After years of debating, I finally make my first attempt
So some background, I'm in my late 20's, I'm 5'11 and I weight in the mid 200 pound range. I'm a bit on the heavy side but I wear it well. I'm about five inches cut. I am best described as Bi-Curious.
I've lived in New York my entire life, and have always walked it's streets. In a sense, I was always aware of the video shops on 8th ave since before I should have known about masturbating in general. I went in to my first one when I was 16 (I look older than I am, and the clerks don't give a fuck so long as you aren't obvious). I found the idea of masturbating in public to be pretty hot, I'm shameless when I'm in heat, having had sex with girls out on the street when we didn't have any options.
A few years back, walking through Chelsea, I stopped in a store and realized that I stumbled upon a buddy booth with an even circle cut out to my right. No one was there, but I remember cumming hard as I thought about watching another man getting off and me watching. For years, I darted in and out but I never got around to it. One night I outright went cruising, trying to find someone I could hook up with in a booth, but just found myself hassled by hustlers.
Then about two weeks ago, I was walking through the lower west side and I was feeling horny. I stopped by one of the shops. I could clearly hear the sounds of sucking coming from behind some of the doors, and I could smell the scent of sex mixed with disinfectant. I slipped into a booth and slid in my five dollars, working myself into a genial froth. There was a hole on my right, but I didn't pay it much mind.
In a blink and you'll miss it moment, the door next to me closed, and almost immediately a cock came through the hole.
I didn't believe it, at first because there was no preamble, and secondly because it was so small. It was clearly two inches hard and didn't have any girth to it. I debated not acknowledging it, of not touching it and making him think I wasn't interest. But I was horny, and I wanted to know what it was like. So while I was working on my own cock with my left hand, my right hand grabbed his shaft. I immediately felt him tense as I worked my fingers over his shaft. He may have been small but he was sensitive, I could feel him throb. So finally I said what the hell and got down on my knees. Without thinking I took his cock into my mouth, my tongue working his lower shaft as I (instinctively)sucked my cheeks in to give the sides some friction.
He pulled back a bit, and I could see he was white male, probably no more than ten years older than me. "Are you going to swallow?" He said.
Was I? "This is my first time," I said. "Keep going and we'll find out. Just tell me when you cum."
He seemed to like that idea, as he bent down and shoved his tongue into my mouth. I was so hot at that point I took it freely. "Do you return?" I asked.
"I don't," he said. "That a problem?"
"No," I said. "Just tell me when you're going to cum." I took my hand and grabbed his cock, pulling him back to the hole and tugging on him, sucking on his head. I could hear him grunt and groan after a few turns. He shouts, "Fuck! you're doing so good! Just keep sucking that cock." A few more twists later and I feel his dick spasm. I expected to feel warm cum hit the back of my throat. I'd never tasted cum and it would be one more first. He pulled back and thanked me.
"Did you cum?" I asked.
"Oh yeah," he said. "You were great." He pulled back in, enjoying the rest of the time on his film. I sat back down in my chair. By then, my cock was raging and already leaking. It took me a few quick strokes for me to cum. Unlike my partner, I shot clear across the corner of the booth, coating the walls. I came hard and loud and at that point I didn't care who heard it.
I stepped out of the booth, nonchalantly fixing myself. The booth next to me opened up and my partner stepped out and winked at me.
That was my first gloryhole and my first session with a guy. It's made me very much aware of how much I like to get my partners off and has affirmed a lot about me. This won't be the last time, and I think another trip is on it's way. I've other stories about masturbation with a high school friend, but I'll save those for later.