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.

Beginner Makeup with Jessica Blackler

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.

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.

Beginner Makeup with Jessica Blackler

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.

Beginner Makeup with Jessica Blackler

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?

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Amy Myers

I'm 60+, hetro, married, and love dressing up! I keep saying and feeling like I'm new to this, but I have dressed from time to time since my pre teens, but just late 2018 it seems to have become of a bigger part of me, rather than just a role I played from time to time. I'm interested in music, cars, photography, and plus other interests.

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Rikki Edwards
Duchess
Active Member
Rikki Edwards (@rikkicd)
11 days ago

Hi Amy, I have to say that I am definitely not ashamed of loving to dress as a woman any more. I used to, when I was a lot younger, and struggling with understanding why it was I loved crossdressing, but now I am in total acceptance of who I am mode. My wife is somewhat supportive in that she knows I like to dress( but I don’t push it in her face…she does allow me alone time to be Rikki these days, which is quite nice), and occasionally she will make comments like “you must be part woman” etc.… Read more »

Patricia Marie Allen
Active Member
Patricia Marie Allen (@triciaxd)
11 days ago

Ashamed? Proud? Not really either. I guess you could say that I was indifferent. My feelings about being a cross-dresser or trans, are about the same as my having hazel eyes or brown (ash blonde) hair. It just is… that is it’s just a part of me.   When I’m out and about in full feminine mode, I’m confident enough in myself that the vast majority of people I interact with don’t take exception in any way, but simply accept me as another person doing whatever it is that I’m doing.   Just yesterday, I was in my local Safeway,… Read more »

Lucinda Hawkns
Active Member
Lucinda Hawkns (@dlgeb275)
11 days ago

wow what a great story and also question to ask i would have to say for my self proud to be a cross dresser but in a way a closet one. no one knows of my cross dressing except my wife. i have been out twice dressed up, one time for Halloween and once for a cross dressing meeting. i enjoyed both times. wish i could go out dressed up and just be free and show my fem side . but with society the way it is and people not ready for the cross dressing world even tho we are… Read more »

Ruby Tuesday
Member
Ruby Tuesday (@rubytuesday)
10 days ago

Hello Amy – I’m from England, live in France, and have been a crossdresser for many years. My earliest memory was when I was about five years old, when I fantasised that there was a drawer full of girl’s clothes in my bedroom. Now, I am 62 and certainly proud to be Ruby, and go out as her, though I don’t pass very well.I love to go to the beauty parlour for a makeover and manicure from time to time. I have another side, too – sissymaidruby, who likes to dress in a pink satin maid’s outfit, with oodles of… Read more »

Krista Writeme
Member
Krista Writeme (@krista12)
10 days ago

What a fantastic article!! I am very happy being a cross dresser.I am so very comfortable with myself when dressed!! I live in an area where going out in public may result in a public hanging,just kidding,or am I?But I am “out” and very open with my life choice.I spen my days dressed,I am retired.I do my yard work and around the house jobs in casual but very fem clothing.I discovered myself fully at age 15.I am now 70.HAs it been easy?Well,you know the answer to that as well as I do.Love your article,love you my dear!! Krista

Bianca Everdene
Active Member
Bianca Everdene (@bianca)
10 days ago

Hi Amy Proud?yes kind of! Ashamed? No, over that! Frustrated? Sooooo much! Societal pressures keep me mentally blocked in. Single father of two school age kids with a job in the public eye, where one has to be squeaky clean. I know my teens would be embarrassed of me if I told them and terrified it would get out in my hometown. Other Kids, and some parents can be cruel, and potential mental harm/bullying this would land my kids is prohibiting me outing myself more. Also fear it would adversely affect how my work colleagues see me. I know there… Read more »

Rita Rainbow
Member
Member
Rita Rainbow (@ritarainbow)
8 days ago

I loved this article. Thanks for sharing your story and inviting others to join the dialogue.

Gail Bingyi
Member
Gail Bingyi (@gbingyi61)
7 days ago

Wonderful article Amy and so very true as a friend of mine once told me you have to love yourself first and foremost which includes everything good bad or otherwise about yourself before you can be loved by others.

Carly Keene
Duchess
Member
Carly Keene (@carlyamy)
7 days ago

I wish I could be a proud crossdresser but I’m terrified how people look at me when I’m dressed up I would love to be Carly 24/7 but very scared of loosing the ones I love. I’m a widow now so I don’t have to worry about hurting her but I’m scared of loosing my kids and grandkids there are many times when I think about moving to another state and live my life as the woman on the outside to match the woman on the inside maybe even finding a man to love me and me to love him… Read more »

Carly Keene
Duchess
Member
Carly Keene (@carlyamy)
6 days ago
Reply to  Amy Myers

Thank you for some inspiration it is very hard hiding in the closet. every day is harder than the last more and more I just hate having to pretend I’m a man but I’m thinking and feeling more like Carly needs to come out and embrace her womanhood and enjoy being a woman but I’m very scared and confused and with my womanhood I’m only interested in men.

Scarlett398
Editor
Trusted Member
Scarlett398 (@scarlett398)
6 days ago

Super article from one one of my biggest fans! And as you well know, Amy, from my photos, writings associated with each photo, my comments to other girls, my written instructional articles, and my edited articles, I’m extremely proud to be a cross dresser. It’s taken me many years of study of YouTube videos on makeup application to take my cross dressing skills to the lever they are at presently. I’m one of the very lucky and blessed cross dressers who fall into that way less than 1 percent of cross dressers who are 100 percent passable as a pretty… Read more »

Scarlett398
Editor
Trusted Member
Scarlett398 (@scarlett398)
5 days ago
Reply to  Amy Myers

Brina did a pile of them over the past two months. She edits articles over on the TG side as well. I’ve just finished 3 articles in 2 days! Was very busy with all of them!

Take care and have a super week ahead, Amy!

XOXOXO Scarlett

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