Crossdressing is the most significant thing I have ever done.
This post is going to rely heavily on how I define crossdressing:
Crossdressing is simply wearing clothes that are typically associated with another gender.
A boy wearing panties, a woman wearing a tie. That’s crossdressing.
It is, admittingly, a very broad definition, but if the world continues on insisting on gender norms and gender as a binary, then I am going to keep defining it this way.
I have been crossdressing my entire life. It’s literally one of my earliest memories… going through a closet in the basement of the house I grew up in, looking for high heels. I was probably four years old.
I’ve wanted to wear girl clothes my entire life and I did so as often as I could. I could change in and out of clothes faster than anyone I knew. It became a survival skill.
When I was in my early teenage years I began accepting that I would always want to crossdress, but I hadn’t yet realized that I couldn’t stop crossdressing. I always assumed that when I started to date I would be able to resist, but it took a few more years to accept that this is who I am. It took even longer to fully embrace this side of me.
But in my teenage years all I knew was that I wanted to keep wearing girl clothes. I never felt I was born with the wrong body, and I never really wanted to be a girl, but at the time I thought the only option was to transition if I wanted to keep wearing girl clothes.
It was right around this time when I started to notice the pattern of me not really *feeling* like a boy. I couldn’t ignore the reality that all the boys my age liked sports while I liked drawing. All the boys talked about how hot girls are, and although I was attracted to the same girls, I noticed their style more than their, ah, body.
Of course, not feeling like the gender you were assigned at birth can cause someone to wonder if transitioning is the right decision. For me, I liked wearing GIRL clothes AND I didn’t really FEEL like a BOY.
So… maybe I should be a girl?
To this day I am still amazed at how quickly I realized that transitioning wasn’t appropriate for me, despite how I felt about gender identity and gender presentation. I wasn’t unhappy as a boy and I didn’t feel uncomfortable in my body and to this day those two reasons are why I still feel that I don’t need to transition.
But I still wanted to wear girl clothes. That would never change.
I knew that a boy could wear dresses and whatever else I wanted. Sure, it wasn’t typical but no one could stop me.
Crossdressing helped me express myself and made me happy. I didn’t need to transition to wear panties and skirts and leggings.
Crossdressing scratched that itch, if you will.
Had I never allowed myself to wear what I wanted, even in secret, I could have easily assumed that the only way I could be true to myself was to transition.
Of course, transitioning is more than just about wearing what you wish, so please don’t misunderstand me. I don’t want to simplify the reason many of us transition.
But crossdressing made me realize I didn’t have to legally or medically change who I was. I could continue to express who I was and I could continue to wear clothes that I wanted. I realized that anyone could wear whatever they wanted, no matter their anatomy. I realized that gender wasn’t binary. I started to understand the unlimited potential that ignoring gender norms created.
Of course, crossdressing was also significant for many people who have transitioned. Many of us feel or felt uncomfortable in their body. That feeling, combined with how crossdressing made them realize “yes, this is right” shone a light on a new path, a new direction, in their life that they didn’t see before.
I know it’s not all sunshine and rainbows. I know that although crossdressing and gender identity and gender presentation can make us very happy, I know that it rarely makes life easier.
I don’t think it’s a stretch to say that regardless of where you are in life or how you identify, the very first time that you wore girl clothes had a significant impact on who you are. I would love to know how you felt the first time you did. Please comment if you feel comfortable in doing so.
Love, Hannah
Hannah McKnight 
I don’t have those same kinds of core memories, or the internal needs that you did, Hannah. It was a lot simpler and more casual for me. When I was about 8 years old a group of medieval reenacters came to visit my school and did a demonstration of armored combat and some other stuff. It was amazing to watch as a kid, and probably the kind of stuff you see every day at the ren faire. After that we were invited to take a school trip to an event they were holding later, and encouraged to dress up.
Basically all the boys in the school wanted to be knights, and all the girls wanted to be princesses. I told my mom I wanted to be a court jester. So she sewed me a red and yellow jester costume, including bells dangling from my hat and at the tip of my curled shoe covers. But one key detail is that jesters always wear tights.
I remember my mom showing me the pair of green girls tights that she bought for the costume and telling me to put them on. I objected, saying those are for girls. She said that’s just advertising, and it doesn’t matter. So I put them on, and the costume was awesome.
It’s not like that kicked off an immediate interest in crossdressing. I didn’t proceed to wearing dresses or anything immediately thereafter. But many years later when Sophie began to make herself known, I remembered that jester costume as a moment of reassurance and comfort. Regardless of what advertising says, and what cultural expectations are, clothes are just clothes. There’s nothing “wrong” with wearing them if they help you feel good.
