Confession #94

I know and lived that confession. First with tights, then with skirts. Took longer for tights cause they were my first foray wearing non traditional clothing as a man. I think skirts were easier for me because I already went through it with tights.

Here’s my advice from experience. Yes, once you do it you will wonder why you didn’t do it earlier. But that doesn’t matter. You have to do it at your speed or you’ll be too uncomfortable. So don’t stress about times.

Baby steps. I’d start with a kilt cause it’s way more accepted. You’ll see people argue “he’s not wearing a skirt, that’s a kilt”. And, often enough, women give you these genuine, spontaneous, overwhelmingly positive comments that give you an elation that’s hard to match. And then you slowly get bolder. At your speed. Never worrying about how long it’s taken.

And don’t stress over how many skirts you’ve have. I go to thrift places and get them cheap and have more than I have in pants. Why? Because I’m experimenting with my look. I know my look in pants. It’s drab and boring but it’s the uniform. Skirts aren’t. And you need to find your look through trial and error.

Parting thought. Have fun. Just let it happen. Don’t overthink it.

I don’t know your circumstances, but I hope you can find a way to go out in a skirt and feel good about it. It’s a tough debut, but the vast majority of men who make the move are glad that they did. I know that I am and I wish I hadn’t waited so long.