Question - Why do I feel so guilty after I crossdress?

by - February 11, 2021


To varying degrees, each one of us crossdressers have felt guilt after participating in what society views as "deviant". Since young we have been taught that boys should only wear boy's clothes, participate in sports and be manly. Playing with dolls, wearing anything with feminine trimmings (let alone dresses) or behaving effeminately is unacceptable and an embarrassment. Society is also swift in passing judgement, branding such any boys/men who do so as "sissies", "ah-kua", "gay", "homo", or a slew of other derogatory names. With the penchant for wearing girls clothes usually manifesting around 10 years of age, it means at least a decade of lessons on how boys/men should behave, it is no wonder that there is an incredible amount of guilt when one enjoys and desires to do otherwise when they participate in crossdressing.

Guilt isn't always a negative. For example, feeling guilty for indulging in so much rich and good food over the Christmas and New Year holidays could cause people to decide to start a diet or exercise regime. Or guilt when seeing others around you participate in volunteer activities or seeing the less fortunate struggle in life may encourage one to donate money or time in the betterment of others. However, the guilt that crossdressers feel tend to be negative, leading to purging, emotional mood swings, depression, self-esteem issues and self-loathing (please note that I'm no psychologist, so this is based on my personal experience, chats with others and articles that I have read). Although not everyone crossdress for the purpose of deriving sexual pleasure, for many, wearing feminine garments is an incredible turn on. How many times over the years have you felt a heady sexual high when crossdressed, only to have guilt crash down on you like a tsunami after sexual release? It manifests in self-loathing (e.g. hating oneself for a lack of self-control) and maybe you purge or swear never to crossdress ever again, only to do so a few months later, triggered by seeing a random pretty girl on the street wearing a dress and the opportunity to dress up served up on a platter (e.g. parents on a two week holiday, leaving the entire house to yourself).

In my opinion, there are a few reasons for guilt:
  • Pleasure from partaking in the "forbidden" or "taboo"
  • Feeling ashamed of inability to live up to society's expectations of a "Man"
  • Feeling ashamed at inability to be normal
  • Feeling ashamed at the inability to have enough self-control or willpower to stop crossdressing
  • Doing something "unacceptable" behind a wife's / girlfriend's / loved one's back
I am no different. I struggled with feelings of guilt until I was in my mid-20s. To manage it, I became very adept in compartmentalising my male and female self. I knew I enjoyed wearing women's clothes and the constant cycles of self-hate, promising to do better and failing was just depressing. I rationalised that just by wearing pretty outfits and wigs at home, as long as no one knew, I wasn't hurting anyone and was still able to enjoy myself. A win-win situation. That said, coming out to my wife and with her acceptance of my female side helped reduce this guilt tremendously, since crossdressing was no longer "wrong". I was also no longer dressing up as Isabelle in secret behind her back.  

Many of you who read this may still be early in your journey, or still deep in the closet. Regardless, it is important to take care of your own-mental well-being, and come to terms with the fact that the female and male sides of us are two sides of the same coin. Stop beating yourself up over what society views as "forbidden"* and learn to enjoy the journey. As long as you're not harming or hurting anyone, crossdressing is just another more peculiar hobby.

[*Note: Although my post is encouraging you to adopt a YOLO mindset a little, it is solely in reference to crossdressing. There are some "forbidden" activities that are truly abhorrent and should not be enjoyed under any circumstances, such as abuse, torture and others too horrifying to list]

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1 Comments

  1. Good article. Well said. Always enjoy reading your post

    ReplyDelete