Every other year our company chooses a Charity of the year. We work in a small section of the business and for the charity we always do something 'horrid' to our boss. However I am running out of ideas and the other members of staff who are newer are reluctant to suggest anything. He is quite a good laugh and up for most things, however he wont dress up in womens clothes. I would really appreciate it if anybody could suggest a few.
How about auctioning him to be a slave for a lunchtime? Or sponsoring him to learn a new skill (magic trick? ventriloquism?) in one week and having to perform it in front of everyone on Friday lunchtime?
I was recently involved in a 'Splash 4 Cash' event. It was basically a jump into the sea (on a cold day!) from a local pier. The tide was out and everybody made a big splash literally.