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Hi! I have no clue where the days/months/years are flying by. Have been heeling pretty regularly (usually weekly, sometimes twice), and have gotten comfortable, in both the emotional and physical sense. Emotionally I get much less worked up, or none at all, when wearing heels, no more anxiety and just get to enjoy it. Yes, it takes mental effort to plan out which cloths I will wear so things match, but otherwise I'm good. Physically am getting better at wearing 5" stiletto pumps for 2-3 hours walking around. 5" boots no problem. Recently saw this boot (in the picture below) and I reeeeally wanted it, they were gorgeous, and I loved the color. $180, and given the number of shoes I have, it's not something that made any sense, so I talked myself out of it. However, a week back, I noticed they were on sale for $70, and upon impulse, walked into the store and asked if they have it in my size. I was doubtful, but the lady brought it out. Took off my 5" boots, and tried these on. They fit perfectly, loved the whole thing, and couldn't resist. YOLO and all that. Few days ago, had a chance to go shopping, and wanted to show off the boots a bit. A bit of chat with AI helped me figure out some color combinations that would style the red well (AI hopefully gave good tips, my style sense sucks, so it can only get better). Ended up with what is in the photo, with a white TV shirt and grey hoodie on top. Obvious I'm a guy, have good facial hair. Felt comfortable. Went to a diner for food, then spent about 3h shopping, book stores and such. Two ladies complimented the boots. I'm sure others looked, but it was comfortable. Guess my unhiding is progressing. Wish family was supportive, but this still is a lone exercise.

I finally got a pair of booties that fit. Nothing special, but they fit. Women’s Fran Bootie by New York and Company Upper: 100% Faux Suede, Outsole: 70% Rubber, 30% Textile, Lining: 100% Faux Suede Shaft height: 5", Shaft circumference: 10" Heel height: 4" Inexpensive, but they fit. Wore them all day at work.

I suppose I should break out my few sweater dresses and try them on while I have some free time. I think I wore one of them one time out in public. That's one of those things which does not really take up a lot of room in my house, but yet, if I'm not going to wear them, why do I keep them around? We'll see.

Here for the record are my challenge heels - my 12cm knee boots