Skip forward to a couple of years ago. I had a girlfriend who helped me explore a lot of kinky things including pegging which it turned out I liked. After that experience for some odd reason, I began to wonder what it would be like with a real cock in me. Something that was new and totally out of character for me.
Wanting to move slowly, I decided to get a male on male massage. This was in South America and I knew this would mean we would both be naked and would be a non hostile experience. If I didn’t like it or didn’t want to “do” anything then no harm no foul.
I made an appointment with a young man named Christian, who was an IT Tech full time and did massages on the side. I went to his apartment which was very clean and tidy and had a massage table set up in his living room. He spoke fairly good English and was very cordial. He asked if I wanted to be fully nude and I replied that we were both adults and sure, it would be OK and he could be as well.
After stripping I got on the table and he began the massage. It was terrific! I had never been massaged by a man before and he was strong and knew just what he was doing. My arms and hands were laying by my side sides and as he moved around the table he brushed his cock against my hand and I thought “what the hell” and began fondling his cock and balls. I was crazy with strange feelings. What was I doing? I had NEVER done anything like this but was loving it!
As he continued the massage we chatted and I told him it was my first time with a man. He was very curious and was surprised I had never even experimented. As he moved to the front of me I looked up and noticed his cock and balls were right in front of my face. He had an erection and again, this was a whole new experience as I’d never seen another mans cock this close.
As we talked he began to massage my ass and explore and massage my hole…or my boi pussy in the parlance…and while doing this he would reach down and rub my cock. OMG! Quickly he had two or three fingers in me and I was loving it, raising my ass to give him easy access.
It was time to turn over so he could do my front. It was then I really noticed he had no body hair except the small amount around his cock and balls. I found this really attractive for some reason. As he started massaging my chest and legs needless to say I had a very big erection.
At this point he asked if I would like to go into his bedroom and I replied yes. We went and got on his bed, when he produced a dildo shaped like a cock and asked if I’d like him to use it on me to which I replied absolutely. He used it with a condom which I appreciated. It was big but felt good though as he slowly ran it in and out of me. He then asked if he could fuck me and I said yes but with a condom. He then began to fuck me and it felt great and really natural he fucked me quite hard until he came and I was happy that he’d gotten off. He then asked me to lay on my back and he began to stroke my semi-erect cock which responded quickly shooting a really big load to which he laughed.
Afterwards, he offered me a shower and we talked a bit. All the while I was thinking what a nice experience.
I saw Christian again some time later on two occasions. The first was at his place again and was basically the same scenario except this time when he was in front of me I took his cock in my mouth and although I did not suck him off, I found it enjoyable.
The third time he came to my hotel room with his “equipment”. It was this time that we showered together. I remember lathering him up and how smooth his body was and when we were face to face our cocks were both stiff as a board…it was fun.
The massage was different this time. It started the same but we quickly got busy. I wanted to suck him and get him hard and when he was, I asked him to lie on his back so I could ride him. I absolutely loved it and found it was very enjoyable. He stroked me off and it was a very mutually gratifying experience. However it created the desire to cum from anal only with no penile stimulation. I've come close but am still working on the goal!
From my experiences I have really began to enjoy anal and being a bottom...Who knew?