My First Time Sex With A Thai Ladyboy

Last updated: December 11th, 2018 | in Ladyboys

At home everyone tells you to be careful with Thai girls especially those that are “too beautiful” to be true. Be careful with what? Well of course the main reason why I’m coming to Thailand (and most other guys I know) are not the beaches which are more beautiful in other countries like Australia or Brazil or the spicy food on the side of the road that I tried to avoid after my first week here. The main reason for any of my trips to Thailand is sex and plenty of it.

Until recently I was not even thinking about having sex with a Thai ladyboy, when out in the bars looking for a hook up I was always trying to figure out ways to spot the difference between Thai girl and ladyboy. Until recently? Well yes, I did it. And not even by accident. After thinking about it for quite a while I thought I write it all down and share it with you guys here. I’m sure a lot of people at least think about trying it out just like me but they don’t really know how to go about it and what to expect. So here we go.

Already from at home I booked my hotel in Bangkok online: I decided to stay at the infamous Nana Hotel for a couple of nights before heading down to Pattaya. I have never seen a place like this. I’m not talking about the rooms which are pretty standard and actually a great deal. No what I mean is it almost makes you feel like in a short time hotel you can basically sit in the lobby and watch foreigners walking in and out with the ladies every two or three minutes. The hotel is located on Sukhumvit Soi 4. Some call it “the city’s beer bar capital” but it’s most famous for being home of Nana Plaza, a three storey building packed with Go Go Bars – and literally right opposite the Nana Hotel.

So on my first evening back in town I went to Nana Plaza at around 8:30 pm – just about the perfect time since most guys are sticking to the beer bars and the 80 Baht a beer happy hour and at the Go Go’s in Nana Plaza most of the staff is already there while the bars are just about to get filled up with the male customers means you have like the full range of girls to choose from.

Ladyboys BangkokI was walking around the complex and it wasn’t so easy to make up my choice as there are just so many bars and the girls were stunning hot and tempting simply everywhere. After ten minutes or so I just thought ok let’s try that one, went in and ordered a beer. However soon I knew that I wasn’t going to take anyone out from there, the girls were more average looking on a closer sight, not really enjoying dancing on stage and the one girl I liked and paid two tequila lady drinks went back dancing before sitting down next to a Japanese guy. I left that place after paying my bill of 500 Baht including some minor tip.

Somewhat disappointed but still in mood for getting laid I started looking at other Go Go Bars. In front of some place on the second floor a fairly slim and tall (around 1.75m) stunning blonde and busty chick started to hug me and whispering “Why are you so handsome” in my ears while uninhibitedly grabbing in between my legs. I was like oh my god and told her “Why are you so sexy” before putting my hands down on her… dick. Dick! She was a ladyboy! I ran into a ladyboy and would have never noticed it by just looking at her. Somewhat embarrassed I said ohh, thank you it’s ok see you naa.. and went off the scene.

While continuing my walk around Nana Plaza, a new thought started popping up on my mind again and again: Why not just trying out sex with a ladyboy? Might be a freaking awesome experience – she was stunning hot and I might regret it later if I didn’t do it. I think it was more or less spontaneous and intuitive that I was suddenly turning around and walking back to the spot I left five minutes ago.

My ladyboy was still standing in front of the bar together with some of her friends and my reappearance put a charming and sexy smile on her face. I asked her for her short time price expectation and after some negotiation we agreed on 1,000 Baht plus 700 Baht for the bar fine and 350 Baht for the rental of a short time room on the top floor of Nana Plaza. Altogether 2,050 Baht – not too bad I thought for this hot Go Go Ladyboy and I didn’t have to spend any more on lady drinks.

Sex With A Thai LadyboySo I handed her the bar fine which she brought inside and after getting her handbag and putting on some more make up we walked hand in hand up the stairs to the top floor where the short time places are found. The atmosphere here was completely different to the bustling scene of the bars on the storeys below, very quiet and there were absolutely no people around. I was really excited by then. We entered the place and found a woman sitting somewhat bored on her desk that I paid the 350 Baht for the room.