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hi Hannah,
two items from your article I can really relate to: 1) “Crossdressing is the most significant thing I have ever done. and 2) “crossdressing made me realize I didn’t have to legally or medically change who I was. I could continue to express who I was and I could continue to wear clothes that I wanted”. From the age of ten when I tried on my mother’s girdle and was able to attached nylons with the garters and managed a satin slip I was hooked..however, feminine desire to dress escaped me due to marriage, family, work obligations. I also refer to “manly obligations.. volunteer fireman and status in a men’s fraternal organization… fast forward to retirement.. I was alone while the wife still worked.. the feminine feelings and the desire to dress came back with a vengeance… as I reached out to my wife’s dresses and make-up!
I started to buy my own clothes,intimates, and eventually forms to enhance my feminine persona… my guilt and shame prompted me to seek counseling, especially “why does a Macho volunteer fireman” embrace feminine and express those feelings by dressing? Counseling has helped to embrace and accept my feminine persona and helped me balance my alter egos… for me there is no need to change who I am, medically, due to marriage, family and “manly obligations.. thank you for listening
wishing you a Happy & Healthy New Year
Hugs, Leonara
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I’m so thankful for the era of exploration that crossdressing allowed me to do!
I remember having a conversation with you about a year ago that really confirmed my need to transition. It was during the 10 year anniversary party, and I asked you if you ever feel sad at the end of the day when you have to go back into guy mode, and you very quickly (without thinking at all) said “nope!” I can remember, in both my crossdressing and genderfluid phases (they are NOT phases for everyone, but they were for me!) how hard it was at the end of the day to “de-Alicia” as I called it. It was after one of those moments that, with my wife fully knowing the reality of things (and ready for me to admit it), that I finally blurted out “I WANT TO TRANSITION!!!”
Four years and one gender later, and I’m so thankful I did it!
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I find it very interesting and puzzling that a cross dresser does not find it sexually titillating! To me there are 2 things – 1. A turn on sexually. 2. Makes me feel like a female to some extent and gives me an idea of what it is like for a female to dress this way. I feel like the female version of me when I look in the mirror, for example, made up facially. I would like to be able to magically change into a female for a few days to a week to know exactly what it would be like, but I would never want to be permanently changes.
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My first time is deeply buried in the long distant past, when I was maybe about 4 years old. I think the first experience involved a satiny slip that belonged to my older sister. No recollections beyond that.
What I do remember is a persistent sense that I was different, and the vague insinuations by family members that I was in some ways acting like a girl, and doing what I could to suppress whatever it was that gave that impression.
For the majority of my life from that point, I viewed my cross dressing and apparent gender variance with a combination of fear, guilt and shame. It is only in retrospect that I have come to recognize the adverse life consequences of deeply ingrained self loathing.
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what a great article. I’m a lifetime crossdresser and I love it more than ever. I remember the first time I dressed completely in my sister’s clothes like it was yesterday. I still remember what the dress looked like. I still think about dressing all the time. I dress almost everyday, it has turned into something much-loved.
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All so true, very well said!
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This was profound….I don’t know what to say
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This is a great blog, that feels like it was written for me! It covers a lot of familiar ground; the unexplained compulsion to wear girl’s clothes from a young age, the confusion and questioning of my sexuality and gender identity, the shame and embarrassment, keeping it all hidden, attempts at denial, gradually accepting it, understanding myself and my need to crossdress… it’s been a difficult and soul searching ride. Finally, I’ve learnt to embrace it. From the confused boy who guiltily liked dressing up in girl’s clothes, I’ve become a confident man who simply just spends some of the time crossdresed. I’m heterosexual and generally comfortable dressing and living as a man, but sometimes I enjoy dressing myself up as a woman. I’m married and open about my habit, albeit only with my wife. She accepts me for who I am and has encouraged me by welcoming my crossdressing into our relationship. My perspective now is that it’s all just a bit of escapism. At different times it brings me pleasure, a sexual thrill, fun, calmness and excitement. If I tried to deny myself those feelings my life would definitely be less fulfilling.
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The very first time I tried on girl’s clothes sparked something in me that remains to this day. I was about 10 and had already developed a keen interest in the lingerie sections of my parents retail catalogues. I wondered what it would feel like to wear some of the beautiful undergarments I saw in the pages of the catalogues. As I went for a bath one day I saw that my sister had left her bra and panties on the floor of the bathroom. Without too much thought I put them on. The excitement was like an electric shock. I gazed at myself in the mirror and couldn’t contain my excitement. That was the very first time, but those feelings are still with me over 25 years later. Whenever I treat myself to a new lingerie set I feel like my young self all over again. I’ve struggled with my compulsion to wear lingerie over the years, but have learnt to accept it because the thrill I get from it is intoxicating. My life would definitely be less fulfilling without it.
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I just turned 64 and have been crossdressing for over 60 years, including now, typing while wearing a beautiful red sheath dress, pantyhose, matching red panties, bra and slip, and red heels.
Hard to remember the first time but the urge has been there since a very young age. The surprise to me is how much the desire and enjoyment has dramatically increased as I have gotten older. Crossdressing remains a power and profound and substantial part of my life.
The internet has opened up a safe space to share our journeys, challenges and successes. Thanks to Hannah for making this crossdresser feel better about what I do and why I do it.
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