Around 19 or 20, I had been finally getting the courage up to go to gay meeting spots. Back then (early 90s), there was 1 gay club in a 20 miles radius-but at least it was only about 7 miles from home. I had been in the parking lot a few times, which was a cruising spot of course. I never had the nerve to go in because I figured I was bound to see someone I knew with it being the only gay club in miles. I was way, way in the closet-only very recently having broken up with my girlfriend of 4 years. These were very paranoid, anxiety filled rides through the lot. But wanting to get out of the depression of the breakup gave me the (strong) desire to finally be with a man. The first several meetings were all so sexy and hot to a young me-all me giving oral to older men in their cars. I was loving it.
Eventually a man invited me back to his apartment. It wasn't far and I was anxious to take the next step down this path. After some fun foreplay it came to the big moment. Was I ready/prepared to actually let a man fuck me? Was this the path I wanted to go on in life?
I was smart enough to realize this wasn't a phase. I had switched to masturbating almost exclusively to men for a while now, even before the breakup.(Again, harder to do before the internet!) Despite trying-really trying, it hurt way to much and I went home feeling like "I'm not up to being gay". I continued to meet guys and found that I was the submissive all the time. Being the first to go down, asking for cum on my face, etc. But, hurt too much to actually have sex-UNTIL...Driving through lot one Saturday night the inevitable happened...I made eye contact with someone I knew! Luckily not someone my family or friends knew though. He was the barista at the bookstore coffee shop I lived near. I was a coffee addict so I saw him often. A good looking Afro-American guy about 3 years or so older than me,We both gave each other the knowing look of "oh-you're here too?Who knew?" We talked a bit-"i didn't know you were..." etc. Then he asked me back to his place. Just about a mile away. I agreed. We went into his apartment. There was a tv on in the other room.
" That's my room mate, he's asleep by now."
I felt a little weird but followed him into his bedroom. We kissed. Feeling weird about it at first because a day earlier we only said hi to each other if I bought coffee. Now I'm kissing him and unbuckling his pants. We rolled around in bed giving each other amazing oral and he asked if I was a top or a bottom...
"Well, I'm a bottom in training! I want that sooo bad but so far I can't get it in."
He said he'd go slow and had lube and he'd stop whenever I said.
I was kind of standing and leaning over the bed. It hurt as usual-burning actually, but we were having such a good time and he was being as gentle as I needed him to be, that we kept going.
or What happened next was the greatest sexual moment of my life. So much so I'm writing about it now. The burning pain got overcome by a wave or a rush of ecstasy. The pleasure actually washed out the pain. The greatest feeling I've ever had. I learned how to fuck that night. I became gay that night. The playing around before was practice. If there was any confusion left, I realized now I loved men. I realized now I loved being totally submissive. I realized I found the total purpose for me during sex is to bottom.
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