I was blessed with a big dick and word of mouth has been good to me. In my younger years, I'd hook up with a girl from whatever random job I had and she would talk. At one particular job, a woman almost twenty years my senior got word I was hung. She happened to be married and taught me how sweet forbidden fruit is. She also exposed me to the excitement of rough sex. I fucked her as hard as I could but she screamed for more and ordered me to spank her ass. I pulled hair, choked, tossed her around the bed but it was never enoigh! I was nineteen at the time and thought I knew how to fuck. That woman exposed how little I actually knew. Over the course of about a year, she showed me the ways of an experienced freak. It was humbling but a very fun learning curve!
I got to fuck a married woman but I still wanted to cuckold someone very much. My fantasy became reality one night out with friends. I was a month removed from a relationship and went out with a group. One of my exes' friends happened to be there with her boyfriend. Drinks were had and ex friend started to flirt her cute little ass off. She kept touching me and laughing at everything I said. She was sitting between myself and her man when her hand found it's way up my leg. I shifted and shot her a "what are you doing?!" look. She said "it's ok, he's fine with it." I couldn't believe my ears. She said those beautiful words loud enough for her man to hear. He looked at me and confirmed it. Check please!
We met back at their place and had a few more drinks. I was young and inexperienced with this so I was nervous. Ex friend would kiss me and all I could think about was the guy sitting across from us staring. Here I had my fantasy come to life and I was nervous as hell! She went over to her man and started sucking his cock so I went to a favorite of mine ate her ass. Apparently her guy did not ever rim her. She let out a long moan and told him he needs to eat her ass like I was doing. For some reason that small comparison that leaned in my favor did it for me. My alpha maledom kicked in. I rimmed that ass while she rubbed her clit to orgasm. Her boyfriend came on himself.
This was my first threesome and first time I really looked at another man's erection. I was honestly surprised at size (or lack there of). He wasn't small but wasn't big either. Ex friend said my ex talked about me and wanted to see my cock. My dick was rock hard and so was my ego! She pulled my pants down and they both looked at my dick. It was one of the best feelings of my life. I felt like the greatest man to ever fuck. Ex friend stared and said "fuck." I think it was that moment that I was hooked on cuckolding other men.
We fucked like animals. I put everything I learned from married coworker into practice. I pounded that pussy in front of her man. At this point, her man was just watching. I used every position I could think of. When I picked her up and hammered her while her legs were open and arms around my neck. Our bodies were slapping when I stuck my finger in her ass. Ex friend came violently and scratched the shit out of my back! I winced at the unexpected scratch and dropped her on the couch with a thud. Her man laughed. She turned to him and said "what are you laughing at? I've never cum that hard with you." That small bit of degredation toward her boyfriend that I caused made me cum. I stroked the cum out of my cock and shot all over her.
I continued to fuck ex friend for months afterward until she moved away. Sometimes her boyfriend knew, sometimes he didn't. The sex was amazing but cuckolding was better. There was no way I was going back to single girls! I signed up with a swingers site and couldn't wait for my next experience, which I got shortly after but it didn't go well.