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1.
To insert one's middle, ring and index finger into a vagina and with your thumb against her clitoris and your little finger on her perinium (better known as the taint). You rotates your wrist to stimulate the clit/perinium and move inside her.
I gave my girlfriend a gentleman's handshake last night.
door Ajedrez 18 april 2007
 
2.
A gentleman's handshake is when one man inserts his hand into a woman's vagina and another man inserts his hand into the same woman's anus and the two men's hands meet somewhere inside her and they give a handshake.
Timmy walked into his mother's bedroom without knocking and saw that his father and uncle where engaged in a gentleman's handshake to the pleasure of his mother.
door Orlando Bich 27 december 2007
 
3.
ejackelating in a females mouth and requesting she spit the contents in your hand, then slapping her in the face with the content filled hand
Gentlemans Handshake

I blew my load in sallys mouth then she spit it in my hand and I gave her

a "Gemtlemans Handshake"
door HeiseKool 2 oktober 2010
 
4.
When a male performs a tugjob on another male with the top of his hand.
The other night Tommy and Jeff were so drunk they stood across from each other and gave each other gentleman's handshakes.
door Biff Webster 29 januari 2008
 
5.
When two gentlemen jerk off another gentleman using a handshake. All gentlemen must be wearing suits.
Hey, I'll give you two guys $30 to give me a Gentleman's Handshake.
door Iloveskeeball 23 mei 2009