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1.
To take an object that belongs to someone else, put it in a bad place (typically your butt) and then return it to where it was, unknown to the owner of the object. This is done in the hopes the person will use it or handle it unaware it has been in a bad place.

This comes from an old story in the 70's of a couple who went to Jamaica on their honeymoon. While out one night their room was broken into ransacked and robbed. All that was left behind was their camera (this is before digital cameras) and toothbrushes. The couple replaced what was missing and went on with their vacation.
Upon returning and developing the photos of their wonderful honeymoon in Jamaica they were shocked to find pictures of their toothbrushes jammed up the perpetrators backdoor.
"Hey, my coworker has gone to a seminar let's Jamaican toothbrush his stapler while he's out.". In this instance one of Jason's coworkers takes the stapler to the bathroom and takes a picture of it in a bad place. In lieu of insertion, possibly in the toilet, or just uncomfortably close to a not so desirable part of the anatomy.

"That plumber who charged me $225 for a quick repair left behind a small flashlight, so I Jamaican toothbrushed it and returned it to him"
by tommyboyO February 02, 2012