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Hi Everyone! I€™d like to talk today about my first experience dating and having sex with a cabaret ladyboy dancer on ko tao island. It was a positive experience and I€™m already looking for another lady to date haha.
About me: 21yo entrepreneur living in Bangkok Thailand for 1.5 years now. Consider myself completely straight, had sex with 18 girls in my life (17 thais 1 korean, yep got the yellow fever, big time), overall open minded and outgoing.
Seeing 2~ normal girls atm while going out regularly to get new girls at route 66 RCA and also from online dating (thai friendly). I never paid for sex in my life, although I€™d consider it if she€™s super hot. Funny note: Every girl I€™ve fucked was on the first day I met her, within 2-4 hours, so I guess I give a player vibe to girls and not a provider.
So my family came to visit me in Bangkok, and we decided to go to ko tao island after 1 week in lovely Bangkok. I was there last year when I turned 20 and learned how to scuba dive.
As we got there I looked up tinder and tried to get a date, found a 35yo Russian girl and met her for a drink but she was very cold and boring (Russians have a tendency like that from my limited experience). I saw a lot of hot tourists on Tinder but they didn€™t seem to swipe right on me, sadface lol. I also saw a lot of sexy ladyboys promising a €œfun time and intense experience€ but I didn€™t give it much thought and declined. Didn€™t feel like going to parties and looking to find drunk tourists as well. I love dating locals.
Then we went to a cabaret show in ko tao, it€™s every day 22:30, and I was kind of blown away. I saw the show last year and loved it as well, but I wasn€™t comfortable enough back then in my sexuality and in general to do something with a ladyboy. I love tall skinny girls so I was naturally attracted to them but I was quite intimated by these ladies of the night and their aggressive behavior.
I was very attracted to 2 of them, and found myself considering to do something about it, yet I wasn€™t willing to initiate anything.
Before the show ends the girls select 4 hot guys from the crowd and take them backstage for one last show, they undress their shirt put a wig and make them dance onstage to the song €œsexy and I know it€ haha.
I wasn€™t interested in performing, I actually did it last year, got quite some likes on facebook but to be honest I was afraid of going backstage again with a ladyboy away from sight.
Meanwhile they selected 3 guys and I was starting to relax. Suddenly a tall 1.76m beautiful ladyboy invited me, and my heart raced a bit. I hid my nervousness and went backstage with her, where I acted very direct, held eye contact, and let her put my hands on her tits while squeezing them, she was then quite surprised and said meet me later after show, lol talk about direct.
I told her you€™re said beautiful but I€™m very shy. Don€™t be shy was her response, I was still skeptical though, I then gave her my LINE and went to the stage with everyone, and proceeded to dance with everyone in a drunk way. My parents and brothers told me I was the best dancer except for some random gay guy that went on stage without being invited. Oh well
I went home with my family telling my brothers (not parents) about what happened and that I was considering meeting her. They were quite shocked but they knew I like trying new things so they were cool with it.
I was quite scared at this point to be honest, I didn€™t mind her dick or giving her a handjob or fucking her in the ass, I was just afraid of getting raped or forced to have sex in my ass, which I€™m still quite afraid of. You see these girls are very feminine but if the guy side of them comes out they can kick my ass for sure.
In hindsight though that girl was very sweet and I could trust her.
She texted me hello after she was done but I didn€™t reply, I was intimidated and not ready yet. Her profile pic on line was also not pretty. I then spent the next day scuba diving and googling about ladyboy stories/first time experiences to see what the web could provide. I found a lot of amusing stories but it seemed that ladyboys would treat you right as long as you treat them well, which I was definitely capable of. I decided to give it a shot. Fuck it, I know if I won€™t try I€™ll regret it.
I went to the show the next day, was quite mesmerized by the ladies, and then volunteered myself to go on stage for the final song. €œHey Mike€ she said to me backstage. I was flattered she remembered my name. €œHey Jenny€ I replied back, which made her quite happy, €œyou remember?!€ was her reply.
I told her again very honest
€œyou€™re so beautiful *stroking her hair*
I want to get to know you, but I€™m very shy.
Can I trust you?€
She then said again I could and I started to believe her, at this point I gave her a big hug, which was a bit weird but I guess I wanted to look vulnerable so she wouldn€™t want to do anything to me. She also showed me her id card, which said born in 1995. Well whaddaya know, looks like she was really 20, although she may have faked it who knows.
After the show I went home and texted her to meet me near my place on the beach. It was midnight and I was very nervous at this point. I waited for several minutes, my heart racing at the sight of every passing motorcycle. Drunk tourists were going home and it was quite nice being close to the beach like that, I€™m talking 30m from the water.
