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16.
Found in their normal habitat of the bars of South East Asia. Large clusters of them congregate in Bangkok, Chaing Mai, Koh Samuii and Koh Phuket. A gender challenged male. Some have become true transsexuals, others are on their way. The computer geeks that have defined this word previously have obviously never been with a real woman and there are several tell tale signs that any red-blooded male can use to spot a ladyboy.
i) Adam's apple.
ii) Size of hands.
iii) Voice.
iv) The way they walk.
All these can be altered but using these guildlines and a modicum of common sense ladyboys can be easily spotted. But only if you want to. The phrase, "I honestly thought they were women" does not cut it with me closet boy.
"Sean, Sean I want your penis in my mouth."
"Put your own there."
"No! No! I lady. I no penis."
"Look 'darling', you've got a face like a slapped arse, an adam's apple the size of a tennis ball and hands that Andre the Giant would be proud of. You are no lady. Ladyboy at best but more like Hellboy."
by The Strut October 12, 2004
 
1.
A Male naturaly with all the attributes of a woman except for the plumbing. A true Ladyboy does not need surgery or makeup to look like a woman, nor is there a need to try and sound like a woman it is all natural for them.
If you go in to a club or talk to a Ladyboy on the street you would not know from the body language or voice that you are talking to a man.

Once the truth is known, one might even want to try him/she out just to see if they can get past the plumbing issues.
by RearEnder April 26, 2005
 
2.
You think you have picked up a sexy girl. You put your hand up her skirt and find a HOT-DOG!!! Oops, you made a mistake....or was it really a mistake? Come on, be honest!
"Hey dude, what are you doin' with my ladyboy?"
by lord nobcheese August 25, 2006
 
3.
Transvestite; a young male dressed as an attractive girl, often practising as a prostitute.
Back in his room, he discovered she was a ladyboy. But as he'd already paid, he thought he'd better make the best of it. It was the best head he'd ever had.
by starflier December 08, 2003
 
4.
A nice surprise you have in the morning after you got so trashed in that club in Bangkhok and you though you'd scored yourself a 10.
"I was so smashed last night, I shagged a lady-boy"
by Flo January 28, 2004
 
5.
A boy or young man who dresses as a girl or wishes to dress or act like a girl, especially from the Thai culture. Often used to describe a young, gay Thai boy. Western society would describe a ladyboy as a young Thai transvestite. This term is used by Thai's when they are speaking English. (The Thai word is altogether different.) Sometimes used by Thai's as a general word to describe any gay boy or man.
My Thai friend, when introducing me to his family, proudly announced that his thirteen year old son was a ladyboy. Looking at his smiling son, I thought he was a girl.
by bangkokboy October 13, 2005
 
6.
An extremely effeminate gay Southeast Asian male, usually in his 20s, who dresses up like a girl, often has tits (fake or grown with hormones), and typically cums like an ordinary male. They often practice as prostitutes in the tourist ghettos of Thailand and The Philippines, and are known for luring/soliciting unsuspecting Western men, as well as their unique ability to suck cock given their personal familiarity with male anatomy and desires. Most ladyboys prefer to get fucked in the ass, though a few (usually those with larger dicks) are tops. Ladyboys are completely mind blowing to sexually confused Western men who are simultaneously bi-curious and into Asians. Large hands/feet and over-assertiveness are usually a dead giveaway.
Last night, one of the most beautiful Asian women I've ever seen in my life tried to grab my cock in Nana Plaza (a red light district in Bangkok). I was impressed. We walked back to my hotel room, where she took off her underwear, revealing an erect, uncircumcised penis. My mind was totally blown, and I had to give in despite not really being into dudes. We had the most amazing gay sex ever, slept until noon, and went shopping together in CentralWorld the following day. It was the total ladyboy experience.
by The Demon Lover June 27, 2010
 
7.
In Thailand (khatooey), a Transexual . A Male who looks and lives as a young woman. Often post-operative.
I Don't Care if that's a Lady Boy, he's HOT!
by Haiti PI September 19, 2007