Story about my first time masturbating with my friend, sorry it's kind of long.
I have this one friend, we're pretty close and usually hang out a lot.
Sometimes whenever we would hang out and his place playing video games or watching tv one of us would pull the other's pants down as a joke, this happened a lot and I never really thought anything of it. Whenever I'm over I usually try using his tablet to check out stuff on the internet and he'd always say no and never give me the password for it. One night though I checked out like usual but this time he had a pic of his dick on it, I kind of laughed it off and he finally gave me the password for it. I couldn't not check out some of his pics after that. There was a lot of normal pictures but there was this one folder that I guessed he masturbated too that had porn and pics of some girls we know and more pics of his dick.
I though it was pretty hot but I didn't really know what to do, I had always wanted to try stroking with another guy but didn't really know how to play it out. Nothing happened for the first few weeks and we just hung out like usual until this one week where we both went to some conference out of town and got put in a hotel together. First two nights were normal and we just went thought the days events and to sleep. I hadn't jerked off in a few days and needed to cum so late at night when he fell asleep I put on some porn and rubbed one out and went to sleep shortly after.
The next night was where it all started. We were both laying in our beds and he was taking pictures but I wasn't really paying attention to him, took me a while to piece things together before I realized he was taking more dick pics. I was getting kind of horny and I started talking to him, it was really awkward at first but eventually I started joking about what he was doing and that I saw his pics before. He was still taking pics while we were talking and I ended up pulling out my phone and taking pics of my dick too. After a few minutes of this he got up to go get something to drink from the corner store and I reached over and grabbed his camera, I was already pretty hard and seeing pictures of his erect dick and him stroking were pretty hot. It took him a while to get back but I was still looking at his pics, things got back into the mood it was in before he left fairly quickly and I started commenting on his pics saying our dicks looked almost the same before I tossed it back to him. We started talking and stroking again behind the little barriers we had up to block each other from seeing the other one's dick but those came down pretty fast. Soon we both had our pants down and cock clearly in sight as we each stroked, things advanced pretty fast from there. I put on some porn on my laptop and set it on a table between our beds, after awhile of that we moved on the same bed together watching it. I was getting pretty into it, we're both very similar in body types and dick size so it was pretty comfortable. (Little chubby, dicks aren't that big)
We were both going at it and the porn clip we were watching had ended so I stopped and put a new one on. As I was looking for a good long video to watch I felt his hand wrap around my dick and it felt so good, my dick seemed to become much more sensitive. I put on the porn video and just sat back and let him stroke me for awhile, the sensation felt amazing and I almost came right away. I returned the favor and grabbed his dick in my hand and started jerking him off, his felt much different than mine and could feel it throbbing which made me even harder. This went on and we started using our different techniques on each other. I spit on my hand and got his dick nice and wet like I usually do to mine and he did the same for me and we jerked each other like that. He started rubbing the tip of my dick with his thumb and playing with my balls and I did the same back. We both were both close to cumming and couldn't take it anymore and each shot huge loads back to back. Normally when I cum I have to stop at a certain point because my dick becomes to sensitive and I can't do it anymore but with someone else they just keep going and it felt so amazing. We sat like that for a few seconds with cum all over our shirts and dicks softening up in each others hands, we each took a shower and went to bed shortly after.
Nothing else happened the rest of the week, things were a bit awkward between us for a while but we eventually got over it and became comfortable with it.
That night we had talked about some of our fetishes and we both had some similar ones like sniffing/jerking with girls underwear and masturbating to girls we know.
We jerked off a few more times together, but I'll write those in another story.