I watched a lot of tranny porn because I've always was fascinated by them. To me they're females with dicks. I'm not attracted to men so i never head any sexual encounter with a man. I like too look at trannies with big dicks but never even seen one in person.

So i'm on this dating website and me and this chick are talking. I ask her if we can meet up. She said ok and we met up at this hotel. She's brownskin, skinny and small titties.

She ask me what I like to get into sexually and asked if I'm a top or bottom. Since this was my first experience with a tranny I told her I was a bottom. I also lied and told her this wasn't my first time bottoming. Anyways, we get naked(she kept her bra on) and she started nibbling on my nipples. then she got lotion and rubbed it on my asshole and her dick. She then tried to penetrate..

THAT SHIT HURT LIKE A MOTHERFUCKA!!!!!!!

For one, it hurt so bad she couldn't even put it all the way in. She only put the head in. Every time she ask if i wanted her to stop I said yes. She's about 7 inches. I was like "Let me suck you off" then she told me that she doesn't cum from head often so i said nevermind. Regular girth(maybe SLIGHTLY thicker).

Also I was nervous a little. I couldn't get fully hard. I only made it to 75%.

Overall I liked it but i was TOO painful. None of us busted. She could only get the head in before i said "stop". Maybe next time i should just suck the girls dick and top her. I don't know if my asshole can take a dick.