My first time with a ladyboy

Ask any guy whose played around in Thailand for a while and they’ll tell you about the allure of ladyboys. Well not all of them. Oddly there seem to be only two main reactions to the ever present kathoey: adoration or outright hatred. Rarely do you find anyone in the middle in my experience.

Maybe it’s odd then that I was right in the middle for years. I never thought too much about ladyboys one way or another. I heard people joke about shemales when I was younger but that was about it. The first experience I ever had with ladyboys was when I used my roommate’s computer years ago in the middle of the night. Guess what was on his screen when I knocked the screensaver off? A video of a transgender Brazilian with big fake tits and tanlines riding a cock. It didn’t turn me off or disgust me but I must admit I was a little transfixed at her cock rotating at high speeds in circles like a little turbo prop as I spent 30 seconds or so watching it.

My next experiences with ladyboys came when I actually visited Thailand a few years later. I heard unsolicited advice from old hands about “how to spot a ladyboy” and avoid them. On the other hand, lots of Thai guys I met strongly recommended that I let a ladyboy suck me off because they are supposedly the best. I pretty much ignored both since I never had any problem identifying ladyboys and had no interest in getting sucked off by one either.

Over the years and many visits I passed many ladyboys in the streets, hanging out in front of bars on streets like Pattaya’s Soi 6 and often working normal jobs at shopping malls and coffee shops (including the Starbucks on Second Road in Pattaya which hires an inordinate number of ladyboys). I chatted a few up here and there. That’s about it.

Then one day when I walked passed the two ladyboy massage parlors on Sukhumvit between Soi 5 and Soi 7 for the umpteenth time, I decided to stop in. Maybe it was because I just blew my fourth load of the day at Dr BJ’s blowjob bar but I wanted to try something new even though I was pretty much out of spunk.

I don’t remember if it was Mantra or the place next to it but I finally gave in to the calls by the big breasted ladyboys outside to come inside for a massage. The ground floor was like a barbershop but no one was getting their hair cut. Chairs will filled with newspapers and blankets. An old Thai lady sat in one of the chairs. The ladyboy who led me in by the hand took me up some stairs to a room that was small but private with a bed on the floor.

She told me to take my clothes off and wait for her. So I did. When she returned I got my first real glimpse of her. She was taller than most Thais but shorter than me. Her face looked womanly but her hands and feet were big. She was obviously a ladyboy but not obviously a man with fake tits, if that makes any sense.

I laid face down on the bed butt naked and she started giving me something resembling a massage. We made some small talk then she asked me what I wanted to do. I told her I was drained but I’d like to watch her cum. I don’t know why this came to mind but it seemed like the easiest “service” to suggest since I couldn’t conjure up another load and I certainly didn’t want to get anything up my ass. She asked a few more times if I was sure that’s all I wanted. I said yes and we agreed on 500 Baht ($14) after some friendly negotiation starting with some sky high number she pulled out of nowhere. I understand that she’d want to save up her loads for big spenders who want to get banged but I wasn’t going to pay more than I would for a handjob or blowjob elsewhere since I wouldn’t even be getting off.

She got naked and laid down on her back. She was feminine to an extent but her body had certain manly features. Besides the big hands and feet her upper arms and legs were a bit too toned. She was no Joe Piscopo but she was no soft and lovely lady either. Her tits looked great to me. I don’t care about real or fake but I like perky and firm. I was never much into saggy tits barring one fetish bender I went on fucking adventurous MILFs. Her cock was pretty damn big and to my surprise stiff as a board. I’d heard rumors that most ladyboys have trouble getting full wood because of the hormones they take. At least in this case that was proven totally wrong.

Up to that point I guess it would be the most “adventurous” thing I’d done depending on who you ask. It didn’t exactly get me going but I must admit it was a little fun. About half way through the ten minute jack off I even started playing with her tits. It was then that I realized that they looked better than they felt. When women get fake tits they usually still have some natural meat in their hooters so while they feel firm they don’t feel like hard coconut shells. These felt like concrete. What’s worse was that I distinctly felt a little stubble in the middle of her chest where hair was starting to grow back, presumably after a shave.

I started to snap back into reality just as my new ladyboy friend shot a big thick white load all over herself, including her phony fun bags. It was a spectacle to say the least. She laid there naked and recovering for a while and we had a chat that was actually pretty decent. I guess that was only possible because the testosterone was totally absent since both of us were totally drained of the poison semen that makes people born with male chromosomes act like fools in pursuit of sexual gratification.

She eventually cleaned herself up and we both got dressed. I gave her the agreed 500 Baht tip in the room than paid another 500 Baht for the massage on the way out. Then I got a sandwich at the Subway on the corner and headed home with another experience under my belt.

Okay, so I didn’t really try having sex with a ladyboy. Well not that time. The experience stayed in my head for a while and somehow started to grow on me. I developed the acquired taste and went over to the dark side or the fun side depending on how you look at it. I A little later I went the whole way but I’ll have to save the story of me butt fucking a ladyboy for another post and many others to follow. This is after all the basis of this entire website. Stay tuned!