Are you Proud, Ashamed, or somewhere in between of being a Crossdresser?

Some might find it an easy answer, but for most of us, I don’t think so. Like many aspects of this life, the truth is more muddled. It is for me, and it has evolved over time. Oh yes; for most of my life, I was ashamed of being a Dresser. For years, (read decades,) I thought I must be the only one in the world like this. Being a child of the early 50’s, I came of age in the 60’s within a small, conservative town. Any talk of what is now called an alternative lifestyle was met with distain, if not outright disapproval. Never mind that regular sex was never discussed or talked about in my circles either. So, I always tried to look like a good boy, and mostly I think I succeeded.

This was so long before the internet. Even though I have now learned there were clubs back then, which provided support and companionship for those folks who didn’t follow conventional dress codes, I hadn’t been aware of any. I felt alone. The pleasure I derived from dressing caused considerable guilt. Silly as all that now seems, given the experience I had over the intervening decades, it was true for the times.

Human nature through the ages hasn’t really changed, though our behavior is modified by the various cultural norms of the times. Basic nature was cast thousands of years ago—for better or for worse.

EnFemme Style

In the early 70’s, an older friend (female) took me to a few drag shows and other events in Toronto. I think she believed I needed an “education.” It was something like that for sure! Those female impersonators were good. She got a chuckle out of my ogling them, and then had fun at my expense, spoiling it by saying, “There’re guys.” I was astonished, as they didn’t look like guys!

Not much later, I found myself working and dealing with customers in the arts community of Toronto. They obviously had an alternative lifestyle, not that it was as open as it is now, but it was there. Generally, the only ones that I knew were gay and lesbians, though a few I realize now were leaning toward being trans.

Back then, a few of these folks seemed to be prominently putting themselves “out there,” and they had a degree of pride to who they were. They weren’t ashamed of themselves. Not how it used to be when it was illegal to have sex with another person of your own birth gender.

There are many of us completely and totally in the closet, and that’s fine, but how do you feel about yourself? If you are here on CDH, you at least realize there are many of us in the world. Although in some circles, this lifestyle is still considered rather taboo, but at least you know you are not alone. Many are living life as the gender they feel suits them best. Not to forget those folks who don’t yet know what they really are as they try to figure it out. Wherever you are in the spectrum, it’s just fine.

Exceptional Voice

Getting back to the question; Do you find yourself ashamed of your love to crossdress or do you perhaps feel a little bit proud?

I find myself on this journey, having run the gamut from my earliest days of dressing, (being so totally ashamed of myself.) From hiding my mom’s things back in the dirty clothes and not wanting to do it again to promising more than once, “This is the last time I’m doing this.” Of course, it wasn’t true!

The next stage was becoming a slightly reluctant and closeted dresser. When I let myself go, I enjoyed the thrill of dressing, finding happiness and not shame when going back to my male self. This lasted some years. A couple of years ago, I was bitten by the urge to completely dress up; I’d had these thoughts way back in the 90’s, but felt it was too far out of bounds to actually act on. Those feelings of guilt and shame resurfaced again, as did the thoughts, “What’s wrong with me,” “I’m enjoying this too much,” and “Why am I enjoying this so much.”

As mentioned in previous articles, in the last year, I’ve gone from not “passing” at all to learning makeup skills, buying better foundation garments, clothes, and learning feminine behavior so that I now generally pass without trouble. I’ve also learned that if I don’t pass, then so what? I am what I am and nothing anyone says is going to change that.

It’s not that I have tough skin, not at all. I’m a sensitive soul who can be hurt very easy. I suspect many, if not the vast majority here are like that, too. It’s simply a part of our feminine make-up, which might be why we are so afraid of going out and being ourselves.

Through this transition, as it were, I’ve come to some other realizations. I’ve found myself actually committing the other sin—Pride. Not in my pretty clothes, or nice wig, but in who and what I am. I am not ashamed of myself. Not everyone in my life knows, but the circle is widening.

This notion was brought home as a female friend of mine, who introduced Amy to one of her friends, had said how amazing it is that I am out and about fully dressed and being me instead of hiding. Honestly, I think she paid me a better compliment than I deserved, but it did get me thinking about how I had changed over time.

Through my outings and travels as Amy, I’ve met many people. I find so much happiness and joy, and yes, a certain amount of pride in what I am.

