A Tale of Two Ladyboy Stories from Pattaya

Ladyboys in Pattaya can be quite fascinating and we all wonder how it feels to date them. Perhaps any straight man wouldn’t want to think of doing it or if that person seems to be the adventurous type – this might be a fantasy for them one way or the other.

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I have collected some ladyboy stories from men who have just recently come back from Thailand and had encounters with ladyboys sexually.

This is a guest post and not written by the blog author.

I am not writing this to judge people who have dated or wanting to date ladyboys. I am just writing to tell you two of my ladyboy stories. Most men that I have heard who have already tried it, says that it is very addictive and the experience will change you.

Story 1

Strolling down Walking Street in Pattaya at around night time could be time well spent for someone who is traveling solo.

The lights and music will not bore you to death, even on a Sunday night. Then I saw this really beautiful girl who is about 27 years of age. She asked me to come over and we started talking after I ordered drinks for both of us. She was really nice and despite her broken English, I could tell that she was really interested and attracted to me.


Until eventually, our conversation started to get really dirty. She took my hand and put it into her crotch and could tell that she was already turned on.

At the back of my mind, I was really nervous thinking of what would happen but at the same time, the feeling excites me. Being a first timer, a lot of things are running through my mind –such as what would be people say back home if they knew that I had sex with a ladyboy, or is this someone whom I can trust or what if she robs me or will I get infected, etc.

It would surely be a different story to tell, but who cares? I took one last swig from my beer and then pay her bar fine of 500 baht. We went straight into the nearby room that accommodates short time stay which costs about 200 baht and we went inside.

We showered together and I got the chance to look at her beautiful, slender and feminine person who had a cock, but that did not put me off instead I got more turned on.

We kissed and made out in the shower and the kiss was more passionate and affectionate. This was my first time and it was really dirty which I doubt I could ever experience having with a girl back home.

As soon as we were finished, I paid her 1,000 baht for the short time and bid goodbye to each other. I went to a beer garden to have a drink and I smiled as I recall my first ever experience with a ladyboy.

My 2nd story

Men who have been to Pattaya have definitely got a lot of ladyboy stories to tell, especially when travelling solo. But this is wicked and definitely the dirtiest I have ever encountered. Soi 6 in Pattaya is the hardcore of them all. If you think that Walking Street is dirty, then Soi 6 is ranked 20 out of 10 sleazy.

Ladyboy prostitutes are more aggressive that any man would think that they are hungry for cock and of course, money. It is like walking in paradise! This is like the haven for hardcore sexpats. The rooms are sleazy and dirty as there were stains in the carpet, walls, etc. and you can see a lot of people walking around the hallway naked without a care in the world.

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This is a place where imagination is your limit. You can have sex with just about anyone in Pattaya. Ladyboys and women are all lined up just to have sex with you.

This is the best experience I ever had with someone or everyone in bed. Everyone, I meant orgy fest. I would definitely want to go back. I would never hesitate to hook up with another ladyboy if I get another chance. But of course, I will make sure that I get tested on a regular basis to make sure I am safe. When I go back to Pattaya, I am sure that I will have good tale to add to my collection of ladyboy stories.

These ladyboy stories are definitely something that goes beyond your imagination. These men are living their fantasy. It is like being on a high after you had sex with a ladyboy.

Does it make you gay if you slept with a ladyboy? I am not sure and these foreign men do not care either! What they know is that it is the best sex experience they’ve had. This is something that they won’t be able to get from real girls back home. Unless they want something in return, but the frequency tends to decrease over time.


If you are interested with hooking up with a ladyboy, there are also dating sites where you can go to such as Thai Friendly. You can be able to choose and check out their photos to see if they are someone that you prefer. You can find thousands of women and ladyboys who would like to hook up with you from these sites. Perhaps, when you find one you can share the experience.

If you're thinking about moving to Thailand and need help or advice, check out my Online Nomad Group by clicking here.
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