We moved on and into the room that wasn’t very spacious but it was clean and had a nice Queen Size Bed with a couple of towels as well as a pack of two condoms on it. I closed the door and without wasting anymore time I put my hands on her beautiful big and firm boobs while kissing her cheek. She started giggling while massaging my dick. We undressed each another and went to the small enclosed bathroom where we took a shower, rubbing on one another with lots of soap. This was also when I first saw her penis which was pretty small like the one of a 13 year old. Her balls hairy and more like that of an adult though.

After finishing our shower and drying each other off we went over to the bed. We started touching each other. Once again I had to start with her amazing boobs but soon I felt doing something completely new, weird and exciting at the same time: I went down with my hand and started masturbating her penis. It didn’t take long for it to stand up and become tight and my ladyboy started moaning, firmly grabbing my shoulder. I got horny by that and got a boner as well.

After a while I was just about to go on to the next part when she put her hand on mine saying “Go on baby I’m coming’. I sped up my movements and so she did moaning even louder and soon after she got her orgasm. She hopped out of the bed and went to the bathroom to clean herself up again.

Now it was my turn. I lay down on my back and my ladyboy started sucking my dick. It felt amazing. She did it without using her hands. It felt so good I had to ask her for small breaks to avoid coming too quickly. After a while I felt like now it was time for the real sex and I told her that I wanted to fuck her.

She put on the condom on my dick, applied some baby oil that she had in her handbag and started to passionately riding on me while I was squeezing her boobs. Her small cock was clapping on my belly. She didn’t break and since her anus was quite tight it didn’t take long until I couldn’t hold it back anymore. Now it was me moaning loudly while cumming in her.

I stayed in her for a short while and looked at her beautiful body before we both went to the bathroom again for another shower. We dried each other off, got dressed and I handed my ladyboy her love reward of 1,000 Baht. We walked back to the go go bar where I gave her another kiss on her cheek before I left. I was so glad I had the guts to try sex with a Thai ladyboy – and I knew it shouldn’t be a once in a lifetime experience.

After arriving in Pattaya a couple of days later I felt like doing it again. But instead of spending another 2,000 Baht for buying a ladyboy in a bar I tried a different way that many of my friends recommended me. I signed up for that Online Dating Site and wrote a message to some random attractive ladyboy in town. Since she was online at the same time it didn’t take two minutes until I received her reply and after some standard small talk I asked her if she wants to meet for some dinner. She said she was too lazy now to go outside and if I wanted to watch a movie at her place instead. Two hours later I’ve had sex with my second ladyboy in Thailand.

It’s really that easy and I did it not just in Pattaya but also when I returned to Bangkok, the site has ladyboys looking to have some fun with foreigners simply everywhere. Are they asking for money? Yes some do but it’s never more than 1,000 Baht. Some just say “up to you” and I give them 500. I still like Thai girls for girlfriends but once in a while it’s just super exciting and fun to have sex with a Thai ladyboy especially what I found most Thai girls have sex primarily to please the guys whereas the ladyboys seem to really enjoy it.

Guest Post by Martin Gilchner

31 Responses

  • Sahil gupta says:

    Amazing man .You are right its best when your partner enjoys the act as much as you do.I have never had sex with a lady boy but after reading your story I will definitely do so

  • Bauer says:

    Can you write more stories like this?

  • Steve says:

    Lived in Chiang Mai almost five years now and dated many ladyboys and had sex with all of them. With the exception of one, they were all versatile, or we fucked each other. Ladyboys are sexy, sensual and can really do what it takes to please a man, and the ones I know aren’t whores, they work in various jobs just like everyone else.
    The ones I’m dating now, one is a lawyer, another is a secretary and the other works in a large shop. They are nice people who work very hard, and play hard too..!
    I’m mostly bottom and love sucking a cock, who doesn’t like a good blow job..? Am I gay, who cares, I like what I do and really enjoy a bareback dick filling my butt up with come or getting a mouthful…
    After years of straight sex, these past five years have made up for 30 so so ones with chicks..

