Was 16 at the time
This is the first story I've submitted and have been wanting to for a while, so I'll apologise now if it's a little amateurish.
It all starts one night when I was 16. Me and a friend, Andy, were over at another friends house, Ryan, playing on computer games. We were'nt really into the game and were just messing around making the characters do stupid things and losing on purpose. Anyway Ryan was getting bored and starts fooling around pushing me and Andy and tickling us. We then started wresting and play-fighting, it ended up with us all on a heap in the middle of Ryan's room exhausted. We were just laying there laughing when Ryan said 'Do you guys jack off?' I was a little shocked by this as I did regularly jack off, but had never spoke about it before. I replied with 'No, but I have done it before' Andy denied it. Ryan then retorted with 'I do!' By this point I was in ecxtasy, I had heard lads at school talk about it but never had the opportunity to talk about it myself. I then thought it was time to come clean 'I do it almost every day actually.' Ryan smiled at me and sat up, as did we all at this point. Me and Ryan chatted for a while about how often we did it and when we started, eventually Andy came clean and told us he did but was really shy about it and didn't talk much.
It came to around 6pm and Andy said he had to be home for dinner so we said our goodbyes and he left. When Andy left I was still buzzing about the fact I could talk to someone about jacking off. We didn't really talk about it much after Andy had left though because Ryan's mum was around and could probably hear us. Ryan seemed a little bummed by this and we just read comic books for a while, he then had a brain wave 'Hey! Do you wanna stay over the night? We can talk about you know...?' I accepted and he asked his mum and she said yes.
I only live a few streets away from Ryan so we set off across the park to my house to get some things. It was just dropping dark as we left his house and we had to go across the park. There was no one on the park so we decided to go sit on a tree we climbed for a while. Again the conversation turned to jacking off. I said 'Ya know what would be fun? I think we should play truth or dare...' Ryan agreed and we began with the simple things like 'Have you ever j/o in the shower, outdoors' etc. It became more heavy when Ryan said to me 'How big is your cock?' I asked 'Erect or soft?' He timidly said 'Er...soft?' I told him about 3-4'. He then asked for a dare. I was waiting for this one to come and I said 'OK. I dare you to show me your cock!' He then went red and said no. I was disappointed at this and pleaded with him to do it. He then came up with a solution 'Why don't we show each other at the same time?' I thought for a second and said Ok if I got to see his cock it would be worth it. We jumped down from the tree and found an area that was out of the way of everything and by this time it was very dark 'After three we show each other OK?' Ryan nodded '1...2...3' we both pulled our cocks out and examined each others soft penises. Ryans was around the same size as mine and very smooth, we were both uncut and had a bush of pubic hair. After around 10 seconds of staring at his cock only a few feet away from me, my soft cock began to stiffen, as did Ryan's. We both got emmbaressed and put them away quickly. We smiled at each other and said we should keep playing as we walked to my house. I asked for truth 'Do you watch porn?' Ryan asked 'Yeah! My dads got loads of videos and stuff' I replied immediately. 'Why don't you bring one over to my house tonight?' Ryan eagerly asked. 'Yeah sure' I replied just as eager.
After we'd been to my house to get the essentials and the video we made our way back to Ryan's house for supper and things, we waited for his mum to go to bed and get settled before we put the porn on. This was my first time watching porn with anyone else and I was sooooo excited I had a hardon thinking about it. Ryan popped it in the VCR. 'Shall we take our tops off?' Ryan suggested. Without hesitation I pulled my sweater over my head. He did the same. We were standing in front of each other topless. We are both fairly athletic and have modest bodies. Although I'd seen Ryan's body before this was spectacular. I wanted to reach out and run my hands over his hairless smooth chest and feel his firm pecks, then move down onto his toned stomach where a trail of light brown hair led down to the treat that I'd had the pleasure of seeing earlier. He was looking at my similar body in an excited way. We both sat down on seperate sofas and watched the movie. We talked about how hot the women were and how much we'd like to do some of the things they were doing on screen. 'Hey are you hard yet?' I asked Ryan 'Yeah. I have been for ages! What about you?' 'Yeah I am' I then asked with a hint of caution 'How big are you hard?' he replied immediatly 'I dunno I've never measured...shall we do it now?' He ran to his room to get a ruler and shot back in the room. He turned away from me and measured his own erect penis and announced '6 and a half inches' He pulled up his pants(to my disappointment) and turned around handing me the ruler. I measured my own member and announced '7 inches' We both then started to watch the porn again.
'I need a wank' Ryan suddenly said. 'Me too. But we cant can we?' Ryan then took off his pants leaving him in just his boxers, that made me want to come there and then 'Thats better' He said 'You can take yours off if you like', and I did we were both staring at each other's hard cocks peaking in our boxers, both with precum leaking out. 'Shall we go up to bed now?' Ryan asked not taking his eyes off my dick. 'Yeah lets' I said taking the video out of the VCR.
We went upstairs with our boners sticking out in front of us both knowing what we wanted to happen when we got to his room. We got there and both got on our beds, Ryan on his and me on the blow up mattress his mum had set up earlier. We both got under the covers and I said 'Lets play a game!' 'Like what?' Ryan answered 'Who can come first?!?' I could see Ryan already had his hand in his boxers and was ready to start stroking. 'OK. But how will we know?' I came up with a quick game play 'Well we say when we've done and then we show each other the cum. OK?' 'Ok then close your eyes' Ryan asked. I did and said '3...2...1...go' I frantically started pumping and could here Ryan doing the same thing after about 10 seconds I opened my eyes in curiosity to see what he was doing as I did I found he had been doing the same thing, looking at me, we were both under the duvets. We both looked at each other both slowly still working our own cocks, I knew what I wanted to do and moved slowly with my sheets around me up on to his bed. I pulled down his duvet to find he was jacking in his boxers. I pulled down his boxers to unleash a 6 and a half inch cock with a glowing head covered in precum. I then removed my sheets revealing my 7' cock for Ryan to grab. We sat face to face both nervous at seeing our first hard cock of someone else. I grabbed his balls that were huge and hanging and worked them in my hand. He smiled and started to breathe heavily. He started to work my balls too. With my other hand I grabbed his cock and started to pump it fast and then slow. He did the same to me. We were both starting to feel the pressure that had been building up all day come to a head. All of a sudden Ryan stopped jacking me and lay back on his bed moaning in a breathless voice 'I'm gonna come, oh keep going I'm gonna come...' I teased him by slowing down and stopping for a second 'No keep going I'm gonna...' I grabbed his throbbing cock again and thrust it fast and hard '...come' he said in a low moan that went on as he shot three ropes on my chest and another four on his legs and sheets. He took a few seconds to recover and then sat up 'Now its your turn' He pushed me back so I was lying down now. I was almost ready for coming before and now I was ready to be finished off. He worked my whole body, firstly rubbing my legs and arms and then worked my cock using his come from my chest as lube 'Do it for me I wanna see you come' He whispered to me. I began to grinding my pelvis in his hands and moaning gently until I couldn't handle it anymore. I came hard...once in his face...once on his chest and 3 more times on his sheets. We lay there for a few minutes and then said that that was the best experience ever.
We are still friends now and I have other stories to tell, but we no longer have j/o sessions. The other stories are hot and enjoyable.