First Time as a Top
I write a decent amount of fictional gay sex stories on this app, but I've never written about my first time. Well, I guess, both first times. I have my first gay hook up as a top and I have my first gay up as a bottom. It happened in that order, so I'll talk about my complete first time with another guy as a "straight" guy who got seduced into not being so straight.
At the time, in the early 2000s, I was a 21 year old college student living in New York City. I played hockey, had an athletic build, clean shaven, and spiked dark hair. I was also on a cold streak with women. So I put on a nice button up shirt, blue jeans, and expensive looking knock off dress shoes to go to one of the nearby popular clubs.
I was terrible at everything in the club. I wasn't comfortable dancing and talking to women was just not working out in such a loud setting. As I made my way through the dance floor over to the bar, a petite feminine person with long wavy dirty blonde hair, who I thought at the time was a woman, playfully grabbed my crotch and continued on their way. I thought to myself that maybe my luck was changing, but I couldn't find the "girl" that did that and just continued to the bar to get my drink.
I had a couple of drinks in the bar area, struck up conversations with some of the women my age that were there, but I was definitely striking out. I figured I was either really out of practice or maybe this just wasn't my scene anymore, if it ever was. Then the petite "girl" with the wavy long hair randomly reappeared and started grinding against me before turning around, playfully grabbing my crotch, and asking me if we should get a cab and take this elsewhere.
Horny and not noticing the clear signs that this sexually aggressive woman was actually a femme male, I agreed and grabbed a cab to go back to her place.
On the cab ride to "her" apartment I kept trying to slide my hand up between "her" legs while we were making out, but was stopped by their hands. They then reached into my pants, stroking my cock, and then pulling it out to suck it, not caring if the cabbie saw us or not. Stopping me from even attempting anything else as I enjoyed the cab ride blowjob.
We got to "her" apartment, I paid and tipped the cabbie, and with my hard cock stuffed back into my pants I entered the apartment. We drunkenly made out and grabbed each other and as I tried to reach between their legs again, they pushed me back onto the couch, pulled down my pants, and started sucking my cock again. I ran my hands through their hair as they sucked and moaned softly telling them what a good cock sucker they were. They must have noticed O was almost at the brink of blowing my load when they pulled off my cock and said we should take this to the bedroom.
We got to the bedroom and started making out again as they quickly stripped me naked. I started returning the favor and as I started taking off their tight jeans, I felt his bulge for the first time. I paused as I slowly moved my hand back, but he quickly grabbed my hard cock and started stroking it, asking me in a flirtatious manner that I'm not going to back out now, am I? Maybe it was the drinks or maybe it was the horniness, but I went with it, told him I wasn't backing out, and we made out deeply as I pulled the rest of his clothes off.
We rolled around on the bed making out as he grabbed my cock and I squeezed his smooth ass. He then rolled over, pulled a condom out of his bedside drawer, ripped it open, and slipped it onto my cock. He got on his hands and knees, reached back to help guide my cock to his hole, and pushed back as I pushed my cock into his tightness. He kept the pace at first, but then I started taking control and started fucking his ass hard and deep. I gripped his hips as I hit his hot ass from behind as he moaned loudly, telling me to fuck his ass like a pussy. He then said he wanted to ride my dick, so I pulled out and got on my back.
He leaned onto me to give me a deep kiss before grabbing my cock and positioning it so he could slide down it with his ass. With my knees up he bounced up and down on my cock, moaning loudly with each bounce. Suddenly he let out an even louder moan as he shot his load onto me as he continued to bounce on my cock. He could tell that caused me to almost shoot my load myself, got off my cock, pulled off the condom and started stroking and sucking my cock. He told me that he wanted to swallow me as he went back to sucking and stroking and almost on command I shot my load down his throat. With both of us satisfied, he crawled up next to me to make out some more. He excused himself to wash up in the bathroom and I passed out drunk on his bed.
The next morning, I woke up to him walking around naked and cleaning up some of the mess we made the previous night. He told me good morning and sat down next to me and told me how good the fuck was and asked if that was my first time with a guy. I told him it was and he jokingly told me not to worry. That it was our little secret. I agreed and admitted I enjoyed it quite a bit. I then got up, used the bathroom, washed up a bit, and started getting dressed. Still naked, he sat on my lap and asked me if I wanted to exchange phone numbers. We did and as I gave him mine, he playfully rubbed his bare ass against my now clothed crotch. Then he got up, turned around, and told me not to be a stranger. He walked me to the door where we made out again, him grabbing my crotch and me grabbing his ass, and I made my way to the subway station. When I got to my stop, my phone went off and it was a text message from him thanking me for being such a giving guest. When I got to my apartment, my roommate asked where I was coming from and I told him about the hot girl I hooked up with from the club as young and stupid straight guys do.