Girl meets boy dressed as girl

I suppose this will be my obligatory Valentine’s Day post about cross-dressing and romance…(nah; not really).

I’ve already talked about how a number of guys have responded to Twist; what about women? I’m a heterosexual guy in a skirt who happens to be engaged. But as ‘Twist’, I’m both more outgoing and rather more coy; I suppose I’d have to say Twist is flertarosexual – nothing more than a flirt.*

I also asked a number of my female friends for their thoughts and opinions; I’ve been swamped with so many nuggets, gems and useful insights I can probably generate three or four posts out of it all. (My thanks to all of them!)

Twist was surprising to my conservative upbringing… with very old-fashioned, strong, gender-stereotypes… The only context in which I would see a man dressed as a women is when they were making fun of women…

I couldn’t quite wrap my head around you at first because, you weren’t gay, you weren’t a drag queen – you were an actual, straight, perfectly regular man who just wanted to dress like a woman, and did it in such a way that it was obvious you weren’t making fun of us… it made me feel amazing in a way I’d never felt before. My femininity was suddenly awesome, not something pathetic for frat boys to parade and degrade themselves with.

Pre-Twistoric relationships

I went to a rather old-fashioned boys-only school in the 80s (pop psychologists are invited to keep their opinions to themselves at this point), which wasn’t really the kind of environment where a boy could express his feminine side, or engage in even the most rudimentary kind of relationship with girls. So when I made friends with girls at university, it seemed a bit mind-blowing at the time.

Happily, I got to know enough girls who were comfortable with the idea of me borrowing their dresses for parties, that I could experiment a bit with cross-dressing. And that’s when I noticed something a bit odd: for some reason, it was easier to hang around women whilst cross-dressed – or was it just me?

I can’t quite put my finger on it but it may because with Twist there’s a bit of feminine competitiveness that comes out when I’m in her company, in that she ups the ante to be funny, wild, a bit rude or risqué.

As a post-adolescent boy who’d had limited female contact, this was bloody fantastic; if I put on a dress, I’d end up surrounded by girls wanting to doll me up with makeup, lend me bras to be stuffed full of toilet paper, and actually – you know – talk with me. All the guys at these parties would end up on the other side of the room, drinking beer and burning through cigarettes, casting glances at the cross-dresser who’d infiltrated the girls’ corner (cuttlefish do this too, you know).

I guess when boys dress like girls it makes them kind of more relatable.

One of them – my psychology lab partner – once said that “if [she] was into girls, [she’d] bang my goddamn brains out” (which was the weirdest and most gratifying compliment I ever received at university, seared into my brain for all time); sadly she wasn’t and didn’t, but one of her friends took me home with her at the end of the party. (Years later, a couple of female friends have joked “dammit, stop turning me gay!”, which I take as the lighthearted compliment it’s intended as.)

Perhaps some bisexual and lesbian women are legitimately attracted to you as Twist, but any straight women (because orientation is not a choice) might simply be saying this because Twist makes you more attractive as a man.

When my improv troupe went to see the then-latest James Bond film, the girls wanted to dress as 007 in tuxedos, and they wanted the guys to dress as Bond girls – because I was the director of the show at that point, they picked out a dress for me (a flirty red minidress, amply padded)… so, as far as cross-dressing went, I think I struck lucky!

You have a very alluring and fascinating character there! Boys and girls are all drawn to Twist…

As for the girlfriends I had back then, some were OK with me cross-dressing, some were weirded out and happy if I didn’t mention it ever again, and one  really liked it. I mean really. (That would have been one of those intense ‘the candle that burns twice as bright burns half as long’ kind of relationships.) Yes, I’m glossing over a lot of details; I already told you Twist is coy. Generally speaking, the ones who met me cross-dressed found it easier to deal with than the ones who found out after we started dating.

So, there are women out there who are quite happy to have cross-dressing boyfriends; I’m pretty sure there’s always someone out there who’ll accept you the way you are and the way you want to be. And there are some who’ll positively encourage it…

(From ViaVia, 8 December 1994)

(From ViaVia, 8 December 1994)

I saw this advert from a newspaper clipping used in a Dutch textbook I read for a university course. It’s asking for women’s summer clothes – “Man must wear girls’ clothes for his girlfriend; therefore looking for a wide range of tight summer dresses, miniskirts, hotpants, blouses, swimsuits…” Forced feminisation is a fantasy for some guys; clearly this dude was living the dream!

Luke, if only you knew the power of the feminine side of The Force…

…[men who] don’t act like MEN (sports, beer, and misogyny)… are generally sensitive, good listeners, not afraid to display their emotions, etc (‘girlie’ qualities)… and ‘Manly’ men don’t like this.

Cross-dressing is great fun; more so when you can find someone to share it with. But I suspect many of the women who are attracted to it might be just as reluctant to ‘come out’ as the guys who cross-dress.

Once you’re comfortable with your own cross-dressing, you’re more likely to find someone else who’s comfortable with it too. Until you find that special someone, just do it for its own sake.

After all, not all women are into manly men:

*It’s hard finding a phrase that means “my sexuality s nobody else’s business”.
I could describe myself as ‘cryptosexual’ (‘hidden sexuality’), but the illiterates of teh interwebz have gotten there before me and defined it as ‘sexual attraction to mythological creatures’, not realising that that would describe a ‘cryptozoosexual’ (attraction to ‘hidden animals’).
I can’t use ‘idiosexual’ (‘private sexuality’); it’s been hijacked to refer to chronic masturbators (that should be ‘autosexual’).
It’s a matter of some irritation to me that the evolution of language is driven by people who won’t read a bloody dictionary. Yes, I know this makes me a bitter snob; deal with it.
🙂

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9 thoughts on “Girl meets boy dressed as girl

  1. Gee says:

    Thank you for the wonderful and insightful comments. As someone who was encouraged to crossdress by a woman friend, I initially had a hard time getting my own head around it. While there was no doubt that I enjoyed it, I kept thinking “why is she doing this,” “why am I doing this” and “when am I going to get caught and regret it?” What started out as fun, daring, experiment in not-so-forced feminization turned into a very exciting embracing of who I might want to be. There’s still a lot of daring and experimenting, but I’ve been fortunate to find women who accept and support me.

    • Miss Twist says:

      Thanks, Gee! (I nearly typed “Gee, thanks!”) 😀

      Sometimes it’s best to heed the advice of Thomas Jefferson in the pilot episode of ‘Jack Of All Trades’: “Shut up and do what the lady says.” At the very least, if you ever get a chance to do something that’ll give you a great story to tell in fifty years’ time, go ahead and do it. 😉

  2. Sophie Gray says:

    Hi Miss Twist, Love this post! It never stops to amaze me how some people’s lifes seem to be a blueprint of mine. I also have a supporting and understanding spous, who dragged me out when I was stuck in circles. And I also feel more comfortable around women, when dressed as Sophie. It’s an awesome feeling to be accepted as one of the girls and to take compliment in their sometimes rude and envious comments about my appearance. Although it’s not always easy to have a foot in both camps, I try to keep a light hearted approach about it and never forget it can also be a lot of fun.
    Sophie

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