What do you dread about crossdressing?

Many an experienced crossdresser will tell you that it’s not all music and roses – being a woman takes hard work, courage and a lot of patience. Many of us endure almost any discomfort for even a fleeting feeling of femininity. But there are those days when being a woman can get so frustrating you just want to scream.

You’ve laddered your second pair of pantyhose and then spilled makeup on your best white blouse. You overtweezed one eyebrow and in an effort to even them out both eyebrows are in a race to extinction. Your heel broke, your nail polish smudged and you emerged from shaving looking like a wounded warrior.

*sigh* Sometimes you think it might just be easier being a guy. Now is your opportunity to vent a little – go to https://www.crossdresserheaven.com/what-do-you-dread-most-about-crossdressing/ and let me know – what do you dread most about crossdressing?

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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.
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Terra Rigg
6 years ago

For me right now I hate the thought of having to shave. My genetics gave me a thick beard and some chest hair and not being to dress up all the time I have had to let it grow and right now I’m honestly feeling like I’m gonna be too lazy to even want to shave it all. It takes me about 2 hours to shave from face to toe and it’s really annoying. Hopefully once I do it enough to times I should be able to get a routine going.

donna misteriosa
6 years ago

My two main issues with crossdressing are the inconsistency with my dressing and then having to transform back to male mode. As closet cd, I only dress when home alone. The opportunities have been few and far between for the past 10yrs. Once dressed, the undressing is a slow and drawn out process, reluctant to remove clothing that feels amazing, back to drab male clothing.

6 years ago

I hate having to return to male mode. That is why I undress as much as I can when i am wearing male clothes.

Samantha Victoria
5 years ago
Reply to  Michelle

I hate it to. the things I hated to take off the most is my pantyhose and panties I just love wearing them.

sandra saunders
sandra saunders
5 years ago

Hi Vanessa, yes you are right it is hard to be a woman, it takes a lot of work to get the make up right and then I make sure I have a good photo session trying new outfits on. Finally as I have gone to the trouble of making up I venture out to get the full feminine experience.

5 years ago

What I hate most about dressing is shopping for sandals & heels.
I have a hard time finding tasteful heels & sandals.
Most shops think since you’re a CD, that you want to look like a whore!
I want to dress, look, & be treated like any other respectable woman!
No insult intended to my bolder ladies (I’m no church lady, myself!)
Towering heels are great if I plan on being on my knees or on my back, but I’m NOT walking in them! LOL 😉

Joanna Paveley
Joanna Paveley
5 years ago

The over riding hate for me and pain about my whole cross dressing experience is that moment when I have to return to Male form. I put it off as long as I can, even keep on things like nix, tights, stockings under my male attire and if I can a bra and camisole. I openly wear womens Jeans and unisex tops and have several baggy jumpers to disguise my wearing a bra. However, when I fully dress its always a skirt and very fem top or a dress that I go for and not trousers. That moment I have… Read more »

Jen Kelly
4 years ago

Looking blah because I cannot seem to get the makeup down. I would just love to be more proficient. First thing when i see girls is how I wish i could copy their makeup….pretty sure most people would not expect that!

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