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Your Feminine Insecurities

by Jessica De Leon on September 23, 2009

Teenage Fear

Is there something specific about your physical qualities that prevents you from enjoying being a crossdresser? Perhaps you feel that your hands are too big, your shoulders are too wide or your jawline is too structured. Try as you might, you just can’t get over how they make you feel about yourself, thus hindering your femme development.

You may look at other transgendered people who you feel look better and because of this you rarely muster up the courage to get dressed yourself, citing various reasons. This post is all about getting over your perceived flaws in order to fully experience your womanly side.

Focus on the Positive

So, you were born a man but want to look like a female. In many cases, you don’t have the most feminine of features and short of hormones and/or surgeries, there’s nothing you can do to change them.

Instead of focusing on what makes you look masculine, concentrate on the things that enhance your femininity. Maybe you have really nice legs that women would kill for or perhaps you have really nice eyes that you could play up with the right makeup. By emphasizing characteristics that beautify your femme look, both internally and externally, you will feel better about yourself when dressed as a woman.

All Women Are Insecure

If you believe that transgendered people are the only ones that feel insecure about their appearance, think again. All women — I don’t care how famous, revered or confident — are anxious about at least one thing about themselves. In fact, there are usually several qualities that they can’t stand.

From small breasts to chunky thighs and everything in between, females are constantly trying different methods to hide what they perceive as flaws. I distinctly remember a scene from “Mean Girls” in which the group of girls each take a turn in the mirror and admit their most prominent flaw.

Don’t be that girl! Sure, you may not always be happy with your reflection, but if you can accept yourself completely then you will be a happier crossdresser.

You Are Your Own Worst Critic

What you may perceive as a defect another person may see as a strong point. Keep that in mind next time you are feeling down about yourself. Tearing yourself down will work against your personal development in life as a crossdresser.

As an example, my wife has a couple of features that she is constantly critcizing. For privacy’s sake, I won’t go into detail but I actually love these characteristics and find them absolutely beautiful. When I tell her this she has trouble believing me, yet I am always sincere.

Don’t hold yourself back with unnecessarily bashing!

Your Assignment

I want you to do an exercise: either on a piece of paper or in the comments section, list something about your appearance that you are insecure about and follow it up with at least two things that you love about your look. In this way, you will feel better about yourself and less reluctant to doll up and be yourself.

Always remember, you are gorgeous girlfriend!

Creative Commons License photo credit: mike_is_scrumptious

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{ 15 comments… read them below or add one }

1 Stephanie September 23, 2009 at 9:48 am

Thanks for this great perspecive. I worte a similar piece on using what we have. It is so true that we crossdressers focus on the flaws and not on the areas that we shine.

Steph

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2 Jessica De Leon September 23, 2009 at 9:49 am

Glad you enjoyed it Stephanie :)

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3 Lindsey Luck September 23, 2009 at 10:55 am

I used 2 be so scared to leave my house in drag because I am a big girl. But hey, now I’m a performer so I take pride in my look. I really love my legs and my chest. Thank you for sharing this I really can relate

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4 Jessica De Leon September 23, 2009 at 10:56 am

I definitely understand getting all dressed up and being insecure with how you look or if you ‘pass’. Kudos on getting over your insecurities :D

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5 SheenV September 23, 2009 at 11:19 am

One thing I learned when I first started fully dressing in women’s clothes in public is how ‘out there’ everything is for women. Women’s clothes are very revealing – skirts show the legs, many blouses are short- or 3/4 sleeved, necklines are more open than men’s, clothing in general is much more fitted. I mean, as a man looking at women, my head turns at every short skirt, low-cut blouse, and other revealing attire that passes me by. Now when I wear women’s clothes I realize how they must feel – there’s not a lot to hide behind if one wants to wear nice clothes and not look frumpy. So all the flaws are also out there to be seen.

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6 Jessica De Leon September 23, 2009 at 11:20 am

That is very true, dressing up as woman leaves you very exposed. Normally men wear shirts with sleeves yet most tops for women are either sleeveless or have a very tiny sleeve. That is why we battle with the dreaded ‘farmer’s tan’ *ugh*

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7 Neutrina September 23, 2009 at 11:55 am

A very interesting post.

I’m not particularly experienced at crossdressing, but I think your point about emphasising characteristics that help enhance our femme look is an important one. I’ll need to try and remember that, because I often wish a lot of things about myself were less obviously masculine. I don’t know, I’ll have to see how I feel when I’ve had more practice!

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8 Jessica De Leon September 23, 2009 at 11:56 am

Thanks, Neutrina. Exactly, we must consciously appreciate our good qualities otherwise we may end up feeling very bad about ourselves

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9 Jessica Sideways September 23, 2009 at 11:16 pm

While I am not a crossdresser (I am a transsexual), I will have to say that I do have an insecurity about my female presentation and it is my voice. I think it is too deep and I worry that it’s one of those things that has a high likelihood of outing me.

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10 Jessica De Leon September 24, 2009 at 2:59 am

Many transgendered people worry about this, I can see how it can be something to be insecure about. Best of luck with it and thanks for sharing :)

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11 Julie M Shaw September 25, 2009 at 12:42 pm

For me, I was cursed with what I call, “Mediterranean Fur” – my Italian heritage sprouts all over my body. However, I have “killer legs” (according to my spouse) and I know that my eyes can look VERY feminine and alluring. So, I wear long sleeves and short skirts!

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12 Jessica De Leon September 25, 2009 at 7:07 pm

I can relate to the body hair thing, that’s why I keep my Philips Bodygroom handy ;)

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13 Kristen Kelly September 26, 2009 at 10:34 am

In the past if there was 1 thing I wish I could change it would be being big boned, but not now. Women come in all shapes and sizes, take a seat center court at a mall (preferable enfem) and watch the women and young girls go by, not all are petite, or totally feminine. Address your Achilles heel, learn to work around it or learn to live with it. In the past I would never wear sleeveless dresses, but from my seat I saw I looked a lot better than many of the women that passed me by. I have an athletic built many women do, and that’s 1 thing no surgery can change.

Posted to http://groups.yahoo.com/group/SandyMartinPhillyTGirls/message/2409

The same question is addressed here

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14 Jessica De Leon September 28, 2009 at 8:10 pm

You bring up a great point: women do come in all shapes and sizes and realizing this does wonders for your self-esteem as a transgendered person

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15 Louise November 14, 2009 at 8:37 am

Jessica, just read this article about your Feminine Insecurities and loved your vision of what is important. My wife and I fight everyday about little things about our looks. My insecurities are only from my perspective and her’s also. Lets all learn from your vision. We need to pass it on to others and help them be encouraged by what they have and not what they think they should have. I have beautiful blue eyes that men love and I am so proud of myself. The glass is always half full and not half empty. Your articles continue to help me everyday. Love you girl.
Louise

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