To initiate a Boston watchman, you must be in doggy style with your girl facing a window. Simultaneously slip out while your buddy slips in without your partner knowing. As your buddy keeps getting it, walk outside and wave from a distance so your girl sees you through the window.
by Please Touch It III April 6, 2016
Get the Boston Watchman mug.i almost got caught breaking into a building but lucky for me the guard was a cock watchman so i just flopped out my dong and he let me go.
by Raoulduke69 January 17, 2024
Get the cock watchman mug.A guy who likes anal...usually recieving it. He act's like he enjoys giving it, but in the end, he likes the pain.
by Kennedy March 6, 2005
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