  • Jamie says:

    Tried it for the first time in Pattaya. Cute 21 year old ladyboy. Very gentle and passionate. Rock hard cock. Let her fuck my ass then cum in my mouth. Sweet creamy cum was nice. Had second helping the next afternoon. Never thought l’d let a ladyboy cum in my mouth but would do it again. Overall nice experience and will go tp Pattaya next time as the selection is good.

  • Tom says:

    I had sex with a ladyboy in Thailand when on a rugby tour last year. We did New Zealand, Australia, Thailand and Indonesia. Went out with the boys one night to a few bars and we got hammered. I have always considered myself straight, but damn, some of those ladyboys are attractive. We got chatting to three of them and eventually me and two of the lads took them back to the hotel, our better judgement impaired and overwhelmed by their looks and dirty talk. We each went to our room with one ladyboy. First we took a quick shower, and she got some condoms and lube out her purse. In my mind I was going to dominate her as though she were my gf, but what actually happened took me by surprise. She started sucking me, and reluctantly I started sucking her – never touched another penis other than my own before. She started rubbing my bum with some lube and maaaan, it felt good. Before I knew it, she’d slipped a condom on and was gently pushing her cock against my bum. I was so everwhelmed by the sensation she just went ahead and pushed in. I have never felt such intense pleasure, and it’s the most amazing sex I’ve ever had, even though my dick was limp for most of it. Will do it again in a heartbeat.

    • Matt Duncan says:

      I totally relate to that. You haven’t lived until you’ve been topped by a ladyboy. I’m straight but it’s mindblowing. I love it

      • Armand says:

        Rofl, gotta love guys who like to take it up the ass but continue to tell themselves they are straight haha

        • FourOwls says:

          I am not sure I quite get this….bit confusing, but I think it simply part of the excitement and trying something new…from something that looks like a girl.

  • Jack says:

    First time I got with a ladyboy I turned it into a special occasion and after many dozens of hours setting it up and planning everything I found an escort who met everything I was looking for and booked her a week. Best week of my life. She was waiting for me at the airport and before we got to my condo in Pattaya she insisted we stop and eat a big meal first because she “want to fuck [me] long time.” Well, she wasn’t kidding. We literally had sex for 13 hours straight, slept for a long time, then woke up and went into ~10 more hours before I insisted we finally take a break and go get some food. The rest of the week was half sex half hanging out. The girl was a total sex freak she had me tie a magic wand to her dick and turn it on for over an hour while she convulsed and screamed like she was being electrocuted. For those who haven’t done this I tried it for 10 seconds at most and had her stop because it was wayyyy too intense. She was an amazing person too. Totally unreal experience and no regrets.

  • Dave says:

    I live in Chiang Mai and have been lucky enough to have quite a few ladyboys, two I could have very easily have considered girlfriends, both wonderful people, good hearts and very kind, plus awesome in bed. I still see maybe two new ladyboys a month, even though I am in a straight relationship with a Thai woman, she knows ands accepts how much I enjoy being bottom and sucking, so we just don’t talk about it. She doesn’t care about sex much anyways, and understands I need a good ass pounding and mouthfuls of come. I consider myself bi sexual, it doesn’t matter, whoever turns you on and makes you happy sex wise is okay..

  • Robert says:

    I have been with several ladyboys and I must admit I found them to be more involved with the sex act then there genetic girl counter parts. I do not consider myself gay even when I suck there lovely cock or bottom for them. Ladyboys just happen to have an enormous clit that demands attention from men.

    • CB says:

      Wow, your mind is very twisted. Since when is a genetic man having sex with another, what you describe? And maybe you are not gay….do you still fuck women? If so, you are bi sexual. Just deal with it but above all, be honest with yourself.

