So this Gender thing… Part 2

Where were we? Trying on my first ever dress1I’ll talk more about this in a later post coming very soon but this wasn’t quite my first ever dress.….

I’m not sure what I was expecting, if it would be momentous or there’s be thunder/rainbows/choirs? Obviously none of that happened, but it was easy to put on. A single zip running from butt to mid-back, then a pair of lovely dome buttons on the collar that do up really easily. I was shaking so much I appreciated that touch, made it possible for me to get it on by myself after I’d stepped into it.

My wife was there with me, encouraging me to put it on, and my usual habit of grinning like an idiot when I’m nervous came out.

Then it was on.

It felt nice, thick pleated skirt with a bit of weight to it, thin ad breezy top in some sort of faux-silk. It fit perfectly, draping down from my hips and hugging my neck just tight enough, and the chest looked natural lying completely flat. I remember distinctly that it swooshed when I spun around. It flared out from my hips slightly, moving gently with my motion.

It felt right. I looked down and saw it hanging off of me and it looked right. Up until that point I’d not really cared much about what I looked like, I’d never bothered to do anything with my hair other than keep it length 4 all over, and I realised that it was because I didn’t really care. Looking down at myself I realised that this is what I wanted to look like, that I was more happy with myself standing there in a dress with hairy legs and hairy feet, a full beard and a stupid grin, than I’d ever been before.

I talked to my wife after this, sat on the edge of the bed in a dress, not able to stop looking down at it, only just able to stop running my hands over it to appreciate that it was mine and I was wearing it. We talked about what this meant, and again what steps I should take next. She asked if it was something I’d ever want to do outside, I said I don’t know but that I was definitely not there yet. She asked about wigs, makeup, underwear? I was all for all of it, in stages. I hadn’t even thought about wigs.

I immediately went and ordered some panties, pictured below. I started with a lot of thinking on this one; the sites I’d browsed included information on tucking and gaffes, which I’ve still not tried yet, but I thought start simple. They arrived and they were another moment of joy, slipping them on and tucking myself out of the way as best I could, they were nice to wear. I left them on for the rest of the day (spent around the house) under my trousers.

My first panties, cheap and frilly, but so pretty.

My wife suggested I tried on a pair of her tights next, to see what I thought of them. We’re about the same size height-wise, so they fit pretty well. Comfortable, functional at hiding my hair, they were another thing to add to the list.

My tights, garter included

Buying these I got 2 things, a pair that were far from standard wear, and a nightshirt that was far more scandalous than I would have ever considered. My logic (what remained of it) decided that if I wanted to try this girl thing I should really lean into it, and the stuff I was being drawn to was the ultra-effeminate, pink and lace. Practical? No, but then I wasn’t going anywhere in it.

This comes up a lot shorter in the picture, but it feels nice enough I didn’t care

That brings us closer to today. I’ve got a small set of women’s clothes I’ve worn. I love all of them, and they make me feel more comfortable in my own skin than I ever have before.

I’m not sure what this means for me. I know I want to keep going, to keep exploring, but does this mean I’m a woman? I’m certainly not 100% happy with being male, but there’s a lot of spectrum past just “male”.

I’ve decided for this blog to go by Sammy, there’s a reason for this I’ll expand upon later, but I’ve taken it from a webcomic that inspired me to talk to my wife in the first place; Raan’s Doll by Kannel Art (warning, very NSFW). I’ve got a few more things to write about before I get to “now”, so I’ll start working on those next. I’m queuing my posts up as much as possible to be regular, but we’ll see how long that lasts!! Probably just until this buffer runs out, but my new years’ resolution is to do this better than my previous attempts so I can look back on this in a few years time and remember what journey I took. For now though?

With love,


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