Saturday, 4 January 2014

A fantabulous night!

I wore a dress for New Year's Eve! In the eight months I'd been crossdressing it was the first time I'd ever worn one, as unbelievable as that may seem. I should clarify, it was the first time I'd worn one as a girl. I'd tried on dresses in boy mode, but that's not the same thing at all.

Carson and Jamey (that's my brother and his wife) had me over at their place to ring in the new year. None of us are the sort of people who really enjoy large parties or spending loads of money at bars, so we figured we'd have a little get-together just the three of us. And just for the hell of it, it was decided the evening would be a formal affair. After all, they both enjoy dressing up fancy, and I hadn't yet had an occasion to do so as a girl.

On the day before I managed to pick out a gorgeous dress that, for some reason, actually fit well and looked good on me. That night I was so excited about wearing it the next day I could hardly sleep! I'm a bit silly like that, I guess. :) The following afternoon I bought some fabulous shoes and jewelry to go with it. I even went so far as to buy some of that shapey hose stuff, which, ironically, ended up being the most expensive part of my outfit.

I arrived at their apartment in boy mode that evening. Jamey and I did our makeup together. She helped me out a lot, and insisted I use several of her products. I learned a lot from her, and my makeup definitely looked better than it ever has before. It was a ton of fun, too!

...aaaand this is what I looked like! Possibly my favourite photo of me ever! :D
Then the three of us had a delightful evening of sushi, boardgames, and drinks, though we missed counting down to midnight because we were busy discussing how Jupiter's gravity causes gaps to form in the asteroid belt. (Yeah, we really do talk about geeky stuff like that, I'm afraid). And it was such a relief for me just to be in the right gender, especially after all the stress I had spending Christmas at my parents' house.

The three of us looking fabulous. (Posted with their permission)
I can't express how grateful I am to have those two in my life, nor how much I appreciate that I can be myself around them. In fact, there was a much more important "first" that night than just my first time in a dress. It was also, technically, my first time presenting fully female in front of them. It's just that, we reached that point so gradually I don't think any of us hardly noticed. Over the months since I came out to them I've let them see increasingly feminine iterations of my male presentation (once even wearing heels in boy mode!), so that by the time they finally met girl-me, it wasn't a big deal.

At one point during the evening I apologized to Carson for how weird it must be having a crossdresser for a brother. (Of course I know I can't help being trans, but I still feel culpable somehow). He shrugged it off: "It's a little weird, but whatever." Then with a smile he added, "You're a crossdresser, but I'm more feminine than you are!" My brother is not a typical "manly man" by any means, and his point, I think, was that I wasn't the only one with an atypical gender.

Depending on your definition of femininity, and that's a very difficult thing to define, he might even be right. I'm a bit of a tomboy; he's a bit of a pretty boy. In the end it probably doesn't make sense to compare one person's femininity to another's, since it's something each person defines for hirself. But it does go to show what a complicated, convoluted thing gender is.

Also, SUSHI!!
It was a great night, both in terms of fun and gender expression, and I'm thinking I just might need to find more excuses to get all dressed up!


  1. What a gorgeous outfit, Ashley! I love the black dress, along with some awesome heels. I know what you mean about the hesitation of buying a dress. I've been so worried about how a dress would work with my figure, that it took me forever to buy one, but it worked out well when I finally got one. Looks like you'll have even more of an excuse to build up your wardrobe, now that you're more comfortable as Ashley. It's so cool you've got a supportive brother and sister-in-law to spend some quality time with, and have fun with makeup. What you brought up is so true, that it's so hard to define masculinity and femininity, one just has to do whatever makes them happy, and not worry about how to define it or categorize it.

    Have a happy 2014 Ashley.


    1. Aw thanks Katie! :) And you're certainly right that "it worked out well"-- you look fantastic!