I Have Worn Women's Shoes

Like many who share this experience, I was fascinated by women's shoes as a child, and I went through the whole phase of trying on my Mom's shoes (both heels and flats) as well as other female relatives. As I grew older, my fascination grew more pronounced to the point that I finally bought my first pair of shoes at Payless Shoe Source. They were a pair of Chinese style mary janes that I've seen some girls wear. This was the summer of 1985 and I was 21 years old. Now at the time Payless was a new presence in my city, in fact I think it was actually the first store in the area (there are now 33 stores in our metro area). I loved the "self-service" nature of the store, but more importantly, I loved the fact that they carried larger sizes. Because of this, Payless became my "go-to" store for shoes (both men's and women's). Years later, I would become just as intrigued by this company and its employees as I was with their shoes. (I'll tell some of the more interesting experiences at Payless in a separate post later on). Anyhow, as the 1980's progressed, I would buy ladies shoes maybe once in a blue moon, I would say once a year. When I made my purchases, I ALWAYS made sure NO ONE was watching me browse the ladies styles. If anyone was in the area, I simply pretended to browse in the men's area till the coast was clear. Yes, I was that nervous... When I wanted to actually try on women's shoes, I took them to the men's aisle and set them by the sitting stool, then grabbed a men's pair and set them next to the ladies pair. I did this to make it look like I was trying on the men's pair and holding the ladies pair for "someone else". I would then make sure no one else was around and quickly set my foot in one of the ladies shoes. If I liked the fit and decided to purchase, I would put the men's back on the shelf, and go to the register. Sometimes I would point out that the shoes were for "her" or "my sister" (even though I didn't have a sister) or "my cousin" or whatever... I always had my excuses ready if any sales clerk happened to ask. Now buying women's shoes was always a deeply personal secret that I told absolutely NO ONE about. I would hide them deep inside my bedroom closet (I was fortunate to have a large walk-in closet). I must note that I lived with my parents at the time (in fact, I still do but in a different bigger house...but that's another story, LOL). The fact is though, I've had to guard my privacy somewhat. In the early 1990's, I became slightly more bold buying more ladies shoes, and wearing them out where I would not be seen. For example, I would go to the local college and wear them around campus during spring break while the school was deserted. Or I would walk on the sidewalks of my suburban neighborhood at night. One time, in 1992, I got really bold and wore some red 2 inch wedge heels in a old used book store. I knew there was always one lady working there, and I was the only other person in the whole store. I had also shaved my legs and wore white cutoff shorts to look more "feminine". She sat at the front register, and she really didn't say anything as I paraded myself in front of her, pretending to be deeply engrossed in browsing the various books. I was sure she had seen me, having glanced several times, and even asking if I needed help finding something. This was truly the first time I "exposed" myself wearing women's shoes in front of someone else. This went on for about 30 minutes before I finally bid her goodbye and left the store. I really got a kick out of doing that... I would later revisit the store wearing the same heels, but with regular "guy" pants. This time another woman was with her, and I could hear her whisper "He's wearing women's shoes". Then, in the corner of my eye, I could see the other lady steal a glance at my shoes. Now these two "exposures" were exceptions, and I would never do something like this for another 18 years. That's because there simply wasn't anyone else I knew that did this kind of stuff. Now I did know there just HAD to be other guys were out there like me, but I'm sure we all felt too much like perverts/weirdos. Remember at the time the thought of having a medium (like the internet) to communicate such deeply personal issues was considered a pipe dream from a science fiction movie! Now my personal preference for shoes at the time tended to be low-wedge flats, up to about an inch high. I did have exceptions such as the 2 inch wedges mentioned earlier, as well as 3.5 inch wedges that I found were sexy, but were somewhat impractical to wear. I have also seen the flat ballet shoes come back into style, but though they looked kinda nice, they didn't have the slight wedge I always adored. Years later my tastes would change... As the 90's progressed, I started to become disenchanted with the whole "buying women's shoes" thing. I liked seeing them on women, and wearing them myself, but I also began to notice the futility of constantly buying women's shoes only to wear them around the house or in other private or secluded places. Please note that I was a record collector since the early 80's, and that's where most of my disposable cash went to. I could easily go out and talk to my friends about the Beatles, the Temptations or Elvis Presley. I could never dare to do that with my shoe passion! Besides, the 29 pairs of shoes I had were beginning to take up too much space in my closet. However much I dreamed of wearing my wedge flats at a record convention or grocery store, I HAD to look in the mirror and face reality: IT JUST WASN'T GOING TO HAPPEN! And so began the great purge of 1996... Little by little, I started