My Experiences With Pattaya Ladyboys

Written by: The Pretender

December 19th, 2012

13 min read

Original published URL:


Dear Stickman Readers,

I have recently returned from a solo holiday in Pattaya and this is my story of engaging with ladyboy prostitutes.

You see – despite considering myself to be 100% heterosexual, as far back as I can remember, I have always wanted to f@#$ a ladyboy. On Sunday, November 25th, 2012, at the age of 33 in a short time room close to Walking Street in Pattaya I finally achieved my goal. I can't remember her name but I do remember the experience. It was one of the best sexual experiences of my life. She was 27 years old, extremely attractive and very feminine in appearance and manner. I met her on Walking Street at the bar next to Linda Bar. At first I was very nervous as this was my first time in Pattaya and my first time speaking to a Thai ladyboy. After she called out to me I walked over and started talking to her. I found her to be very pleasant to talk to even given her broken English so I sat down at the bar and ordered myself and her a drink. She told me how handsome, fit, well dressed and how young I was compared to the other guys in Pattaya and I could see in her eyes that she was genuinely attracted to me physically. After a few minutes of conversation and flirting she asked if I had ever kissed a ladyboy before and I said no. She then kissed me and it felt just like kissing a woman. She started talking dirty to me and told me how horny she was and that my subtle resistance to her charms was making her crazy with anticipation. She grabbed my hand and put it on her crotch. She was erect. She really was attracted to me. It was the first cock I had ever touched other than my own. I ordered another drink and mulled over in my mind whether or not I was going to have sex with this ladyboy. All sorts of things went through my mind as I had heard all the stories about the ladyboys in Thailand. Can I trust this person? Will she rob me? Could she have an STD or be HIV positive? What would my friends, family or work colleagues back home say if they could see me talking to this individual? As I finished my drink I thought 'f@#$ it – who gives a shit what other people think of me – I'm attracted to this person and I want to and I am going to have sex with her'. And with that I looked into her eyes and told her I am attracted to her and I wanted to go to a short time room and do all the dirty things she kept telling me she wanted to do with and to me. I paid her bar fine of 500 baht and she lead me down a soi off Walking Street where there was a short time room. She directed me to pay 200 baht for the room and we went inside. We showered together and I looked at her naked for the first time. It was an extreme turn on for me as I saw this beautiful and feminine person who also had a cock. Sexually, let's just say that we both experienced each other completely. It was quite different to having sex with a woman. This was much more full on, dirty and exciting. She was very affectionate and we kissed passionately and deeply. It was exciting because we both knew just by looking into each others eyes what we wanted and for the first time in my life I was with someone who knew exactly what I wanted as a man and gave exactly that to me and vice versa. It was like having sex with a woman who is as horny, open-minded and dirty sexually as a man. Her smell did not turn me off at all. I was worried about this being a factor as a woman's smell is important in turning a guy on in general and I thought this would be an issue but it wasn't really.

I paid her 1,000 baht for short time which was 500 baht less than she said that she usually asks for because she said that she really wanted to f@#$ me as she was so attracted to me physically. I gave her a 200 baht tip because the sex was so great. After we left the room I thanked her, we both hugged and gave each other a kiss. She then gave me the traditional Thai wai which I also gave her in return. We looked into each other's eyes, smiled at each other and then I turned and walked off. I went back to the Pattaya Beer Garden to have a drink and think about my experience. I could not stop smiling as I recalled my first sexual experience with a Thai ladyboy. It was far better than anything I had ever imagined. Certainly better than any of the female partners I have had in my life and I have had a lot of them over my 33 years. As I sat there I realised that this experience had changed me in a deep and profound way. How could I go back home and go on dates with biological women and put up with the nagging, complaining, bitching and all the rest of the crap that we men have to put up with in the west just to receive a bit of sex which is mostly bad quality sex and less frequent sex over time at that. I knew that I would never be the same again and that I had ruined myself for future dates with women back home. Many thoughts went through my head about my future. After I finished my beer I knew exactly what I needed to do – at least for the short term – I knew what I needed to do whilst here in Pattaya – of that I was damn sure:

My job was to f@#$ as many ladyboys as possible!

The next 2 weeks were an orgy of unbelievably mind bending, hot (but safe) sex with ladyboys and the occasional woman. Walking Street became boring after only a few nights. Soi 6 was where I needed to go I was told as it was the place where the hardcore sexpats hang out. The first time I experienced Soi 6 I loved it. That place has the dirtiest, filthiest, most wantonly aggressive ladyboy prostitutes that I have ever encountered. It made Walking Street a tame tourist hang out by comparison. The short time rooms had stains on the carpets, stains on the walls, were grotty and filthy and the showers and bathroom were shared and I saw other people naked and walking around casually just as they saw me naked and I didn't care even a little. f@#$ that place was exciting! The experience of walking down Soi 6, and the alleyway to the side was very, very exciting. As I walked along women and ladyboys would approach me and tell me that they wanted me to f@#$ them or they wanted to f@#$ me. It felt so dirty and so sleazy to walk down Soi 6 and in particular down the alleyway at the side. Here I was – a tall, very well dressed, young, fit and muscular, 6'2" ex fitness model farang flying solo and didn't the prostitutes respond – calling out "handsome man", "oooiiii", grabbing my hand, grabbing my crotch, grabbing my arse or grabbing my arms trying to pull me into a bar. These were not half hearted calls like I heard them make to the older guys. These women really did want me as well as my money. The ladyboys were the most aggressive. One would come up to me in front and 2 others from the side. All wanting me to f@#$ them. This was so exciting – I knew I had finally arrived in paradise! For 2 weeks, every second night I was here, sometimes one night after the other, walking up and down, engaging with these "ladies" of the night, drinking in the bars, going upstairs for short time encounters and generally enjoying everything that the Soi 6 ladyboys had to offer. Here I was – this highly educated farang engaging in things I was raised never to do. Things that back home would have my family, my friends and my work colleagues shocked and appalled and lead to me being ostracised and labelled a disgrace. Things that left me excited and wanting more, more, MORE!

