Every discussion we have spawns more discussions so here we go again.
I'm gay and extremely active in the queer community with a lot of friends in activist circles who are trans, genderqueer, bi, pan, and so on. Literally until Femboy Hooters I'd never even come across the term. Here's what I think I see and y'all tell me if I'm off.
Femboys themselves seem to mostly be gay boys, although some are potentially trans eggs waiting to crack, but largely they seem to be comfortable with being gay and cis and male. They all seem to dress up pretty hardcore in feminine clothes and wear make up, but they're not drag queens or genderqueer, or they don't identify as such at least.
What's weird to me (yet still makes sense) is that the vast majority of people attracted to them are straight guys. As one dude said, "Men make better women." So of course there's the overtone of misogyny there. I've been approached before by straight men asking me if I'd be willing to wear panties or take hormones or get a tit job, but I hadn't really thought about it until I saw the preponderance of femboys out there in the world. Now how can I say these guys are straight if they want to fuck a cis man? Pretty simple, they don't see me as one. They see me as a woman who they want to feminize more.
I tried looking at the etymology and history of the term but there's nothing much. I did uncover a trove of femboys who hate trans people and who also differentiate themselves from what they call tr^ps. If you hate trans people your gay card should get revoked automatically so fuck them, but it seems to confirm my suspicion that this seems to have a misogynist bent to it. This may just be a label for the types of gay guys I knew who were very feminine and liked to date straight men, who treated them like garbage and both of them had really conservative personal politics.
But I don't know and I want to learn so tell me what's up, I'm old and I need my porridge.
Femboys aren't necessarily gay, my impression is that most are bi and some are straight. As far as the evolution of it, the closest I can think of is the term "sissy" which is a term used in the BDSM community which has a similar meaning to femboy but more... derogatory, I guess? Not malicious, necessarily, but like the term assumes that you're into degrading dirty talk so you wouldn't mind being called that. Femboy is a much better term because it allows you to describe someone who fits into a certain combination of presentation+identity, without forcing them into such a narrow box or having negative connotations. In fact it's kind of an awesome term because it doesn't seem to have the same stigma that is usually associated with men being effeminate. Anecdotally, I have a bi (leaning gay) female friend who told me she loved the term because of it describes the exact kind of guy she's into, and she never really had a word for them before (she used to be active in the kink scene, and said "sissy" always left a bad taste in her mouth).
Anyway yeah there are some femboys who are transphobic or nazis or whatever, for some god-fosaken reason. But there's also nazi furries and nazi bronies and so on. I wouldn't read too much into it. Being a femboy doesn't really say anything about your personality or sexual orientation, it's more like a style, you might say.
AH. Now this one makes a lot more sense. It also kinda fits into that forced feminization thing I see a lot of.