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 Watchmanmug. 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
Get the the watchmanmug. 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 watchmanmug.