Your First Sex Experience With a Thai Ladyboy

Your First Sex Experience With a Thai Ladyboy

Having sex with a Thai ladyboy for the first time is likely to fill you with a mix of nervousness and excitement. For most heterosexual males it can be a rather anxious occasion. If you’re a heterosexual male who has had no sexual experience with another male, you are going into whole new territory and are likely to have a lot of concerns.

While your fantasies may already be running wild, your actual comfort zone may not quite be on the same page, so it’s important you meet the right person and in the right situation.

Meeting the Right Ladyboy

The kind of ladyboy you meet, her stage of transition, and where you meet her can have a significant influence of the kind of first experience you have.

Femboy Vs Post-op Vs Pre-op

For some a lot of the nerves of a first sexual encounter will revolve around the sights, smells and touch of another body that wasn’t born genetically female.

When taking a femboy or ladyboy who has had no real operations, only hormone treatment, you may find yourself making love to a body that is somewhat more male than female. For some that may be a large part of the thrill and excitement, while for others it may take them too far from their comfort zone and not fit the fantasy they had in mind.

Typically, femboys will dress, act, and even smell feminine, but they may well have a more masculine figure, with no hips and little or no breasts, and they may even have some hair on their legs and even stubble on their face.

Meeting a post-op will typically mean finding a far more feminine figure and lessen the likelihood they will have any or much bodily hair or facial hair. They may even have a much more feminine voice and mannerisms, and in some case it could be almost impossible to tell that they are a ladyboy rather than a female.

However, the big difference is that they still have a penis. For some first timers there’s a fascination to touch and enjoy a ladyboy’s penis for the first time, while for others there’s a need to take it much slower and even ignore that part of a ladyboy’s body. It all comes down to personal desires and your level of comfort.

The third option is to meet a post-op ladyboy. In most cases you’ll find post-op ladyboys to have a high level of femininity and female like behavior, with often one of the only clues that they are not true females being that they are simply too beautiful. While this may be a better option for super nervous newbies, for many ladyboy lovers a post-op doesn’t seem like a ladyboy at all (more a lady with a man-made vagina), and almost doesn’t  count as being your first ladyboy sexual experience.

Bar girls Vs Escorts Vs dating sites

Your encounter will also depend greatly on the attitude and experience of the ladyboy you meet.

Meeting a ladyboy from a beer bar or gogo will mean having someone who is likely to be experienced in the bedroom, but a lot can depend on their mood and attitude. It’s hard to describe a typical attitude as they can vary greatly between sweat and lovable, to jaded and disrespectful.

However, meeting a ladyboy in a bar means you have the time to judge for yourself, and it’s important to find someone you have good chemistry with. It is also worth telling them that it’s your first time and even discussing what you want to happen – that may sound like a bit of a passion killer, but it can be quite the opposite, as most Thai ladyboy bar girls love meeting first timers and feel happier knowing what you want and how to please you.

Taking an escort is a slightly different experience. If it’s your first time this can instantly take away any nerves to do with discretion or danger, however there is some risk that the chemistry might not be there. A good escort agency will want to know that it is your first time and what you would like to happen, and then they’ll do everything they can to supply the right ladyboy and prepare her correctly. It’s fair to say that this is a pretty safe bet for having a good first experience, albeit a rather expensive one.

Meeting a ladyboy on a dating site is a bit of a different scenario altogether. Typically, meeting a ladyboy online means you’ll have plenty of time to talk and get to know each other before hand, and even discuss the fact it is your first time and what you imagine will happen. You may even get a good sense of whether the chemistry is right, but ultimately, all this close and open talk will leave things in the realms of relationship territory and cause some form of commitment; if you’re just looking for a sexual experience you have the freedom to walk away from after, this isn’t your best option.

Relax and Enjoy

I’ve mentioned the word chemistry a few times in this article and that really is the key to having a good first experience. Having sex with a ladyboy for the first time isn’t something you have to do, and if you set things up correctly you have the freedom to back out at any time you want. However, this should be something you really want to do and so it’s up to you to put yourself in the right situation with the right person.

Once in that right situation with that right person, take it slowly, explore the boundaries of your sexuality and try to edge out of your comfort zone if you can, and then go and have a mind blowing experience you’ll smile about for years to come.

Posted on Gods of Thailand March 4, 2015 in


Kal is known as the Ladyboy Guru of Thailand. In addition to this article, Kal will be sharing his Ladyboy advice and expertise every week on Gods of Thailand. Click here to sign up for our Ladyboy Newsletter and get these updates emailed directly to you in real time.

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  • Dee says:

    My first experience was what I thought was a woman. And after getting pleasured, I felt like I should reciprocate, that’s when I found it was a ladyboy. At first, I would only touch it, just out of obligation. But found a penis is actually fascinating. I ended up with it in my mouth, and not out of obligation.

    The second one pressured for anal. That was a step too far for me, and it ended badly with me not doing it. I was still new and feeling that some things were too “Gay.” I’ve still never done it, but wish I was less offended, and her not as pushy. I needed a patient one. I could be talked into it now with a patient one.

  • JulioC says:

    Thanks for this good article. I’m not a newbie regarding Ladyboys, but it will be my first time in Bankgok next september? I wonder if there is any kind of “personal” tour guide thru the good ladyboys areas, bars around Bangkok.

  • Weng says:

    You’ve made a mistake and have written post-op twice, the first time I suspect was in reference to pre-op ladyboys.


  • TexasJeff says:

    Well written and you make excellent points. One thing I might add. I have several TV lovers in the U.S. I guess they are somewhere between a femboy and a ladyboy, i.e. beautiful, nice bodies, but no boobs. After several experiences, I discovered an interesting fact. At first, they are nervous about you reaction to their penis, even if they can hide their anxiety. But once I had ‘paid attention’ to their ‘junk’ they became wonderful, enthusiastic top and bottom lovers.

    This may be a cultural difference, I don’t know. I’ve never been with a Thai femboy or ladyboy (yet!) From what you’ve written I will be on guard for different reactions from them.

    Thanks again.

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