Well, you asked about “why”, so hold onto your pantyhose because that’s a complex and thorny issue that nobody can fully answer except you.

Now, first the obvious. Cross dressing, aka transvestism, isn’t inherently gay, nor is it inherently a sign of anything other than having a desire that is met by adopting the culturally normative garb of a gender other than your own. If you were trans, to cover that, it wouldn’t be transvestism because you would dressing as your own gender.

Thing is, some people discover their trans self by exploring gender norms via clothing, so only you could say if that’s in play here. I’m just saying that cross dressing isn’t the same thing.

So, since we’re assuming you aren’t trans and exploring your gender, we can move on to other possibilities.

The first one is easy enough to examine. Is it a kink? Some transvestism is kink based. It turns people on to wear clothing of genders other than their own. If you do not experience sexual arousal from the act, then you can exclude it entirely and move on. If you do experience arousal, then it definitely includes a sexual component, even if it isn’t the only reason.

The reasons for having any kink are already complicated enough that if it is part of your reason, it would take a book to cover the possible root origin of it. So, if that’s the case, unless you’re feeling distress related to it, or it has become obsessive and/or interferes with the rest of your life, you’d want to consult a good psychologist to help guide you through that part of things. But, just to be clear, cross dressing isn’t inherently a disorder. There’s also nothing wrong with it, but anything can turn into disordered behavior/thought.

If there’s no kink involved, the next thing to look at would be what feelings it either causes, or reduces. Some cross dressing is rooted in self soothing of one kind or another. The process of it ameliorates some inner stress. As an example from a guy I used to work with, he would dress in styles similar to his mom, after she died. It helped him feel closer to her memory.

There’s also the possibility of other stress relief. Donning an other self can give people some distance from their daily self. There’s some folks in cosplay and furry communities that first stepped into those hobbies as a form of escapism. In that regard, it’s the same as any other hobby tbh. Putting on heels and some make-up is no different in principal from playing d&d, or call of duty. Sometimes, we just need to step away from the daily grind and be someone else for a while.

Hell, some people will do it just for the lark of it. It’s silly and fun to explore clothing and other gender norms. That tends to not be a long term thing, but what starts as a bit of humorous fun can turn into other things.

There’s still other reasons you might have found your way into it. More than I can list with the absurdly shitty internet connection I’ve been dealing with lately lol.

But I think the important thing is to realize that it doesn’t necessarily say anything about your sexual orientation at all. It could, but you’ve stated that you’re attracted to women only, and I assume you know yourself well enough for that to be true.

You can be a trans lesbian, you know. Or you can be literally anything else.

Welcome to the character customization screen. Pick whatever sliders you want.

I think @southsamurai@sh.itjust.works pretty much hit the nail on the head, but just to sort of reiterate

Wearing “women’s” clothes (I always liked the Suzy/Eddie Izzard quote “They’re not women’s clothes, they’re my clothes. I bought them”) doesn’t necessarily make you gay or trans or anything, it just means you’re wearing women’s clothes.

If you’re comfortable identifying as a man, and you’re attracted to women, all that means is you’re a straight male cross-dresser or “transvestite” (I believe some people find the term transvestite offensive, others have no problem at all with it. I’m not a cross-dresser myself so I won’t weigh in on that debate) or perhaps a femboy. It could be that you just like wearing women’s clothing and there’s not much more to it than that. It could be some sort of kink/fetish thing, it could just be that you find it comfortable or feel cute, or maybe you just think it’s fun and silly.

And you could probably go down some pretty deep rabbit holes trying to unpack why you like it. There’s probably as many reasons for it as there are people who enjoy cross-dressing. But unless it’s really causing you severe emotional distress not knowing, you can always just take a page from Popeye the Sailor and say “I yam what I yam an’ that’s all that I yam”

Or it could be that you have some sort of gender dysphoria, and this is your way of working it out and coming to terms with that. In which case you might figure out at some point that you identify as a woman or some flavor of non-binary.

But at the end of the day, clothes are just clothes, and the person wearing them is just a person. I don’t think it’s worth getting too hung-up about putting labels on things, go ahead and try some different labels out for yourself, maybe you’ll find something that sticks, but a rose by any other name would smell as sweet.

You’re autogynephillic, which is something some straight men have. It just means you’re actually very straight

You don’t have to want to date men to want to be feminine. I’m a femme lesbian who prefers other femmes. I’ve known straight and bi women who like their men more in touch with their feminine side (just as I’ve known some who find femininity in men unattractive).

There are infinite variations on how to live, only you can decide how you ought to.

Gender and sexuality are separate things. Just because you have a feminine side doesn’t mean you have to be attracted to men. I’m trans, and when I was 16 I would also dress femme alone in my room sometimes, so I get what it’s like. (Not saying you’re trans, it’s perfectly okay to be a guy who likes to dress femme.) Figuring out why and what it means for you takes a lot of introspection and is only something you can answer.

