Seven Things I Hate as a Crossdresser

Conchita Wurst

Image: VIPevents

Unfortunately, I’m in one of those negative moods today. Enough so to make me hate everything… well almost. Slipping into some Wolford tights, however, just isn’t the same, seemingly lacking in joy of digging into my femme side to ease the bad vibes. I don’t think new heels could even cure my case of get the hell away from me today.

So, in honor of negative bullshit, I feel it is my duty to call out on the seven things I really hate as a crossdresser, not in any particular order. They all pretty much suck, er, I mean can go suck.

1. Hair, That Which is Not on Thy Head

Have you ever shaved all of your body hair? It is a fucking tedious process that takes a minimum of two hours. And don’t get me started if the Remington isn’t fully charged. Afterwards, though, is a bliss of silky smooth delight, sliding around on your sheets and your pantyhose not having to hold back the wild forage overgrowing your crotch.

Then a week later, back to hairy and hours trimming. Maybe this time, I’ll remember to charge the damn shaver.

We’re not even talking about the beard either. Not even Estee Lauder can hide that 5 o’ clock shadow when you doll yourself up. Oddly enough, some other Eurovision winning singers can pull it off with class. Just don’t let this become a trend though.

2. Shoe Sizes

Not too long ago, I saw some knock me down shag me now (thanks @pollypantyhoes) shoes on Zappo that I would have purchased right there on the spot. Then there was that problem of a size 8 being the largest size available. OK, spend and hour looking for the next sexiest pair. Only a size 9? No new shoes today I guess.

There seems to be a Murphy’s Law of buying women’s shoes if you’re a crossdresser. The cheapest, ugliest red pumps straight out of the 80’s will always be available in your womens’ size 12, anywhere, whenever you’re in the mood for some new heels. Just remember that.

3. G-strings

In concept, the g-string is a fantastic, ultra-sexy invention… on a genetic woman that is. Packaged, so to speak, on a crossdresser unfortunately looks like a handful of grapes hanging down from the vine. Not exactly elegant. Sure, you can try to put them over a pair of tight fitting pantyhose to cut down on the bulge factor only to get annoyed when they start sliding to the left, the right until the triangle is pretty much under your ass.

4. Shoulders

I bought a cute little light sweater some time ago thinking it were perfect for lounging around the house or even a quick stroll down the street. It’s the kind with a couple buttons down low leaving the upper part a bit open letting you show a little “cleavage.” Then came the surprise when I actually put the thing on.

I nearly ripped the new garment at each armpit. I could eventually squeeze into it only to notice it looked rather ill fitting in the mirror. Great, now I look like I just stole some kid’s bathrobe ready to do an Incredible Hulk impression by bursting out of it. At the very least I have healthy shoulders, and a sweater to give away as a Christmas present.

5. Control Top Pantyhose

For me, my whole feminine identity started with a simple pair of pantyhose, sheer to waist. To this day, nothing has changed except for the higher quality and the discovery of Wolford. Pantyhose are just an extension of the feet, legs, butt and crotch whose duty is to leave a lovely glistening hue behind.

So looking at those silken feet then on up and discovering that awkward divider line in the middle of the thigh leading to a wannabe-panty looking thing is just… wrong. Sure, they may have a purpose in shaping up if you will but why ruin a gorgeous invention by doing so?

Buy a goddamn shaping panty and put it over your sheer to waist pantyhose please, for the sake of pantyhose purity.

6. Men

Sure, I’m a man on my off days. I concede that I’m disgusting, creepy, filthy scum. If you are a man, part time or not, then you are too.

7. Post Orgasm

I’ve had mostly regular orgasms while crossdressed but I have had a few incredible come-squirts here or there. Yet all of these have the same thing in common: the “OK what now?” feeling thereafter. There were times I use to feel guilty (read: OMG I can’t believe I’m a male in female clothing!) but, nowadays, the orgasm is usually followed by a severe disinterest in the thing that I couldn’t get enough of just moments earlier.

And if I have to clean up fresh hot come stains off of my lingerie, then I swear I’m never doing this again.

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Anything you want to add to the list? Make my day and leave one in a comment.

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4 comments on “Seven Things I Hate as a Crossdresser
  1. Lisa T says:

    Hi Sheery, I hear you girlfriend! Even with something we do for pleasure it’s not too difficult to find things that annoy or disappoint us. My comment goes along with your number 7, and I’ll call it “Fast Food Sex”. For most of us that moment of glory we call an orgasm also means one other thing: GAME OVER! For me, an orgasm is like the desert at the end of a great meal that I’ve taken my time to enjoy. Unfortunately it seems that for many these days, they go for the desert right after the appetizer! So many who are out there looking for meetings are only interested in brief encounters, you know, get in, get dressed, get off, and get out! The last person that I met with some time ago was a nice and attractive person, but our actual time together was less time than it took me to do my hair and makeup! Have we become so impatient and so accustomed to instant gratification that sex has become the equivalent to wolfing down a burger and fries at the fast food joint? Not for me! Life is too short and I want to totally enjoy and savor every precious second! If you want a sexual encounter with me you had better plan to budget some serious time!

  2. Sheery says:

    That is the whole point of being a CD… enjoying every moment and ending with a splash, right? Well said LisaT!

  3. Lisa T says:

    I guess the thing I hate the most is the closet. I don’t mean not having enough room for two wardrobes, but rather the one we’re forced to hide in. I hate the double standard for men and women when it comes to how we dress and present ourselves. Women who have short hair, who don’t wear makeup, who like to go out in baggy jeans and a sweatshirt and old sneakers are not labeled as crossdressers. They can and do dress and present themselves any way they chose, and while they may not be viewed as attractive, they don’t have to face the real possibility of public humiliation, loss of respect from friends and family, being labeled as perverts, being harassed by authorities, being attacked physically and verbally, and the list of abuse goes on and on. I know that for some the taboo aspect is part of the thrill, but really, this is ridiculous! If we human beings can’t get our shit together over something so ultimately meaningless as physical appearance, how can we ever hope to achieve something valuable as say, world peace? That’s my rant for the day!

  4. Sheery says:

    On one hand, I hope the taboo stays a taboo (more fun that way!) but, yes it is pretty ridiculous to judge on something so trivial as physical appearance. I believe, unfortunately, it will stay this way for some time until Jesus is proven to have been a crossdresser himself.

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