She then came from behind the meeting location, to keep discreet I guess, I was surprised, she looked a bit like a ghost/vampire on the line of the beach and the darkness of the sea. I said hi and she told me to walk to my place and she€™d follow me. I guess she thought I didn€™t want to look with her in public, but at that moment I obeyed even though now I wish I treated her like a lady and walked with her.
On the short walk home I was starting to relax, told her again I€™m very shy, and she took it quite well. At my place I let her in and closed the door (funny sidenote: I actually made my little bro sleep with my sisters in a different room so I€™d have a sex location available. That€™s like the 5th time I made him do it, thanks brother!)
We set on the bed, she was sitting on top of me, and then she pushed me into the bed falling on me. We started making out, she loved it when I breathed hot air and licked her ear, and I was enjoying her as well. She took of my shirt, and then went for my pants, which were holding a hard dick. I was excited to let her touch my dick, recalling the stories saying that ladyboys give amazing blowjobs.
She put my dick in her mouth and started sucking, she wasn€™t amazing but it was the 2nd best blowjob I€™ve got, considering that the first was from a 38yo experienced woman I€™d say that€™s quite impressive.
I felt her hair and it felt very nice. €œI never fucked a girl in the ass before€ I said, and told her I€™d be very careful as I know how much it hurts them. I started sliding my dick inside her ass (with a condom!) while we€™re both lying on the side and felt her body. I could feel a bit of hair on her arms but that was pretty much the only male thing I felt about her.
During the entire act she didn€™t take off her underwear, but rather let it slide in the behind to let me fuck her, I never got to see her dick, and I was totally ok with it. Going easy on me haha. In hindsight I wonder what she thought and how nervous she was about the situation.
I was uncomfortable fucking her hard to cum in her ass as I thought it would hurt too much for her, although in hindsight I guess she would like that. After some more pounding I let her make me cum twice from two blowjobs that was fun.
She stayed over to sleep although it was already 4am and she left at like 5:30 or something dunno why. She was very sweet and I tried to treat her like a woman and I think I did well.
I ended staying in the island for 3 more days, going to see the cabaret show every day as I genuinely enjoyed it. I met her two times after the show and one time before the show. She gave me a blowjob on the beach while people were occasionally passing by for two days in a row, as I couldn€™t meet her in my room again cause my brother was there. My dad got pissed at me for kicking him saying I give him bad values or some shit lol.
On the 2nd time she wanted me to cum in her ass on the beach at 1am, but I was uncomfortable for doing it publicly and also didn€™t want to be inside her that much, not sure why. Told her I wanted a blowjob and she willingly agreed without mentioning it again, which was pretty sweet of her.
My favorite time with her was when we met at 6pm and she rented a motorcycle and drove me around the island to a beautiful viewpoint. She paid for the bike rent and wanted to pay for the smoothies we ordered but I wanted to pay so I did. I always like though when girls buy me stuff and pay for me, and appreciate the gesture.
She was super skinny thin, exercised every day 1-2 hours, then would practice for the cabaret show and would put on makeup for 1 hour to prepare (some girls do it for 2-3 hours!), saying it was a very boring part, although she enjoyed performing in front of people.
She would get 400 baht per show, and would get tips from people in exchange for photos, averaging an extra 400-600 baht. Funny enough the ladyboys never in my life asked me for money for pic with them, although they ask girls and unattractive men. A music university student in Bangkok learning to play the flute, which I didn€™t understand how since she was living in another place.
On the last day she wouldn€™t come out for pictures after the show, later she told me it was because her friends teased her about me being her boyfriend haha. Guess she was uncomfortable like a normal girl. I just feel bad because I know she lost some money because of me.
We went for food after the show one time, she took me to a really cheap local place and I understood she probably was poor or trying to save money. Again she wanted to pay and to be respectful I paid only half.
Funny note: I actually took a picture with her 1.5 years ago on my last visit to ko tao, and we both were quite surprised when I showed it to her and she confirmed. Anyways here they are, I blurted my face to keep anonymous although I€™m not sure why, just to be cautious I guess.
new pic
jQRC4ZH.jpg
old pic march 2014
4r0eolN.jpg
funny enough she left 2 huge bite/kiss marks on my neck, which everyone would see for the next 3 days, even my scuba instructor asked me randomly if it was some mosquito bites or if my date went really well. He then added jokingly was it a ladyboy or something. I later told him that it was and we had a good laugh about it
It was a great experience, and I€™d like to see her if I come to ko tao again, although I won€™t be interested in meeting in Bangkok, but I€™d consider it. She treated me very nice and in many ways was more feminine that many other girls I€™ve dated.
