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 an auction for him to be a slave for a lunchtime? Or you all sponsor him to learn something new (ventriloquism/magic tricks/a song) in a week and then he has to perform for you all on Friday lunchtime?
If you are near the coast and he aggrees you could get the lifeboat crew in full kit to "Kidnap" him. In my experience they are always good for a laugh if it raises funds for the RNLI.
For comic relief I organised a pub quiz at lunchtime in our conference room - that was great fun and raised �106. My line manager dressed as a maid and made tea and coffee all day for 50p a cup.
Swear boxes are always good in offices, we were going to have a Perv box for two of the guys here. 50p everytime they say something suggestive or gawp at us females!