I hadn't thought about the issue of whether I'd be comfortable wearing a skirt, until I read this piece of yours.

Personally, I'd like to try out experiencing the physical comfort of it. But I'd also want the emotional comfort of being amongst other men similarly wearing this style of garment. More effeminate men already harbor trauma from being targeted by those who subscribe to toxic masculinity, so there is something to be said for the cliche of strength-in-numbers.

As far as your points about sex...are you thinking mainly in terms of heterosexual intercourse? As a gay dude who only partakes in NON-anal forms of sex (only with other men), I'd think a skirt would just get in the way. I'd rather just go naked.

Regarding high heels: I've never worn them, and I never have any desire to. I'd always viewed them as something that would be outright dangerous for ANYONE to wear, regardless of your sex/gender. But I have a phobia of falling, so the shoe style itself is pretty much a baked-in trigger for me, individually.