I Like Ladyboys

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I Like Ladyboys
It seems that everybody knows somebody who has accidentally made out with a ladyboy, or worse. I never thought I’d be one of them, but then again, nobody ever does.
First off, let’s establish what a ladyboy is.
A ladyboy is a transgendered or transvestite individual in Southeast Asia. In Thailand, for example, they are openly tolerated if not embraced and even regarded as good luck charms.
My story takes place between Christmas and New Year’s last year, on Phuket. I would normally avoid what has become such a seedy place like the plague, but it so happened that I had to head there to get a chest x-ray for my Australian visa. While there, I met a group of friends who wanted to check out the ladyboy cabaret. Given that I had nothing better to do, I tagged along.
Ladyboy shows are often a way for ladyboys to save up for the final step of the surgical procedure to become a woman. The performers tend to at least have breast implants, and are quite often absolutely beautiful, and convincing!
I sat through an hour or so of performances in Russian, English, Chinese, and, of course, Gangnam Style, so that every possible member of the audience would be satisfied hearing a song in his/her native language, performed by crystal-adorned ladyboys dancing a little out of sync with smiles plastered on their faces.
After the show, we had an opportunity to take photos with the various performers. One of the more beautiful ones I had noticed on stage beckoned me over.
He (she?) grabbed my hand and slung it over her (his?) shoulder. My friend, Dylan (who attended with me on the pretense that ‘the journalist in him said yes’), snapped a photo just as the unthinkable happened:
The ladyboy stuck my hand down her (his?) top. 
It rested there for a few seconds (though it felt like hours) before I realized what was happening. I pulled it back out at lightning speed, completely flabbergasted, as the ladyboy laughed at me.
For the remainder of the night I just kept looking down at my hand, unsure of what to do.
Do I wash it? Sanitize it? Chop it off?
And so, without even meaning to, I made it to second base with a ladyboy. I have now joined the rank and file of tourists in Thailand who have befallen such a fate.
I think the best course of action for me now is to do as the locals do, and regard this as a good luck charm. If nothing else, it makes for one hilarious story.
*This post is for Chelsea, who so eloquently said one night, “The title of Kristin’s Southeast Asia memoirs: I Made it to Second Base With a Ladyboy .” 
*Special thanks to Dylan Lowe for the photos, and you’re welcome, Dylan, for getting to be the one to witness this account first-hand. 
2015 Update: Transgendered individuals have a hard enough time with acceptance into the societies they were raised in without the burden of someone like me writing a post like this. I’m ashamed for highlighting our differences and instead want to celebrate the beautiful (inwardly and outwardly) and strong women who have the bravery to embrace their lives as transgendered individuals. If this post offends you, it’s because I’m a silly girl without an understanding of the difficulty those who dare greatly to be different. I support you in all that you do, empowered woman. I respect your struggle and promise that moving forward, all that I do in my writing and attitude will reflect that. Much respect where it is due.

