Happy Accidents

I met a guy online and we had been talking for about three weeks about potentially playing out a fantasy he had, in which, someone would happen upon him jerking off and they would jerk off together.

We agreed on a place to meet and a scenario, he would be sitting on the steps to a back entrance of an old brick building, he could be naked and already masturbating when I got there. When I arrived I saw a slim, muscular man, in his early 20s, with black hair. As arranged he was naked seated on the steps and jerking off.

I approached him and asked if he needed help, he nodded yes to me so I undressed and stepped into the doorway with him where we began jerking each other off. We managed to stay out there jerking each other off for about half an hour before we decided it was time to cum, I faced him a way for me and began to jerk him off at full force while I slid my dick up and down the crack of his butt. He came hard all over the steps and my hand, once he came down he took his place behind me and jerked me off until I was spilling my seed on top of what he had just left on the steps. When we were done he gave me a kiss thanked me and walked away still naked. That's when I realized I had never seen his clothing anywhere and figured he must have had an undressed in his car.

 The part that makes this an accident or a mistake is that when I got home I found an email from the guy apologizing for not showing up. At first I thought he was messing with me but after a few more conversations we found out that his straight but bi curious brother decided to go in his place when he chickened out.

I had a boyfriend named Zack, he was a tall, slim built Asian guy with short black hair, brown eyes and abs sculpted out of marble. A couple of important things to note are that like myself Zack had a lot of jerk off buddies and while we did not have an open relationship we still maintained relationships with our jerk off buddies. The other important thing to note is that Zack has an identical twin brother named Chad and the two of them were each other's original jerk off Buddies. Zack and I had had a few conversations about having jerk off sessions with Chad. Zack wanted to do some mistaken identity role-plays during the sessions. So when Chad surprised me in the shower and was very obviously pretending to be Zack I made the mistake of thinking this was a role-play and knocked him trying to trick me. (They are identical twins but there are subtle differences in their bodies and I definitely knew my boyfriend's body.) Chad and I were making out and jerking each other off in the shower. The whole time I kept expecting Zack to show up any second. After we were finished he whispered into my ear I'm Chad by the way, I laughed and told him I knew that. He was very confused as to why I didn't put a stop to things if I knew who he was, his confusion made me realize that this was not a set up and I had to explain to him that Zack and I had talked about having a jerk off session with him with this exact type of scenario.

 I was visiting some family when I was 15. My cousin Josh, also 15 at the time, had gone to his friend's house. I don't remember his name so I will just call him friend 1. Josh was a skinny, shorthaired blonde guy, with brown eyes. Friend 1 was 15  like us a bit stocky, had reddish brown hair and I think green eyes. I'll give you the description of friend 2 now so I don't have to disrupt the story later. He was 16, extremely tall and skinny, with a surprising amount of muscle definition for his build. He had bleach blonde hair with a pink streak running through it and brown eyes.

 Josh and I had gone over to friend 1's house to go swimming, no one was there but others so we decided to go skinny dipping. Inevitably we all got hard and decided to jerk off together. The three of us were laying on three lounge chairs by the pool jerking off when friend 2 to showed up and caught us. He ended up joining us so this impromptu session turned out even better when we accidentally got caught.