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To take an object that belongs to someone else, put it in your ass 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 your ass.

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, Curt has gone to a seminar let's Jamaican toothbrush his favorite pen while he's out.". In this instance one of Curt's coworkers takes the stapler to the bathroom and takes a picture of it mostly up his ass but enough out to recognize it. In lieu of insertion, possibly in the toilet, or just uncomfortably close to a not so desirable part of the anatomy.

"That plumber Norm charged me $225 for a quick repair left behind a small flashlight, so I Jamaican toothbrushed it and returned it to him"
by tommyboyO June 10, 2016
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