Things I Really HATE About Crossdressing

Sheery in pink bodysuit and Wolford pink tights

A while back I told of my absolute joys of being a crossdresser, so why not get all dolled up and let out all my frustrations today? Don’t get me wrong though. If you came here looking for reasons to really hate crossdressing and give it up, you would be out of luck. I LOVE my crossdressing life and the way my new bra hugs the natural curves of my chest. Like anything in life, however, it does have its pet peeves and annoyances from time to time.

Sometimes those pesky problems can get the best of me. Most times I brush them off. Well, now it gives me a little writing material.

So, as I sit here in my black Wolford bodysuit, Neon 40 tights (black) and a black miniskirt (plus my favorite heels), time to begin the tales of things I really HATE about crossdressing…

The Guilt

This use to be an issue in the past but not so much over the last decade or so. Nonetheless, it’s worth a mention… getting that urge to slip into some pantyhose, throw on some lingerie and get a quick wank out of the way. Then the post-climax being the need to stop doing this from now on.

I can safely say this was due to me not being comfortable in my own skin. Hey, once I realized this crossdressing thing won’t go away at all then there was no choice but to embrace it, pervertedness and all.


Smooth legs are awesome. Smoothness everywhere else is nice. Shaving sucks. So do those little nicks and cuts from shaving. Why do I have to make an appointment in my calendar every week or ten days to do it? My god, shaving sucks.

Pantyhose Runs

Runs are seemingly trivial, just go out and buy another pair of pantyhose, right? No, I feel like my best friend was just shot and died. I have a cemetery of runned pantyhose (AKA a shoebox) where they go to rest forever. A few weeks ago I added a pair of black Wolford Neon 40 to it and it depressed me for a good day and a half. Yes, I was really in a depression but that is the life of a pantyhose addict I suppose.

The Secrets

My friends and family are still in the dark about my lifelong hobby. I strongly doubt I ever will come out to them about it and I’m totally fine with that. I don’t need for them to know. However I do go to great lengths sometimes to keep this a secret. For example, when having friends stay over, how would you go about hiding twenty boxes of high heels? Or make absolutely sure they do not open that drawer or closet? Or open that odd-looking locked box that happens to contain all my makeup?

Then there was that one time I was asked about “that pink stuff” on my lips which were little flecks of lipstick leftover from an earlier beauty session for miss me. I sheepishly quipped “I like cotton candy, OK?” One day I’ll run out of excuses for my carelessness.


Makeup was probably the biggest catalyst into me going full-on girl mode when crossdressing. I just love the transformation and smacking my lipstick here or there. This is of course after the damn hour and a half it takes to put all of it on. Also, from all the Youtube videos I’ve seen up until now, I am still doing it wrong too.

Don’t get me into the cost of it either… expensive as shit! Cheaper stuff is no good either. While I love and enjoy the final product (miss me) I do find it hard to justify all that time and expense.


Ditto here, I actually love glitter in eye shadows and even lipstick. It makes me feel sexy, sophisticated and cool even though I am none of those.

But that shit is really hard to get off. Sure, the makeup remover can get 95% of that glitter off but that last 5% is nearly impossible! Not to mention, it isn’t something you can let slide by since everyone notices it. Having to scrub my face off for an hour is not my idea of looking sophisticated and cool.

Crappy, Ill-Fitting Lingerie

Why is it that I can’t just throw it away forever but instead keep it all sitting there along with my old tax returns?

Wig Care

My favorite wig (shown above) has nice long flowing blonde hair and makes me feel and look like a goddess, ahem, in my humble opinion that is. Untangling, washing, untangling some more, brushing, etcetera etcetera makes me feel like I’m doing weekend chores.

I don’t have this issue with my shorter cut wigs. I don’t look half as sexy either (ahem, in my humble opinion).

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