That really IS a deceptively brutal roulette. The endless scaling of it seems to be getting out of hand already.
I assume by "failing the roulette you mean 'cumming without permission or failing to complete your task that day'.
So I think there should be a failure roll added to make you worry about failing, but also keep your hope alive for earning a release.
if you do ever find yourself failing, grab a Dice and see what punishment you have earned for the rest of your game.
1. Naughty Boy.
- 1M
- Spank your ass 10 times for every 100 strokes you complete. 'cumulative'
- Optional: instead, add 5 ball slaps
2. Bondage Bitch.
- 2M
- Add a new piece of gear every time this is rolled. Applies for all time spent on the roulette.
(Ball gag, Nipple clamps, Cock ring, Collar tied to something solid, Bound Ankles/knees/arm, Add 5 clothespins to your body - starting with your balls)
3. Filled Fucktoy.
- 3M
- Plug your ass when playing. Escalate toy each time. (Plug S, Plug M, Plug L, Dildo S, Vibrating Plug, Dildo L)
4. Desperate Denial.
- No touching for (24/48/72/96/120 hrs) Increasing each time.
- For each time you slip up and touch yourself +1M. For each full day you manage not to touch -1M
5. Public Property.
- Take a sexy selfie and save it into a 'Roulette Whore' folder until you complete the roulette.
- Beg in the shared roulette for someone that would like to see your selfie. If you cant find anyone to share with +3M
- If they like your selfie, ask if they would like another. -1M for every additional selfie they want to see.
6. Sixy Sissy.
- add a piece of feminine attire each time this is rolled. (Panties, Bra, Stockings, Heels, Skirt, Top, Lipstick, Wig, Makeup)
My hope is these should scale along with the rest of the roulette, making everything more intense and becoming progressively more punishing if you do fail repeatedly.
I'd love to know how they go, and also if anyone else enjoys the idea we can easily add to your punishments as you play
Good Luck