This Is How I Fucked A Ladyboy (On Purpose)

As y’all know, Thailand is full of a rather odd kind of human beings. They’re usually called ladyboys, also known as shemales, trannies, chicks with dicks, and some more creative terms.

They are dudes (this is the first and last time I’ll say this, cause really, it’s kinda gross if you think about it), but they feel like they’re chicks, so they look like chicks, but they still have their… assets. I think they’re usually gay, but wild ladyboys have been seen banging girls – srsly, search the internet for it some time, it’s kinda fun to watch.

Anyway. I was in Thailand on a business trip (wink, more like a vacation) and I had taken refuge in a normal bar in downtown Pattaya, one of the biggest cities in the country. I was just minding my own business, having a drink, looking at hookers hitting on foreigners and trying to kick them away from myself. I succeeded quite nicely, until a really cute – uhm – not-so-much girl sat down next to me. She (I’ll call it “she”, I bet she would have liked that) didn’t say a word, so I reckoned she wasn’t after my money. I said hi and we ended up having a really nice talk about Thailand, sex tourism and work. I bought her a couple of drinks and we got legitimately tipsy. I really wanted to know whether she was actualy a girl, so I decided to ask her, having already accepted the fact that she probably wasn’t. She grabbed my hand and stuffed it under her dress. They were clearly a ladyboy.

Do I care, I asked myself? Some part of me did, another didn’t. I decided to jump right in and if I really got freaked out, I could always just apologize and leave. Now before I explain my next move, remember she absolutely looked like a girl, and a very, very hot one, too. Beautiful eyes, a crazy hot body and fake, but huge boobs. So… I kissed her. My hand was still kind of touching her dick and I kissed her. She joined me and shit got fairly passionate. When I told her I wanted to fuck her, she stood up, grabbed my hand and took me outside. We took a cab and drove to my hotel, kissing and touching the entire trip. As we had made it to my room, she immediately undressed and sat down on the bed. Her dick was hanging down and she wiggled her ass at me. I raincoated myself, stood behind her…

I alternated between nearly shooting my load inside her and jumping out the window out of pure shame.

…and had a huge WTF moment. I mean really. She started stroking herself, leaving me with the strangest view I’ve ever had. A girl-ish creature, fully naked, yanking on a 7 inch rod and waiting for me to fuck her ass. She started begging me to get to it. I thought about videotaping everything, but I couldn’t do that to future me. So I grabbed her hips, pointed my dick at her asshole and slid the tip in. She moaned, so I figured she liked it. Then I went in all the way. I was surprised by how easily it went down the rabbit hole, trying not to think about the other guys having stretched her out.

I kept thinking weird thoughts all the way through. The one that kept coming back was “Dude, what the hell are you doing”, but there were also ones like “Hmm I better go slow before I cum too early” and “Are you kidding me? You’re never gonna be able to cum”. I alternated between nearly shooting my load inside her and jumping out the window out of pure shame. I did manage to keep myself alive, though.

At some point, “What the hell!” changed into “Oh, what the hell”. I couldn’t be grossed out by myself any more anyway, so I thought: might as well get it over with. I even grabbed her dick and started jerking it off. It took her not more than 30 seconds to get rock hard and shoot her load on the bed. My mind was blown, but I kept fucking her, encouraged by her cumming all over the place. When I got really close, I pulled out and turned her body around. I sat down on her belly and started jerking really fast. Her boobs helped me pretty well, and so did her face. Now it just looked like I was about to cum all over a cute little asian girl again.

Kthxbye, don’t forget your panties, maybe we’ll meet again some time.

And that, sir, is exactly what I did. About seven or eight bursts of the dirtiest cum I had ever produced, landing on her boobs and her face. She laughed and cleaned her nose, then smiled a very cute and satisfied smile. Needless to say, I immediately felt regret and wanted to slowly and painfully kill myself, but I also felt pretty good about what had happened. If she can pretend she’s a girl, I figured, I can pretend I’m fucking a girl, right? Just pretend she’s on her period or something, so anal is the only option, and go with it. After I realized that, I felt amazing (I had just had quite an intense orgasm, remember). I thought about offering her to be a top, but I all my brain cells knew that would be a bit too much. So I just sent her away. Kthxbye, don’t forget your panties, maybe we’ll meet again some time. Which didn’t happen cause I obviously didn’t go back to that same bar ever again, but still.

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