This happened about five years after my first encounter with a guy. The only other experience I had before this was with a bookstore guy where we traded blowjobs.

So around 2003, I was hanging out in a Yahoo chat room for gay/bi guys, feeling pretty relaxed after smoking a bit. I noticed this guy offering full body massages at his place, just a couple towns over. I figured why not and headed over.

When I got there, we went straight to his bedroom. He told me to strip down, lay on the bed, and place a towel over my ass. He came back and started working on my shoulders. We chatted a bit – he mentioned he was a licensed massage therapist but wasn’t practicing professionally and liked to keep his skills sharp. The massage was completely professional and absolutely amazing.

While he was working on my feet, his hands started sliding up my legs, then turned inward as he reached the bottom of my cheeks before going back down. I was getting pretty turned on, so I spread my legs a little wider, hoping he’d get the message. And he did – the next time up, his fingers slid from my thighs across my crack and back down. I let out a soft moan and tilted my hips up to expose my ass. When he came back up again, his fingers went right into my crack and dragged across my hole. My breath caught and I pushed back slightly against his finger. He started swirling around my hole, teasing it but not pushing inside. I was going crazy from his teasing.

Then he told me to turn over to finish the massage. When I flipped over, I was rock hard and dripping precum. He didn’t touch it directly but placed the towel over my erection. As he massaged my front, he’d occasionally brush against the towel, making me moan. After a few minutes, he asked if I wanted to take things further. I eagerly said yes, and he leaned in and started kissing me. I wasn’t really into kissing guys back then, but he had me so damn turned on that I eagerly returned his kisses while he stroked me.

Finally, he moved down and started sucking me, which felt incredible. He turned onto his side, and I reached over and pulled his dick out of his sweatpants. We started 69ing, sucking each other off, then he started pushing a finger in my ass. He asked if I liked that and if I wanted more. He got off the bed and grabbed a medium-sized dildo and some lube, telling me to lay back and spread my legs. Even though it wasn’t huge, it was bigger than anything I’d had inside me before, so when he pushed it all the way in, I yelled at the sudden pain. But that quickly turned to overwhelming pleasure as he coordinated thrusting the dildo in my ass with sucking me.

After keeping me on edge for a few minutes, he asked if I wanted the real thing. I was so wildly turned on that I loudly begged him to fuck me. I turned over and got on my knees with my head on the bed. He mentioned he didn’t have a condom, but I wanted it so fucking bad I didn’t care. As he started fucking me, I was moaning and begging him to fuck me harder. He called me his good boy and told me how tight my ass was. When he said he was going to cum, I told him to cum inside me, and he filled me with a huge load.

Since it was my first time, I had no idea that semen comes back out later. So I went to work without cleaning up. A couple hours into my shift, while talking to a customer, I suddenly felt cum drip out of my ass and coat my crack. That kept me wildly turned on the entire shift, and when I got home, I immediately jerked off. That day I learned that I was a bottom, and from that point on, I wanted to get fucked every single time.