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Eventually I started a new job that had me travelling to Thailand regularly. I was certainly happy about that, both because I was keen to explore a new place and because of the amazing trans ladyboys they have there. After my work was done during the day, I would explore the local cultural offerings and definitely stopped in a few ladyboy bars to enjoy the shows. Despite the temptation, I never bar fined any though as it wasn't my thing. I have nothing against working girls but always wanted more of a connection with anyone I was going to take to bed. Call me romantic...

I have been lucky enough to have had quite a few partners who were into anal sex. My ex-wife and I did that more than anything else and since my divorce I have had a couple of great lovers who shared my preferred kink. But there is just something different about being in a ladyboy's ass. Maybe it is tighter somehow. Maybe sliding past the prostrate gives a different sensation...but whatever it is it just feels different. Perhaps it is just that this is, in a way, another taboo that gives it an extra flavour of excitement. Whatever the magic is though, it definitely works on me. Watching Suri below me as she began taking more and more of my cock was the sexiest thing I could imagine.

Although kathoey is often translated as 'transgender woman' in English, this term is not correct in Thailand. As well as transgender people, the term can refer to gay men, and was originally used to refer to intersex people.[4] Before the 1960s, the use of kathoey included anyone who deviated from the dominant sexual norms.[5] Because of this confusion in translation, the English translation of kathoey is usually 'ladyboy' (or variants of the term).

Trans prejudice has produced discriminatory behaviors that have led to the exclusion of transgender people from economic and social activity.[37] World-wide, transgender people face discrimination amongst family members, religious settings, education, and the work-place.[8] Accepted mainly in fashion-related jobs or show business, people who are transgender are discriminated against in the job market and have limited job opportunities.[35] Kathoeys have also experienced ridicule from coworkers and tend to have lower salaries.[10] Long-term unemployment reduces the chances of contributing to welfare for the family and lowers self-esteem, causing a higher likelihood of prostitution in specialized ladyboy bars.[8] "Ladyboy" bars also can provide a sense of community and reinforces a female sense of identity for kathoeys.[8] Harassment from the police is evident especially for kathoeys who work on the streets.[8] Kathoeys may be rejected in official contexts being rejected entry or services.[10]

In series 1, episode 3 of British sitcom I'm Alan Partridge, the protagonist Alan Partridge frequently mentions ladyboys, seemingly expressing a sexual interest in them.[citation needed]

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.

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.

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 nice sex and I told her that I wanted to bang her.

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. 041b061a72