As you continue to dress to whatever vision of femininity you believe suits you, don’t be ashamed of yourself, but instead find happiness and at least a bit of pride in what you are. I don’t feel as if I’m anything special. My hope for all is that if I can, maybe you can find the way, too.

Where do you find yourself on this trajectory?
How do you feel after you have had time to dress up?
Are you comfortable sharing this part of you with any others in your life?

EnFemme Style

More Articles by Amy Myers

View all articles by Amy MyersTags:
5 2 votes
Article Rating
Notify of
Inline Feedbacks
View all comments
Sami Dee
2 years ago

Amy I love the article. I know for years I like you dealt with guilt and I believe that was a product of my growing up catholic and how this seemed to be tied to shame.
Thankfully after a bunch of counseling I am over that hump and really accept both my sides. I am so happy with myself and that shows. I no longer require meds for depression and can look in the mirror with joy when I am in Sami mode.
Thanks for this article Amy!!!!

Rozalyne Richards
Rozalyne Richards
2 years ago

Hi Amy like you I’m a child of the 50’s started dressing in the 60’s when it was still a taboo subject to talk about, The only role models we had were the drag artists and women impersonate’s like Danny LaRue, Like a lot of people who liked to dress up i thought i was the only one who took pleasure in wearing women’s clothing so hid it away because at the time i was ashamed of myself, I even thought it was some sort of pervertion so hid from everyone including my family even my wife when i got… Read more »

Gianna Bonita
Active Member
2 years ago

Amy, dear friend, yes I could not have expressed myself better. I recently watched the entire series of both series of Tales of the City on Netflix. Anna Madrigal, the transgender heroine, well she’s my hero anyway, said a line that resonated, namely, “Living in the shadow of my shame”. It was not relating to being trans as such but it has a meaning in the wider context of living our lives with this blessing that sometimes we allow to become our shame. To me, it’s a signal to be proud, cautious but defiant of negativity and make choices to… Read more »

Bettylou Cox
Bettylou Cox
2 years ago

Hi Amy, and thank you for another interesting story. I wouldn’t use the word “proud” to describe my CD relationship, but only because it isn’t something which I accomplished; it’s simply part of who, and what, I am – like Hazel eyes and big feet. Now, if you asked if I have come to terms with my CD status; am I happy and at peace with it, then the answer is a definite “Yes”. And do I care about being outed” Not a bit (other than the restriction my wife has placed on me). Growing up, I always knew I… Read more »

Olivia Livin
Trusted Member
2 years ago

Hi Amy, great article
For me, this came about much later in life than many and its possible that because of that maturity or wisdom? I seem to have been able to bypass much of the shame, guilt and denial that so many others have shared.
I can’t surely say I’m proud to be a crossdresser, but I am proud to feel the self confidence required to show Who and What I am, thats something I didn’t have before.

Abigail Kingston
Active Member
2 years ago

Hi Amy, Great article as I believe I am going through the stages you mentioned. I am a little younger than you, a child of the eighties, and I am not sure this was much different for us GenXers. We too grew up in the binary world and boys are boys and girls are girls. At least that was how I grew up. So yes, when I indulge myself in a dressing session I have had the exact same 3 thoughts as you, “ What is wrong with me “ and “Why do I enjoy this so much” and of… Read more »

Tiff Any
Tiff Any
2 years ago

Hi Amy , a beautiful read.
Indeed my wife and I are proud of the gender fluid crossdress I am & how we’ve adjusted & strengthend our relationship as a result.
We’re out to those that are important in our daily lives . Tiff

Stevie Steiner
Managing Ambassador
2 years ago

I find I am neither ashamed or proud. I just am being what I feel I am. Though still ” in the closet ” where family and most friends are concerned, I after a lifetime of being alone, have my CDH friends to share my life with. Amazing feeling after 40 years of wandering through my journey alone.
No shame. No regret. Not proud either, per se. Just content and satisfied.

Kathryn Lynn Peters
Active Member
2 years ago

Great article, Amy. I have lived your life as well. The guilt and shame followed me most of my life until I decided on Halloween night to come out to my wife of 20 years. From that time forward, I have been able to be Kathryn whenever I desire (which is daily) and I’ve been able to come out to a few others. The response has been comforting. Am I proud? I don’t know. But I am at peace with myself for the first time in my 71 years! CDH has been a safe harbor for me and I now… Read more »

Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials


Forgot your details?

Create Account

If you don't see the captcha above please disable ad and tracking blockers and reload the page.