I'm using a gamify-your-life app (a home-made one) that lets you make your own "classes" and "quests", and I've been using it for masturbation challenges.
Each class unlocks quests that give XP for that particular class. Earning XP levels up the class. The higher level you reach in a class, the more challenging/unusual/risky the quests are unlocked.
The current classes I have are:
Camera Man: Take pictures/videos of your masturbation antics
Example quest: Take a picture of your dick in a hot-dog bun
Connoisseur: for masturbating to unusual (non-)porn (at least, unusual to me)
Example quest: Masturbate to a movie poster
Sneak: Masturbate secretly (with others nearby or almost-completely hidden from view)
Example quest: Sneakily masturbate during a work Zoom call
Adventurer: Masturbate outside of your own home (or car)
Example quest: Hump a tree until you cum
Researcher: Experiment with masturbation acts and improvised toys
Example quest: Make a hole in a pomegranate and use it as a Fleshlight
Home Alone: Freaky things to do when the family/roommates aren't home
Example quest: Close the curtains and dance naked around the house for at least 10 minutes
I won't really put up my entire collection of quests, since that would be quite a bit (and a lot of them are very geared to my specific situation and tastes). Still, I could post some of them if there's enough interest.
With this topic, I'm mainly looking for ideas for quests (and maybe classes) so I can expand my collection of masturbation challenges. Any suggestions?