What are some extremely humiliating fun game ideas for the submissive?

There is a whole section dedicated to humiliation and degradation, what type of humiliation physical humiliation or through clothing, verbal, exposing him as chaste/submissive?
If you can give us a bit more info, we can help better.
For instance my madam enjoys humiliation through clothing, she tells me what to wear when we go out, I have a selection of bdsm/cuckold shirts that I wear, and other things to.

 

I think that would depend on your sub and what he might have to be humiliated about. Once you know his dirty little secrets, they can be used to exploit whatever level of humiliation you want.

 

That's not nice Donna. Lol

 

My Femdom Roommate writes these Dares involving her girlfriends and then lets strangers chose which dare I must do on their weekend get togethers.

CHASTITY # 9: My roommate and/or her friends will pick out and lock me in one of the 27 chastity cages my roommate has for me and sissy panties or thong for me to wear. I must role play while she or they watch a “Sissygasm” porn video successfully to be released. If I fail to have a Sissygasm I have to be their sissy chastity slave for up to 4 hours. My roommate has me pull down the thong to my ankles, lube up my butt and squat and insert an 8-inch realistic cock dildo suction cupped to the floor to fuck while roleplaying the video.

CHASTITY # 10: Girlfriend Maid Service: My roommate will offer to the any of her girlfriends that will accept for me to be their sissy chastity maid. I’ll lock myself in chastity cage her girlfriend chooses and wear nothing but the thong or panties she chooses around her home for four hours cleaning and doing her bidding while being teased and humiliated however she chooses.

CHASTITY # 11: Sissy Chastity Glory hole Hand Job Hooker: My roommate and/or her friends will pick out and lock me in one of the 27 chastity cages my roommate has for me, sissy panties or thong for me to wear and thigh high stockings. They can then offer my services to give hand jobs at a gloryhole for up to 2 hours to whoever they want'

CHASTITY # 12: Sissy Chastity Slave Gloryhole Roleplay: My Roommate will invite her girlfriends over for a sissy chastity gloryhole roleplay show. When they arrive, they will pick one of the 20 plus cages she has for me and lock me up. Then they will select just a sexy thong for me, and I will dress in my regular street clothes. My roommate will mount an eight-inch realistic suction cup cock dildo on a door mirror visible from the Livingroom. She will cuff my hands behind my back, unzip my pants and pull out my caged cock. They each will take 3-minute turns with the hitachi wand to get me to cum. When I cum it will be coated on the dildo, my pants and thong will be pulled down to my ankles and I will get on my knees and suck it clean. They can repeat as many times as you say with a different cage up to 3 times.

CHASTITY # 13: Sissy Chastity Slave Forced Bi Roleplay Show. My roommate and her invited girlfriends will lock me in chastity and dress me in a thong and a garter and stocking set, They will cuff my wrist behind my back and put on a collar and leash. They will finish by putting red lipstick on my lips. They will then put on strap-ons and each one will take turns leading me around, making me get on my knees and suck the others strap-ons while one of the others take turns teasing my caged cock and balls with a hatchi wand. If I cum it is used to coat the strap-ons I am sucking.

CHASTITY # 14: Sissy Chastity Slave Femdom Strap-on Gangbang: My roommate will invite her girlfriends over for a sissy chastity femdom strap-on gangbang party. When they arrive they will pick one of the 20 plus cages she has for me and lock me up. Then they will select a pair of sexy crotchless panties and thigh high stockings for me to wear. They will generously apply and reapply during the dare hot pink lipstick to my lips. . My roommate will have me get on the coffee table on my hands and knees and will cuff my wrist and ankles to the table legs. Each one of her girlfriends will get to choose a different colored strap-on from my roommate’s collection and then the fun will begin. Wine and cheese will be provided of course

CHASTITY # 15: Chastity Ballerina. My roommate bought a black Tutu and black thigh high stocking for me to wear while locked in the chastity cage of her and her friends’ choice. I am to serve them wine and whatever else they please. Whenever they or my roommate request I must do a releve pose in front of them on my tip toes with my arms up over my head while they tease my caged cock for no more than 3 minutes. If I come off my toes, they are allowed to slap my balls. This is my femdom roommate's rendition of the "Nutcracker Suite".

Chastity # 16: Chastity Condom Cuckold: My femdom roommate will lock me in one of her chastity cages from her collection with me totally naked on my knees. She will stick a suction cup realistic cock dildo to a door mirror. I have 30 seconds to apply a condom on the dildo using my mouth with my wrist cuffed behind me. If I fail, she zaps me on my balls. I have to keep trying until I succeed 3 times in a row. She says this skill may come in handy in the near future