I’ve been dressing since I was around seven. I remember thinking, why can’t I dress like my sister? Now over 50 years later, why am I still asking that same question regarding womenswear? Why can’t I wear them?

It’s an everyday occurrence now. Whenever I see a woman beautifully dressed, I’m usually asking, “Why didn’t I get to dress like that?” It causes me to think back on all the wonderful outfits that I missed out on while growing up. All the cute little dresses and all the pictures my mother would’ve taken of me. All the special events we went to required a beautiful gown, and all the dolls I missed out on.

I could have been raised to be more girly and feminine, as I really wanted to be. I’ve missed not having a Barbie doll collection complete with a Ken doll. The fun in giving Barbie different outfits to wear for all those special occasions. I’ve missed having my first vanity (Makeup table) where I would have learned the proper makeup techniques. The many ways my hair could have been done in cute ways. Getting to learn it all from my mom, mostly, and then my girlfriends at pajama parties. That’s all part of learning to be a woman. How to act and dress properly.

On a different level, I now look at women and wish I had their features. I know I could have them with surgery, but I really wish I could have it all naturally. At least lived my teen years with a beautiful feminine body. Be that beautiful girl. I can imagine all the gorgeous outfits that I could’ve worn. I wish I could’ve had that experience. Good or bad I want it. All I can do now is to grow out my hair. You won’t believe it; I even get comments from older guys about the length of my hair. Good and bad. It’s all I have girls.

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When I’m noticed checking out other women by the women I’m with, they might get jealous but I’m usually thinking, “Look how she’s dressed and how she carries herself.” I look to see how she pairs things together. I want to be her. I’m sure we’ve all done that at some level.

There are so many things a woman can have. Pretty things and useful things. All sorts of clothing styles. Purses to match any outfit. Jewelry in endless combinations. When women go shopping they can buy anything. They’re not scared to have an item in their possession ready to purchase or when a friend sees them. They’re free to buy whatever they want. I have to be sneaky. I’m so jealous. 

When a woman has extra big features, I usually ask, “Why couldn’t you have given me some of hers.” That sounds silly, I know. It’s just my desire to be a woman. The perfect woman I picture in my head; She’s elegant, poised, and proper. Not with her nose up in the air towards others, but she is truly accepting of others and caring. I am basically that person, but I’m in the wrong form.

People see guys as being more tough. When they see a guy who’s a little “Too caring,” they are labeled soft or some other derogatory name. It’s literally hard every day to be a guy when you see women living the life that you want for yourself. Believe me, I don’t hold that against them at all. On the contrary, it’s who I want to be.

I’m just so jealous that I wasn’t raised as such. I don’t mind being my male self, but if I could switch, I honestly would. Therefore I’m jealous. I could be the perfect housewife if that’s what it takes. I could be a wonderful mother and Dr. Mom, too.

One day, they will be able to swap our gender in a better way. Maybe through brain surgery. Put my brain in a woman’s body. Hey, it could happen. If it does, it’ll be way after I’m gone. Therefore, I’m so jealous and maybe a little silly too. 

I know there’s much more to add. Believe me, I’ve thought of it all. I want to know, does anyone ever have these thoughts? To what degree? And finally, what would you add or not do?

Baily Marie Lovejoy

EnFemme

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carla
Lady
Member
2 months ago

Great article, unfair not being able to dress like them. And envy when you see a woman dressed up as you would like to be, and angry when you see women who do not take advantage of everything they have at their disposal. And I would take advantage. If it is becoming more and more tolerant, today the waiter who served us had his nails painted. And I have been left wanting to ask him. But what would my family with whom I was eating have thought. It’s not so easy if there are people you don’t want to lose.… Read more »

Paula Dene
Lady
Member
2 months ago

Probably not any more, but many years ago I suppose I was jealous of girls and women I knew (to be honest, only the more attractive ones) and always wanted to know more about their clothes, including the ones I couldn’t see, and how they chose what to buy and wear. As a teenager – without sisters – I was especially fascinated to listen to mothers of teenage girls talking about their daughters’ development into adulthood and their “problems".  I realised that girls went through an intense learning period, helped by their mothers, their older sisters and their schoolfriends, working… Read more »

Fatima Abrams-Cohen
Lady
Active Member
2 months ago

Well yes I do have those nice thoughts at times, especially when looking at a woman whom I find very attractive. I want to be her. But usually I’m happy enough being a guy’s guy. Then maybe twice a week I open that little box that is labelled Fatima and she blossoms into womanhood. I haven’t had trouble controlling her yet but sometimes I wonder that I won’t be able to get Fatima back into her box and then…..

