tagGay MaleMy First Time

My First Time


I was going to grad school in NYC. I was 27 and had never been with another man or really even considered it. Well actually, there was a time when I came onto a really close friend at home. We were sleeping in the basement of my parent's house, when he awoke to me kissing him, he freaked and ran out the door! Not a good experience. I had started thinking about it again the last year or so, especially when my long distance girlfriend started cheating on me. She lived in a ski town, where I spent nearly 4 years being a ski bum. We broke up in a messy scenario when I visited the town for the entire winter break between semesters that year only to learn she was seeing someone else a few days prior to my arrival. Man, did that suck! She was by far the best sexual partner I had ever had to that date and we had great sex while I was there anyway, but our relationship was never the same and we were no longer mutually exclusive when I returned to NYC.

The very night I returned to NYC I met a 32 yr old gal, whom I had admired from afar, through a mutual friend, who was also a student. We instantly hit it off and I asked her out. At first she said no because she was too busy to consider a boyfriend. Then one night when I knocked on her door just to say hi, she invited me to dinner and I I won her over. After tons of sake, we had amazing sex that night and she even let me fuck her in the ass. It was a steamy sexual start to a great no strings relationship that lasted several months.

We started dating, albeit it was never to be serious and she always reinforced that it was only sexual. During our lovemaking we would fantasize together about different things. She confided to me that she had bicurious yearnings and I guardedly shared with her I also had bicurious feelings. She was the first person I ever told and this was a crucial step in my recognizing that fact and I believe she helped me move toward validating those feelings.

All of a sudden, men started to become attractive to me. In the past, I always thought male bodies were gross, but now I was looking at men and thinking they were cute! And I would actually check out their ass or their package in their jeans! This was huge and so were some of them! It was very exciting, too.

Then it happened. I was partying out with friends that weren't associated with school and thus I was coming home alone on the subway about 1 am. I was walking up the stairs exiting the subway and ahead of me was a cute, tall guy in a pair of jeans. I immediately like his ass and when I said something to him, something unimportant like, "Hey - how's it going?"

"Fine," he replied in a flamboyant effeminate sort of way.

I was pretty hammered, so I just said, "Are you bi?"

He was floored, but responded, "Maybe," as he looked me up and down. Then I really noticed he was very cute with blonde hair and a slim build. I walked very close to him doing my best, in an amateur, haphazard kind of way, to give off signals.

When you live in NYC you get hit on all the time by other guys in very subtle ways. A glance at your cock, a seductive smile. It happens quite often, especially in the Village near the more popular Gay Bars. Most hetero guys never even notice simply because they're not looking for it. When you look for it, you find it, and that night we found each other.

We talked a bit of small talk as we walked and it turned out he was an a student at another school that leased space in my same building. We were neighbors. This freaked me out a bit, because I wanted an experience well removed from my hub of life for secrecy issues. But hell be damned, I invited him up to my room to smoke some pot and he said sure. The art school packed 2 and 3 kids into the same rooms that my school used as singles, and believe me they were very small to begin with. So he was psyched I had my own room.

We went into my room and sat on my small couch. I loaded my bong and we both smoked a hit. As he let his hit out I reached over and rubbed his cock through his pants. He responded positively and grabbed for mine. I looked deep into his eyes and kissed him. We french kissed and massaged each others groin. He slid off the couch and got between my knees. He undid my belt, slid it out and unzipped my Levis. I was getting so hard. He took off my shoes and slid my pants off. Then my under wear. I had the hardest cock of my life. He complimented me and said I had a beautiful cock. Before I knew it, I was getting a hand job from another guy. A cute guy!

I stood up and brought him over to my bed. I undressed him and almost gasped at the size of his cock. It was huge!! I mean, I couldn't believe how big it was.

I asked him if he liked it in the ass and he said "Sometimes." I told him I was a virgin and that he would have to go easy on me. He was quite a bit younger than me but obviously much more experienced and at ease with his sexuality.

That night was unreal for me. We made out, gave each other blow jobs and had safe anal sex. I was able to fuck him, with a condom, quite vigorously while he was barely able to do me, as it hurt pretty badly due to his unusually large size. When we woke the next morning, side by side, naked, in the bed, I did an immediate guilt check. I felt funny, but my uneasy feelings were more about anyone finding out and implications associated with the possibility of me truly being gay rather than feeling guilty for the experimentation itself. I even felt fine enough to have the urge to reach over and start playing with his glorious cock as I woke him up with kisses on his body. I got him hard and tried to do him one more time in the ass. But he couldn't take it.

He said, "Sometimes it's easy and sometimes it's not, just like with you last night!"

With that we kissed and I begged him again not to tell anyone. He told me not to worry and that our secret was safe.

Over the next few months I ran into him on several occasions. We would both be with friends and we would exchange greetings, nothing fancy. We never ran into each other again after a certain point and I was afraid to go to his room because he had roommates and they would likely know he was gay. I didn't dare risk it. As far as I know, he kept his promise and never told a soul! That was very sweet of him. He took my virginity and he kept my secret. Now, of course, I wish we would have played more!

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