Top Definition
A type of sexual position originating in Windsor, NY. In it the man and the woman have sex with rear entry facing a ground floor window. In the middle of sex the man pulls out and has a buddy of his take his place without the girl knowing. He then goes around outside and waves to the girl through the window. This usually will freak her out somewhat!

It is important that your buddy has the same size penis as you!!
"Why did you and Allison break up man?"

"I did the Windsor Stranger on her and she did not like it dawg!!"
by awheel February 28, 2008

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