For young crossdressers who are confused and scared

I started to write this as a private response to a young person expressing concern about why he likes to dress this way and how it affects his social life, but then I figured maybe there are others who stumble across this site in search of answers.

First, the quick summary: You aren’t alone, and there’s nothing dangerous about your compulsions (depending on how you act on them). There’s a good chance that you are neither gay nor transgender. Maybe you are, and that’s fine too, but don’t just *assume* you are transgender just because you don’t act like what society tells you a man should be like. You could very well just be a man who happens to like doing and wearing things that historically have been reserved for girls, but that doesn’t in and of itself make you a girl.

Now, my own story: A family friend who was often my babysitter had to leave suddenly while I was very young, and it was a huge trauma for me. Up to that point, she doted on me constantly, made me feel safe and loved, and losing her left me broken for years afterwards. We moved to a distant city, and life went on… until I happened to run across a box of her things that somehow stayed with us when we moved. It included some tights and a fur-lined satin winter coat. By then I was 7 or 8, still smaller than she was, but they fit me OK if a bit loosely. I have no idea what compelled me to put them on!

That moment changed me forever. It was like bringing a piece of her back to me, or perhaps it seemed like if I couldn’t have her with me, I could transform into her for a moment by wearing her clothes.

I was what they called a “latchkey” kid in the 70s – both parents working, my older sibings with jobs and on the cusp of moving away from home, so I had the house to myself for hours every day and a relentless curiosity. I discovered my mother’s lingerie drawer and found that her girdle was pleasantly snug at its smallest fastening, like having a satiny hug all over my body. Sometimes I would wear it under my t-shirt and jeans when I went out to play, and one day while I was doing this a friend stopped by on his bicycle to chat. That’s when I learned the dark side of what I was doing: If my friend knew what I was wearing, usnpeakable horrors would ensue, I just knew it. I would be mocked and ridiculed and likely beaten to a pulp by every bully in the city. So I made my excuses and hurried back inside, and over the years learned to be more careful about when and where I experimented.

I spent a lot of time watching TV in those days, and girls looked different back then. Rarely any trousers for them, always long dresses and pleated skirts. And wow, the prairie dresses on Little House on the Prairie rocked my world! I so wanted a calico dress from neck to toe with ribbons and ruffles on it like Laura Ingalls wore. I still do, but you’d be surprised how difficult it is to find one with a 46 inch waist.

All the while I explored and experimented in secret, I also obsessed over my sanity. What was wrong with me? Was I gay? Was I insane? Was I meant to be a girl trapped in a boy’s body like Renée Richards who was in the news at the time? We didn’t have the internet for quick research, nor was there any easy way for me to find others like myself. I didn’t even know there were others like myself. I had to find books on abnormal psychology in the library that defined “transvestic fetishism” as a disorder best treated by shock aversion therapy.

It wasn’t just the dressing; I just didn’t act like a boy in many ways. I was physically inept, no strength or agility or stamina. So I was excluded from sports, unable and unwilling to defend myself in a fight, socially awkward because I used juvenile humor as a defense against my physical inferiority, afraid of confrontation, prone to crying easily for no apparent reason… all of which added up to also not having any kind of female companionship or romantic interest as I got into my college years. I was a virgin until age 22.

By that time I had learned to mask some of my more eccentric characteristics. I came across as funny but sweet, and latched onto a girlfriend who found that attractive. I even came out to her a bit – I wore her leotard as a joke (or so she thought), and sometimes an old-fashioned dress… always as a joke, just kidding around, ha ha.  We broke up soon after, and I drifted deeper into a confused world of crossdressing and sexual confusion… until I got married.

I somehow once again managed to present myself as a more or less normal man long enough to convince a young woman who was also a bit flaky to marry me. We are still married and have some wonderful children, and it was only after we were engaged that I was finally convinced that I am fully male, inside and out. This, my anonymous young friend, is the part I wanted to tell you.

Sex was great! I never wanted anything else but to be a man having wild, ecstatic sex with a woman, and now more than 20 years later I still feel that way. What’s more, she accepts me for who I am, weird clothes and all. Before we married, I told her something I had never told anyone else in my life: I can’t stop wearing dresses. I made it clear that I very much identify as a man, I had no interest in becoming a woman, but I couldn’t stand to wear trousers. She finds it a little weird and perhaps a bit unsettling, but she accepts that we both have some quirks that we put up with in each other because that’s how love works.

A few parting thoughts for you:
First, don’t despair of finding the perfect match. Look for unattached people who share your interests, join an online dating service, whatever. Because our personality type is a bit off-center, it may very likely take you much longer to find someone who can handle you. That’s fine.

Second, don’t hide who you are from the person who will spend the rest of your lives together. You may not be comfortable letting the public, or even your parents and best friends, know about the crossdressing. Bringing it up on a first date may be more than she’s ready to handle. But once you’re sure she is “the one”, once your mate has every reason to know that you care about her and want to make her happy, don’t go into marriage with such a huge secret. I pretty much followed my proposal with my confession in the same conversation, leading up to it gently: “Before you say yes, there’s something else you should know about me… that time I dressed up for Halloween isn’t the only time I do that stuff. It’s a part of me that I have lived with for my entire life, and I don’t want it to be a secret between us. If that bothers you, I understand… but know that I love you with all my heart and I want to do anything I can to make you happy.” Something along those lines, anyway.

Third, don’t obsess too much over analyzing yourself. I know there’s something deeper than “I feel more comfortable in a dress than in trousers”, because I don’t just wear any random thing off the women’s side of the store and call it good. I am attracted to specific types of dresses, mainly overly-feminine, old-fashioned styles (remember Laura Ingalls!). That scratches some psychological itch I don’t understand, and after 50 years I just don’t care enough to explore it any further. If you want to see a shrink about it go for it, but I doubt you’ll get any answers that satisfy you.

Finally, never ever let your compulsion control you to the point that it harms your relationships, or job, etc. It’s like alcohol: A little bit once in a while to help you relax is one thing, but if you get to the point that you can’t stop thinking about your next drink, you miss work or social/family obligations, you lie to cover up your activities, you even commit crimes to get more of what you desire… then it’s a major problem that will leave you alone, unwanted, dead, or in jail. So if you find yourself lying to your wife, stealing her clothes and wearing them without her permission, shoplifting, avoiding time you could spend with family and friends, missing work, etc. just to satisfy your need to wear that special something… that’s when it’s time to get help.

If you still have questions or concerns and you don’t want to discuss them here in the comments, feel free to email me on the Contact Me tab at the top of this page. Of course any private communications are your property and I will never share them with anyone else.

About Ralph

Male. Straight. Married.
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