After reading so many hot stories, I (24M) decided to finally share my own. This was during the summer of last year, a few weeks after I broke up with my ex-girlfriend. I was quite devastated about the break-up then and was looking for all the attention I could get. This is something that is quite hard with women, as I have dwarfism as the name suggests (this will be relevant later on). I've always been a bit bi-curious and had been enjoying a lot of femboy and trans porn then. So after a night drinking, I decided: "f- it, let's try Grindr". I had been experimenting with some toys already at that point (a small buttplug and a small dildo) so it was not like I was diving in head first, but I never had experiences with guys before.
There were a lot of creeps that really turned me off, until I got messaged by this 35 year old guy without a picture. In contrast to many others, he started a conversation interested in me and why I was on Grindr. This was a refreshing change of pace and I noticed I started fantasizing a bit already as he described how he looked. Naturally, this ended up with him sending a picture of his cock. My gods that cock was amazing: 18 cm long, girthy with a bit of a curve as well. I immediately got so turned on. We sexted a bit, we sent some nudes to each other and his complements were driving me insane. He told me my ass was so thick and that he would love to play with it. He described how much he loved rough sex (again, important detail for later). After a while of sexting, I told him I was a bit too drunk and that I really had to sleep.
The next morning he initiated the chat again and asked if I wanted to continue this sober. He again asked why I was here and what I was looking for. I told him my story, the details about my physical condition and that I kinda was just looking for my first hookup with a guy. I was super nervous to agree, but we decided to meet up and traded our snapchat. We sexted some more the upcoming week till out agreed time during the weekend.
I got on the train and was absolutely shaking but also so insanely horny. I went in plugged which also aroused me so much. He picked me up in his van from the station after which we drove to his house. He was as sweet in real life as through chat. He had everything prepared: a shower to prep myself, some toys in the shower to loosen my self up and tons of lube. He told me to take my time to get ready and that I should remember that whatever he does, if i feel uncomfortable I can say stop and he'd stop immediately.
I got nice and clean in the shower, reinserted my plug and entered his room naked. He was already laying there in bed, with a rock hard bulge in his underwear. I was warned, but still taken aback by his shift in demeanor. He just looked at me, started dirty talking and commanded me around. Things like "Now look at my little slutty toy" and "come show that ass for me little one". My god it was so hot to be degraded like that and for him to be so assertive. He was also certainly in the mood, as I was his bulge twitch as I showed my plugged ass. He commanded me to come over and suck his cock. I removed his underwear and it seemed even bigger than on the pictures. I remember that I started kissing it and licking his shaft, before he said "no like this" after which he proceeded to grab my head and force his cock down my throat. I am pretty sure I was already leaking at that point. After a good session of roleplay with me throating his cock (apparently I was a natural) and him fingering my ass, it was time for the real deal.
He pushed my head of his cock, picked me up and easily threw me on my stomach on his bed due to me being quite small. He quickly switched out of his dom mode to quickly ask me if I wanted him to use a condom. That small moment was the hottest thing ever for me. I told him I'd prefer that, so he put on the condom and went back into it. He commanded me to get on all fours and get ready for the fuck of my life. I was already quite loose from all the toys, but damn it was a bit uncomfortable when he put that massive rod in me doggy style. That discomfort quickly turned into pure bliss as he slowly kept fucking me, slowly increasing the speed. It felt like hours that we fucked (which was I believe 15-30 minutes though haha) and we tried tons of positions. Me on to, missionary and he even tried to pick me up to use me "as his personal cocksleeve". That last one was sadly a bit impractical, but damn the idea was hot.
After a while, I came from the anal and him jerking my cock so he stopped fucking me. He wanted me to finish him with his mouth, so he removed his condom and got ready. I gave him another blowjob until I felt his cock twitch in my mouth and his facial expression changed. I looked at him and he said I didn't need to swallow, which was my immediately cue to kept blowing him until he came in my mouth. Such a lovely feeling of that warm liquid in my mouth and his complete surprise when I swallowed it. After our encounter, he let me shower and brought me back to the train station.
For some reason, I've never gotten the courage (although I've also been a little strained on time) to meet up with a guy again (really hard to know when someone is safe/trustworthy). Sadly we didn't stay in touch either, but god I recently have been missing a cock and good fuck like that.