So this Gender thing… Part 1

These first couple of posts are being written in bulk. I decided to create this about a month after things started, so I’ve got a month’s worth of writing to catch up on. I’m going to try and write them in a single go, so they’re going to follow on a bit more fluidly than can be normally expected.

So this Gender thing?

Well it’s the reason I’m here, writing this, at least. I was born male and for my life up until now I’ve identified as such. I’m also bisexual so I’ve never had an issue with fluid or queer sexuality, and this has really extended to gender as well. I couldn’t care less about what gender people are or what they have in their pants (or if they match), but that’s been something of an academic point for me as it never meant anything to me personally.

About a month ago now I told my wife, cuddling in bed at about 1am, that I was interested in crossdressing and femininity, and that I wasn’t sure about anything else. Was it just a fetish thing? Was it something I was interested in from afar but not for me? Was I trans? I couldn’t really answer.

It’s worth pointing out here that my wife is awesome. She’s amazingly supportive, bisexual herself, and a firm supporter of gender, sexuality, and neurodiversity rights. I can already feel a post just about her coming up, but for now I’ll keep it simple (so she can check what I publish before I do it!).

My wife told me that it was okay, she supported and loved me regardless, and asked me about what I thought the motivation was (I didn’t know), how long I’d been thinking about this for (that month), if there was any reason I’d told her today (I promised myself I’d tell her that day so I’d stop putting it off), and what I wanted to do about it.

That last one caught me out. I hadn’t considered I could do something about it. I felt odd and uneasy, I was terrified that I’d told her, worried what she would say, and I didn’t even want to think about what came after that. The relief that she just went “okay” was indescribable.

So what next? What could, or should, I do? As a bit of an academic the first place I started was research. I’d done research already in the month leading up to telling her but very perfunctory. I realise now that I didn’t want to admit anything to myself or make any definitive statements in case it proved true and caused me problems, but now I was able to take a moment to look around I found a lot of friendly and helpful advice. The best piece was that things take time.

As someone who has always considered themselves male by default I am about as far away from the femininity that intrigued me as possible. I’m not tall but not short, reasonably thin but with a bit of a belly developing over the past year, short hair when I remember to cut it, a thick very dark beard ranging from short to bushy, and hair on basically every other part of my body.

My wife suggested taking things slow and bit by bit. First place to start was try on some female clothing, see if that did anything for me. We might be able to work from there to see if it was purely sexual for me or if there was an element of identity in it.

But what should I get? Just start buying women’s clothing and hope? Measurements were no problem to get, we had a tailors measuring tape, but what style? What sort of clothing, even?

Again my wife was to the rescue. She suggested that she had a set of fashion books she had bought in preparation for sewing and that, although she’d not looked at them in a while, we could go through them together to see what I liked.

We spent a chilly Sunday afternoon pouring over these books before moving to the related websites full of patterns, her explaining what things were and all the components to them, what would work best for my figure (rectangle, if you were wondering), what fabrics were a good idea, what styles were flattering…. it was a lovely experience, something I smile at remembering. It made me feel utterly comfortable.

We moved to amazon for the purchase, and wrangled the sales page on the women’s dresses before I finally settled on the piece below. A simple dress, sleeveless, pretty material and a lovely coloured floral pattern. The nervousness as I hit “buy now” was almost overwhelming and I remember she had to encourage me to actually take the step and do it.

The first dress I bought

The waiting was intense. I had work the next day and spent most of it checking my phone for the live postage updates. I knew when it arrived and I was a mixture of hyper-excited and hyper-nervous at the same time. The walk home was terrifying.

There it was waiting for me. Lighter than I thought (although maybe I just expected it to weigh more from my expectations?) and smaller, but when I opened it it felt wonderful.

My wife once more reminded me to be careful, not to be too excited and not to be too disappointed if it didn’t “work”. Neither of us were sure what would happen, if anything. So I went upstairs, carrying my dress, and tried it on.

With love,


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