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Tough to remember, because i progressed gradually. All started with 2" block heeled Frye Campus boots and cowboy boots, always looking for cowboy boots with taller heels. I made many thrift store purchases also. My first actual purchase was online, a few pairs of Pleaser boots.

My first heels were acquisition from my first wife in about 1977-78. It had (I think) 2 inch heels. Had them till the mid 1990's when they wore out. In 2011, I determine that my numerous ankle injuries was due to men's shoes not fitting my foot shape, so I switched to only women's shoe. No ankle issues since. I Started with mild 1.5 to 2 inch heels. It took a lot of nerve wracking to get over the clicking sound, but now I enjoy it. In February 2015 I had a (medical) need to raise a heel 4 inch, but I couldn't raise just one foot, so I went to DSW and found a pair of 4 inch heels in the clearance area. Put them on and within a minute found my balance and have been high heels since.

My first attraction to feminine footwear was for the shiny white go-go boots worn by a very pretty red haired girl in my seventh grade class. I didn’t just admire them, I longed to have a pair too. At the same time I was also acutely embarrassed by the thought that I fancied wearing girls boots. I put such thoughts out of my mind, or at least tried to, although I still really wished I could have a pair of go-go boots and thought it grievously unfair that I couldn’t. It wasn’t an obsession, this curiosity and desire to wear feminine boots - it was the feminine styling, not so much the heels themselves that appealed to me - it was more like something I’d be reminded of from time to time. Some random style would catch my eye and send my imagination wandering down those corridors again. And always with regret that such a thing was impossible. About ten years ago, I had this damascene moment when I realised it wasn’t impossible. It was only me that was making it impossible. I decided that I didn’t want to go the rest of my life having never worn heels or feminine boots, and so I ordered a pair. I splurged and bought some beautiful black suede OTK boots from Jean Gaborit with 10cm slender - nearly stiletto - heels. They were beautiful and fit like a glove, my first feels. And from the moment I stood up in them I knew it had been worth the wait. I never did get a pair of go-go boots, but I want to…

I remember the 90s as being some pretty dark days as far as being able to purchase decent looking shoes. My memory isn't what it used to be, but all I can remember is giant ugly platforms with lugged soles, and the jeans that girls would wear too long on purpose so that the hem would get stepped on and get all ratty looking. I also fail to remember my very first high heel purchase. I can remember my first pair of heels, but I didn't buy them, I actually found them. Inside the bass drum of the drum kit in the high school choir room. I know they were some girl's show choir shoes from a previous year, because I recognized them. I paid attention to such things. They sat in that bass drum for quite some time, probably unbeknownst to anybody but me, and I finally decided that they needed a better home. In retrospect, they were kind of ugly. I'm not going to waste a lot of time trying to recreate their likeness, but they were very 80s looking open-toed pumps with fake stacked heels, dangerously close in lack of height to being kitten heels. And they actually fit me. I remember wishing many times that they were 4 inchers, but alas, they were barely half that. I have to fast forward us about 25 years before I bought actual real heels for myself to actually wear in actual life.