I am a highly visual person and I remember intimately every sexual encounter I had with each and every ladyboy. One of them had the most beautiful face I had ever seen. She was 21 years old. The sex with her was absolutely incredible. To stare at her beautiful face and into her eyes as we enjoyed each other's company was a privilege and an unforgettable experience. I was on a MASSIVE high after having sex with her. Another ladyboy was beautiful physically and personality wise and I enjoyed our 15 minute conversation after we had finished having sex. Another had the body of a supermodel but with tattoos and she was very submissive and kept saying 'yes darling this and yes darling that'. She was so excited when I f@#$ed her up the arse.

All up I had sex with eight ladyboys and 2 women. It was a f@#$ing great experience! I cannot wait to get back to Pattaya to experience it again. I knew from my Stickman readings how addictive it would be. I have read every article on Stickman and I used those articles to develop my own personal "Rules of Engagement" whilst in Pattaya which are essentially a distillation of all the experiences from Stickman writers of what to do and what not to do. These rules were essentially to protect myself from the bar girls and very importantly – to protect myself from myself. Rules like never giving out my contact details to bar girls, not establishing a long term romantic relationship with any of them, not sending them money from back home, not frequenting the same bar, not allowing the girls to take photos of me or me of them and so on. My rules protected me very well and came in very handy but before I left I was very worried about my hard and fast rule 1 which stated "ALWAYS REMEMBER – I AM ENGAGING IN AN ADDICTIVE ACTIVITY – DON'T DO IT EVERY NIGHT". After living through this experience, and doing it mostly every 2nd night so as not to break my rule, I can categorically say that this lifestyle is absolutely addictive. I can completely understand why western men love it so much. Despite the fact that I was having sex with women as well as ladyboys – the underlying cause of it being so addictive is biological of course – men have evolved to have sex with as many different beautiful women as possible. I now know that yes – even if that beautiful woman has a cock – it is still exciting as you still having a sexual experience with a beautiful looking individual who looks physically like a woman. For me it was even more exciting given these ladyboys will say and do pretty much anything and are not lazy bitches in bed like most women. She is up for it at the same level as me as a man and that is a huge turn on. She is not using sex as a reward or any of the crap that women use to control men back in the west. Yes she is in it for the money but she can still be attracted to you if she likes you. Didn't I know this after my 2 week holiday! I was very popular amongst the local ladyboy population. I treated my partners with respect, they treated me with respect. I conducted myself honestly with them. I did and said all the things I would say back home when meeting an individual for the first time. Respect is a two way street and the ladies of the night I engaged with seemed extremely pleased that I treated them so well, paid them a fair price and appreciated that I didn't lie or promise them anything else. All I asked was that we have a great sexual experience together and 80% of the time I found my partners were attracted to me physically and we did have great sexual experiences.

For the record – I have never had sex with a man before back home ever in my life neither do I plan on ever doing this. I am not attracted to men at all physically. Does this experience with Thai ladyboys make me gay? Who knows – maybe – probably in some people's minds and certainly in others. Personally I really don't care. I am going to continue f@#$ing ladyboys every chance I get when I am in Pattaya and if that makes me gay then so be it. I don't care if my close friends make fun of me for it. I told them straight up – it was the best sex I have ever had. Period. Some were shocked. Others smiled and told me they "always knew I was a dirty c*nt". Will I tell any future female partners that I have had sex with ladyboys? Maybe not – because the women here in the west – every woman I have ever met and ever been involved with would not understand nor tolerate this. I will however be responsible and I will ensure that I have safe sex and get tested for both STDs and HIV on a regular basis. I could not live with the thought of infecting a partner through no fault of their own. It is highly likely now that I have experienced Thailand and sex with Thai women and ladyboys that I have ruined myself for relationships with women here in the west anyway and will stay living alone and if that is the case and my lot in life never to marry – so be that as well! The women I were with in the past getting the better part of the deal anyway.

Here is a warning to you Stickman readers who might want to follow my path. Getting home after an experience like this is like coming off drugs. It has been without doubt a very unpleasant withdrawal experience over the last 10 days and I know that the withdrawal is not over. I am in real trouble here: I will need to keep going back again and again to Pattaya to get my fix.

I read somewhere that a man hasn't truly arrived in Thailand until he has had sex with a ladyboy.

Gentlemen – The Pretender has arrived!


Stickman's thoughts:

The other half has joked with me on occasions never to have sex with a ladyboy – not that the idea has ever entered my mind. What she says – and what I have heard a number of Thais say – is that sex with ladyboys can be very addictive and once you've gone down that path it is hard to go back…