I have had a polysoydnal (that is not even remotely close to spelled correct, I merely sounded it out) sinus operation on my backside long in my past. Basically they open the sinus glands in the crack of yer butt.
I was permitted to wear pads for several weeks as a result, yippee I felt so glad

Here's your truck load of sarcasm Lesley hehe.
I also suffer from roids, oh I know full well the thrill of needing to wear something to protect against periodic bleeding (no pun intended), or the problem of stray random seeming discomfort. I have only missed out on the bloating I think.
How far will I go in 'simulating' my womanhood?
Hmm I will NOT simulate anything at all.
I am what I am, I deal with what I deal with and I will not actually go LOOKING for grief though.
If the weather is dreadfully hot, I still wear my top, hey I don't actually have breasts, and as such, it's not like I am in a situation where going topless is going to be me casually exposing hooters to view eh. But I feel like a woman and that means acting like a proper one.
My health simply doesn't look kindly on me forcing my posture to be like how a female normally would sit. It just leads to a lot of knee and hip joint discomfort. I won't sit legs wide open if I have a skirt on though.
I talk like I talk, I am just more aware of why I say what I say now. It just makes more sense to me now is all.
I like what I like, I just have a better understanding of why I like it now.
I personally am of the sort that thinks women wear dresses and skirts and pants are only for garden work, servicing the car, and warmth in winter. I don't actually consider pants to be women' wear. That's just me though. I'd rather be in something very female in manner of clothing all the time given a choice. I am not in a hurry to buy women's jeans, I hate jeans in the first place.
I often wonder, will HRT make me less anti male?
I often wonder, will I finally make peace with my own sex organ, or will it be the case I will never be happy till it's gone.
Will I ever over come my own built in brain washing and be able to wear women's swimwear? I never go swimming anyway.
The truth is 90% of my life as it stands currently, is indoors, and in no way in need of my impressing anyone. If there is no reason to expect company, odds are I am wearing a shirt and nothing else. All I see in the future, is my eventually sitting around the house bare assed in something meant for a woman, rather than me just wearing a longish male polo t-shirt. I don't think it is an odd notion, my wife lounges around in her night gown, and my mother tends to be about the same, and my niece is prone to sitting around her place like that.
I like to be bathed and perfumed and wearing some jewellery when I go out. Currently it is really all I have to work with. Doing none of that just means I have nothing at all to make me feel good. Its for me in the end, I don't do it for the observers.