This is a wonderful thread. I am a straight male and I am in the lucky position of having a female friend who loves getting messy. Cross dressing has never been on my list of things to try but reading this thread I wonder whether that is because for many years I have regularly been able to experience the reactions of my friend while she gets messy. Oddly enough we were taking last month about her choice of clothing to get messy in. She usually wears casual clothes but has worn smart office wear and a few old dresses that she no longer has a use for from time to time. I generally wear casual clothes and she is happy with that. We do have a mutual transgender friend but although she doesn't know about our messy sessions I have no reason to believe that she is into WAM so I can't really compare the reactions of my friend getting messy with those of a transgender woman or crossdresser.

Long time lurker poking my head out for this one because it's a topic I've thought about for a long time who is almost the same age and into the same things. WAM isn't my only fetish but in all of them I crossdress to participate in them. Rarely in my fantasies I am a woman but mostly I'm forced to dress that way because I'm a "weak and submissive" man getting dominated by a powerful woman. Either way there's no gender dysphoria and I'm always fantasizing about being with women in them.

My conclusions on why are mostly the same as yours. I'm also a pretty small, nerdy guy who saw gender roles as bullshit in my teens and ended up friends with gay people at a time when "gay" was still a synonym for "dumb" in that edgy South Park way. I think testing those gender lines is fun on its own, plus women get such better clothes and options than men do. I have t-shirts and button downs and my partner has, well, a whole closet full of fun stuff to wear. Also, when I'm watching videos of whichever kink it is, I'm watching women be humiliated and I don't fantasize about being the person doing the humiliating, I'm fantasizing about being humiliated and that means putting myself in their (heeled) shoes. I think that has kind of lodged into my head as being in those fun dresses and lingerie but hasn't gone to the extent of I want female parts.

My fiance likes that I'm submissive and wear panties at home, which I am incredibly thankful for as I really do feel like that's a part of me and not just a kink anymore. I haven't introduced her to WAM, and I'm unsure if I will as it's like #3 on my kink priority list irl (and I don't want to push the limits of her patience and am constantly terrified one day I'll go too far and she'll find me unattractive), but if I do I'll be wearing lingerie while doing it. Like you, I've never been messy in men's clothes, they're just so boring!

Edit: Just to clarify I'm making it clear that I separate my crossdressing from transgenderism not for any "no homo" bro mentality, but because I am very much aware they are not remotely coming from the same mindset and think it's real weird when people do think they do. In fact, the only time I got what youngins call "the ick" in a relationship was when I told a partner I like wearing panties and she said she was afraid I'd "become trans."

Looks to me like there are several common themes.

One is that it's a turn on to see an attractive woman get covered in mess, especially if she's taken a lot of time and effort to look nice.

Two is the humiliation associated with being covered in the mess.

Third is wanting to experience it oneself, which is why it's much less appealing to be sploshed in male clothing.

Maybe it's also about the reduction of the male ego, too. No better way to reduce that than to wear feminine and restrictive clothing, make a real effort with your appearance and then to put yourself in such an inappropriate and normally unwanted situation where that pristine and beautiful clothing gets gunked on.

It's also nice to trust another person who understands all this.

There was a Domme in Glasgow called Megara Furie who used to splosh crossdressers, I don't think she does it any more. It amazes me that people on here don't organise a safe event for this sort of thing though. There aren't a huge number of folks into it, but if someone hired a venue and everyone paid a fee to come along, imagine the incredible weekend that could be on offer! You can spend a day as your feminine self and all have dinner in the evening with the clumsiest waitresses you've ever met...!