I gave my first hand + blow job to a middle aged man I had just met in his car in the middle of the night when I was 22

So I went through yet another quick and fast ended relationship with an ex girlfriend and had just moved to a new area far away from most of friends and family right after college so decided hey ya know what maybe I’ll take things slow and experiment just a little bit, ease u to things.

Well anyways I started innocently just watching some gay porn being definitely into it but then discovering cross dress and sissy femme content and was excited and intrigued even more. After lots of more time passing next few weeks I couldn’t get enough. So I bought my first dildo, I bought my first femme outfit at a good will far outta town. I took pictures (of course later purged all this shortly after but as I’m sure you guessed I came back to it all eventually) and was just honestly having a very sexy (and kinda wholesome?) blast exploring and focusing on myself and playing with toys with myself and stuff!

But… as my title suggests, and I’m sure many many of you maybe have felt a similar feeling before, one night all the excitement caught up to me and I wanted something even more exciting and real. I wanted to please a man for the first time in my life, and after getting so excited I couldn’t help myself. I downloaded grindr made a still very private account just bio and no face pic. I didn’t even know what I was doing or who I was looking for until eventually one account messaged me that piqued my interest enough to actually push forward and respond.

He was an older man, maybe middle aged? He’s single but also on the DL has a few frequent friends with benefits he’s explored with. He was swooning me and getting me so excited talking about all the things he’s tried with toys and group play and it was very exciting.

Eventually he offered an initially meeting, that same very night, just to chat first face to face before meeting in the future to have some further fun. I was shaking my cock was leaking and I wasn’t even dressed femme (was just one tiny step too much for me at that very point in my journey haha but I wanted to). So I agreed knowing full well that he never said anything about sex or expectations, that I wanted him. I had never touched another man’s cock before I hadn’t even come to terms yet with my sexuality fully. But that made it all more exciting.

Anyways I’m very nervous he can tell as he picks me up late at night. He’s nice and genuinely comforting, promises nothing is expected and I trusted that. Didn’t make me any less nervous though haha! But we chat for a bit driving down empty city roads til we get to a large empty parking lot. He parks and talks about how he’s a dom I suppose in the local area lgbtq community or circle. He’s just a dom who plays a lot essentially. He started asking me things I’m interested in and he would tell stories and explain things. It was hot.

Maybe a little too hot though because even though we were just talking and I wasn’t touching myself, a precum stain became forming on my crotch and while the darkness of the area helped a bit, eventually it became impossible to not notice on my beige pants, and he saw.

We both nervous giggled and to be honest for my first irl encounter playing with a man I have massive respect for how he felt. So much so I told him I was extremely horny and wanted to jerk him off and he of course said yes.

It was huge. I mean BWC. Circumcised, smooth too I mean smooth. I was a bit shocked. Regardless he relaxed and I started stroking, I had no idea what I was doing but I figured it out fast I was eager. Eventually I started spitting and using two hands but realized my spit wasn’t enough lube. He was big and circumcised and needed lubrication, and spit wasn’t going to cover it, so, I went down opened my mouth and licked. Then sucked. And I have to tell you, loved the smooth textured, loved the taste of cock. He was very well groomed to be fair maybe that helped.

I kept going and going and he told me after 10 minutes or so he was going to cum so while the thought crossed my mind to swallow I knew I was getting ahead of myself and not ready for that so I instead stopped sucking and finished him off with my hands. And wow his loads were thick and big. All over my hands I was just speechless.

He thanked me and we drove back to drop me off. Thing was he only had a few spare napkins in his (actually very clean) car but it wasn’t enough to get all the cum off my hand, seriously. I pretended I did just so I didn’t come across weird or I dunno make a scene and was still processing the fact I just had my first gay experience.

But the drive was short and eventually he got to the spot a few blocks away from my apartment to drop me off (was and still am closeted so I told him to do that). This was in the dead of winter, and I had cum dripping down my hand and freezing on me too. In public. At must be 2AM small city sidewalk.

I got back home washed the other cum off, collapsed in bed, touched myself maybe for at most 20 seconds and before I physically got fully hard I just came, not thick necessarily but definitely big big shots of cum. I passed out I was so tired covered in my own cum. Woke up the next day and we’ll it’s been a sexuality exploring journey ever since :)