I'm a late 30s married guy and started to get curious about sex with guys ever since I started really enjoying anal play a few years ago. I really enjoyed using dildos and vibrators on myself however my wife always mentioned that while dildos were great, nothing compared to a real life dick. I wanted to experience what that was like at least once. I went to a conference in Vegas a few weeks ago and thought it would be a perfect opportunity to explore my fantasy.

The thought of using apps or trying to hook up organically seemed risky so I decided to hire a masseur/escort. I called a service, explained what I was looking for and made an appointment for the guy to come to my hotel room. Later that night I get a text that he's in the lobby so I nervously go downstairs. My heart was beating out of my chest at this point but I was determined to make this happen. We finally spotted each other, shook hands, and went up to my room. I'll call him Sergio for this story. Sergio was an absolute specimen. He was eastern European, about 6-2, 190 lbs, cut muscular body with a six-pack that looked fake, it was so defined.

We both chatted for a few minutes before getting started. He mostly wanted to know what I was looking for, and anything that was off limits. I told him it was my first time and that I wanted him to start with a massage, then "seduce" me into going further. At first, I felt pretty embarrassed and ashamed that I was actually going through with it, but Sergio was super normal, nice, and really put me at ease. Sergio set his massage table up, turned the lights down and told me to strip naked and lie face down on the table. Sergio stripped as well which was one of the hottest moments of my life. His body was incredible, he didn't have any body hair, and his cock was absolutely hypnotising. He was soft but he was thick, and it hung down nicely with a foreskin that covered his tip.

The massage started out just like any normal massage. I won't bore you with the details, but what started as normal slowly progressed and became more sexual. He kept getting closer and closer to my ass crack as he massaged oil into me. Every so often, I'd feel his penis brush against my hands or on my cheek. I wanted to spring up and just go crazy with Sergio, but I wanted to savor the tease. I finally lost my patience, and touched him the next time his penis brushed my hand. At first I brushed it gently with the back of my fingers, then I closed my palm and slowly started to stroke him. It literally felt like electricity pulsed through my body. I had fantasised about touching another cock for a long time and it was finally happening. As I stroked, he started to get hard and his head started to peak out from his foreskin. He continued his massage, however he really focussed on my ass/balls. He spread my ass cheeks and started pouring warm massage oil into my crack, lightly massaging my hole. Then, he asked me to turn over.

By now, I was aroused on another level and my cock was standing straight up leaking precum. He starts massaging my chest and his cock was right next to my head. I couldn't resist, so I angled my mouth towards his cock, and licked the tip which tasted amazing. As I took him into my mouth, he started to rub my penis. I was so aroused that I immediately jerked away and told him I didn't want to cum right away so he rolled me back on to my stomach and covered himself with a liberal amount of oil. He straddled my ass and started to rub his cock between my ass cheeks. It was an incredibly raw, and erotic sensation. I could literally feel his foreskin sliding and that drove me absolutely wild.

After a couple minutes, I knew what needed to happen; he needed to fuck me. I had fucked myself with dildos before, but nothing as girthy as he was so I knew I needed a little stretch first. So I got off the massage table, and found my butt plug. Sergio lubed me up, and slipped it in. I got on my knees and absolutely devoured his cock. I had no clue what I was doing but found a nice rhythm by pulling his foreskin back and forth over the head. After what seemed like 10 minutes, I told him I was ready.

We both moved to the bed, I got on all fours and he lined himself up behind me and slowly pulled the plug out of my ass. I felt the head of his cock pressing at my entrance so I made myself relax. At first it was very uncomfortable, it was a struggle to get his head up there, but then it finally popped in. It didn't hurt, but felt stretched so he held still before pressing more and more of it into my ass until I felt our thighs touch. I looked down at my own cock and notices a steady stream of precum just flowing from me. I had to take a mental snapshot of this scene. I couldn't believe how sexy I felt bent over with a thick penis all the way up my ass.

Once I adjusted to his girth, I gave him the green light and that's when it got really intense. He started by pulling almost all the way out, then slowly sliding the whole thing back in. Every Time his cock brushed my prostate, I moaned in a feminine way that almost surprised me, but I was loving every second of this. As he started to fuck me harder I got way more verbal shouting things like "give it to me" and "fuck me like a slut". He keeps going at it, then he announced he was going to cum soon and that it was time for him to "make me his". So he took my arms out, and forced me into the prone position where he absolutely railed me until he came into the condom while still deep inside me. I had erupted too and I couldn't tell if it was from the prostate stimulation, or from my penis rubbing against the bed but it didn't matter.

He left after a few minutes of small talk, and I went to sleep, absolutely spent. I'm so happy I finally made this a reality, zero regrets!