True story of my first gay encounter in 1999.
I lived on a Caribbean island in my early thirties and had been chatting with a guy from NY for a while on the old free chat platforms. We talked about hooking up but as I am married it was next to impossible. Then the stars aligned, my wife went to visit her parents in the states, so I told him, and he said he worked for an airline and could get down for free and get a hotel room.
It was put up or shut up time! He arrived two days later around 11am so I took lunch early and told the guys I’d be late coming back. I got to the hotel and went to his room. I was so nervous I almost chickened out, but I knocked. This older short guy in his fifties answered, he was wearing silk pajamas and has a semi-hard-on. I asked him to show me it, and he told me to do it myself, the moment of truth, all those fantasies of sucking cock coming true.
I fell to my knees, pulled his pants down and became a cocksucker. He was 6.5″ uncut and average thickness. I spent the next ten minutes sucking and licking, tasting his musk and precum, I was hooked!
He pulled me to my feet and pulled me to the bathroom. He had told me he had a mirror fetish in our chats so I knew what he wanted and followed.
We traded blowjobs in front of the mirror nude and ground our bodies and cocks together. I was in heaven! We never kissed because I didn’t have the nerve and he wasn’t particularly attractive, it was all about the cock! He turned me around and he started pinching my nipples and jacking my 6.5″ cut fat cock. I could feel his cock between my ass cheeks and I was over the edge horny, so I reached behind me, took his cock and sat on it. I can remember his gasp and shudder as I took him bareback in one motion (risky, I know, but he swore he was clean and I knew I was). He fucked me standing in front of the mirror forever it seemed like, bent over the counter, spread by the sink, anything to please each other.
We moved to the bedroom. He fucked me in every position we could get into. I started out face-down with my legs spread he fucked me hard into the bed as I rubbed my cock underneath me. I then laid him down straddled him and rode his cock forward and reverse cowboy. I was in heaven!
I then begged him to fuck me doggy style on the edge of the bed, my favorite fantasy position and, go figure, my favorite real position also! He started pounding me and I loved it. After about ten minutes he pulled out and said he was cumming. I spun around on my back with my face under his cock and told him to cum on my face, I did not have the nerve to swallow, yet. As he covered my lips with his hot load I jacked and came so hard, one of the biggest loads ever. He rubbed his cock all over your face enjoying the show.
I washed the cum off my face and stomach and returned to bed. We talked for twenty or thirty minutes and I started playing with his cock. He started getting aroused and I asked him if he would like to fuck me doggy style again. He said he would and I jumped to the side of the bed to assume the position. He came up behind me and played with my ass while trying to get hard, I begged him to PLEASE put it in me! He was about half erect and worked it in my wet hole. As he started to fuck me, I could feel him pulsing and swelling inside me rubbing my tender prostate. I lost control, my ass spasmed and I came, and I fell face-down and came all over the comforter, thrashing around in ecstasy. To today, that’s one of the most powerful orgasms of my life.
Hope you enjoy this series.
