You're a guy who loves to wear women's clothes and that's ok - A letter to crossdressers

by - April 01, 2023


Hello fellow sister,

This is a letter to you, especially if you're relatively new to crossdressing or have been in the closet for the longest time. 

While our origin stories and the winding routes that we take through life are different, we all share a single commonality; our penchant for wearing women's clothes. It may have started inexplicably when we were 5 years old, or it only started in our 20s as part of a dare. But regardless, the activity of dressing up as a woman brings us great joy.

There is an unparalleled thrill solely reserved for us crossdressers when we unwrap our online purchases, to slide that new little black dress up our body and step into a pair of stilettos. The heart thumping in the ears and the quivering fingers as you feel the rear zip enclose your body in the dress. How is something deemed so wrong by society able to feel so damn right?

We live in a world that isn't fully accepting of our proclivities, but it is slowly changing. For the Singaporean readers, while our country is conservative and generally does not encourage expressions of gender identity beyond the binary, it is a relatively safe place to be if you are a member of the LGBTQ community. Some domestic violence or ostracisation is still present, but we don't need to be worry about having a gun pulled on us if we go out in public. With easy access to information on the internet, each generation is becoming more aware of the gender spectrum and non-binary nature of sexuality; with awareness comes greater ease of acceptance and gradual normalisation. While the reality is that male to female crossdressers and others in the transgender spectrum face the biggest challenge, we are progressing forward, inch by inch. 

Take your time to figure our who you truly are, your likes/dislikes, your tastes and desires. You might identify as transgender, femboy, non-binary, sissy, genderfluid, crossdresser or any other labels that society has conjured up over the years. You might be sexually attracted to women, men, both genders and everything in between. Or you could be confused about your inclinations, swinging from one to the next. In your explorations you may realise that your sexual appetite is kinkier and more out of this world than what most folk can imagine in their wildest dreams.

And that's ok.

You might be much taller or larger than most cis-women and extremely self-concious about certain parts of your body that holds you back from going out in public. While being petite and slim does help in being passable, watch a few seasons of RuPaul's drag race and you'll realise that the biggest or buffest guys can slay on the runway. And remember that cis-women also come in all shapes and sizes.

Many of us carry around a mountain load of shame, built up over the years. Shame for seeing a pretty girl and wishing you were her instead of your rougher male self, only to chide yourself for not being a "real man", being weak for giving in to such sinful thoughts. Shame from passer-bys' lingering stares that confirms the niggling thought at the back of your mind; that you aren't passable and people easily recognise you as a guy. Shame for wanting to do what society deems as "depraved". It's very normal to feel that way after years of programming by society to behave a certain way. I'm still working through my shame, so continue to work on yours too. 

Remember, this is your life. While we are accountable to the people closest to us and have different responsibilities, this is the only life we have and we have to live it to the fullest (sorry readers who believe in the afterlife or reincarnation). So make plans to be financially secure and enjoy the female side of you, hopefully in public too. 

Most importantly, love yourself, always.

We are all cis-men who love to wear women's clothes, and that's ok. After all, women's outfits are f***ing gorgeous and better than boring men's clothes 😆

Yours truly,
Isabelle

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1 Comments

  1. Hey Isabelle,

    You might recall that I reached out to you some time ago, before this post. I want to thank you for your honesty and authenticity in what you shared. This post feels especially heartening and encouraging , building on your advice from our last conversation. Even today, I still find it hard to fully embrace and express my inner self, but I hope that one day I’ll be able to truly be Gwynna. Continue doing what you. You are such an inspiration for all the sisters.

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