I’ve never been attracted to ladyboys, but since going on sex vacations, I’ve told myself that I shouldn’t indiscriminately avoid all contact with them. If I met one somewhere and felt an attraction to or a connection with her, I should take the physical contact as far as I could stand. Besides, it’s likely the revulsion is a product of society instead of any sort of ingrained taste, and as I’ve matured and advanced my own sexual desires, I’ve grown more tolerant of the range of sexual desires that exist in the world.

If I had sex with a ladyboy, I wouldn’t feel judged by society. In fact, I may feel that anyone who judged me was not worth knowing. However, there is still the ick factor, and for whatever reason, it exists in me, it isn’t something I can will away, which is too bad as I’ve heard that ladyboys give the best service.

Tinder in Pattaya is simply a means of hooking up with freelancers, and there are lots of ladyboys, most of which are clearly identified. After all, it would do them no good to show up at a customer’s request and deal with an irate man upset that he wasn’t getting a pussy to fuck. “Top and Bottom” is a phrase I was introduced to which means they give as well as they get.

I spent hours in my first two days while jet-lagged browsing through the selection on Tinder and weeding out all the ladyboys. Of the girls that were left, most of them were very clear on their profiles they were freelancers only, having links to other social media and a statement that said: “100% lady, don’t ask me!” Mary’s profile was one of those that said 100% lady, but along with that contained an actual profile that talked like a girl looking for a husband.

“Looking tall and handsome,” and, “want man to take care of me,” were some of the phrases on her profile. Her pictures, well, they were beautiful. If her pictures had been on a profile in America, she’d have her selection of wealthy, handsome men.

When we matched and she began having a real conversation with me, instead of straight to “wanna fuck?” I suspected something was rotten in the state of Chon Buri, but while my sex tourist instincts were sounding alerts, there were some signs that she might be just a regular girl turning tricks on the side while looking for a man. First, her English was near perfect, and that seemed to back up her claim that she had come to Pattaya to be a teacher from the Philippines.

I worked out a strategy for when I chose to meet her. My first consideration was if she turned up and looked nothing like her pics. That would be easy, I’d just tell her to meet me in the lobby so I could turn her away without knowing which condo I was in. The second consideration was if she was a ladyboy. If she was, she’d certainly be a post-op, and figure she could pass for a lady completely. She probably couldn’t, but I figured if she looked like her pics, it would be worth the experience.

I was on the treadmill around 8 am when she messaged me, asking if I wanted to fuck her. At least now she was sounding more like a freelancer, and she caught me at the perfect time. After getting a price of 1,500 baht, I told her to come straight over and I finished my workout while waiting. When she messaged again she was pulling up to the condo. 

I ran down the stairs to the lobby just in time to see her walking up. There was no doubt it was the girl from the pictures. She looked ravishing. She looked so good, my instincts went on high alert again. The other shoe was bound to drop at some point.

She had slightly tanned fair Asian skin and wasn’t wearing any makeup. There were no pimples anywhere that I could see. She was wearing short white jean shorts showing off the same skinny gorgeous legs from her profile, and a green tank top exposing thin lady-like arms. Her boobs were certainly bigger than the average Asian, but I could not tell at that point if they were silicone. She had long flowing highlighted hair and smiled a mixed-race smile with big full lips that looked European.

When she spoke, she sounded like a lady, but I did pick up the slightest ladyboy twang. I began to figure that she was a post-op like I had suspected, but I still wasn’t 100% sure. Besides, I wanted to go through with it either way, so long as a dick didn’t pop out. I was 100% sure THAT wasn’t going to happen.

“Hi Nathan, it’s nice to meet you, I’m Mary,” she said as I showed her to the elevator. Her English was fluent, she may even have been able to speak it better than me and she had the distinctive educated Filipino accent I’d heard many times. Besides being a higher-level conversation, and even though I was looking intently for an Adam’s apple, the interaction seemed like any of the other interactions I’ve had with sex workers. She was comfortable, I was comfortable, nothing but two people about to go screw.

When we arrived at the condo, I offered her a drink and jumped in the shower. This is not something I’d recommend with a freelancer, but I had most everything locked up in the safe and anything else of value she could grab was in my closet which I could still see from the shower. While in the shower, I heard her go through a plastic bag from the Nike store that was still sitting on the floor by the door. I guess she thought something new might still be in it, she’d be wrong, it was just my trash bag. In any event, I took my shower in a flash before she got any better ideas.

