I got home from work after a really long day and sat down with a glass of wine to just chill. I wasn't planning to go on any hook ups, I was just surfing the sites to see what I could arrange for future dates, but then I got hit up by this very hot guy, a model, who also lived really close by (again my local hook up thing...) We chatted for a while online. At least an hour.
He’s only been with non trans boys before and wants to try fucking a pussy, said he's been fantasizing about it. He said it needs to be real discreet because his friends would make fun of him..... I said well you get that i'm a guy right, I look like a guy, he said yeah, that his friends however are asses sometimes.
He wanted me to come over in an hour which was way past my bedtime, but he convinced me so I hopped on my bike around 2am (I love biking late at night), I was there in five minutes. He was very hot in that stereotypical gay boy kind of way – big, muscular and toned, brown skin, tattoo across his chest.
This big, incredibly hot, muscular guy who could easily literally pick me up and toss me out the door if he wanted was scared. Petrified is probably a better word.
He kept chatting about random things, couldn't really look at me, he kept saying how nervous he was. It was actually very cute. I kept reassuring him that there was nothing to be nervous about.
I had to lead him to his bed - he lay back on it. He already had his shirt off. I sucked his nipples some. I asked him if he wanted me to take off my shirt (no top surgery) he said yeah. So I stripped and then pulled off his shorts and boxers. He was not hard yet so I sucked him off for a while, my lips stroking his cock, i felt him growing hard down my throat. He moaned. I stopped, slipped a condom over his cock and guided him into me slowly, he was not that big or thick i just wanted to enjoy the look on his face as he entered me - his eyes wide open watching me.
I rode him for a few minutes, slowly, loving his look of pleasure, and he told me he was gonna cum, after a few more strokes he shot into me. It was quick but hot.
Afterwards as I was getting dressed he thanked me and said it was "different" with this kind of confused expression on his face. I smiled because the way he said it was very cute - like he just didn't know what to think about what just happened. Then i hopped on my bike and was home in five. It all took less than an hour.
I texted him thanks and he texted back "Thanks bro, have a good nite."