Roll After Dark

Feminisation, sissy play

Clothes, makeup, or a name that feminise the person wearing them.

Why people do it
Clothes, a name, a way of moving. For some it is humiliation, for others it is euphoria, and the two look identical from outside — which is why it has to be asked about rather than assumed.
Smallest way in
One item and one hour at home. Find out which of the two it is before building a scene on the wrong one.
What to watch
Ask which register this is in — degrading or affirming — and use that one. Getting it backwards is the failure mode here and it is not a small one.
In the planner
8 different things carry this tag, and switching it off removes every one of them. The mildest of them sits at easy.