I keep batting this difference around in my head. I am someone who prefers to call themself “crossdresser” instead of “sissy”, though is also active in sissy communities. Why do I have that preference? I wrote up a few comparison bullet points below, let me know what you agree/disagree with. And feel free to mention other points ❤️
Crossdresser:
- A little old-school but gets the job done.
- More fluid in sexuality/gender identity
- Not inherently sexual
- Not particularly demeaning
Sissy:
- Feels newer/trendier
- A little more focused on sex with men
- Very sex-focused
- Often used as a demeaning word (consensually)
I wouldn’t bother with thinking about it in terms your first point. Old-school vs newer isn’t really relevant to the comparison you’re looking. Crossdressing is something that has a clear definition - dressing in a way that is contrary to the societal expectations for your gender. As you mention it is also more of an objective non-sexual term.
Sissy is a lot more ambiguous and tends to mean something different to each individual. Because of this it’s going to difficult to get a clear answer. It’s a term that, in the way you’re referring, carries a clear sexual implication and usually in my mind comes in tandem with idolizing/embodying feminization(not necessarily crossdressing) and has D/s BDSM roles baked into it generally.
At the end of the day though, do what makes you comfortable and don’t worry so much about labels.