taking a pair or two of my ladies shoes and throwing them in various public trash cans and dumpsters. Two pairs went into a dumpster by McDonald's. One pair went into a trash can by Sound Warehouse, my favorite record and CD retailer-and so on... In a matter of days I got rid of 23 of 29 pairs. I kept six pairs that I simply could not let go. I considered them keepsakes of an earlier time, only to be used if I ever had an occasional urge to wear them. I would occasionally go into Payless maybe once every year or so to look around, but would come out empty handed. There was a period between 1999 and 2003 where I only visited Payless once...just to replace my regular men's shoes! I did check the ladies section but the selection seemed too boring. Most of these years were spent getting my first PC, getting games and software, and exploring the recent phenomenon called the internet...and of course buying great 1960's music. Since 2003, I would stop by Payless every 18 months or so as an after thought of running an errand. I stopped in a store in November 2007 during a BOGO sale with a lot of shoes on clearance. There were a lot of pretty new styles, but I really didn't want to spend much money, so I stayed with the clearance items. As I browsed the ladies section, I did my usual "no one else is around" routine. Now my "ladies shoe urge" had been returning recently so I decided on 2 pairs of 3 inch wedge heels and a pair of ballet flats, all for less than $30. This visit would turn out to be important for several reasons. One, it was the first time buying ladies shoes in ten years. Two, I bought my first true pair of ballet flats (I had begun to notice how sexy ballet flats were beginning to look). Three, the sales lady was a Filipino woman who unknowingly would turn out to be the most important figure in my "shoe liberation". In April 2008 I would revisit this particular store to check out the latest styles. I would buy two more pairs of wedges deeply marked down. By coincidence, that same Filipino woman was at the register when I bought them. I would swing by this store once again in the summer of 2009, but the lady from my two previous visits wasn't there. What I DID see there was a pair of very pretty low wedges with three rings on the vamp of the shoe. I did not try them on, but I did notice they were in all large sizes. They weren't on sale so I figured I'd buy them later on...little did I know these shoes would play a role in my "liberation". I should note that during this time, I have gotten the courage to compliment women when I see them wearing a nice pair of shoes. I used to think they might see me as creepy, but I've found that women really appreciate it when a guy notices they dress well. In October 2009, I met a lady who walked out of a grocery store wearing those wedge flats with the rings I saw at Payless. After telling her how nice they were, she said she got them from Ross. I could have sworn they were from Payless. Whatever. Seeing how good she looked in those shoes reminded me that I needed to get to Payless and buy them. But again, I put it off...big mistake. About two weeks in the new year (January 2010), I finally made it to Payless. When I walked in the front door, that familiar Filipino woman greeted me: "Hey! I remember you..." she exclaimed as I said hello to her. I told her I was going to browse real quick and went to the ladies section. As usual, I made sure she was out of sight before looking at the ladies side. Now before I went to the store, I noticed they were out of stock in my size (11) online. This usually meant they were being discontinued. And sure enough, I couldn't find my size. I found the shoe in a different size and asked her to check if another store had a size 11. She said no other store in the area had it in that size. Uh-oh...busted. Just missed out on one of the best shoes I ever saw due to procrastination. DAMN!! She then said "I think I can help you" and directed me to the ladies section where she pulled down a pair of size 10 wide off the top of the shelf. She then explained that a 10 wide would fit very similar to a size 11. She took one of the shoes out of the box, looked me straight in the eye and said "TRY THEM ON" and then walked away. She didn't say it with anger or sarcasm...she just said it with a straight face. Now I was absolutely FLOORED by what she just said. In the 25 years since my first woman's shoe purchase NO ONE has ever let me know that they know I like ladies' shoes. I froze for what seemed like ten minutes. Oh my god! She knew my deep dark secret! How did she find out?!?! I pulled myself together, tried on the shoes (they didn't quite fit) and started thinking of two things. One, she must have known I was buying for myself the last two times I've seen her. And two, the fact that she encouraged me to try them on was a sign of her acceptance of me wearing women's shoes! Wow, what a defining moment in my life! Just the same, I decided to go ahead and buy the shoes just so I could have a keepsake of that great moment. I would not visit Payless again until September of that year due to the fact that I wanted to save up my money and pay off some credit card debt. But every day, I would replay the events of that day in my mind. I was simply haunted by those three immortal words: "try them on". Little did I know those words would lead to bigger and better things that September. That will be the second part of my story..... For those of you that have read this far, thank you so much for reading this. I really had to get this off my chest. Please post any questions or comments you may have. Thanks again- it's time to go to bed now...