Sex and Gender can have ramifications beyond the academic or purely personal interest level though of which one is just the whole business around buying your own clothes and specifically the area of underwear cos while some forms of attire can be seen as for either or any gender underwear brings its own things such as actual physicality.
Like most boys, until you got to certain age usually connected with either romantic involvements or leaving school your mother bought your clothes and if you were lucky, you'd have some say in it.
Because I was around as a child/teen in the nineteen seventies and early eighties, you were bought boy briefs because your sex was that and for most they would be Y fronts even though it was also the start of point I was trying to figure out why my gender preferences didn't always line up with other boys.
Around late February 1987 when Nick Kamen was stripping off in the Laundromat to his boxer shorts , the very short lived LM "Lone Male" magazine had a feature on boxer shorts which I did try for a while but did find that the tended to ride making for an uncomfortable experience 'down below' and why they may of been cooler than my polyester mix Y fronts they provided no support where I at least needed it.
Under the influence of some in the transgender community, specifically transexuals who thought *everything* I experienced growing up and since came down to my gender being trapped in the wrong sex body the issue became one of which sexes underwear do I wear.
And yet briefs are just that beyond being cut for your sexes anatomy and I couldn't see how anything cut for females could really fit well.
I then found I was starting getting much more into regression which in some respects made what was something I didn't feel actually helped me, so the idea of presenting in a more feminine way was more redundant because school age regression with uniforms isn't something you 'pass' at in city centre coffee shops and I started drifting back to where all this started, being a school boy who was a boy but had different gender preferences in some areas.
Through my exploration of age regression as a boy and adult school boy I started to move toward putting together a uniform and more boyish 'play' clothes but that returned the focus back to underwear because I knew what I had worn first time round but had not changed since.
Though ASB I found out the standard of choice was what I had worn in my childhood and feeling that that whole period of female presentation in any form had not done anything for my actual problems like feeling good about my sex and finding a way of handling doing both masculine and feminine things and still feeling 'a boy at heart', decided to bite the bullet and put myself back into Y fronts and ditch all else.
One thing I noticed straight off was underwear actually designed for my sex fitted better where it needed to which was a far bit more comfortable on me when doing more physical things.
I am finding ASB age regression is helping me learn to love being a boy all over again, feeling able to hold my own accepted without prejudice as a boy and nothing less and making one decision to embrace my sex and wear our standard has helped in re-integrating me back to being the best boy I can.
That ironically was all I ever wanted from the issues I had around gender preferences and presentation.
* This is where I feel most comfortable, a boy in his uniform, playing wearing his Y fronts and happy*