Well in my husband’s case I started off slowly and eased him into the humiliation. We haven’t done anything extreme I know my husband’s limits and will respect them. Below are humiliation things that my bull and I have done:
Verbal humiliation: This one is the first one we started on. I would tell my husband his small cock didn’t please me while my bull would tease him about his cock.
Standing in the corner nude: We would make him nude and watch us. Also at times he wasn’t allowed to touch himself if he did my strong bull bend him over his leg spank the crap out of him.
Cleaning up: This was a big adjustment for my cuck at first he didn’t want too but my bull would grab him and his mouth on my pussy and lick up all his cum. After awhile my cuck started to lick and was eager to clean up. Lucky for him bull would shoot about 3 to 4 tablespoons of cum. Cucky started to become a big cum slut.
Transition into panties. This was easier than I thought it would be. I purchased some sissy satin panties off Etsy and presented it as a gift for him. When he opened the package he thought they were for me. I said no dear they are for you Since you are mouse hung you do not need male underwear anymore. He went and tried them on and I could see he loved the soft satin material. I removed all his male underwear and now only wears panties. We forced to stand in the corner and watch in them. My bull would call him names sissy panty boy or sissy cuckold. When my bull is over he can only wear panties around.
Chastity device: This didn’t workout unfortunately it was too painful and would turn my husband’s cock black and blue. We decided after trying different C Rings to give it up.
Not allowed to watch: At times my bull and I make him listen outside the master bedroom with the door lock. He is only allowed to come in and clean up in his panties. Usually my bull stays the night and my cuckold husband has to be in the other room.
Lingerie Shopping for the Bull: I take my cuck husband shopping with me for lingerie for my hot bull.
French Maid: I had cucky recently fitted for a custom French Maid dress from a local seamstress. He was totally humiliated because the lady knew he was sissy cuck. The dress was fitted hoop at the top the which allowed me to lock it with padlock. Also it has matching satin and lace panties. I bought him heels, garters and thigh high stockings. He now has to shave his legs and must be dressed in the outfit when my bull is over.
I probably forgot to mention some of other humiliating experiences we have done on him but that’s the majority of them.