"My first gay experience came a couple weeks after my High School graduation. Some kid from my class had a roommate he lived with in Bethlehem. It just so happened that his roommate was gay. This kid then set us up on a date. The gay roommate was black, and he was one of the first other gay people I had ever met. I took a chance and went to his place. I didn't have a car yet so my mom had to drive me there. Anyway we walked around town for a while then we went back to his place and started watching Will and Grace. I had never seen it before. As we watched TV he makes his moves and I give in of course. Next thing you know we are 69ing on his bed! He continued to give me head and I finally blew my load in his mouth. He wasn't a swallower, so he spit it into a can, in which he also kept his change in. Whatever happened with that change I don't know.
"When I was 17 I had just joined one of the online gay dating/hookup sites. I was working at a local grocery store at the time. One guy, a few years older than me had seen me cashiering there, and then messaged me online. He began to talk to me for about 2 months online. I started to recognize him when he came food shopping and even began speaking with him in person when he started coming through my checkout line.
Soon after we started speaking in person. He invited me over to his place one night after I got out of work. His parents were out of town and he knew I had absolutely no experience with guys (and being a gold star gay, no experience with girls either!), it wasnt a date. I was going for the pure reason to hookup with him. I was so nervous because I had to tell my mom some made up story about where I was going after work. I went to his house and I was shaking the entire time, even when we were sitting on the couch. He put his head on my chest/shoulder he could hear my heart pounding. Soon I was making out with him, and feeling him all over, clothes were coming off at this point. The one problem that I clearly remember is that we both wanted to do things to the other one more than getting things done to us (both givers, what can I tell you). So we kept pulling each other off of one another. He was very well hung so naturally I was drawn to it the entire time we were hooking up.
When all was said and done, I have to admit, I didnt really like it (at first). I think because it was all so new and I had no idea what I was doing. But I will never forget my first time. I hooked up with him now and then over the years, but very sporadically and we still keep in touch a little to this day."
"My first gay sexual experience occurred in college. I was a junior, and the guy I was dating was a freshman. We were each other's first (of any gender). Everything was a progressive step forward. We never got as far as home plate on the base pads, we got to 3rd base. You know, I don't even know how the bases are allocated for the gays. I guess it goes: french, jerk off, suck, fuck Anyway, I'm digressing.
Each night we were together our hands ventured further down the bodies until "oops, I found a penis". He always made the first move, he was the first one to reach his hands into unknown territory. I of course let him. Who was I to argue. This all happened in a dorm room, where I was one of the Resident Assistants, so at any moment my door could be knocked on or the phone could ring (which actually happened once).
He was out like a fat kid playing dodgeball, whereas I was still pretty much in the closet, minus telling a very few select friends. So each time hands ventured into mysterious places. It was all intimate, and comfortable. And I think it helped that we both had no idea what we were doing, we both learned together. "Don't worry I've done this before" was not part of the conversation. One night we ventured down there, and I don't remember if juices flew or not, but at least we got a look at the goods. Then another night it was 2nd base, each of us jerked the other one off. He was kinda picky with cum, he wouldn't swallow. Me, haha, I have no problem swallowing! Then of course the next night we were together we went down on each other, made each other cum, of course he didn't swallow, but it was very affectionate. Later experiences, we tried different positions, nothing terribly kinky, but it was great to explore with someone, and it meant even more knowing he was exploring too.
Now the first anal experience I had, wasn't that. Remember those M4M chat rooms on AOL back in the day? I met a guy on there, and went to his place. First night we only did oral, I had NO idea about anal sex. Didn't know how to prepare, totally oblivious to it. He wanted to fuck me, but I said no, and he was cool with that. I was 22 at the time, and he was 29. I can't quite remember what I did to prep myself for getting fucked. I pretty much determined that I'd be a bottom. I've topped for 2 people ever, the rest on the receiving end. But I did a couple of things to "get ready" for the act, and it seemed to work, and still use it to this day.
Tuesday nights were the unofficial "gay night" at The Ugly Oyster in Reading, and I ventured out quite a bit. So I was at the bar and the same guy I hooked up with was there, and I eyed him from the other side of the bar. Blah blah blah he mouthed that "I'm gonna go [home]" and I followed him out of the bar into the parking lot. He asked if I wanted to come over and "hang out", so I followed him home. Obviously we did more than listen to records, and I let him fuck me. BIG mistake!!! Why? Cuz he was HUGE. Probably about 9 inches, and thick. I know it hurt going in, and of course I had to pick the guy that could go hours before cumming. And he did! Might I say BEST SEX EVER!!! But the next day, I could barely walk, and every time I coughed my insides hurt. Even when I pissed it hurt. I thought I was gonna die. But I got with him about 4 more times after that, still the BEST SEX EVER!!"
I was talking to this one guy who found me interesting, but I cannot say I returned the interest. So as the night goes on people begin to exit the bar and my friends decide they want to leave. At this time it's about midnight and I convince them to have one more drink before we depart. Right when I convince these gents to stay, the clouds open and god smiled...well at least I thought she did...
We ordered our drinks and then this older gentleman comes up to me (probably about 35) and tells me that although he thinks I am adorable, his friend has been eyeing me up all night! He said he was shy and he wanted to meet me. So I told him I would go to the bathroom and then he could introduce me to his friend. Of course I went to freshen up and then when I came out this gorgeous man in his mid thirties was shaking my hand and was completely into me. I was floored! He was well built, in great shape, and had a touch of salt and pepper in his hair. We talked and exchanged numbers that night. When I returned to my car he asked me to meet him at his apartment to hangout, but I told him it was too late and I wasn't that kind of gurl. I suggested a movie night and dinner. He then invited me over the next day.
What happened next is one of the most embarrassing and shameful moments I have had in my entire gay experience. I drove over with the anticipation of having a date and left wounded and full of regret!
When I arrived I should have known something was going to happen. I was escorted up to his apartment and he was so full of compliments that he had me in the palm of his hand. His apartment was pretty barren and he said it was because he had just moved here. If we wanted to watch a movie I was told we would have to watch it in his bedroom. I was swooning and cannot even tell you what movie we watched. We started cuddling and making out almost immediately! What happened next still shocks me.
In what felt like one quick swoop, all of my clothes were off and we were lying on his bed. Things got very hot and heavy! He suggested that I close my eyes and when I did I was handcuffed to the bed. The feeling of pleasure left my body and I was filled with extreme dread and regret! I was completely in over my head!
Next he un-handcuffed me and I slumped into his bed. He exchanged some pleasantries about how enjoyable he thought it was and I forced a smile through my lips. Assuming that after that I would spend the night I laid down and began to get comfortable. He asked if I wouldn't mind going home because it was late. I got dressed in silence and excused myself. I heard from him a few days later when he asked if I would come over, I never responded.
Now that I am older I take this as a learning experience. I am very lucky that I was at least with someone who wore protection, but as a young gay male....I was a stereotype and most importantly an idiot. I want people to hear this story in the hope that they will be smart and never go home with someone they do not know. Although sex is a desire, it can also be a very intimate moment shared between two people who care about eachother! This is what I have learned and hope to teach!"
Remember no glove, no love. Be safe everyone and for god sakes make good decisions.
For my first time story please see the post Like A Virgin
If you would like to share your first time experience here please EMAIL ME or click on the blue comment link below.