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Transvestites are cross-dressing characters encountered during the Leisure Suit Larry series.

Background

They are relatively uncommon, and are generally play the part of some gag on Larry's part. They are generally treated as stereotyped homosexuals in the storylines ("no wonder Shablee knows what a man likes!").

The two notable transvestites during the series are Shablee and Koko.

The first of these 'transvestite' twists occurs in LSL6 as noted in the design documents:

"Shablee is our perky little black transvestite spa guest. Beautiful babe, good dresser, nice make-up, hair. She "hangs out" in the Make-Up Classroom, trying to powder over her beard, although no one will ever suspect this from her picture...
...When you give it to her, she discretely turns away to put it on "herself".
Click the condom on her. Learn she's no she. Wake up in your bathroom the next day, gargling your heart out.
If you gave Shablee the evening gown, he/she is waiting for you here....Larry's body covers her genitals, but its plain to see her new gown is riding up noticeably in front. Larry does a take sickens as he realizes what he's done, and begins spitting, trying to get that taste out of his mouth.
Complimentary Condom: ...Used on the beach with your girlie-man, Shablee.
Warm Champagne: Take from the Beach the morning after your first (admitted) homosexual experience...

Although Larry is forced to dress in drag a few times throughout the series he himself is not a transvestite (or at least not publically admitting to it, though he does list occasional cross-dressing as one of his hobbies).

Depending on the choices made Larry Lovage brings up transvestites in many of his conversations, as well as 'transsexuals'.

Quotes

  • Yeah, so like two months later, I caught my dad under a bridge with a seven-foot-tall transvestite, and he's like, "You see what I've been reduced to? What the hell happened to the escort pages?"
  • Wait a second, did he play that blind transvestite dude on Welcome Back, Kotter?
  • And don't take me to any more transvestite bars. You know I'm easily confused!
  • The term 'transvestite' first appears as one of the possible quiz answers in the LSL1 age quiz.
In some personal ads, TV stands for
a. television.
b. transvestite.
c. trans-venereal.
d. terre-voracic.
Correct answer: b.

Notes

Koko uses initially uses a female voice but reverts into a more masculine voice after "he" propositions Larry Lovage to give him a blow job. The Strategy Guide stresses the male genitalia by pointing:

Just when you thought you were going to tuna town, you hit hot dog city. That shock is enough to make any man weep and take a long, burning-hot shower.
You got a jumbo wiener as a token of affection, but let’s try to forget this incident, shall we?
Then she unloads her package on you, causing you to assume the fetal position in the corner. Even a hot shower won’t wash away the memories of this encounter.

Behind the scenes

These games were released long before terms such as 'transgender' or 'transwoman' were used publically (though "transsexual" does appear in Larry Lovage games & Laffer Utilities (as topic of jokes, with little context)). The dictionary defines transvesites "as a person, typically a man, who derives pleasure from dressing in clothes primarily associated with the opposite sex."

transvestite
tranzˈvɛstʌɪt,trɑːnzˈvɛstʌɪt,transˈvɛstʌɪt,trɑːnsˈvɛstʌɪt/
noun
noun: transvestite; plural noun: transvestites
a person, typically a man, who derives pleasure from dressing in clothes primarily associated with the opposite sex.

As Webster Defines;

a person who wears clothes designed for the opposite sex : a cross-dresser
An older term for crossdresser is transvestite. Crossdressers often dress only in certain situations. They do not usually identify as transgender—most identify as straight men.