I live in a small town, relative to the big picture, but it's the biggest and only city in my country. I'd known about this sexy little spanish crossdresser for a while, I had been interested, I had been turned on, I wanted her so bad. But I was hesitant. Is this really me? What does it say about me if I fuck some guy? I had gone to see her I think only once to get a blowjob, so we'd met before.

She is a short and petite, Spanish slut. Always dresses up so well, with makeup and a wig. She's so convincing, just what I want.

One friday night I was terribly horny. The weather outside was really bad, snow storm and dark. I messaged her on the dating website and we made arrangements to meet that night, I had a knot in my stomach from excitement and nerves. I felt like I was taking some step that you could not turn back from.

All of a sudden my doorbell rings, it was my best friend coming for a surprise drop-by. Not totally out of the blue, we live close to each other and we like to hang out. I message my crossdresser "Sorry baby, my friend just came over and we're going to hang out", I'm sure she thought I was bailing or got cold feet.

Me and my friend sit around for a few hours, drinking whiskey and beers, shooting the shit. I never mentioned my plans to him, I was embarrased, I was ashamed. Now it's getting close to midnight, and we're both quite drunk, my friend needs to get home to his wife and get some sleep. His kids will be up early, and taking care of them at that age is relentless work.

I messaged my crossdresser again "I'm free now" and she tells me where to go. It was like a 5 minute walk from my place, well that's convenient. With the alcohol in me, I have less qualms about the whole thing. I know what I'm going over there for, so I get naked and dress in the winter clothes, protective pants and a warm jumper and head over there.

She's dressed to the nines, in very sexy and slutty underwear. I sit down on the couch and she starts sucking my dick. I can tell you that this little slut is one of the best cocksuckers I have ever met in my life. It's like mana for her, the more she can suck dick the better. After a while I ask her "Do you have condoms?" I was beyond horny and I wanted to fuck, screw the prejudice and what people may or may not think. I need to pound that ass.

She gets on all fours in front of a mirror, and I slide into her ass. "OOOOHHHH .... OOOWWWWW" she moans from the pain as I slide my thick cock in her ass. As soon as I am inside her I just start pounding away. I'm having a great time, I fishhook her mouth with both hands and fuck her relentlessly until I can't take it any more and explode in her ass. I collapse on the couch, and she removes the condom and starts sucking my dick again. What a slut, I love this.

We say our goodbyes and I walk back home in the storm. I felt guilty. What have I done? I cheated on my girlfirend with some crossdresser, what's wrong with you? But the overwhelming feeling was "God damn it, that was so hot! I should have stayed longer to fuck her again".

This was the firsst of many, many times that I fucked this sexy crossdresser. She might be my favourite fuckhole of all time. This was 11 years ago today, and since then I have fucked her so many times. At that time I'd always message her after I'd been out for drinks, to drop by and dump my load in her slutty little ass. Every time I've broken up with someone, she's my go-to cumdump. I've cheated on many partners to fuck this little crossdresser, and I don't regret a single time I have done so. She is a legend where I live. Hundreds, if not thousands of men have fucked her. She is a well known slut that can take cock for hours, and I love her for that.