The one that (almost) got away
5 years ago I started a new job. One of the first people I got to know was my supervisor, Lets call him Brian. I thought he was a good looking guy but really kind of straight laced. We started hanging out some at lunch and after work and I discovered he was a lot different than he appeared. He is married, but talked a lot about going to massage parlors and getting his "happy endings". He also told me a lot about things he'd done in the past (like fucking a watermelon in his backyard). Things I never pictured him doing. I also learned he smoked weed. Like I said, he's good-looking and I fantasized some about having sex with him. But he seemed totally straight, so I gave up my fantasies and just enjoyed him being a friend. Well at one point, I'd been going through a dry spell so I finally decided to post on Craigslist. I posted an ad looking for a guy to let me suck him off. A lot of bullshit replies mostly but one was interesting so I answered back. Things were ok until I gave him directions to my house and told him a certain bit of info about me (that I'm amputee, I didn't want him to be surprised when he showed up and saw me sitting in a wheelchair with one leg) This was his response "You sound like someone I know, I don't want this to be weird. Is your name *******?" Well, it was my name so I replied "Yes, who is this?" His reply was "Sorry dude, I'd love my cock in your mouth but it's too risky" That was it, I heard no more from him. That left me wondering just who it was. Based on the minimal description he sent it could have been Brian but there was no way to be sure. A couple of years later Brian left for another job. We didn't see each other much but kept in touch through texts and phone calls. Now back then I didn't smoke weed. I actually started smoking a short while later as I found out it could help control the phantom limb pain I'd been having for years. Around the same time Brian had promised his wife he wouldn't bring anymore weed into their house. When I let Brian know I had begun smoking he asked if he could come over and smoke with me sometime.(His wife didn't want it at their home but didn't mind him smoking elsewhere) So he started coming over a couple of times a week to get high. Of course being high meant we were even more open in our conversation. At some point we were talking about some of the crazy ads on Craigslist and Brian admitted he had once answered an ad and said it was mine. So that was one longstanding mystery solved for me. He told me how he'd been so horny that weekend and his wife was out of town but when he realized it was my ad he just couldn't go through with it. He was worried about anyone finding out he said. He me told being with another guy was a fantasy and he had thought about it a few times but didn't think he'd ever actually do it. We had a laugh about it but nothing did happen then and aside from occasional jokes we never really talked about it. I decided it wasn't going to happen and found other fantasies to jackoff to. That changed tonight. He came over to smoke. We were just relaxing in the living room, talking about random shit when he stood up, unbuttoned his pants and pulled his dick out, stuck it in my face and said "Wanna suck it". So I did. I sucked for a bit, then we moved to the couch beside each other. I was leaning over, sucking his cock, when he started rubbing my ass. Then he reached down and started to my dick through my pants. He told me to take them off. I did and he started stroking my cock while I went back to blowing him. After a minute he pulled me off and pushed me up straight. Then he leaned over and took my dick in his mouth. I wish I could say he gave an amazing blowjob but it was obvious he had no real experience at it. Still in none of my fantasies did I imagine him sucking me so it was still a pretty awesome experience. I told him I wanted to suck him some more, so he moved over and we got into a 69. (Not easy to do on a small couch) After a bit of this he started playing with my ass. He rubbed it and pulled my cheeks apart. I felt his finger pushing on it, he must have stuck his finger in his mouth because it was wet. He slowly pushed it up inside me and finger fucked me for a bit. Then pulled away and changed position so he was on his back, his legs up in the air and holding his cheeks open, he said "Lick my ass". I got down and started giving him the best rimjob I could. He was really enjoying it, moaning and wiggling his ass. Then, again, he suddenly changed position. He was up on his knees and pushing me onto my back. "Wait a second" he said. He grabbed his pants and pulled a condom out of his pocket. (That's when I realized this wasn't spontaneous. He had planned to do it or he wouldn't have brought a condom.) He put it on, then spit on his hand and rubbed it on my ass, the only lube we had but the condom was pre-lubed. I was fuckin nervous as hell. Brian didn't know it but I had never been fucked before. The biggest thing that had been in me was a very small dildo I'd had, and Brian's cock was THICK. But I wasn't about to stop him either. When he pushed into me it felt like my ass was splitting. He went slow but never stopped pushing and I just gritted my teeth. He was finally all the way in and started fucking slowly. As my ass loosened up he started going faster and it stopped hurting so much and started enjoying it. The whole time he was just staring down at me with this big grin. As got close he said he wanted to cum in my mouth. He pulled out, pulled off the condom and shoved it in my mouth. He fucked my mouth and after few strokes he grabbed the back of head and shoved me down on his cock. He shot a big load in my mouth and I swallowed it down. Afterwards he leaned back, just kind of playing with his balls. I kept jacking my dick, which was still hard as a rock. He reached down and began stroking me. It didn't take long for me to shoot, getting all over his hand and arm. Afterward we sat there just talking. It was almost surreal. We were both naked. On the couch we had just had sex on. Talking about movies and shit. The weirdest part was it didn't feel awkward or anything. It seemed like the most natural thing in the world. Finally we put our clothes on and he got ready to leave. I was back in my wheelchair. Before going Brian leaned down and gave me a hug. Then he moved over and put his lips on mine and gave me a kiss. That was really a surprise. He left, telling me he'd see me again in a couple of days probably. All this happened just a few hours ago. I'm still trying to wrap my head around everything. At this point I don't even know what kind of relationship this really is. Friends with benefits? Lovers? And the fact that Brian's married is another complication, not to mention that, up to this point, Brian's always identified as straight. I guess I'll just go with it and see what happens.