The world of the “ladyboy” is an interesting place and one I felt I needed to explore. We all know that transexuals exists and can vary from the Eddie Izzard’s of the community who simply like to wear womens pants on the weekend — through to women who have simply been unfortunate enough to be born with an extra bit of skin between their legs.
Thailand is the birthplace of “the ladyboy” and most ladyboys can be found outside the bars in the nightlife districts trying to bring punters in and buy them drinks. What is very hard to hard your head around once you are actually with a ladyboy in person is just how sexy they can be and this is coming from a red-blooded no-homo male. Yes, you will get the odd-one that looks like your plumber Barry with a bad weave, but generally most of the ladyboys try so hard to look feminine that they actually spend more time on their appearance than the “genuine” females.
I felt I had to “try it out” so got myself on Tinder to find myself a ladyboy to take out on an all expense paid date and hopefully during the date I can get a deeper understanding of who they are and learn more about the ladyboy world on a personal level…
It didn’t take long before I found my date called Jossy Berry who is a makeup-artist / blogger and works for a botox clinic in the day, not a “bar-girl” which I thought would make it more interesting. As you can see from the picture, she’s pretty hot, and after some small-talk we agreed to meet the following day at a fancy rooftop restaurant. I was actually quite excited for the date, but was also feeling a little bit deceitful in leading her on a bit, but I justified these thoughts by thinking it would be a good night for us both anyway and as long as she has fun, then who cares.
So the below, is what I wrote as soon as I got home from the “date” , enjoy… Tonight has for me been the most interesting time I have had so far during my travels in Thailand, so without further ado, I will go ahead and explain exactly what went down on my “date” with Jossy… In my opinion there are two types of ladyboys, those who simply likes to dress up in women’s clothes and use this as a career to make money, for many ladyboys who travel to Bangkok to make a living, this is more of an act than anything else.
Then, there are girls like Jossy, who I genuinely believe has simply been misfortunate enough to be born with a penis and is every bit a woman as anyone I have ever met , in-fact even more so in many cases.
She has obviously had her boobs done and has had a chin implant to help “round” the face as well as botox injections just under the ear every 6 months to give her a more feminine and softer jaw line, as you can tell from the pictures, it would be almost impossible to suspect that she was to put it bluntly a “man” in the physical sense. I actually feel a little bit dirty writing about the experience I had tonight with Jossy as after meeting her I don’t want to be openly discussing any private details about her, simply to protect her but I will take this opportunity to discuss the date and my thoughts about what happened during the evening.
So…It has been a really great night, let me get that out straight off the bat, but I have gone home feeling confused, not in my sexuality or anything like that but I have to keep reminding myself that the person who I have just spent the last few hours with having a pretty romantic dinner overlooking Bangkok in a fancy rooftop bar, has a penis..
I met Jossy at Siam station and we made our way to the restaurant and I have to say that I was a little taken aback as despite the filters on her Instagram profile she really was hot, more-so than many girls i’ve dated. Initially the conversation was a little bit stuttery as despite her English being very good I felt that she was a little shy so I was leading the conversation on the way to the restaurant.
What I have learnt abut Thai culture during my time in Thailand is that women in Thailand do not openly display much emotion in public, especially around “farang” men like myself as there is a stigma attached to it, girls like Jossy can be judged quickly from fellow Thais for essentially “selling themselves out”, if that makes sense. Public displays of affection are also a no-go and can be quite the turn off for anyone considering dating a Thai girl / ladyboy.
We made our way up to the rooftop terrace of “The Nest” in Bangkok which is a fairly exclusive restaurant in which we were given the VIP treatment of our own “bed” on a make shift sandy beach within a buzzing nightclub style atmosphere.
In the bed next to us was a middle aged European with a “girlfriend” half his age sipping on some Echo Falls wine, clearly he was new to the game of Thai dating and was all over her like a sweaty rash. She didn’t seem to mind though as he kept sending shots over throughout the night to keep her happy.
I wasn’t particularly hungry so I settled for a beef salad which despite me asking specifically to not have many chillies in , still blew my head off which meant that I spent most of my time trying not to appear like I was having some sort of chilli induced seizure, whilst picking off the chillies in my salad like inspector morse at a crime scene.
About halfway through the date I had to be honest with Jossy, I couldn’t keep up the lie and lead her on anymore, she is such a nice girl that I felt bad to think that she was essentially content for this website, so I revealed everything expecting a slap, but her reaction to me explaining this, completely surprised me..
Actually, Jossy felt happy for me more than anything and felt that the blog was a really good idea, after this Jossy opened up even more to me and went into a deep conversation about the mis-conceptions about ladyboys that people have, and how my experience with her and that fact I will write about it will hopefully help change the perception that many people have about, “chicks with dicks”.
We talked about her dating history, her previous boyfriends have all been straight, she sees herself as a woman in all senses, and lives like a lady even when she is at home alone watching TV. She is very open and honest about the fact she is a ladyboy and has no immediate-plans as yet to have the”chop”, but told me that it would be something she would consider in the future.
I know that nothing will ever happen sexually between me and Jossy, but by the end of the date I could have quite happily gone in for a kiss and felt fine about it, I think many men secretly would go with a ladyboy to try it out, I’ve seen in with my own eyes around the party strips, young straight guys walking off to hotel room with ladyboys and having great fun, but I doubt they would ever admit it. The will always be an “intrigue” to it, the other thing to remember is they probably have more experience in how to please a penis than their female competition.
So all-in-all the date was great, we both had fun and I would happily do it again, I think I was lucky to find Jossy to go on a date with rather than a working bar “ladyboy” as I think the experience would have been much different. I can’t recommend going out with a ladyboy enough, just give it a go – there is nothing “gay” about it trust me and you will have great time.