About a month ago for reasons I can't remember, had a few hours of personal time, and I tried on a mini-skirt to see how it would look with heels. Never experimented with it before, and didn't know what to expect really. I really liked it, and ended up buying a few skirts at a second-hand store. Not the greatest skirts, but they were a good place for me to start. Both were mini skirts. A few days after that, no one else was home and I had some time to explore different heels with pantyhose and my two new-to-me skirts. I experimented a bit until I was happy with it. But boy was it an overwhelming feeling!
Up to this point, I've ventured outside in heels, with the heels always under jeans. Even then, it's usually difficult to get out of the car, but I usually manage after I stop thinking, and "just do it". But now I'm standing in front of a mirror, with my 4" stiletto heel boots, black pantyhose, and a gray mini-skirt, finished off with a white T-shirt and a short black jacket, and I stopped thinking straight. The look was amazing. I grabbed the car keys, drove about 15 minutes away to a neighborhood I've walked in a few times in the past (in heels & jeans), and without barely any self-talk got out of the car and started walking. In a mini-skirt. With the heels completely visible. And it was so liberating! I can't remember the last time I felt such freedom. Some cars passed by, some of the trip was under heavy lighting with apartments nearby, but I didn't meet anyone.
It all felt like a dream, but it was so awesome! I don't know how I went from "let's hide those heels as best as possible" to "let's wear a mini-skirt with 4inch stileto heel boots". All in a span of a few weeks.
Since then I've been doing a lot of soul searching, about what I want, who I am, what I'm trying to represent and the image I wish to portray. I'm straight, and do not wish to pass or become female, that's not changing. I'm just a guy who wants to borrow some stuff from the female side of the closet.
Since that walk, I've bought a few more second-hand store skirts. I also completely accidentally came across a store with a clearance section where skirts were 2-for-$5, and I ended up buying a few right then. I guessed at my size, but for that price I couldn't pass it up. One skirt looked so amazing (sort of like this, but much lighter brown: https://d2h1pu99sxkfvn.cloudfront.net/b ... GO9/P0.jpg]! I had to go out again in it, and I did. Another walk after night-fall, 15 minutes or so. During this outing, I made mental plans to go back to that clearance and look through the selection more methodically (2-for-$5!!), but decided to push myself and wear that skirt during my trip. A few days later I ended up going back to the store, wearing that skirt, beige pantyhose, brown jacket, brown ~2" chunky heel boots. Stood in the parking lot by my car for a few minutes before having the courage to go in. But I did go in. Looked through the racks, picked like 20 mini-skirts that looked like they would fit, went to the fitting rooms, and tried them on. Ended up buying like 7? A few other customers were in the store, but it was actually very liberating looking at skirts while wearing one! I didn't have to pretend... "This is for my GF, can she bring it back if I guess the wrong size?". And I could try them on without worry or shame! No one said anything.
I haven't been able to recreate this type of experience since then, this virus derailed all my plans. My family doesn't know. My wife would have deep problems with this, she's been struggling with the heels throughout our relationship.
Having said that, I was able to go out one night a few days ago. Recently I bought a red plaid mini-skirt (my all-time favorite look), something like this [https://www.trashandvaudeville.com/medi ... _zoom1.jpg]. Black pantyhose, 4" stiletto heel boots, white T-shirt and black jacket. The look was simply amazing. The skirt very comfortable. It took a bit of effort to get out of the car, but I ended up walking around several blocks, including by a large road, for 30 minutes. It was dark, and I was stressed out of my mind for the first 5 minutes or so. Then I started relaxing and enjoying it. It was an amazing experience...
I don't know where this is heading, but so far it's fun. I've read quite a bit of this forum, and hope to contribute my share...