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Ha! those lady boy shows are definitely entertaining but I missed out on the second base bit… lucky you!
Haha what an experience! I wasn’t able to watch a single lady boy show when I went to Thailand last year 🙁
You’re not realllly missing out on much, honestly.
She doesn’t seem to have silicon… were they real or fake? 😀
Too funny! I’ve been to Phuket twice. I went once with the teachers at my school and once with John because he had never been. Both times, there were funny incidents with lady boys, but the best by far was sending John out to get a few bottles of water one evening and having him come back completely traumatized after a lady boy exposed him/her self at the convenience store!
Ahhhh, goodness. Their faces look so fake!
Not the fakest part, let me tell you!
This is brilliant. Best blog post title I’ve seen in ages! Good on you for being so lighthearted about it. Did no one capture Dylan in any compromising positions?
Good stuff! I just discovered the ladyboy phenomenon in Bangkok, but from a more of a distance than you!
You see them all over SE Asia. Very special
The good news is that he/she was definitely the prettiest of the bunch 😉
Nice and not sure if you’re sunburnt of they are loaded in that ever popular white powder which makes the contrast so intense. ;]
Maybe we could just say I’m tan…Yes, I like tan.
Oh lordy! You poor thing.. but entertaining
Once any straight man spends a night with a pretty lady body, he will very rarely be 100% satisfied with a normal women again. Don’t ask me how I know… I just know ok, lol.
Most amazing comment I’ve seen in a while!
Don’t worry happens to us all eventually – or is it just me. Great blog post btw thanks for sharing.
Haha just dancing with one is no issue, I think people mistake them for women and find out when it’s too late.
Hey, just a heads up, you would call them “she” if they identify as women. If you call a transwoman (which Kathoeys are) “he”, you are misgendering her. If an individual is presenting as a woman, if they have gone to the trouble of undergoing dangerous surgical interventions like these ladies have, if they identify as female, then you most certainly should call them “she”. Not “he-she”. “He-she” is the trans equivalent to the “n” word for African people, or “ f@ggot ” for gay men. It is very offensive. I’m sure no one here meant to be offensive, but now you know!
You’re absolutely right, and I appreciate that you were patient with your response. I don’t mean to offend anyone but I can see how my post could be seen as insensitive.
Hi there 🙂 im glad you had a good time. I am Thai and let me tell you this…I don’t think we consider ladyboys as a good luck charm haha! they are just individuals… but yes they get a lot of attention from the tourists of course 😉
Well Wikipedia was wrong then! Thanks for the correction 🙂
Ladyboys are considered goodluck charm in subcontinent (India, Pakistan, Bangladesh). I’m from Pakistan, thts why I know this. This might not be the case in other Asian countries. So Hanna is right
Specially when a ladyboy is very hot and a good entertainer, you will surely don’t have a second thought!
Thats one lucky ladyboy i tell ya, cuz your absolutely gorgeous miss kristin
Hahaha, loved this. It certainly is a strange experience over there – very confusing!!!
The real challenge is to get to third base ! They do say it’s like cooking with gas once you’ve tried it you can’t go back to electric if you get my meaning. So a friend of a friend says…..
You’re an extremely hot and sexy lady. and I mean that not just in a physical way, but your whole vibe and style is like that. This is the only travel blog I’ve ever read where I didn’t feel angry at the person who wrote it. Thank you.
Your initial response was natural as transgender is quite different and is hard to understand (especially for me who is raised conservative…talking about understanding, not accepting as that implies I am judging them). Nonetheless what one of the ladyboys did to you was inappropriate. Being different and being treated equally means embracing others for their differences. However it also means that everyone takes responsibility for their actions and doesn’t use his or her difference as an excuse for harassment. What was extraordinary was how in 2015 you had gained sensitivity about transgender and made a sweet appeal to them that you love them like everyone else. It is not easy to admit these things and you keep growing! More things to write to your 21-year old self as a 31 year old!
So you got sexually assaulted by a ladyboy and now you need to apologize for your reaction to it. Got it. No wonder the west is collapsing.
That’s true. I apologize for not recognizing her as a her and making fun of the transition, but she should not have done that, either.
I really see no reason to apologize for writing your experience. Yes ladyboys might have it rough but they don’t have a right to sexually assault you which is exactly what happened. Ladyboys often try to trick unsuspecting people about their gender and often when intoxicated anyone who has been to south Asian knows this for a fact. Respect should be a two way street if you’re not gay you shouldn’t have it pushed upon you and if your gay no one should be be harassing you simply for being gay. Since most people are actually straight it logically follows that the lb in fact knew it was more than likely that your not interested and should know that straight people find the same gender disgusting with respect to sexuality. To argue against that last sentence is to argue against biological necessity and evolution. I can logically be ok with someone practicing their sexuality and at the same time find it not for me.
Interesting that you apologize for not “recognizing her as her”. But, as a biological woman wouldn’t it be normal to not perceive a transgender (man to woman) as a a “real” woman? As a woman you have a whole different set of physiological and life experiences, which are bypassed by a man who becomes a woman. Nothing wrong with a guy becoming a woman, more power to him/her, but it seems a bit of a cheat
I am still trying to understand the nature of your apology that you appended to this article.
What was so offensive that you felt that the need wrote the apology?
Was it your reaction to what some would consider to be tantamount to sexual assault?
You see, there are different ways to spin this.
It seemed like a honest reaction to a real situation to me.
I mean, as a man, if someone with a penis grabbed my hand and put in on their penis, I’d probably be reeling back and looking for hand sanitizer, too.
Does that make me a bad person? I don’t think so.
I don’t even want to imagine what would happen to me if I forced someone’s hands onto my naughty bits.
Anyways, I found your “original” article to be very entertaining and enjoyable.
In reading through the comments I seem to have noticed that perhaps your apology is related to the pronouns.
Well, I was told never to assume pronouns. If you did not ask, and you don’t know… listing both like you did seems to be a valid option.
There are straight gays the cross-dress, but the identify as “he” still. I see plenty of women that dress like men, and at a first glance may even look like men, yet, they go by “she.”
I mean, they call themselves “Lady Boys” in English, so that has both genders mix right into their name.
I would say to any of the trans-folks who chimed in, “shame on you for assuming.”
I think that you did the right thing, initially.
Honestly, I personally don’t feel that it is my job to validate someone else’s subjective view of themselves.
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Communities > Sexual Health > My boyfriend likes shemales does that make him gay?

