Men are cute when they blush. Unless your man is very jaded, you can have fun making him blush, using humiliation. It is not meant as abuse however. So, know what you have to work with and what needs to be avoided. Keep it light and remember there is life after your fun, don't leave him with something he can't explain at work the next day. (Unless that's what he likes).
Most men get fidgety about things like women's periods, girly things, and so on. Make a list of things you know will bother him. How about being exposed, even if it's not likely anyone can see him. Think of it, a tall building surrounded by shorter buildings and him standing naked in the window. Would he get butterflies?
There is a lot of humiliation in age play scenarios. I wrote some of my own ideas in my erotica for Chris. Things like taking him to a restaurant and making him order from the kids menu, wear a bib and ask for the crayons and activity sheet usually given to children.
Another thing to keep in mind is how your scheme for him affects others. Public nudity might seem great fun while you're in the planning stages but it's indecent exposure if there are other people around who don't feel quite the same way you do about it. Plan, think and scheme and you can make your best ideas work.
I personally don't like forced feminism, though that is a popular humiliation. I just don't think it's very complimentary to us, the real women.
Need more ideas? Keep him nude all evening while you remain dressed, doing everything as usual. Have him acting as your footrest for the evening. Send him to the store for the big box of maxi pads, flowery underwear (in his size), cosmetics, or scented bubble bath. Have him join and graduate from a sewing class. Make him take a map into a gas station and ask for directions. Whatever works.