You can wear women’s clothing without ever developing or having an attraction to men; you seem to have a firm attraction to women and fem-related clothing. There is nothing wrong with wearing a woman’s outfit in your bedroom and enjoying the experience, it’s not going to make you bi or gay. If anything, you clearly enjoy feminine coded clothing close to your skin. I don’t really think you need to do much of anything, once again, I feel there is no harm that is being caused.

It might make your egg crack, but that is something you’d need to interrogate yourself about deeply before learning that answer.

well, it doesn’t sound like you’re confused about your sexuality, but rather, your gender. in case you didn’t know, those are separate concepts (what gender you’re attracted to vs what gender you identify as)

have you taken some time to consider if you really enjoy being a man? when you look into the mirror, and you look at your face, does it look right to you? or does something feel wrong? these are just a few of many questions that might help you uncover any underlying gender dysphoria (or lack thereof)

i’m about to go to bed, but you can read about it more here: https://genderdysphoria.fyi/ i’m a transgender man (so, ftm), but i know a lot of transgender women, as well, so feel free to ask follow up questions if you have them

Time to get back to basics: Genderbread Person

Why do you do it? Probably because femininity turns you on. It’s nothing to do with being gay. Maybe you have more of a fem side you’re discovering? Idk I’m not an expert, but there’s a bunch of the queer/etc community here (crossdressers probably too) that could give better answers than me.

My advice would be, don’t be self critical on yourself, or feeling bad because of what society says men should or shouldn’t do. You’re allowed to be a complex person.

I wouldn’t spend too much time looking for a lable to apply to yourself because you’re probably not going to find one that perfectly fits. Reality is way too complex to be neatly categorized like that.

Sexual and romantic interests doesn’t need to match. This has probably more to do with the dom & sub dynamic than about being gay. It’s a kind of a mismatch between how you feel and what you think is expected from you based on your gender.

I was in the same situation at your age. I’m just as confused 15 years later but I’ve stopped fighting it. I like what I like and I don’t need to explain it. Most people deal with stuff like this but they just keep it hidden to avoid judgement. You wouldn’t believe how many comments I got online starting with “I’m not gay but…”

I’m gonna agree with what some others have said. You’re not wearing a woman’s clothes, you’re wearing your clothes. You’re not dressing like a woman, you’re dressing how you wanna dress. I think that’s fine.

A lot of the women in my family (and, my wife) buy clothes from the men’s department. I buy my young nieces, who are not old enough to have a differently shaped body than the boys their age, shirts from the boy’s section. When my youngest niece was six, the only NASA shirt was in the boys’ section. I think every kid should have a NASA shirt at some point, and it doesn’t matter if they sit or stand to pee. That became her favourite shirt for a while, until she outgrew it. We didn’t tell her it was a boys’ shirt. It was her shirt.

These days, skirts and dresses are definitively feminine clothing, especially in the west. In the east, men wear kimonos and yukatas (I think) and other such robes which are functionally the same as dresses, and they are considered elegant and formal. The problem with a guy wearing a dress is that dresses are tailored for women. They’re meant to accentuate and show off the breasts. Even a dress made for a little girl typically is cut the same way, and it’s fucking weird. If a tailor wanted to design a dress for a man, they would make the waist wider, and either it would stop at the waist, it would be cut to show off his pecs, or it wouldn’t show anything, but it would be almost a different garment. Take everything you know about “manly” clothing design, and say you want to put that into a dress. What would it look like? It could be denim, or flannel, or that rigid material Dickies are made from. I imagine it would be pleated and I imagine it would have long sleeves to keep you warm. Honestly, if I were a clothing designer, I would take this as a personal challenge to make a dress the manliest man would be proud to wear. But even the name “dress” is ingrained in our head as being a feminine article. Yet Scottish men wore kilts, which are totally not skirts. You wouldn’t say a man in a kilt is any less manly than a man in pants, so why do we assume a good past-knee-length skirt of denim or even a thick cloth is less manly than the kilt (which I think is about knee length)?

If you look at what is happening in the crotch with dresses/skirts, and pants, you might think, minus any social conditioning, that skirts and dresses are for men, to accomodate their external genitalia; and pants, with their tighter support in the crotch, are made for women, to help hold sanitary napkins in place. Since their genitals are internal, pants make more sense. But, both genders go the opposite way. Men hold their external genitals tightly in pants (even those of us who wear looser fitting pants and boxers, or boxer briefs), while women “let it all hang out,” though nothing hangs out. Boys on the school yard love to flip a girl’s skirt or dress up, showing everyone her underwear, but other than embarrassing a classmate, what’s even the point? Her genitals are internal, you can’t see anything but her white cotton panties. It’s not like if it were a guy, you could see a bulge.

I say fashion is backwards, which is why fashion makes no sense to me.

I still (47/M) wear pants, though. I would wear a kilt if I had one. Like, a nice kilt. Wouldn’t bother me in the least. They generally aren’t sold in stores (maybe in Scotland? but I’m not even part Scottish). I’ve seen them online but I’ve never thought to order one. I’d want to try it on in a shop first, decide if I like the feel. I’ve never worn anything like one. So I’d have to get used to it.