We chatted for a while about her time as a teacher in Thailand and where she was from in the Philippines. I was making a bit of a connection with her, that only deepened when she said, “I never thought I’d become a hooker.” She didn’t seem new to the business, but like many other girls found it an easy way to make a living while in between gigs.

“Can I have my money?” she asked.

I had nearly forgotten my previous worries when she asked this question, but they came rushing back. When asked for the money upfront, I’m always worried there will be some reason I may not want to pay afterward, but since the price was only 1,500 baht which I probably would pay just not wanting to cause a scene, I ponied it up.

“Ok, are you ready?” she asked. Yes, yes, I’m always ready!

At this point, I was still not convinced she was a ladyboy. There were a few inconclusive hints, but when she took off her top, leaving her shorts on and crawled into bed, and I was exposed to a perfect set of silicone implants, I became convinced… I was about to have a sexual encounter with a post-op ladyboy that I had already paid. Oh well, I might as well dive in. I sucked on those tits while she pushed my head in for several minutes and as I pulled her nipples as deep in my throat as I could, she began to moan an indisputable ladyboy whine.

“Honey, do you have condom?” she asked.

I jumped up to open the closet while she got up and headed for her purse and took her shorts off. Of course, I wanted to see the shorts come off. In the back of my mind, I was still a little afraid a dick would pop out, though if it did, she’d be the most feminine ladyboy I’d ever seen.

I never saw a dick, but things got real when I saw her butt. It was not a feminine butt, it was an Asian man ass, just like all the ones I’d seen in Asian porn. A perfect lady upper body, a perfect set of legs, a perfect face, and then there was this Asian dude ass. Somebody should have told her to do squats. I began to get a little nervous and wasn’t sure I’d be able to go through with it, but the sight didn’t last long. She knew to hide her backside. She turned around quickly and applied lubricant to a big, but normal-looking vagina, at least as normal as I could make out in the dim light.

The blowjob was great, just as it should be from a ladyboy. It was my first, but I’d heard about them from many other sex tourists. Ladyboys give the best blowjobs and I’d have to agree with it, and that’s even despite that she did it with a condom on. “I’m a safety girl,” she said, and never backed off even in the face my strong objections. If I had it to do over again, I would have told her to finish with the blowjob, but I suppose then I wouldn’t have had this experience to tell.

When she climbed on top, I got a better look at her vagina. It was huge! There was a long slit running from deep between her legs all the way to the front. There was no clit, it was all lips and I couldn’t even make out a hole where she was going to put my dick. At the front of the vagina, I could make out a scar, obviously where her previous plumbing had been removed. I couldn’t help but point it out and lean in closer for a better a look.

“Oh yea, I had an ovarian cyst when I was younger,” she said—a statement she had prepared.

All I could do was laugh, I didn’t even realize she still believed I thought she was a woman – or born a woman to be more precise. In respect to her, everything about her except a man-butt and a strangely shaped pussy was very feminine, and to a total naïve man, she might have actually passed off the ovarian surgery explanation.

“Sure. Just bear with me, this is my first time,” I said.

“What? Do you think I’m a ladyboy?’ she asked.

“It’s ok, I’m ok with it,” I said.

“I’m not ladyboy! I’m lady!” she said.

It should have been me who was insulted. I’d decided before she even came that should this scenario play out, I was going to go on with it, but I would have much preferred to be able to discuss it. I had questions I wanted to ask. However, with the nervousness that already existed and being completely new to the situation gave me pause and instead I just said, “Ok, let’s flip.”

Seeing her body stretch out on the bed helped with my feelings of manhood. I thought she was a truly beautiful creature I was about to fuck, what does it matter if she used to be a man? I mounted myself on my arms and positioned my dick to enter her as she grabbed it and helped to coerce it in. It was tight! By God, it was tight. It didn’t even feel like a hole that was possible to enter. I definitely wasn’t trying to enter an ass, her legs were almost flat on the bed, this crafted pussy had the strength of a vice grip.

“I didn’t have sex all day yesterday, you are my first customer for two days,” she said.

I smiled at yet another lame excuse. Sorry girl, real pussies just don’t work like that.

“Ok, push,” she said after half a minute of trying to work my dick inside. That’s what I did, I pushed. I put all my weight on my erect penis and it didn’t go anywhere.

“Ouch, wait wait wait.”

I was becoming amused at the situation and the thought hit me that if she was a real girl, I’d have hit the jackpot.

