I guess this thread is a bit stale but here's mine. I'm very much into consensual humiliation behind closed doors or at least semi public in a safe space.

I'd love to get caught by my partner doing something shameful like cross dressing or playing out a sissy fantasy while I think she's away on a girls trip. Then turned into a part time sissy behind the closed doors of our condo as well as taken out to fetish parties in my sissy persona and maybe even registered to a weekend sissy training academy where I work my normal Mon-Fri day job in my male persona but on Sat/Sun I go into sissy mode and attend a private school type "finishing academy for sissies".

I definitely need to flesh out this concept/idea more in writing since my thoughts tend to go everywhere when I even start to think about it.