A very good question Mistress Anna!
My own working definition of a sissy is simply a submissive crossdresser, which rules out guys who like to dress but not submit and guys who enjoy submission but not dressing.Â
This definition, of course, still leaves a lot of room to include both the formerly-arrogant male who’s being chastized through enforced feminization and the sweet natural sissy, who understands the worthlessness of his little willy and longs to become as much like the superior female as he can.
Personally, I prefer the latter type. So long as he’s obedient and well-mannered I prefer to spend my time playing with my sissies rather than chastizing them (though admittedly even the best need disciplining sometimes). I suppose I think of them as life-sized fashion dolls, ones with more interesting features than closing the eyes and wetting the bed. 😉
xox
Cherie