I'm going to post my outings in this thread, just to share.
A few things about me: Have been married for a long time, with kids. My wife knew about my heels before we got married, but was never supportive, and eventually all heels became hidden (hence my alias) from view, we didn't talk about, I didn't wear it in front of her, nothing. Recently the topic came up, and the conclusion was that she said is OK if I go out periodically, she might join once in a while. It's slowly been improving, I showed her my heels, we discussed them, etc, but she doesn't want me wearing them at home. I'm used to that, so it's OK.
Traditionally, 50% of my outings have been at night, with noone around, lasting about ~30 minutes. 50% of my outings have been to parks, or other more-deserted locations, during the day, hoping noone would be around.
I usually wear jeans which cover the heels, and the heels vary depending on my mood. I much prefer boots, or ankle-boots, so it's almost always that. I have never ventured into a store or anything like that. Now I'm working hard to change that...
More recently however, I've been getting really angry, sad, anxious, etc, most of it I am convinced is because of my inability (self-imposed or otherwise) to wear heels out. These emotions have been really difficult, and have preoccupied me greatly. I am getting really fed up with it, and have decided to try to challenge myself a bit and try to wear them outside. This is all recent, and has been happening in the last 2-3 months...
A while ago I had to go downtown for work, and was in a huge mood to wear heels. I decided to take the required cloths with me, and a ~3.5" ankle boot that looks professional, no platform. After I was done with my work stuff, I quickly changed... Jeans covering almost the entire heel (about 1" was showing), and off I went. Broad daylight, with your general downtown population moving about, roads, etc. Put in headphones and walked around downtown, looking into stores, just browsing. Obviously lots of people saw me, but I was having fun. Didn't bother me who saw, and I didn't hear, was busy listening to music.
Once I was done walking around, I walked too far from the car, so I decided to take the bus back. Got on the bus, in heels, sat down, and paid no attention to anyone. Was a bit self-conscious, but it was great. This was the first time I went out in public, ever, in broad daylight.
I had a blast, still processing the experience.
Cloths were: jacket, white shirt, very dark blue jeans, and black ~3.5" chunky heel ankle boots. The outfit I think worked perfectly.
A few days after the above adventure, I got another chance. Was near a shoe store that I don't get a chance to go to often. Was coming home from a work-thing, and wanted to challenge myself. After my work-thing, I got changed, put on very long jeans, and a pair of 4" stiletto boots which I simply love. So comfortable. The heels could barely be seen.
I got out of the car, shuffled around a bit, battling my thoughts, but then decided to just go for it. Ventured into the mall, past some coffee shops, and into a large department store. I looked around a bit randomly, just enjoying that I'm there in my heels. Then walked around the mall for a few minutes before making my way to the shoe store. I looked around, found nothing of use, then walked around the mall for a few more minutes and out to the car. The entire thing took 30 minutes or something, but it was broad daylight, with lots of people around, and I loved it. I was just a bit self-conscious.
Cloths were: dress-shirt, black sweater, long blue jeans, and black 4" boots. I think it looked OK, upon reflection the outfit could be improved, but am still trying to figure that out.
OUTING, OUTING, OUTING, OUTING
A few days after the above adventure, over the course of ~2 weeks, I had the chance to be alone during the day once in a while for some hours to do my own thing. I wanted to challenge myself again, and wear heels. This time I decided to go to a coffee shop and grab a drink & some food, and work. So I did just that, picked a coffee shop that was far enough away from home, packed myself into the car, and went. This time I was quite self conscious in my brown wedge ankle boots, and long jeans covering most of it. While standing it was OK, the heels weren't showing, but when sitting I'm sure they were. I tried it out before going to the coffee shop and the jeans would ride up if I sat down, so I assume people could see some of it. But I sat down, enjoyed my drink, ate a bit, and worked on my laptop. Spent about an hour there. Got to repeat this 3, maybe 4 times over the course a few weeks. Quite enjoyable, but doesn't beat the above two adventures.
Cloths: Varied, but long blue jeans with 3" wedge ankle boots covering most of it.
The above outings might show progress, and they are huge progress compared to what I was doing a year ago, or further back. But I am still very much conflicted with this heeling thing, and I am sure these emotions will not go away for a while yet. I am trying to challenge myself, and in the process wear my heels, and so far so good. I am still very uncomfortable showing photos or URLs of the heels, or myself. I love it when others post photos of themselves in coffeeshops, etc, but I am not comfortable with that, for various reasons.