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When 2 girls lie on their stomachs while you insert one foot into each vagina and you pull on their hair while you attempt to walk with your feet still inside them.
Me and the ladies are going bootstrapping tonight! Oh boy!
by Billy Lurker September 20, 2017
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Adverb, fucking a girl after she has bent over to tie her shoes
A surprise fucking if you will call it it. (Surprise fucking may classify as rape in some areas).
John ran over to this bent over bitch and did some good ole boot strapping.

John "I just boot strapped some chick in the park."
by Theycallmemighty March 31, 2011
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To plus one your own self to an event, usually resulting in social exile.

Derived from the saying: 'Pull yourself up by your bootstraps,' as it involves paradoxically gaining entrance to a party through means possible only if oneself is already invited.
Ricky got kicked out after he tried bootstrapping his way into the party.
by NineHill June 18, 2018
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