My miserable first time with a Man

NSFWStory about ‘straight’ boy going gay

So I'm 26... Several month ago I had my first real-life experience with a man. Looking back, it’s something I learned a lot from — mostly about listening to my intuition and respecting my own boundaries.

At the time, I was curious, excited, maybe a little too horny, and I posted an ad on a local site. A guy replied quickly with a very nice dick pic that made my mouth water. We exchanged a few texts, and I decided to meet him. I got ready, took a shower, and drove almost ninety minutes to get there.
When I arrived, he wasn’t there. He let me wait twenty minutes, I already thought he wouldn't come. When he finally showed up and brought me to his apartment the place was a nightmare, dirty everywhere, and the atmosphere made me tense up immediately. First thing he did was he pouring himself a full glas of vodka and lit a cigarette, even though he knew I didn’t smoke.
Despite all that, I tried to go along with it, striped down, finally hold my first dick and played with it. However I wasn't really feeling sucking it... He then turned me around and groped my ass and even though that was exactly what I wanted I felt dirty and not comfortable at all. He continiued licking my hole for quite some time and it felt great but with everything else I wasn't getting in a mood to enjoy it. When he put on gloves and startet fingering me very fast I tensed up and that hurt so much but I endured it... hoping to feel that dick. After I dont know how long... maybe just 5 minutes, maybe 30 he was done fingering my ass he tried to push his dick in, without a condom although I clearly said I wasn’t okay with that. But it hurt way to much since he was very thick. So I finally managed to just ask him to stop after several tries and left.

I drove back home feeling disappointed, shaken, and honestly a bit ashamed, even though I shouldn’t have been.

I just want to share this as an bad example and to raise awareness to be carefull in who to meet up with even though you want to feel the first time getting fucked.

But now I'm back again.. thinking about sucking dick and hoping to be fucked some time (soon), feeling the cum hitting my face or my back, feeling it filling me up. I hope the ones looking forward to that as well won't get discouraged but rather motivated to look for someone nice to enjoy it with even though it might take a little longer.

Posted Dec 7, 2025, 11:44 PM UTC

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