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1. Ladyboy
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 Apr 26, 2005 add a video
2. ladyboy
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?"
3. ladyboy
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 Dec 8, 2003 add a video
4. ladyboy
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.
5. ladyboy
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.
6. ladyboy
a feminine girly man who couldn't fight his way out of a wet paper bag. A male with female qualities who behaves in a womanly manner. One who is a bitch. One who gets laughed at constantly.
Sal is known as the ladyboy of the internet.
Vitale is a ladyboy.
7. ladyboy
Drink consisting of a Baileys, a gin and tonic and a pint of lager.
A drink one might order at a travel tavern.
by LoopyL May 4, 2005 add a video
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