  • Crash69 says:

    Hi bros,

    Great article. I read every post. I am traveling to BKK for the first time in Feb for 5 nights. I have always been attracted to girls but have been hit on by many guys too. I signed up for Thai friendly and my first 3 hits were from LBs. one was super cute.

    I’ve been doing my research for the trip, but until now, I have been thinking of only girls to sexcapade with. You all may have changed my mind. The videos and pics on the web got me aroused. And now this article might persuade me just enough to try it with an LB.

    Thanks for the inspiration.


    • John Dean says:

      Crash. Dont think i am gay but the best orgasms i ever have are with ladyboy. Especially when being drilled.

      • Jac Dupuis says:

        They have a dick, but they’re not into gay guys. My best sex so far has been with ladyboys and I’ve been fucked by them as well. Gay? I don’t care. Sex is about pleasuring your partner, and some ladyboys are versatile, which I prefer.

  • Andrew says:

    Has anyone tried a post op lady boy?

  • Anthony says:

    Great write up! It echoes my experiences well.

    The ladyboys that I’ve been with have all been keen as, they like fucking just as much as us guys.

    One guy asked if we consider us to be gay or bi… myself, I just consider it as I don’t give a fuck what the label is… it’s just a great time. Don’t think too much about it and what others may want to label me or perceive me as.

    Some times after a good romp I even take them out for a cold drink at Mc Donald’s for example. Had some good conversations… nice to get to know them as well.

    Enjoy the world. ;-)

  • James says:

    IMO real women were put on this earth to procreate. Ladyboys exists to pleasure men. Once you’ve been with one you’ll know exactly what I’m saying

  • Jack says:

    Great post. I would love to do this, especially helpmg that tiny LB cock get release while she goes down on me. I think it transcends labels, that is: it is sex, nothing more, nothing less.

  • donkey55555 says:

    You guys that had sex with the ladyboys. Do you consider yourself Bi sexual or gay?

  • Horny ultraman says:

    I had a fantastic massage and pounding with a Pinay ladyboy in Malaysia . She massaged my rectum until my prostate leaked mil then she pumped me bareback with her thick mushroom cock head so good . Oh we also did 69 for half an hour before the pounding .

    • JayZ says:

      FWIW, I had a similar experience with a male masseur, because I was curious to feel how good of a blowjib by a guy could be. Excellent two hour nude massage, and while he was working my shoulders I could feel his erection on my head. I lifted my head up and held it first, then licked the shaft, and ended up taking a cock in my mouth. Surprised at how easy it fit (!), and although I gagged a bit I enjoyed it. Didn’t let him CIM but that got him excited enough that he gave me an outstanding prostate massage and blowjob with CIM finish.

      At one point I told him that maybe I could try taking him up my butt, but his “professional opinion” was that I was too tight.

      Haven’t repeated but am now curious about going with a ladyboy.

  • JC Rezonna says:

    Had sex with a (Japanese) ladyboy for the first time, yesterday. Very pretty, great kisser, and I must say the feeling of my cock in a tight, sexy butthole was as intense and pleasureable as any sexual experience I’ve ever had.

    • James says:

      You are now addicted to ladyboys my friend. I was the same way fantasizing about sex with a hot ladyboy. Then when it finally happened, I was instantly addicted. They give the best head. It feels so good in their tight ass. They love sex as much as us men, and often are the ones that want it more. Watching a ladyboy cum while fucking her is so hot!

  • Chris says:

    Great article. My experience is more with Filipino ladyboys. I agree with what John says although my experience with Filipino lbs is they tend to like it bareback.

  • John says:

    Sounds like a great time.

    One thing if I may offer as a recommendation…Baby oil is not condom compatible. Meaning it makes condoms loose their integrity and therefore may allow disease to spread more easily. So the suggestion is to only use water based lubricants.

    BTW – Nice site. I’m enjoying the reads.