SHORT SUMMARY: A young, preppy man in his 20s goes to New York and right when he assumes he'll not get lucky on his trip, he encounters an older leather man. What follows is a night of uninhibited pleasure for both as the young man orally services every inch of the leather man's body.
The following short story is true. I am not releasing names in order to protect the identities of the people involved. This story involves consensual sexual pleasure between legal aged guys. If you find content like this offensive or if it is illegal in your area, please do not continue reading.
Last Call One Night in Manhattan
It happened one night back in 1997 when I was visiting New York for the weekend. I had traveled there by train after work on Friday to meet up with some friends that had also traveled there separately. The plan was for us to meet-up for drinks and do some sight-seeing. I was in my early 20s at the time and looking forward to getting lucky with a local at some point during the weekend.
The night I met up with my two friends, I started out rather early at a bar in the Chelsea area, just around the corner from the hotel where I was staying. It was dead and so I had my drink and wandered around the city for a while before meeting my friends at another bar in the Village. We went to two bars that were both happening and despite some flirting with several guys at both, nothing materialized.
Closing time was nearing and my friends and I went out separate ways. I went back to Chelsea, assuming that I would sleep alone that night.
Despite the very late hour, I felt like another drink and so I returned to the bar where I had started. This time the bar was packed with guys trying to get in a last drink and no doubt a hook-up before the closing bell rang.
Like I said, I was in my early 20s at the time and had a straight preppy look that didn't necessarily fit in with the very gay looking twinks and muscle boys in the bar. Nothing was really catching my eye and I was resigned to the fact that nothing was going to happen. And then, in he walked.
Two men in their late 50s walked in and while one of them looked like an average guy off the street, the other one definitely caught my attention. He had a trashy, hybrid Levi and leather vibe to him which was out of place for the rest of the crowd. I can't say that he was attractive in the traditional sense. He had gray hair, gray moustache, and beard. His shirt was really a couple of studded leather cross straps and his pants were skin-tight jeans. On his feet, what else? Black boots. His wasn't tall and his body was in the average category. His friend was dressed the exact opposite: normal jeans, long sleeve shirt, non-descript shoes. They were an odd pairing for sure.
I caught the leather man's eye, and some cruising began. At this point, I was starting to feel turned on. This man was not my type but something about him was triggering erotic and perverse thoughts in my head.
He came over and we introduced ourselves. His friend was clearly drunk and could barely speak. Leather man was on the prowl and when he asked me what I liked, I told him what I wanted and would he be interested.
What I wanted was to take them back to my hotel around the corner. I was to be in charge, and they were there to please me. How was I going to be pleased? By pleasing them. I was feeling horny in my throat and on my tongue and I needed to put both to good work, on them, with no reciprocation at all.
He seemed taken aback by my bluntness but quickly said yes and off we went to the hotel.
The walk back was very short, and I was feeling hornier and hornier about what I was going to do with this older man and his boyfriend. In the hotel we went and right past the no visitors sign, to the elevators to my room.
Inside the leather man excused himself to the restroom and I made my move on his drunk friend. He laid down on one of the beds and before I could bend down to touch him, he immediately passed out cold. Oh well, I was now free to turn all my attention to the hot leather man.
He emerged from the bathroom, mostly naked except for his cock ring, boots, and some studded leather bands around his upper arms.
I didn't even bother to get undressed. I told him to get on the (other) bed and down I went.
We kissed each other passionately, tasting the whiskey on each other's tongues. I was the aggressor and sucked that wicked tongue of his, giving him a precursor for what would come later.
His hair chest called to me and so down I went, licking his neck and stopping along the way to suck his earlobes and run my tongue into the crevices of his ears.
His nipples were big, and they were hard -- perfect for sucking. He asked me to bite them and so I did which rang his pleasure zones. I was fully in heat at this point and wanted to taste every bit of him from his head down to his toes.
He seemed surprised by my aggressiveness and thankfully did not resist. When I took his fingers into my mouth one by one, he groaned with pleasure.
Skipping his torso, I went down his legs and pulled off those black leather man boots and his socks. Again, I wanted to taste every inch of him and he went wild as I worshipped the steamy soles of his feet and sucked his toes, one by one. I don't know if anyone had worshipped his feet before because he was in a state that conveyed both pleasure and surprise. Here I was being submissive and yet I was fully in charge: A clean-cut young preppy taking control of this older leather man, in all probability, a dominant top.
I could have sucked his toes all night but that throbbing penis and his big testicles, made even bigger by that leather cock ring called to me. At last, I was going to shift my attention to his official pleasure zones.
His testicles were warm and felt good in my mouth as I tea bagged him before I took my tongue on a journey, up the shaft of his penis, around the base of his head, into the slit of his urethra and his entire manhood into my mouth and esophagus. The g-spot in my throat was happy and so was my leather man's penis.
My throat got to the point where it needed a break and so I pulled away then looked down at his face. You could tell that he couldn't believe he had hooked up with me and that I was much sluttier than my first impression had conveyed. I gave him a devilish smile, reached my arms down under his legs and lifted them up in the air. His forbidden fruit was now calling to me.
He was a hairy man and in the midst of his hairy crack, his pink rosebud looked back at me. As my tongue came into contact, he erupted in pleasure, pushing up his hips and spreading his legs as far apart as he could to give me full access.
It was warm and sweaty from the body heat we were creating. The salty taste immediately turned me on, and we were in mutual ecstasy as I introduced my tongue into the most taboo part of his body. Up until now, he had been mostly quiet other than lot of moans but now he was in full trash talk mode which further turned me on.
I think I spent more time on his ass than I did any other part of his body. His ass was all mine. I was making him feel incredibly good and that more than anything was what turned me on.
I could tell his couldn't last much longer and as his testicles started to twitch, announcing that the volcano was about to erupt, I shoved the tip of my tongue into his asshole which he was not expecting. I don't know who was in greater pleasure, him or me as I felt the walls of his anus twitch around my tongue as he ejaculated all over himself.
That was pretty much it. He got dressed, thanked me then managed to wake up his still drunk boyfriend and off they went into the early morning. I had expected a disappointing night alone and am grateful that it turned out to be one of the most erotic experiences of my life.