When a man cups a womans breast, gently moving it up and down similar to a handshake
Clinton reached through the crowded bar and gave Emily a Boston handshake. "Pleased to meet ya!"
by 619 Special Case January 18, 2011
1 more definition
Light tickling of the shaft of the penis.
I took her to The Parisian; and all I got was a Boston handshake.
by Elvis Wearing a Bra on His Head November 13, 2007