and smashed, and it wasn't hardcore by any means, but at least you could see some cocks and pussies and boobs lol)

By 11pm, my parents had gone to bed, and we were in my basement bedroom, watching HBO - hoping for the elusive shot of a breast or pussy during some soft-core skin flick. We had all the lights out and only the light from the TV, and I had talked him into getting his cock out while we watched. I also had mine out and was stroking. I was on my bed and he was laying on the couch, so neither of us could really see much of the other - only the TV. I think maybe I could see the head of his cock but nothing else, and only a glimpse at that. The movie was lame, and so I kept saying "If this doesn't get better soon, I'm turning on the lights and we're getting the real porn out!".

Well the movie didn't get any better, and I kept "complaining" so he agreed. I got up, got the mags out of my hiding place, and turned on the lights. I was fully hard and so was he. I'm about 6.5", but he was easily 8", cut, and pretty thick too, with a nice bush and two big balls hanging below. It was one of the hottest looking cocks I had ever seen, and I had messed around on quite a few sleepovers before this! To this day when I see a pic of a cock like that, I take notice and remember our sleepovers.

So we continued flipping through the porn mags, plus we had this thing he brought which was trying to look like an academic journal about sex but had a lot of photos of couples (but no penetration). We were both rock hard and I was stroking, but he was only "sort of" stroking. The conversation turned to cumming and what it was like. Pretty soon it was clear that he didn't know how to really jack off - he was only getting precum and he said "I cum in little amounts, but not a big load". I think he had gotten a hand job once from a girlfriend, but wasn't really into jacking himself! (Or at least that's what he said)

Taking this as an open door, I told him he didn't really know what cumming was and he was probably doing it wrong. Naturally, being the good friend, I offered to do it for him if he wanted - just so he could see how it was done, and then he would know for himself. He took me up on the offer and we both sat on my bed. We were both in tshirts and socks, but nothing else, both rock hard. I sat on his left (I'm left-handed), and reached over to start stroking him. Everyone talks about the feel of a cock - hard and soft at the same time - and this one did NOT disappoint. It was really impressive.

He leaked pre-cum which I really loved, because I don't get much myself. I put my thumb on the back of his shaft and first two fingers on the front, and started stroking up and down in short strokes. Through this whole thing he was kind of ignoring me, his nose buried in a mag, looking through the pictures and trying to find the perfect shot. I kept going without much feedback from him, although at one point he asked me to hold the shaft higher up, so my fingers went up and over the ridge on his cock head with each stroke. I remember it because I don't like to go that far up on the upstroke when I jack.

This went on for about 10 minutes, and finally his balls started to move up, one on each side of his shaft, and so did he. I kept going and eventually he tensed up and came. It was a nice sized, thick white load. Not a lot of distance - maybe a couple of inches - but a constant flow onto my hand, his bush, his stomach. I stroked him all the way through and also milked out whatever was left in his shaft. I had a decent amount of cum on my thumb and I clearly remember licking it off. It tasted a lot like mine - warm and slightly salty, but not bitter.

That was the beginning of an excellent year. We got together at every chance - on sleepovers, scout camping trips - wherever we could, and did a LOT of jacking off. On weekends we would do 4 or 5 orgasms in a day. We eventually moved onto more advanced masturbation: he did me, I did him, and we experimented a lot with cumming in different places - on each others balls, bushes, cock heads, even once on each others' anus. I will never forget how hot it was when he shot on my hole, it was so hot and I asked him to rub it around with his cock head. I blew my load almost instantly after he did!

Once he even tried to cum on my face, but he couldn't get himself to cum. It had to have been a funny scene, with me on my back, a porn mag on one side and him on the other, trying to nut on my face lol. I also got to blow him twice, but without real porn at our disposal I didn't really know what I was doing and it wasn't very good. He never did me orally though.

After about a year, he got a girlfriend, and that was the end of our fun. I've since found him on social media, but haven't made contact. I definitely wonder if he still thinks about our sessions - I know they were some of the best orgasms I've had.



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