I remember my first time with a girl, I had met her through a friend and it was nice, but I wanted to get out of there as soon as possible. It was always like that. I had a lot of trouble in high school "hooking up" with girls. I also remember another night when I felt like I was stuck going to a dance with this girl - disastrous night; long story short, I was very uncomfortable all the time trying to fit in and date like everyone else. There was always something wrong with me, or at least I thought, that was until I was 21 and had a night I will never forget.
I entered a time in my life that should have been very fruitful but I was fucking it all up. Picture this: I'm 21, living on the beach in south Florida, hanging out in a cool bungalow I rented with my older brother and his girlfriend, had a good crew of young, crazy, cool, and fucked up friends. We frequently hit the Fort Lauderdale scene, the South Beach (Miami) scene, and having another brother that lived a short road trip away in Key West, we hit that scene too...fuck I had it all...or I should have had it all...and for nearly two years of living that kind of life my grand total of fucks, sucks, macks, or any other kinds of action was zero. I was struggling. I tried to date, but it felt as uncomfortable and unnatural as ever. I really thought eventually I would have a break through and get over the awkwardness of it all; little did I know I would, just not in quite the way I expected. There's a bit of a story to this; I'll explain.
I ended up at a club one night with a gay friend of mine when he saw an ex-boyfriend or just some guy he knew - there was definitely a past between the two of them - so he gets visibly uncomfortable and asked if I could just hold hands with him and pretend that we're together. Okay, no problem, help the guy out. Fast forward to a while later when the same guy ends up coming over to us while we're sitting in an outdoor patio area; he was with some friends and they were all being dicks. He ended up asking if we were with each other and my friend said yes. I guy asking was kind of being an asshole to us, so I went with it, again, no problem, help a guy out. He didn't seem convinced so I leaned over and gave my friend a peck, nothing more, nothing less. Seeming satisfied or maybe unsatisfied that he couldn't get under my friend's skin, he went away. My friend thn turned to me and said he was surprised I would stick up for him like that, or more accurately, in that way. It really wasn't a problem and I told him that. Done, end of story right? Well not quite.
We ended up getting a couple more drinks, relaxing, and this is where my recollection is a little fuzzy. I don't remember our conversation or the timing of it all or anything, but I'll try my best.
At some point we ended up in another outdoor area that had a cool lounge vibe to it. We're chilling with a couple of drinks and my friend notices a drag queen sitting alone at a table. I forget why the drag queen was even important; I think my friend wanted a glow necklace that apparently the queen gave out during her act. Being shy, he didn't want to ask for one himself so I took the lead and went over. We talked and I found out she came to the club on the wrong night and therefore didn't in fact have a show that evening. I asked politely for a glow necklace and she gave me one. I think I complimented how nice she looked and I may have even given her a little kiss. Finished with my business and mission accomplished, I went back to me friend and gave him his new necklace.
You probably thinking that for a supposedly straight guy I was teetering the line, and maybe I was. I don't know when, but at some point things began to change for me. It may have been there, a little later, when we held hands, but I think it was even earlier.
I left out the details of how we ended up at the club together, so long story short; we were out as a group earlier that evening at the very same club and everyone wanted to go home early, I didn't feel like ending the night that soon and when all of us drove back to my place and the others made plans to head home, I was thinking I wanted to head out again. I thought two or three of them would be up for heading back out, but in the end it came down to just me and the one guy that I ended up going out with. If I recall the ball was set in motion by that point, because I remember being a bit excited at the opportunity to go back to either that club or another gay club with only this guy. I don't recall how much I felt it or specifically what I felt, but I definitely was feeling a bit dizzy with excitement about it being just the two of us hitting the gay scene. Was there someone (me) in my closet? Did I even have a closet? Let's get back to the story.
A while later, we were back inside the main club at this point, my friend, again being shy, or coy, or maybe he was working me at this point; the more time I have to reflect on it I really do think he was working me. And you know what? No big deal. I think I wanted to be worked. In fact I hope he was for a couple reasons. For one, it means that he was more of a player and less shy and helpless then I originally thought - good for him, and secondly, if he was working me it was because he was attracted to me and wanted me - good for me. Any way, we're back in the club and apparently we just missed a show of male dancers and they were giving out CDs and other stuff. Disappointed, or maybe he was working me more, he asked if I would go over and see if one of the dancers had any left over stuff to give away. He didn't and I went away, but not before complimented him too, by telling him he was cute and giving him a kiss.
There I was with my gay friend, in a gay club (a dance club that although was gay, was very straight friendly), I'd walked around holding my friend's hand pretending to be his boyfriend, even given him a kiss, I'd flirted with a drag queen (giving her a kiss too), and I'd flirted with a mostly naked male dancer; where on earth was this going? Where ever it was I can honestly say that being there represented something that was a bit taboo for me, a source of arousal, and more importantly, I was at a place where I was stripped down to nothing, me naked so to speak. What I mean is that this was me without societal, family, or any traditional expectations as baggage. I was in a sense free to be myself and these were the choices I was making, the most honest me, and it was blazing a path that was taking me from the straight world into this new world, but I digress.
Again, all the details and the timeline are not perfect, but by this time I was beginning to get aroused, excited, horny, nervous, a bunch of things. The important thing is that I was into it. I don't know what I thought was happening or where it would lead, and prior to that I had never had a homosexual thought or feeling, and I wasn't
sure I was completely at that place yet, but I was feeling all those things I just mentioned and it was like a new drug. Looking back, I think it was the most erotic moment of my entire life.
Back to the club, my friend, and me. We ended up dancing, standard dance floor separation that you do with friends or strangers. Slowly with each song we got closer and closer. The dancing and the music might have been fast, but we were definitely engaging in a slow dance with each other. So after a while we're pretty much friction dancing and I'm even grabbing his ass. That's when I started to want it. I was very close to the point of thinking, "I would go any where to fuck this guy." I don't know if you can imagine what going from not ever having an inkling of homosexuality to practically wanting to fuck this guy right there on the dance floor was doing to me, but there you have it. I had a full fledge boner at this point, pre-cum is already staining my underwear. This I remember.
Was I gay? Maybe that's why I'd been so uncomfortable, awkward, and bad with women? Most of the time it had been in a sort of force manner, almost like it was against my will, so maybe this did mean I was gay. Or was I bisexual? It didn't really matter. I was 21 and would have fucked a signpost, so maybe that's all it was. Okay, probably there was more.
We ended up sitting down for another drink, and I think this is when I breached the subject and told him I was hot and bothered in not so many words. If I recall he said he wasn't sure or didn't really believe me (working me again, now I'm sure of it), so he asked me to kiss him (just like he asked me to go along with it and hold his hand, and go along with it and pretend I'm his boyfriend, yeah, he was working me). He asked me to kiss him, but not a quick peck; I think he said, "I don't believe you. If you're into this then kiss me for a least 20 seconds." So I did, we did. I've always been a big fan of making out, and really what's the big difference? Making out is making out. Sure some people are better kissers than others, but generally making out is making out. So we made out, it was no big deal. He was a fine kisser. I was horny, loving it, and practically creaming my pants; I wanted to get out of there with him and jump his bones and I told him that.
We made out some more and started thinking: your place, my place? He mentioned that he wished he was a little more prepared - he had some creams or something - looking back with a more experienced mind, he was probably taking about lubes, condoms, and that kind of thing. He didn't want to go back to his place (lived with his parents?) and I didn't want to go to mine (my brother and his girlfriend were there and I wasn't about to come out of the closet by waking them up via loud vigorous man on man sex), so we ended up finding a parking lot to "park".