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My first time was totally unplanned. It started off as just oral, the guy was going to give me a blowjob. Then I started sucking his cock in return, but he wanted my ass...I made him put on a condom, but he took it off after a bit and finished inside me bareback. After he pulled out I noticed the "dry" condom on the floor and only then noticed that his cum was leaking out of me. It was worth it though.

my first time was really similar to yours, only from the other end. I was doing some heavy kissing with this guy, we had fucked before, but I loved the idea of kissing him with my mouth on his, while at the same time kissing the lips of his entrance with the lips of my cock. Before we knew it, I was deep kissing him in both places, then slowly entering him deeper and deeper. He loved it and the fact that he loved it made me completely crazy, the feel of him opening to me completely in that way was so hot and wonderful. Before I knew it, I was slamming a load home into him. Afterward I didn't pull out, but just left my cock in their while I kept kissing him. I remember how wet he was with my sizable cum and, between the feel of his ass all dripping with my cum and our kissing, I got hard again fast and gave him another load pretty soon thereafter. When he finally got up he had some much cum in him it was running in streams down his hairy thighs.... I never looked back.