She repositioned my dick a little more and commanded that I push again. This time, my dick found the target and my entire shaft slid inside between two walls of solid cartilage.

“Oh, that’s the way, honey, fuck me!”

I had indeed found “the way,” and I proceeded to pound that manufactured pussy as hard as I could. I didn’t feel any need to hold back. At that point, the genuine ladyboy wail made another appearance, and I realized I was fucking my first transsexual – or lady that was once a man – or just fuck it, who cares about labels? I looked at the lady below me… beautiful. Then, I leaned in to suck on her tongue.

“Oh no, honey, I don’t kiss on the mouth,” she said.

Well, this girl was acting as much like a stuck-up female hooker as I’d ever been with. Oh well, I just got back to plowing her. Though I was very turned on by the idea of adding to my sex inventory, between being lied to and now denied so simple a thing as a kiss on the lips, I was ready to bust my nut and be done with it.

As I thrust deeper into her, I tried various tactics to see if I could cause her any type of discomfort. I’d very my angle a bit, pull out slowly and then pound back in as hard as I could, but nothing seemed to bring out any kind of pain in her. In fact, her pussy was loosening up. The vice grip that felt like two bones squeezing my dick at first now felt more like two filled balloons. One thing is for sure, this self-expanding pussy could never pass for the real thing. I wondered if the doctor that did her was one of the best or if she merely looked for the best deal.

After I finished and pulled out, she bounded up towards the bathroom giving me another peek at the Asian man butt. That was truly a hideous sight, she got everything right except that.

“Oh, I love fucking!” she said.

“How long have you been a freelancer?” I asked.

“Two months, since I broke up with my boyfriend,” she replied.

I got the story she met a Japanese man while teaching, that took her on vacations in Thailand and spoiled her to death. I guess she got used to the good lifestyle and decided to take up hooking. I believed her that she came to Thailand to teach. She was obviously well-educated.

“I think you should tell your customers the truth, you will get yourself into trouble someday,” I said.

“What do you mean?” she asked.

“Never mind,” I answered.

I wondered if she was in denial about it. Did she want to forget that she was ever a man, or did she simply feel it would be less profitable to admit to being a post-op? I’m sure it is way less profitable to be a post-op ladyboy. She really isn’t a girl, but definitely not a man either. Many men have an attraction to ladyboys with dicks. I don’t fully understand that desire… but those men don’t go for post-ops, and men who like girls would just rather find a girl that had always been a girl.

You can find some sympathy for post-op’s, like a person born of parents from two different races, who are limited to choosing partners from tolerant individuals. A post-op will be attracted to heterosexual men but will be limited to those men who will be attracted to her despite her post-op status, and never because of it.

After she got dressed, I asked her to turn around so I could lift her shirt and check out her ass in her shorts. It looked like a sexy girl’s ass, just like some girls who wear clothes well but look terrible when their fat flops out.

“Wait, I will walk you to the elevator,” I said to her as I looked around for my headphones. I was planning to finish the workout that I interrupted to meet her. Looking back, there was an awkwardness in her demeanor as I fumbled about the condo searching for where I had laid them down.

At the time, I only thought her as impatient and told her she could go. It took a couple of minutes for me to realize the most likely location of my headphones: in her purse. I assume since she couldn’t find anything of value to steal, she simply grabbed whatever was laying around. I had not included them among items that needed to be locked up while I was in the shower.

I ran out of the condo and towards the elevator, with all the speed I could muster, but by the time I got to the lobby and outside the building, she was gone. She must have had a driver waiting for her, as there was no way she could have ran out through security without being stopped to ask what all the rush was about. The security of the condo will stop lone Thai girls but tends to let vehicles in and out without much fuss.

So, my first ladyboy pay-for-sex experience went down in the manner they are often described: liars, cheats, and thieves. Despite having the experience mostly under control, I spent the rest of the day in a state of depression. I felt like I was scammed with being lied to about her ladyboy status, and even though I knew the truth from the start, I don’t enjoy being played.

By itself, that may not have affected me, but when my headphones were stolen, it made me feel like a total mark, and though being a sex tourist means I must put up with being marked occasionally, it isn’t very common anymore for me to feel actually taken advantage of.

The headphones weren’t expensive, but they fit me well when walking, and even in the States, I have trouble finding ones that fit. I replaced them with a pair that didn’t really fit at all.

Never, ever, leave a freelancer alone in your room.