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'Sooo I think you might like boys a little bit huh?' he said. 'Maybe' I said blushing, not sure what this meant for my sexuality and not really wanting to think about it. I just knew I was happy in the moment and wanted more. Now that sex was out and in the open, he started asking me more. What I like, what fantasies I had, what other boys I had crushes on at school, etc. He asked if I wanted to try fucking him, but I told him it didn’t' really interest me, that I very much prefer to take cock, not give it. I also told him how I loved how dominant he was, and it felt natural being more submissive.
We spent another hour or so just lying in bed naked and chatting before going at it again. This time he fucked me missionary first, with a pillow propped under my hips, my legs wrapped around him, and him passionately kissing me and slowly thrusting in and out of me. I'll never forget us being face to face, looking into his eyes as we moaned together as one. I wanted him to cum first this time, and when I felt he was getting close I told him I wanted to taste him.
He rolled over and ripped off the condom. I instantly was on him and swallowed him, choking as he pushed my head down and thrusted up simultaneously. It didn't take long before hearing his familiar roar and feeling ropes of cum fill my mouth. I wasn't sure how I would like it, if it was gonna taste nasty or good. It was amazing! After pumping a few times, he pulled out of my mouth, while I made sure I didn't spill a drop. Looking at him I smiled and swallowed; doing my best to mimic all the girls in porn I'd enviously seen swallow a load. He had me sit on the edge of the bed and then gave me my first blowjob; which again didn't last near as long as I had wanted until I flooded his mouth.
He swallowed, pushed me on my back onto the bed and laid on top of me, trading little kisses and giggling as I ran my hands through his hair. 'This was amazing and perfect' I said to him. We made a little more small talk before we realized his parents were going to be home soon and I better get going. Otherwise, we wouldn't be able to stop and would prob have them walking in on us as I was begging for more of his cum.
So that was how I lost my virginity. Sadly, not the moment I fully understood I was gay. Just that I liked boys, cock, and giving myself to them for their pleasure. It would take another 15 years before I fully understood that lesson. However, in the meantime that weekend, I spent daydreaming of Brendan and the next time he’d be inside me. That Monday at school I hung out with him in the band hall. Neither of us overtly doing any PDA or letting on what had happened. But from the looks and smiles of the girls in Brendan's group; they knew. Talking to one of them a few years later, she said it was written on both our faces. 'We all knew you two fucked' she said before adding in 'and it was about time, we were getting tired of him talking about you, and seeing you stare like a weirdo at him'.
Brendan and I would go on to hook up several more times before I left for college that summer. Word got out among a few other of the openly gay guys in the band, and I wound up in their beds as well. It was an open secret amongst Brendan and 3 other guys that I was open to hooking up. Brendan and I grew close and had amazing chemistry, even talked about dating for a minute. But I wasn't ready to come out, was going to college out of town, and not wanting a relationship. So we just kept it physical, and still to this day is some of the best sex I've ever had.
I did have sex with a girl before leaving town. She was in Brendan's friend group. I found out a few years later that Brendan had arranged it, saying he thought I should try having sex with a gal at least to help me decide which team I wanted to play for. I won't go into the details, but it was way way awkward. Seeing a naked girl just wasn't doing much for me, and frankly a vagina is nowhere near as attractive or pretty as a cock. Her response to Brendan after we slept together...'yeah, he's def gay and he's all yours'. If only it had been that easy and clear for me to understand.
I would continue hooking up with guys on occasion in college, mostly off Craigslist or a local gay bar. I met a few that ignited my love for lingerie and being feminine in the bedroom...opening up a sissy side of me that has never gone away (grown to overwhelming strengths tbh). But then the day came about 3 years ago that I met Aaron who cemented, showed me, and helped me understand what I am, what I need; and had a passionate love affair with. But that’s a story for another time!
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