hiddenheels

Hey! Been a few years since I started this thread. Much more comfortable with skirts now, don't really give it a second thought. I told my wife, she's not supportive, so like with heels, it's something I need to work through myself. Skirts and heels, usually no problems, but still wished it was more mainstream. Or at least you could see guys wearing them once in a blue moon, but never. Agree with HappyinHeels, it's likely that this was always in me, but just came to realize it now. The good thing is that the anxiety has gone away. I'm not saying that there are no butterflies at all, or that I don't sometimes get into my head before getting out of the car, but the progress over the past 2 years has been huge. I've often shopped for heels or skirts while wearing heels or skirts. I tend not to wear both at the same time, maybe one day. Tend to frequent malls or restaurants and just enjoy myself. It's a LOT of fun.

Depends on if it's painted or if the entire bottom material is formed from a material of that print. Do agree, if it's painted then it doesn't last too long (have a few shoes with painted bottoms).

Completely agree! I did try out the square-toe style, but it just repulsed me. And see-through toe-space, not my thing...

I get what you are saying, but sometimes I do want to look as masculine as possible, and in those cases the boots above are what I would be looking for. Other times I am in the mood for 5" stilettos. Depends on my mood, no need to exclude one for the other.

That post was intense, but pebblef's interpretation rung true for me too. I was my worst enemy. No one cares. (well, my partner does, so it's a no-go at home) Blamed myself for so long, and acceptance did not come until recently, after decades of struggle and confusion. If I could go back, and provide some wisdom to myself, this would be one of them. Alas, that is not to be, but hopefully I still have a good number of years ahead of me.

Look really nice! I don't have any of these styles, but still working figuring out my style, so am not opposed to it. If it's wood, does it provide more stability?

Exactly! No one should be *required* to do anything. However, I have found that I *desire* to wear them, and that desire is strong enough to push me to wear it, even though am a guy. Some do ask how I can wear what I wear, well..., because I don't look for excuses not to.

Alright, I'm completely confused. Can't make heads or tails of my thoughts. Haven't slept well for the past few days. For the past two decades I have worn heels exclusively at home, with very very infrequent outings, at night. In the last year I started wearing them out more, have bought a few boot-cut jeans to hide the heels, have become more comfortable with myself, and being outside in heels. The jeans cover most of it anyway, and thus far I have not received any comments. Have been to a few stores, and coffee shops, usually quite self conscious, sometimes am able to relax and just enjoy things. Never been interested in more than heels. Then on Saturday I find some black pantyhose in my stash of jeans, don't remember how it got there, but thought I would try it on with one of my black knee-boots. Ended up thinking that a skirt would complete the look. So Sunday I stop by a second-hand store, quickly grab two mini-skirts that look good and will probably fit. Monday I had a few hours at home, and the first thing I do is try things on, black pantyhose, 4-5" stiletto black knee-boots, and a grey mini-skirt that went down to mid-thy. Now, this is probably the first time I try on skirts, and never considered it, never was curious about it, but the look and feeling was amazing. I have no ideas how to match the top with the bottom, meaning, what shirt or sweater I need to complete the look because I don't want to "pass", I have stubble and am not going to put on makeup or wear a wig (no disrespect, but that's not my thing). But I don't know how to complete the outfit, well, because I have never thought what I would wear if I wore a skirt. After some brief trial-and-error I figure the jacket completes the look quite well, and thus the shirt is largely irrelevant. And look in the mirror. What I saw confused the heck out of me. It was comfortable, I felt comfortable, but at the same time super-weird. That was the most unusual look I have seen on me, and I couldn't place it at all. WTF was I doing? Given my pattern with heeling outside, never obviously showing the heels, the logical thing at this point for me would have been to enjoy the experience at home, in private. But no. I had this indescribable urge to be outside. It was overwhelming. It was dark outside, late evening. I got into the car, and went to a place that I infrequent for heeling, a small park in a residential neighbourhood. Park, and without any major self-talk, get out of the car and start walking. The entire walk took about 15 minutes total, beside some houses and roads. Some cars passed, I met no other person walking. Parts of the trip was under heavy lighting, beside some condos. I didn't meet anyone, nor talk to anyone. Skirt was mostly visible. Boots completely uncovered. I felt "normal", didn't care that my legs showed. I frequently get the fight-or-flight response, trying to stop my heart from jumping out. After a while that goes away, and I become calmer. If I'm able to relax more, I end up usually happy/thrilled with the experience. This time I was rather calm the entire time, no panicking, no low or high emotions. Was focusing on just walking. Would say it was more like a state of "what is just happening, I can't comprehend this"? In short. The experience was fantastic. I loved it. But my mind hasn't stopped reeling since that night. I can barely sleep. I have all sorts of mixed up feelings. Why did I do that? I'm not ashamed, but it was completely out of character. What the heck do I want with this. What was I thinking? Where is this going? Is this something new that I will eventually want to explain to my wife? Why can't I be "normal" (according to society)? [I'm not comfortable sharing images, this is as good as it'll get]