Feel free to write in the comments below your thoughts, I€™d love to hear them as I€™d consider writing about future experiences with other ladyboys. Or ask questions and I€™ll answer.
more pics
G9j0K2q.jpg
The most beautiful girl there, the only one I couldn't imagine born as a guy
About me: 21yo entrepreneur living in Bangkok Thailand for 1.5 years now. Consider myself completely straight, had sex with 18 girls in my life (17 thais 1 korean, yep got the yellow fever, big time), overall open minded and outgoing.
Seeing 2~ normal girls atm while going out regularly to get new girls at route 66 RCA and also from online dating (thai friendly). I never paid for sex in my life, although I€™d consider it if she€™s super hot. Funny note: Every girl I€™ve fucked was on the first day I met her, within 2-4 hours, so I guess I give a player vibe to girls and not a provider.
So my family came to visit me in Bangkok, and we decided to go to ko tao island after 1 week in lovely Bangkok. I was there last year when I turned 20 and learned how to scuba dive.
As we got there I looked up tinder and tried to get a date, found a 35yo Russian girl and met her for a drink but she was very cold and boring (Russians have a tendency like that from my limited experience). I saw a lot of hot tourists on Tinder but they didn€™t seem to swipe right on me, sadface lol. I also saw a lot of sexy ladyboys promising a €œfun time and intense experience€ but I didn€™t give it much thought and declined. Didn€™t feel like going to parties and looking to find drunk tourists as well. I love dating locals.
Then we went to a cabaret show in ko tao, it€™s every day 22:30, and I was kind of blown away. I saw the show last year and loved it as well, but I wasn€™t comfortable enough back then in my sexuality and in general to do something with a ladyboy. I love tall skinny girls so I was naturally attracted to them but I was quite intimated by these ladies of the night and their aggressive behavior.
I was very attracted to 2 of them, and found myself considering to do something about it, yet I wasn€™t willing to initiate anything.
Before the show ends the girls select 4 hot guys from the crowd and take them backstage for one last show, they undress their shirt put a wig and make them dance onstage to the song €œsexy and I know it€ haha.
I wasn€™t interested in performing, I actually did it last year, got quite some likes on facebook but to be honest I was afraid of going backstage again with a ladyboy away from sight.
Meanwhile they selected 3 guys and I was starting to relax. Suddenly a tall 1.76m beautiful ladyboy invited me, and my heart raced a bit. I hid my nervousness and went backstage with her, where I acted very direct, held eye contact, and let her put my hands on her tits while squeezing them, she was then quite surprised and said meet me later after show, lol talk about direct.
I told her you€™re said beautiful but I€™m very shy. Don€™t be shy was her response, I was still skeptical though, I then gave her my LINE and went to the stage with everyone, and proceeded to dance with everyone in a drunk way. My parents and brothers told me I was the best dancer except for some random gay guy that went on stage without being invited. Oh well
I went home with my family telling my brothers (not parents) about what happened and that I was considering meeting her. They were quite shocked but they knew I like trying new things so they were cool with it.
I was quite scared at this point to be honest, I didn€™t mind her dick or giving her a handjob or fucking her in the ass, I was just afraid of getting raped or forced to have sex in my ass, which I€™m still quite afraid of. You see these girls are very feminine but if the guy side of them comes out they can kick my ass for sure.
In hindsight though that girl was very sweet and I could trust her.
She texted me hello after she was done but I didn€™t reply, I was intimidated and not ready yet. Her profile pic on line was also not pretty. I then spent the next day scuba diving and googling about ladyboy stories/first time experiences to see what the web could provide. I found a lot of amusing stories but it seemed that ladyboys would treat you right as long as you treat them well, which I was definitely capable of. I decided to give it a shot. Fuck it, I know if I won€™t try I€™ll regret it.
I went to the show the next day, was quite mesmerized by the ladies, and then volunteered myself to go on stage for the final song. €œHey Mike€ she said to me backstage. I was flattered she remembered my name. €œHey Jenny€ I replied back, which made her quite happy, €œyou remember?!€ was her reply.
I told her again very honest
€œyou€™re so beautiful *stroking her hair*
I want to get to know you, but I€™m very shy.
Can I trust you?€
She then said again I could and I started to believe her, at this point I gave her a big hug, which was a bit weird but I guess I wanted to look vulnerable so she wouldn€™t want to do anything to me. She also showed me her id card, which said born in 1995. Well whaddaya know, looks like she was really 20, although she may have faked it who knows.
After the show I went home and texted her to meet me near my place on the beach. It was midnight and I was very nervous at this point. I waited for several minutes, my heart racing at the sight of every passing motorcycle. Drunk tourists were going home and it was quite nice being close to the beach like that, I€™m talking 30m from the water.
