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.

I think a crossdresser is someone who wears clothing typical of the opposite gender, while a sissy is the male equivalent of a tomboy with a little stigma attached. These definitions would mean most sissies are crossdressers and many crossdressers are sissies

Crossdressing isn’t inherently sexual, being a sissy is in almost every case, sexual. Many if not most crossdressers are straight, most sissies are at least a little bisexual. Crossdressers look at the clothing they wear with pride, it’s an entirely positive thing. For a sissy, the frilly dresses and such are mean to demean their manhood and provide the humiliation that most sissies crave I have also found that while nearly every sissy is submissive, many crossdressers are dom or neither

You’re not alone in this and I think this is natural for anyone figuring out their identity on the trans/enby/cd/fem-spectrum. I’m also still figuring things out and it’s okay to defy categorization.

I’ve researched some angles and I’d like to share them with you:

I think what many of us in this community might experience is some form of autogynephilia. We derive some sort of pleasure from seeing ourselves as feminine. It can be especially difficult to find the difference between this and any form of gender identity other than your assigned sex at birth because the lines tend to blur sometimes. While theory states autogynephilia is by definition sexual in nature, I think the mechanism also exists for nonsexual feelings coming from the same principle where a feminine version of yourself is the source of positive emotions.

But let’s not rely on theory on sexuality too much, let’s focus on what’s important, which is who you are. Not who you’re attracted to. Attraction does matter, but it’s secondary to your own identity.

Starting with my current understanding of myself, this is my interpretation of Fluidflux. See, the “official” description does not quite align with my experience. The best way to describe it is to look at gender as a finite number of “skill points” (because games are always a great way to model reality). Some days my build is purely FEM, while other days I’m rocking a more balanced build between MAS, NBI and NUL. I like all those gender identities and I feel that it’s fine to just flucuate between them in various degrees for the time being. You might say “that’s just genderfluid” and you might be right, but the fluidflux flag is just way cooler.

Either way, I consider both crossdresser and sissy to be part of who I am, but neither paint the full picture. It all depends on what you enjoy and you can be anything you want kinda thing.

Your take on crossdressing is exactly right, it’s an expression of your tastes in clothing. You wear feminine clothing because you want to and the reason why might be strenghened by kinks, a feminine gender identity or just your fashion sense. All are valid.

Sissy is a kink, and while I’m not really fond of the word itself, the main elements of the kink I do agree with. It is focussed on sex, where you are either on the receiving end or on the submissive side of the power dynamic. I don’t think it needs to be exclusively men, but it seems that part of the fun is for people to discover their attraction to the concept of sex with men this way and deriving excitement from something that will stay in a grey area until they accept that 100% straight is not a thing. To me, it is mostly about taking the role traditionally fulfilled by women in straight relationships and doing so either voluntarily, or with help (hypno, coercion, force, etc).

But the main takeaway is that everyone is different and everyone will cherry-pick different aspects of popular concepts to form their own identity, and that is what makes us beautifully diverse.

For relatability I’ll list some of the things that make me who I am:

• I experience both attraction and envy towards beautiful women. I want to be (with) them. Which was quite confusing at first but it makes sense. I am attracted to femininity, both in myself and in others.
• I am bisexual, though I am less interested in a romantic relationship with men than with women. I’m not sure where anything defying those categories will end up yet.
• If I had a choice to be reborn and pick my assigned sex I would choose female. Some days I feel like I am transgender and I want to transition, but I can’t commit because I’m still not sure.
• One of my ultimate dreams is to experience pregnancy and childbirth myself. Though I am not sure we will ever see technology able to fulfill this dream in my lifetime.
• Shopping for feminine clothes is still one of my favourite things to do and I’m slowly trying to figure out a way to shift my daily wardrobe more ‘towards the middle’.
• I think my barber knows something is up because of my long hair. He has adviced against certain cuts because they can make you look feminine to which I’ve replied that I don’t mind that.
• Removing body hair leads to amazing results and I like the clean look both in men and women. I usually remove anything beneath the eyebrows.
• Relationships can be difficult as it is usually a big step to tell your partners about your true self, especially if you are still figuring things out. I firmly believe that if someone does not fully support who you are in private they are not worth investing in. But anyone might take some time to come to terms with something they weren’t expecting.
• Being referred to as female in public (which is usually hastily corrected) makes me feel great because of two reasons: I get the validation that I can pass as feminine and I like watching them squirm trying not to offend me, because I am a sadistic little shit.
• When it comes to kinks I’ve fully accepted that I am just a degenerate. Though the main categories are sissy and anything BDSM. Which would make for a great combo but sadly there is not a lot of content out there.
• I am 100% okay with the fact that ones identity is something that will change over the years and figuring new things out is part of the fun. It’s a shame that society doesn’t always provide the freedom to do so.