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My First High Heels!


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I wrote this autobiographical essay in 1987 when I was 41 years old. Eventually, I published it on Jenny's High Heel Site. A thread in the Guys forum asking about our first high heels inspired me to repost it here.

My First High Heels! by On Your Toes

Well, here's the true story of "My First Real High Heels"

I'm not sure exactly when my fascination with high heels really began. Maybe it was when I was 4 or so. I was just about to put on a pair of my mothers heels when she came in and told me to stay out of her closet. Maybe if I had put them on, it would have ended right there.

When I was about 12, my cousin had a pair of cowboy boots that I used to plot to get to wear. Sometimes I'd go to his house when I knew he wasn't home and tell his mother we were working on a model plane and I wanted to get started on the next step. I never got caught, but never got to wear them for more than a few minutes before I was sure my cousin would come running into the room.

Fast forwarding a couple years I was visiting a friend and noticed a pair of his sister's heels in the bathroom. Friend's sister's shoes seem to figure into a lot of stories like mine that I've read over the years. The family started to wonder if I was sick that evening. I must have "gone to the bathroom" 10 times. They were almost my size and I eventually managed to steal them! They were sandals and really too small so my feet stuck out about a half inch over the backs. The heels weren't very high either. This lead me to decide that if I wanted real heels, then I had to buy them.

About a year later, maybe age 15, one evening I went to a discount department store on the other side of town and bought a pair of red 3 inch heel pointed toe pumps, size 10, the largest they had. I must have circled around the shoe department for an hour waiting for nobody to be around.

When I got to the register, it turned out they were unpriced so the cashier held them up high and shouted "Doris, how much are these spike heels!?" Managing to keep from passing out I paid the $3.97 and as she was putting them in the bag, I noticed that in my nervousness, I grabbed a pair of size 7! I nearly died.

Being in this deep, I walked in a daze to the returns counter and managed to stutter out something about my sister buying the wrong size. Of course the clerk just doing her job, probably didn't even notice that I was a guy returning "ladies" shoes. She pulled out a form and said "name, address, and phone number." Willing to do anything to get out of there I wrote my real information. I'm still waiting for them to call my mother and that was almost 40 years ago.

I went back and got the right shoes this time, paid without incident and was going out the door when I saw MY HOME ROOM TEACHER coming towards the entrance!!

I was sure that somehow the bag had turned transparent or the outline of the shoes was clearly visible. So not only was the store going to call my home, but I was probably going to get thrown out of school. Well, at least that's how I felt at that moment.

It was about a half hour walk home. I was about halfway there when it started raining. I didn't care if I got wet but bags were paper back then, and the bag started to get awfully wet.

Then I ran into a couple friends from school. They said "Hey, what'd ya buy?" and I said oh, just a toy for my little brother. While we were talking I noticed that one of the spike heels had poked its way out of the wet bag and was clearly visible. They seemed to just keep talking and talking while I stood there just nodding my head sure they were about to start screaming "look at those heels!" Once again nothing happened.

I got home and sneaked the shoes into the cellar. I was too jangled from all the close calls to risk even opening the bag for fear the family would come running down to see what the noise was.

Eventually I realized that people hardly ever look at feet so I started taking long night walks around my residential part of the city. Rainy nights were best because there we fewer people out, it seemed darker, and the rain drowned out much of the sound of the metal-tipped spikes. When winter came, I bought a pair of "Rain Dears" brand overshoes. They were translucent plastic and made for high heels. They had a metal reinforcement inside the heel which kept the spike from poking through, and pointed toes. They really didn't look like heels and were very quiet so I wore them a lot.

Those shoes are long since gone.

In the almost 40 years since then I've probably owned 500 pairs of shoes. I have owned or still own: pumps, clogs, sandals, spike heels, wedge heels, wide heels, flat heels, every conceivable heel height from flat to 6 inches, snow boots, fashion boots, cowboy boots, Dutch wooden shoes, Chinese cotton shoes, Japanese geta, lace up, zip up, Velcro up, pull up, elastic sides, cork soles, plastic soles, wooden soles, leather soles, 39 cent flip-flops, $400 custom cowboy boots, every color ever made, a lot of combinations of everything in this list, and that holy grail of shoe fetishists everywhere-the pointe ballet shoe with an 8 inch spike heel....

The End

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