My First Man Experience

For a long time, over twenty years, I had fantasized being with another man. I was a professional Marketing Rep and traveled continuously, from state to state, some international. Mostly one nighters, arriving, meetings, motel, out in the morning to the next stop. Some, those meetings closer to home were best done by car. I spent the nights alone, ate alone, I was never one for solo drinking. Back in my room, my trustee personal laptop, I spent the night with porn and developed a hunger for gay porn, slow motion cock sucking, slow motion anal penetration.

Over time I enjoyed a good episode of man kissing, especially older men, not kids. I would sit through a long video, the meeting, the kissing, the manhandling, the cock sucking, the anal. Over time I would fantasize with the man beside me on the airplane, the man across from me at the terminal. The man in the booth at Denny's. Would I want to kiss with him, would I suck his dick. What if he fucked me? I started carrying condoms and lubricant, just in case.

I had a meeting in Cincinnati, downtown. The meeting went south, no sale. I walked past a small bar that advertised sliders and walked in and sat by myself at one of the small tables near the window, a beer and a slider. I tried to get my mind on the next sale, but I was really pissed that I had lost out to a competitor. The waitress, a woman past fifty, kept interrupting my thoughts trying to push another beer on me. Frustrated, I paid and left and walked to my hotel and my room.

I got out my laptop, tried to get into some videos, I called up some of my favorite anal sex but I couldn't get into it. I went to a web site I had cruised and joined a long time earlier and looked for someone traveling to Cincinnati. A post said this man was in Cincinnati downtown that night and the next one. I reached out with a post, 'traveling sales alone, could use some company' and hit send. A half hour later I got an answer, he was downtown and I agreed to meet him at the bar where I had stopped for a beer and a slider.

He wasn't far and we met and sat at the same table. We ordered a beer and talked, he was originally from Harrisburg and I told him I was from Philly. We got along, and he picked up his glass 'your room or mine' and I said I was closer.

I tried to imitate the men on the videos, soon we were naked and he was sucking my dick. I was hard, much harder than when I masturbate. He fished his finger around and poked my anus. I squeezed my cheeks together and that broke the ice. I grabbed his hard dick in my hand, it was a great feeling, and dick other mine and I lowered myself down and put his dick in my mouth and started sucking and licking. He stopped me 'first time?' he asked me. 'First time' I told him, but not in my mind I had been fantasizing about this for a long, long time.

He let me explore sucking his dick, getting comfortable with it. while he played with my dick with his hand. After a while, it must have been a half hour, the room was to warm, I thought about turning down the heater. He got up, and straddled me, lowering his dick in my face and sucked me with his body over me. He used his position to 'fuck my face' which caught me by surprise but I liked it. I knew right then I wanted to be fucked, I just wanted it.

It took a while to get to that, but not before he had fingered me, and I had 'adopted the position' and he lubed me up with my tube and refused a condom. I lowered my head into the pillow and he positioned his dick at my anus and started shoving, until with a breakthrough he was in and going. Deeper and deeper, I said to myself, I wanted it all the way in, every last silly millimeter. His balls banging against my ass he fucked me, and came with a series of thrusts and then slowly withdrew his dick and wrapped it in the hand towel he had handy.

'Want company?' he asked me. I said I did and we lay there, naked with that feeling. 'For a beginner you did good' he told me. I told him I had imagined it so many times, I couldn't believe it was real. He put some porn on the tv, and we watched the pool boy get it from the gardener. He suggested we shower and we spent quite a while under the hot water, using the time to wash each other down, and wash our dicks and up our butt cracks. He told me to get down on my knees and give him a licking, which I did, I licked his asshole, with the hot water rolling down his back over my face as I licked all around and poked my tongue against his asshole.

'You have to get used to man sex' he told me. A man isn't like a woman, a woman needs a lot of talking, a man just wants to get down to it. And with that we lay back down on the bed, and started kissing, jerking each other until we wanted to go back to sucking dick and he opened his legs so that I could get my tongue back up his ass crack. I found I liked licking his ass, a lot more than I would have imagined. And then he fucked me.

Comments

Anonymous

by Anonymous on Dec 21, 2023 at 10:39 AM

Lots of similarities in how I gradually came to my first man to man experience like yours. After my divorce at 33 I spent 10 years renting gay videos especially ones with lots of kissing and slow sex. I fantasized about letting go with a man all the way and allowing myself to totally get into it.

The desires led to many nights of masturbation. One day I saw an ad in an alternative paper and since it was the 90's pre internet the ad was a telephone gay line where you got a paid membership and talked to real men on the phone. I nervously got my membership and chatted with a few men on the phone often getting into hot chat and jerking off together. One divorced gent I had chatted with a few times suggested we meet. He was older than me and been with men before. In fact he preferred sex with men now. We met in a bar and he seemed like a normal nice masculine guy. He had silver hair and was around 60 while I was early 40's at the time.

We ended up at his place kissing on his couch. He was a great kisser and had me deeply aroused. In his bed he sucked my cock real slow and made me cum in his mouth. Later I sucked his cock for the first time and enjoyed it. We hit it off and began having regular encounters. I lost my inhibitions and he lubed me up one night and fucked me nice. It hurt a bit but was also very pleasurable. After a couple times fucking me he went in easy with some lube and I took him deep. I loved it. We were lovers for over a decade then he got cancer and his daughter took care of him. I have had other men since and now prefer men myself.

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