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bald head scaliwag 

a bitch who does not have any hair and wears wigs to cover it up.
bald head scaliwag, aint got no hair in back. gelled up weaved up, that girl looks fucked up.

scaliwag 

the definition of scaliwag, according to the inventor of the word, is whores that got picked up by pirates and other sailors in port. Then got fu*ked in every oriface imaginable, using any and every available blunt object (specifically including the pepper shaker). When the whore was so utterly abused and disgusting that nobody wanted to touch her, the sailors would just throw her overboard.
Paris Hilton is a modern day scaliwag.
scaliwag by Joe "Burnsy" Smith December 2, 2004

scalywag 

A barhag whore, you'd never really date her. Also known as a "scally" or "scallies", they are good to have around at parties and good to occasionally hook up with. They're usually okay with this, no drama involved.

A scalywag is the opposite of a carpetbagger.
There were a bunch of scalywags in that bar last night.
He hooked up with some random scalywag.
scalywag by JordanP January 5, 2006

I'm done scalywaggin 

I'm done whoring around.
girl to ex: "Stop wasting your time with those scalywags, and let me back in your life!"

ex to girl: "I'm done scalywaggin baby."

scaliwag 

arrrrrr! behold the scaliwag. make him walk the plank.
scaliwag by old pegleg July 2, 2004

Scalywag 

When a woman gives a blow job while sitting on a heineken bottle.
Did you see brandon with that scalywag at the party last night?
Scalywag by atown84 October 7, 2009