Me And My Best Friend Rob Wanking Together For The First Time

I had slept over at Rob’s house a couple more times since the events that took place in my first story but nothing else had happened. I’m not counting me having a sneaky wank either under the covers or in the toilet, that was standard for me at age 13 else I would be too horny to get to sleep.

When the Summer holidays started I arranged for us to sleepover at my house for a change. At the time my house was just me and mum. Without getting too deep in the weeds, my Mum is gay and I am adopted so it has mainly been just the two of us for most of my life.  She has a high paid job so we have a pretty good sized house all to ourselves with three stories where the top story is a loft room running the full width of the house that is just for me. It has a bedroom area one end with a lounge in the middle with a sofa, TV and desk, with my own bathroom the other end. The house is also heavily soundproof, and the staircase up to my room has a door at both ends so privacy is great.

Back to the story, after dinner we watched a movie in the main TV room with my Mum before moving up to my bedroom with a supply of snacks and drinks to last the night. We set the room up like we had at his, with two mattresses on the floor (my bed has a spare pull out mattress underneath so luckily we didn’t have to drag a mattress up the stairs). The only downside of my room is that it gets pretty hot in the summer being in the roof, so both of us immediately stripped down to our boxers. I gave Rob control of the remote, and pretty quickly he found his way to the more risqué channels. We still had the light on so out of the corner of my eye I could watch in real time as Rob pitched a tent in his boxers. I said “well, I can tell you like what you see.” At first Rob was confused then he looked down and saw his bulge and started blushing before saying, “Oh, sorry about that,” to which I replied “Don’t worry about it dude, it’s not like I can complain.” I grabbed my dick through my boxers and shook it to draw his attention to it which made him laugh and relax again. I didn’t let go of my dick though, I just kind of held on to it giving it a squeeze every now and again and maybe even a light stroke whilst watching the women on the TV rubbing themselves through their panties. I noticed Rob was looking at me and for a second I thought that I had gone too far, but then he got hold of his own member through his boxers. He was going a little farther though,  not just squeezing his dick but noticeably stroking it back and forth.

It got to an advert on the show we were watching and I asked Rob “Do you ever watch real porn?” “God yeah, my computer at home is full of it.” “Would you like to watch some?” “Yeah, go for it!” I hooked my laptop up to my big TV as a 2nd monitor and we took turns picking clips to watch, and our wanking became more and more full on. I kept sneaking glances at Rob out of the corner of my eye. As he started stroking faster I started being able to glimpse his shaft through the fly of his boxers. After a little while I decided I needed some direct contact so I slipped my hand into my boxers so that I could wank as normal, and Rob soon followed suit, which slightly disappointed me as I had been enjoying the glimpses of his dick I was getting previously.

In the end I picked one of my favourite movies which Rob also approved of so we decided to stick with that for a bit. Rob said, “There is no way I will be able to get to sleep after this, I think I will have to go and finish myself off in the toilet before we go to bed.” I briefly considered telling him that we should just do it in the open as I had already seen him during our first sleepover but I didn’t have the nerve. Instead, I reached for my sock that I had already positioned for a planned covert wank later and threw it to him, “You can stay here and finish in that if you like in that,” and I got another for myself. He put it into his boxers and started trying to wank in it but it was too cramped, but he quickly came up with a solution. He asked me to turn around for a second, and when I turned back he had his dick in the sock, poking through the hole in his boxers stroking it with one hand whilst his other hand was in his boxers holding the sock down. He asked, “Is it cool if I do it like this?” I gave an approving nod before doing the same set up myself.

So there we were, both stroking away with our cocks pretty much out in the open just inside a sock-condom. After a while we decided that we both wanted to cum, and we made a race out of it. We picked a random video and started wanking at full speed. I thought for sure that I was going to cum first as I was super horny, but just as I was getting there Rob gasped “I win,” so I looked over to see him thrusting into his fists with the sock darkening as he filled it with his cum. I had stopped to watch Rob but carried on and came almost immediately under Rob’s pretending not to look gaze. I got a bit carried away and felt the base of the sock slip out of my boxers as my left hand moved down to squeeze my balls, so Rob would have gotten a pretty good view of my then hairless shaft as a pumped what seemed like my biggest load ever into the sock. We both just laid there for a couple of minutes letting our cocks soften inside the socks whilst we caught our breath. Rob turned away to pull the sock off but I was a bit more daring and just pulled it off and tucked myself back in giving Rob a quick peek. By this point we were exhausted and both fell asleep pretty much immediately. When we woke up we both had morning wood, so we had another session before breakfast.

Rob slept over at my house probably once a week during the holidays and it became standard for us to wank into socks through the hole in our boxers, I even remember changing my boxers one time to put on a pair that I thought had a better slot for access. We probably had three or four sleepovers like this with two or three wanking sessions each time. Then things went to the next level, which I’ll talk about in my next story.