Fatima Abrams-Cohen
Lady
Active Member
2 months ago

@Baily Marie Lovejoy Oh Yes, my male buddies would be absolutely dumbfounded if they found out and saw me as Fatima. On the other side of things the girlfriends I have (other crossdressers) are loving and wonderful and I’m so happy to have found them.

Chrissie Smith
Baroness
Trusted Member
2 months ago

Baily, I think most of us have regrets. I posted a while ago that I was playing in my band at a wedding and I was just so distracted by all the beautiful dresses, heels, hair, jewellery and makeup. I’ve told my story here too many times but I’m a bit consumed by ‘what if’. I’m not even in a position to make up for it now. So frustrating 😥.
Hugs, Chrissie xx. 

Chrissie Smith
Baroness
Trusted Member
2 months ago

@Baily Marie Lovejoy thanks Baily xx.

Harriette
Lady
Active Member
2 months ago

why am I still asking that same question regarding womenswear? Why can’t I wear them? Recently, I finished reading The Naked Neanderthal and I didn’t find the answer to my question (What made Neanderthals go extinct? *) which made me read it in the first place, until the last chapter. Also in the last chapter, I found this: “There were many distinct Neanderthal cultures. We Homo Sapiens Citadensis are absolutely normalized by our society. You just have to walk down any street to see that our expression of diversity is more or less limited to the case that we put… Read more »

Harriette
Lady
Active Member
2 months ago

@Baily Marie Lovejoy I wished that the author had included clothes as a form of expression in our society because at least women have that medium to do that. Women’s clothes are so varied around most of the world.

Krista Crawford
Krista Crawford
2 months ago

@Baily Marie Lovejoy Like many others, I get it and feel that way. The past I need to let go of is that in my teens, I could have been a lovely woman. With a baby face, slender figure, gorgeous curly hair, and very little body hair, I was sometimes mistaken for a girl. Maybe they were not mistaken :-)Decades later, I sometimes like to present as a woman but the curls aren’t as nice, the baby face has wrinkles, and age spots mar my once lovely legs. I am doing what I can – staying in the present! I… Read more »

Krista Crawford
Krista Crawford
2 months ago

I had to read twice to get past you calling me cute! LOL! I love the validation we receive in here. Thank you for your thoughtful response, Baily.

Krista Crawford
Krista Crawford
1 month ago

LOL! I’ll own the humor part at least, though my teenaged kids deny it! I also can’t count…humor…"looks"…and…?

Krista Crawford
Krista Crawford
1 month ago

Interesting that two continents of people lay claim to that word. Where I work we do significant work with American Indians and at one time I lived near the Lakota. Also, such lovely dark eyes!

Krista Crawford
Krista Crawford
1 month ago

I was told that Columbus (or some other white dude) thought he had reached India. History back then though….who knows?

Alex L
Lady
1 month ago

A lovely insight Baily, and a very common tale I bet. I’m not sure which is easiest though, growing up with a mother and a sister (you did have access to clothes and Barbie) or growing up without. In some ways you haven’t truly missed out, your dreams and fantasies…and that secret dressing up?? of course you did haha. I’ve kinda done it without a brain transplant but with the good comes the reality of not being perfect, like not fitting in that dress how you thought you would! And those other women can be bitchy when you are one… Read more »

Jennifer
Lady
1 month ago

Hi Bailey, I could not help but feel like I was reading something I had written! I absolutely feel the same as you do. I would switch in a heartbeat and live the rest of my life as a woman. I admire and envy women so often but I also find myself thinking “I could do better than that” when I see a woman who seems not to care as much about her appearance as I would my own.
Oh if only!
Thank you so much for your article; it was a joy to read! 🥰

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