She then came from behind the meeting location, to keep discreet I guess, I was surprised, she looked a bit like a ghost/vampire on the line of the beach and the darkness of the sea. I said hi and she told me to walk to my place and she€™d follow me. I guess she thought I didn€™t want to look with her in public, but at that moment I obeyed even though now I wish I treated her like a lady and walked with her.
On the short walk home I was starting to relax, told her again I€™m very shy, and she took it quite well. At my place I let her in and closed the door (funny sidenote: I actually made my little bro sleep with my sisters in a different room so I€™d have a sex location available. That€™s like the 5th time I made him do it, thanks brother!)
We set on the bed, she was sitting on top of me, and then she pushed me into the bed falling on me. We started making out, she loved it when I breathed hot air and licked her ear, and I was enjoying her as well. She took of my shirt, and then went for my pants, which were holding a hard dick. I was excited to let her touch my dick, recalling the stories saying that ladyboys give amazing blowjobs.
She put my dick in her mouth and started sucking, she wasn€™t amazing but it was the 2nd best blowjob I€™ve got, considering that the first was from a 38yo experienced woman I€™d say that€™s quite impressive.
I felt her hair and it felt very nice. €œI never fucked a girl in the ass before€ I said, and told her I€™d be very careful as I know how much it hurts them. I started sliding my dick inside her ass (with a condom!) while we€™re both lying on the side and felt her body. I could feel a bit of hair on her arms but that was pretty much the only male thing I felt about her.
During the entire act she didn€™t take off her underwear, but rather let it slide in the behind to let me fuck her, I never got to see her dick, and I was totally ok with it. Going easy on me haha. In hindsight I wonder what she thought and how nervous she was about the situation.
I was uncomfortable fucking her hard to cum in her ass as I thought it would hurt too much for her, although in hindsight I guess she would like that. After some more pounding I let her make me cum twice from two blowjobs that was fun.
She stayed over to sleep although it was already 4am and she left at like 5:30 or something dunno why. She was very sweet and I tried to treat her like a woman and I think I did well.
I ended staying in the island for 3 more days, going to see the cabaret show every day as I genuinely enjoyed it. I met her two times after the show and one time before the show. She gave me a blowjob on the beach while people were occasionally passing by for two days in a row, as I couldn€™t meet her in my room again cause my brother was there. My dad got pissed at me for kicking him saying I give him bad values or some shit lol.
On the 2nd time she wanted me to cum in her ass on the beach at 1am, but I was uncomfortable for doing it publicly and also didn€™t want to be inside her that much, not sure why. Told her I wanted a blowjob and she willingly agreed without mentioning it again, which was pretty sweet of her.
My favorite time with her was when we met at 6pm and she rented a motorcycle and drove me around the island to a beautiful viewpoint. She paid for the bike rent and wanted to pay for the smoothies we ordered but I wanted to pay so I did. I always like though when girls buy me stuff and pay for me, and appreciate the gesture.
She was super skinny thin, exercised every day 1-2 hours, then would practice for the cabaret show and would put on makeup for 1 hour to prepare (some girls do it for 2-3 hours!), saying it was a very boring part, although she enjoyed performing in front of people.
She would get 400 baht per show, and would get tips from people in exchange for photos, averaging an extra 400-600 baht. Funny enough the ladyboys never in my life asked me for money for pic with them, although they ask girls and unattractive men. A music university student in Bangkok learning to play the flute, which I didn€™t understand how since she was living in another place.
On the last day she wouldn€™t come out for pictures after the show, later she told me it was because her friends teased her about me being her boyfriend haha. Guess she was uncomfortable like a normal girl. I just feel bad because I know she lost some money because of me.
We went for food after the show one time, she took me to a really cheap local place and I understood she probably was poor or trying to save money. Again she wanted to pay and to be respectful I paid only half.
Funny note: I actually took a picture with her 1.5 years ago on my last visit to ko tao, and we both were quite surprised when I showed it to her and she confirmed. Anyways here they are, I blurted my face to keep anonymous although I€™m not sure why, just to be cautious I guess.
new pic
jQRC4ZH.jpg
old pic march 2014
4r0eolN.jpg
funny enough she left 2 huge bite/kiss marks on my neck, which everyone would see for the next 3 days, even my scuba instructor asked me randomly if it was some mosquito bites or if my date went really well. He then added jokingly was it a ladyboy or something. I later told him that it was and we had a good laugh about it
It was a great experience, and I€™d like to see her if I come to ko tao again, although I won€™t be interested in meeting in Bangkok, but I€™d consider it. She treated me very nice and in many ways was more feminine that many other girls I€™ve dated.
Feel free to write in the comments below your thoughts, I€™d love to hear them as I€™d consider writing about future experiences with other ladyboys. Or ask questions and I€™ll answer.
more pics
G9j0K2q.jpg
The most beautiful girl there, the only one I couldn't imagine born as a guy
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