This is the story of my first time with a man. And my last time... So far. I was always curious, even when I was very young. Looking at men in magazines, especially if they were in revealing underwear and had big, well-defined bulges. I had messed around a little as a kid, but nothing more serious than 'you show me yours and I'll show you mine'. But as the years went by and I slipped into high school, I had girlfriend after girlfriend, and my sexual history was strictly hetero.
I was very exploratory, enjoying BDSM, chastity, anal play, and roleplaying, but my experiences with gay sex remained nothing more than fantasy as I graduated from high school. I entered the army straight away afterwards, and I really went wild sexually. Girls loved the uniform and I managed to sleep with a string of conquests, stole a couple of wives, and started really getting into chastity. I bought pvc hot pants that zipped from front to back, a male chastity device, and spent whole weeks locked up by my girlfriend. In retrospect, I think I loved the chastity play so much because of the need for prostate milking that went along with it. When I was unlocked I fantasized about cock while I masturbated, and when I was in chastity I got fingered by a girlfriend who I'm amazed never put two and two together.
I made it out of the army in one piece and moved back to Florida, got a roommate, and settled into civilian life, and that's when the story gets really interesting. It was shortly after a break-up; I was feeling rebellious, extremely horny, and I had the apartment to myself as my roommate was out for the weekend. I started fantasizing about cock and hopped into bed to masturbate, but as I got myself more and more worked up, it occurred to me that there was no one to stop me cruising down to a gay bar and finding someone big and hard, someone with a bulge. My most potent fantasy had always been to sit down next to a guy and reach over under the bar to feel his bulge. In the fantasy, the guy was soft initially, but immediately got hard when I started touching his cock. I feverishly jacked off thinking of that cock, growing under my touch, when I suddenly decided to stop, just short of cumming - I knew that after I came, I would become suddenly and extremely 'hetero', ashamed of my fantasies, and certainly would never have the courage to do what I was deciding to do.
I put my cock away, got out of bed, and grabbed my car keys. I had seen a gay bar on the main road in town several times, and it had always excited me to think of guys in there, picking each other up and flirting. It was called the Male Room, and the sign had bright pink neon. I hopped into my car and drove out of my neighborhood, my hands shaking, as I made my way to Tampa's main drag. All the time thinking I could pull out at any time, I drove closer and closer to the club. My mind was racing with how reckless I was being, my cock was rock hard in my sexiest pants. Before I knew what was happening I saw the familiar pink glow as I arrived outside the Male Room. It was smaller than I had thought. The entrance at the back rather than on the street as I had expected. I pulled around, not sure if there would be a guard on the door, or a cover, and I parked as discreetly as I could. The attendant on the door barely registered me as I entered the club nervously, just a twenty-two year-old kid with his heart in his throat and an erection secreted away in his trousers.
The place was crowded - it was a Friday night, and the music was pumping. I didn't consider myself a dancer, but I was intoxicated by the possibilities all around me. I was completely free, for the first time in my life. I tried dancing a bit, but I was nervous, and I wanted a drink. I made my way to the bar and ordered one, and then looked around. Most people seemed to be there with friends and everyone seemed to know everyone else - It wasn't like my fantasies at all. No one was noticing me, and I felt pretty alone. I wandered around a little bit and ended up at the quiet end of the bar where I sat, sipping my drink and looking around, on my own. I felt foolish. I had assumed everyone got lucky at gay clubs, that it was different from trying to pick up girls. I felt shy and like an outsider.