So as my signature below reads, I'm not out and I'm not on HRT and I'm not growing my hair out long. I'm also Not interested in shaving my head like I have been for the past 20 years anymore at the moment. I'ts been about 6 months since my hair has been cut and its starting to look like a mess. I was thinking next time I go in for an eyebrow waxing I might like to have my hair styled in somewhat of an androgynous style. Can anyone share experience; is this even possible with a widows peak?

It might be possible if your hair's long enough for bangs, even short ones. If your hair's longer than a few inches, you could go for something sideswept. Anything to obscure the hairline, really. My hair's not more than a couple inches long, but I wear it combed forward rather than spiked up. You could try something like that. I can post a picture when I'm not on my phone; I think it's rather androgynous, and I shaved my head six months ago too.