side winder

A woman that is wearing her thong or G string improperly; usually crooked of to the side.

Hey girl, fix your thong, it's a side winder.

by The ConTessa November 26, 2007

Side winder

When your penis must be tucked to the side when wearing dress pants or slacks to avoid a bulge at a formal event

Jimmy you need to side winder that hog!

by Boxmuncher829 September 21, 2023

Side Winder Special

Typically used to describe the action in which a man tries to reenter his significant other during intercourse with a considerable amount of force and missing resulting in either a broken penis and or a wounded sense of pride

Me and my girlfriend were going at it last night and I accidentally ended up pulling a Side Winder Special instead. Now I can’t walk right and can’t look her in the eye

by Clumpph March 17, 2021