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 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

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