What was your first time receiving anal like?

My penis never felt so tiny in this situation. The two women seeing my babydick with his much much bigger cock pushed up against it made it look extra tiny and that was verbally noted.

 

It was with a man that I had a few encounters with previously. I was on a work project, and was in the Bay Area for about a year and a half. We had a few encounters, and we attempted anal, but he wasn't able to maintain an erection wearing a condom. He was pretty adamant about safe sex, and asked me repeatedly if I was clean. He's going to deposit fluids in me, so I should be the more concerned of the two of us.

We talked it over and exchanged a couple of emails about it as well. I/we agreed to bareback anal one night when I was there. It was all I could think about that day at my client site. I was going to get fucked in the ass that night. I had wanted it for years. I attempted it with some well endowed men, but I wasn't able to accommodate them. His cock was average sized, so I figured I could handle it.

He met me at my hotel room that night. After some conversation, we retired to the bedroom. I took my clothes off and was sitting on the bed while he got undressed. I was very excited that I was finally going to experience this. I sucked his cock to help him get hard.

When he was ready, he lubed up his cock, and rolled me over face down on the bed. He entered my ass with relative ease. It felt absolutely amazing. He proceeded to pump his cock in me and got incredible aroused. He grunted and moaned as he fucked me, and then I could sense that he was about to cum. With a couple of harder thrusts, he shot his load deep inside me. Having his warm cum inside me felt fulfilling.

For me, it was another experience to add to my "gay resume." We did continue seeing each other for a while, and again recently when I returned for a pleasure trip. I certainly appreciated him initiating me to receptive anal.