For a month, every work email the loser sends must end with one new sentence of a continuing adventure story, composed live, one line at a time, in signature position. Colleagues follow the plot without ever mentioning it. The league compiles the finished novella at month's end.
The long haul: this is not a one-afternoon sentence. With a time commitment of one month, the punishment keeps paying out (for everyone else) long after the season ends. Long sentences need a written end date and a league-appointed enforcer who checks compliance.
Seen in the wild: fantasypunishments.com