I get a bit of a thrill from crossdressing in public. I've got myself to a point where I'll attend most parties some degree en femme - my favourite is when I wear a skirt. My work and most of my family don't know I crossdress though, so my limit at the moment is with friends and parties. I'll wear nail polish and even eyeliner alone in public, but probably wouldn't go further without company unless I'm on my way to meet a friend.

It's taken time to get comfortable with getting glam on the town though, and I've gradually pushed myself to develop my look from ladies jeans and black nail polish to skirts and stockings. Eventually I hope to work up the courage (and wardrobe!) to start wearing dresses out too. 💖

I'm definitely getting more comfortable with presenting somewhat femme in public, yeah. I'm often wearing nail polish, I recently got my ears pierced, and I've been known to wear makeup once out when there's a reason to. I've worn kinda femme clothing before, mostly to pride events (short shorts, floral romper, crop tops, etc). Haven't worn a skirt/dress out, not sure if I'll get there soon but who knows! I do wear a small amount of jewelry sometimes, but I need more of it for sure. Also, I mean, context is everything. Am I gonna be a bit femme at a cool show or concert? Sure. Am I gonna wear it when going to the hardware store in a rural area? Nope.

Not sure where the line really is for me. Or really, where the HARD line is for me. Because like, skirt in public, not absurd. I'm not going to do it right now, but it's not off the table.

Challenges, I mean, internalized homophobia/transphobia/etc being the big one lol. A few things that helped me: having a remote job, cuz previously I would definitely encounter some right-wing jerks in my office. Having a very supportive partner. Coming out as pan to people. Making the decision to be more outwardly queer. Moving to a new city, too.

Thanks to MaybeALittleBitWeird and K.K. for keeping this place going ❤️. I have a lot to say about this month's questions, so I'm just going to dive in.

confusion and shame that comes along with subverting societal expectations regarding gender and sex

I've been a sissy on and off for about 10 years. 85% of my lifetime experience of presenting more femininely in public has been in the last year. It's been illuminating about many things. It's illuminated that I have/had much more confusion and shame about presenting femme than I realized. I think that's because for a long time I did not feel safe presenting this way in public, telling people close to me that I wanted to, or even privately acknowledging it to myself. The Tl;Dr is that I realize I have this vestigial (i.e., outdated, obsolete) 'gender police' in my head that I have built over years; it's still quite powerful and it unconsciously biases me to sense more risk about being feminine in pubic than my lived experience ever has suggested is warranted - and it's not even close. It's surprised me to clearly see after a while that I have more introjected transphobia than non-bigoted cis people have transphobia or even lack-of-acceptance for trans people. (I think as a crude test of internalized transphobia, see how comfortable are you making polite eye contact with and smiling at an enby or trans person you pass by on the street.)

presenting as in public

Just to add that there is no singular public. Presenting feminine in a cab to a gay nightclub and back is different than being feminine around your parents, going to work, running an errand, etc. I read a study of enby people recently and the norm is that people are 'out' to varying degrees with different people or groups in their lives.

How feminine are you comfortable with presenting in public (if you are at all) and where do you draw the line with what is and is not okay to do in public regarding your gender expression?

Long hair in a bun, double huggie earrings, clean shaven or waiting for my next shave (sensitive skin, laziness about things I don't see :P), and a plain anklet are my baseline. For the last few weeks I've been rocking painted fingers and toes full-time. I just shaved my legs 😝

Legally, bathroom-wise, and socially (e.g., pronouns, brother/sister), I think I plan to stay identifying publicly as a man. I don't think I ought to limit my gender expression for anyone's sake per se, but my choice is to present in a way that I think cishet people will understand; and I see that as a somewhat feminine man - not far off from a feminine variety of gay. Wearing makeup and a dress would not fit that mould, imo (although special crossdress nights might be fun). There are some environments where I don't (yet) feel that comfortable wearing colourful fingernail polish in - like my neighbourhood fitness gym. (A lot of people trying to stifle mtf-curiosity do so with excessive exercise, whether or not they're aware of it. I was one of them in the past. There will be more looks than usual at the gym - ha!)

What were some of the challenges you needed to overcome to get yourself to that point?

So, nail polish has been my big drive lately. I started off wearing 'barely noticeable' colours, but I found it better psychologically to gain my 'comfort footing' with more noticeable colours. If my nails were subtle enough that many wouldn't notice, I was hypervigilant about people noticing. But, when I made the choice to wear black polish, for example, and accept that people would notice - I realized that noticing isn't bad. In fact, most of us like being noticed most of the time, I think. But we don't like be stared at, or worse. I recommend that latter experience of - just go with something people will notice and see how safe it actually is [eg, how many genuine stares or negative remarks you actually get] - with whatever you want to try. And, if your thing is also nail polish and you want a 'plausible alibi' just in case, do black around Halloween. Or just Halloween in general.

I think I also shifted from seeing things in black or white about whether or not something is or isn't safe to wear out, to more of a "try it and let's see" approach. I don't think there's anything wrong with painting your nails, feeling like you're getting more attention than you're comfortable getting then and there, taking it off, and trying it again another situation. In fact, I think it's very useful to appreciate to recognize how important personal comfort level, versus objective riskiness of the situation, is to our perception of risk in expressing femininely out and about

The fear of being judged blocks me at the very start. I'm not comfortable at all appearing feminine outside of my own home and won't be in the nearly future. I'll go as far of wear black nail polish if I ever find the courage