Previous stories relate to my first massage experiences. Fast forward a bit and by now I’d had a range of great massages from different guys.

I’ve always been a top with guys but I was getting curious about bottoming. After all, the bottoms always seem to have a great time in bed. What was I missing out on?

I chatted to a handful of masseurs on different sites explaining my curiosity and nervousness. One guy in particular seemed to understand my nervousness, and eventually I got the courage to actually book.

I arrived at his flat in central London. We’d exchanged messages and photos, and I was glad to see that he did look like the ones he had sent. He was was about 30, latin, cute while not the best looking guy in the world. His body was muscular and ripped. He was about my height so I didn’t feel too intimidated. Once the business side was dealt with he led me to the bed.

The massage started nicely. He used his full bodyweight to work my muscles. He had a good touch. We weren’t long into the massage when I felt his heavy cock brushing my glutes. I felt around for it and squeezed, it responded pleasingly.

It didn’t take long for him to get fully hard, and I felt it testing my hole. I was very tight and he didn’t get far but the intent was clear.

He continued massaging for a while then he got me to flip onto my back. We kissed and it was bliss. It felt so natural. He had a great energy about him. He kissed and caressed my upper body, and I wanked his solid 7” cock. It felt quite thick, and this made me nervous.

I started to wonder how this was going to go. Would he double check that I was still keen to give this a try? He distracted me by taking my cock in his mouth. I groaned. Nice cock, he whispered.

He got me into a frenzy with his mouth and hands, kissing, wanking, licking, sucking.

Soon the massage oil was being massaged into my hole. Was this really happening?

Are you ok? He gently asked? Yeah, I murmured.

He lifted my legs up, propped them against his ripped body, and grabbed my hands with his hands. We were holding hands him facing me. He then pressed his cock against my firmly closed hole. I didn’t know how to open it up for him. By this point he had dropped the professional persona of a massage therapist and was in full on macho male mode. He was out his own needs now - I was secondary.

He pushed in. I was in serious pain, the burning pain overriding everything else. Part of me wanted to stop, but part of me thought we’re doing this and we’re committed.

Are you fully in? I asked through gritted teeth? I wanted to know if it was going to get any worse. Yeah I’m in he purred, you have a hot ass.

He seemed to he enjoying it. His thrusts were purposeful. I was still in a lot of pain but there were also enjoyable parts. I wasn’t feeling the wow factor than some bottoms seem to feel, but it wasn’t so awful. My cock was soft but it was drooling pre. He asked if I had cum already. No, I groaned.

He sped up. He was really getting into it. He grunted and groaned. He seemed to be close. I felt his thick cock get even thicker and harder, and then he was orgasming. He grunted hard, face screwed, clearly having a great time. I felt his hot cum shooting into me and wow I wasn’t expecting it to feel so great. It felt like there was a lot and the feeling was really intense. I was still in pain but also enjoying the sensation of hot seed in me.

As his orgasm faded he pulled out and gently wiped away the excess. He lay down next to me and we kissed as he wanked my load out of me. While I hadn’t had the prostate orgasm I had hoped to experience, my own orgasm was definitely improved from him fucking me. I shot a huge huge wad over my belly. It ran down from my belly down my side onto the bed. Wow, that was a lot he said.

We collapsed into a warm embrace on the bed. I could have stayed for hours like that. It felt like a genuine connection.