When I’m usually slipping into one of my million pairs of pantyhose, sometimes I like to slip those hosed feet into one of my, now, many pairs of heels I’ve collected over the last few years. As of now, I have a dozen plus a pair of boots (I guess those are a must). I normally go window shopping online and if a pair catches my eye, I’ll bookmark it, look at it several times later and then just buy them if I’m still interested. More often than not, they are at a sale price which doesn’t take anything away from heels, I just happen to get them a little cheaper.
However, there was one pair that I had my eye on FOR FIVE YEARS. And they were absolutely stellar, a pair of black Sebastian (Italian) patent leather stilettos with a natural wood platform. Why five years you ask? They retailed for 500€ (roughly $600) and went on a clearance sale online, ahem, five years ago for 200€ which I dismissed as too much yet I was drawn to those size 41 beauties. I also had a feeling those would be around for a while. After all, a size 41 is not the most popular womens shoe size, but for this crossdresser it was the perfect fit.
So, every once in a while, I kept coming back to that bookmarked page, just to check up on them.
It’s no secret that succession of crossdressing phases goes something like this: slip into your mom’s pantyhose as a wee-tot, then try on a bra and heels and maybe her makeup a few years later. Then at point when you can pay for all this shit yourself, you buy them all for your very own. So shoes and in particular, high heels, would typically be a part of that equation. I’d say for most crossdressers in my opinion.
Well, somehow after all these years from the wee-tot stage, I still seem to have an aversion to high heels. I think they look sexy and I want to love wearing them since they are clearly the perfect accessory for gorgeous pantyhose over freshly shaven legs. I even splurged on some gorgeous leather clogs thinking that would spur my lust of the heels world. Sadly, those very lovely clogs have gotten few uses to grace my pantyhosed feet ever since.
“What gives?” I’ve been thinking to myself. I can’t go out with just pantyhose and regular shoes. My high heels just aren’t “doing it” either for me if you know what I mean. Then I finally realize the issue while browsing for heels one day: I never chose the right heels… duh.
Here’s a quick rundown of my collection of high heeled shoes…
- Six inch clear plastic heels and, yes the stripper kind. Cheap, uncomfortable and painfully obvious what they are for. Seemed like a logical purchase at the time.
- Six inch over-the-knee glittery boots. No, they are not made from leather or even faux leather but fish-scale shiny fabric. Bought with the heels above. Ditto on the logic.
- Wedge sandals. Found in a steal of a deal on eBay. Had to glue a strap back in place not too long ago. They still haven’t made me feel quite like a supermodel.
- Leather clogs. Definitely the most upscale high heels I’ve ever had but they are just not quite me and are, therefore, rarely used. I must not like heels then?
Yeah, I can see other crossdressers shaking their heads at me. Enough said.
First, let me start out by saying that one telltale sign of a true woman is her ability to look through and pick out a pair for herself. I found this to be quite a journey through hell at first. There aren’t just a few high heels to chose from but THOUSANDS. I’m talking just high heeled sandals, too, not boots, flats, casual and whatever else to which there are millions more to browse through. OK, so this is what it is like for a woman when shopping for shoes… I almost call it a day. Almost.
I have a confession to make… I never really liked heels or women’s shoes for that matter. That is, up until now. Of course, I’ve had a few pairs for a while but they never really did anything for me unless you count the falls and near ankle breaks while prancing around in them. The deal breaker, though, was that they never turned me on wearing them.
Then again, I always thought that the sexiest shoes were the ones that either were clear, five inch heels, or were like a spandex boot going up your thigh. You know, the kind you see on strippers in strip clubs or even on porn-ish models in those jpegs you’re jerking off to online.
In other words, those are cheap pieces of plastic that make you more or less feel the same way. OK, so I like feeling cheap. Just not in what I’m wearing on my pantyhose covered feet.
So recently, I splurged on some high-heeled Dune clogs as you see above. Somehow, they really caught my eye reminding me of Oktoberfest and gorgeous women in their lederhosen and wooden shoes. Don’t ask for an explanation of this, but I just had to have them. Now I’m wearing them as I type with the utmost joy hampered by one near ankle break as I tried to stand up moments ago.