Jimmy Surprise Edit Meaning

1.

A Jimmy Surprise is when an innocent look into your buddy's room through a fire-escape with unusually good clarity results in the unexpected viewing of your friend masturbating buck-ass naked on his bed to Sportscenter.

I thought my roommate was asleep and I could run in real quick to borrow his stapler, but when I opened the door I was greeted by a Jimmy Surprise.

See jerking off