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Here's an easy one we did for our boss. Sign him up for a crossdresser weekly subscription or some other form of perversion (North America Man Boy Love Association). Address it to his name but under his neighbors address. Do this several times. Also, if you have his home phone, there's nothing like placing his name and number in homosexual personal ads...
At one job I had, the boss man got the idea that the IT department should be living up to the slogan, "Giving every user what they need." I politely requested, "How do we get them to turn around so we can kick them in the ass?" It went over quite well, the room fell out laughing. I don't work there any more.
Toward the end of their senior year in high school, students were required to take a CPR course. The classes used the well known mannequin victim, Rescue Anne, to practice. Rescue Anne was legless to allow for storage in a carrying case. The class went off in groups to practice. As instructed, one of the students gently shook the doll and asked "Are you all right?" He then put his ear over the mannequin's mouth to listen for breathing. Suddenly, the student turned to the instructor and exclaimed, "She says she can't feel her legs!"
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