Hi, I recently learned that my boyfriend is into shemale porn and it freaks me out! He keeps denying that hes into that stuff, but i've seen that **** on his phone on several occasions. It makes me wonder if he's gay or bisexual and it also makes me wonder if he imagines me with a penis while were having sex. And i know that sounds funny, but it's really really bothering me. I also had the thought that he might leave me for a tranny someday. LOL. Please can anyone tell me if this makes him gay or bi? Are the any "straight" men out there who are also into that so you can explain this to me? Please i want to understand..I love him very much and this ***** :(


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Am straight, married for almost 30 years. At first it was a fantasy. I see it as role reversal. As a guy its a lot of pressure to perform and being able to enjoy yourself gives you the free reign of either being dominant or submissive. He may want to dress up as you be touched like you but if he is  turned off by your breasts or clitoris that is a good sign he's either bi or gay.
Dress up in his clothes and be gentle with him..best wishes.



gotta say this topic sure get people wild up. If u ask for my personally opinion and experience, i am straight, i started getting into shemale porn though, but i can only watch shemale on female. Personally i was scared that there a chance im turning out gay, both female and trans excite me. I have told no one about this of course and i keep it all to myself. i hang out around my male friends a lot lately i a came to a conclusion i was in no way attracted to guys i wasn't gay, Nor would i ever s**** or f**** a trans. I guess i only liked watching it.


Story of my current life. I've seen it in his phone now twice but he denies he's gay, because I've asked him. I don't know what to do. Im just as frustrated as you sound. And what makes this even sadder some times he doesn't try to have sex with me because he's already jerked off. I call him out on this with, "oh I know why you don't want to have sex, you already took care of it". I'm afraid to marry him now because I am worried I am going to end up with a future Bruce Jenner.


Indeed they can, and the men who receive anal sex in this way, as you say, are not 'gay'. But that is only because of the extremely narrow definition of 'gay' used in the USA, where it was coined; so they do have a right to define it. It is 'attraction to the same gender'. Thus it derives all meaning from 'attraction' and none from sexual practice.

But 'gay' and 'homosexual' are not synonymous (although this is the sleight of hand that is being attempted here.) 'Gay' has existed for all of maybe 50 years whereas homosexuality has been recorded for 6500 years. And homosexuality does indeed take into account sexual practice.

So you are right; men who are 'pegged' by women are indeed, not 'gay'. But they are homosexual, or at least homocurious. (There's no such thing as 'bi-curious' and a moment's reflection should make it obvious why.) And if they want it a second time, then they are no longer curious: they're homosexual.

By induction, then, men who are 'topped' by TS women may not, in the strictest, US American sense, be gay, but they certainly are homosexual.

Most of your other comments seem to rely on similar, somewhat slippery, semantic manipulation. When you're not just using ad hominem and calling people 'idiots' that is.


TooyoungtohaveSTDs
Jun 01, 2016


I wouldn't worry a lot of dudes have an inner gay side to them that rarely comes out it's only natural.. Doesn't make him gay... The only thing that matters is that he stayed with you...


As a shemale (Mistress) myself, I think it depends on a shemale if she will pursue and encourage the guy to have sex with him. Yes, most straight men are curious how it feels like having sex with a shemale. Shemales/Male knows how to do oral compare to a woman. I have dated straight men (curious) and mostly I was their first. I remember when I was in University and bunch of Foreign student Doctors who asking me out...of course i am choosy and afraid of getting diseases... Sometimes some men (homophobic) can easily fall to someone like us in a good approach and how you make him crave for something different in sex.
If your bf really love you, he would tell u everything but of course secret is always a secret. Everyone have a darkest secret...So as a woman, you should know how to know and find it yourself what is it, but you must take and accept consequences.
Your bf wont take serious with the shemale, unless if your bf find something and reason why he will leave you for her (shemale). But if you are loyal and good for him, then there is nothing to worry about, dont be curious. Know his fetish.


Danv86, I to later in life saw a shemale on Maury that I thought had to be a girl. My gf at the time went on A shemale website and I was so turned on by only the beautiful ones. We both had fun with this together. I also shared this with later gfs and it excited them both. One thing though, I had a young guy in his 20s hit on me and he looked cute to me. If he was to put makeup on and dress like a girl he would pass. This happened 10 years after I started looking at  shemale porn. I never did anything with him, but since him, I have seen 4 other younger guys that I really liked over the past few years.....So maybe this is just an extension of my liking of shemales or I am turning from bicurious to bisexual...... See if he likes looking at twinks and that will give you an answer.

Good luck


I am a Natural occurring Shemale. I feel inside I am a woman when a man engages me. In His mind too at that moment I think he considers me a female. So in My humble opinion and own experience,  it is the Feminine pleasing the Masculine and that is just  pretty much a normal event.

He may have bi tendencies or just curious. If he is sleeping with you he Obviously wants You his Girl and do not forget that as his Presence with you should be enough as he has voted with his feet and his penis. Do not be afraid as most people really are Bi-sexual its just not all have the courage to admit that due to our
Puritan and Racist Society when it comes to any
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