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Going Out Dressed Like A Girl Wasn't Necessarily What I Was Planning,

I was young, probably about 8 or so and I had been playing all day with my sister (10 year old stepsister actually). My father passed away about a year earlier. It didn't seem like a big deal but somehow I let my sister talk me into dressing like her girlfriend to play house.  It seemed harmless ...and my stepmother thought the same when she came to get us for dinner. The meal was put on hold and she took me into her room and we talked about our game.  Somewhere out of that she curled my hair and put lipstick and makeup on me.  I remember thinking how much older i looked.  We had fun that day, and during dinner I listened how to stand, walk, sit, talk and otherwise behave "like a young lady". After two days of developing a new feminine persona under her steady tutelage, I was dressed up in one of Cin's Sunday best dresses. Before i realized what was about to unfold, we were in the garage, and then in the car pulling away from the house. It was still exciting up to the point she pulled into the parking lot of the mall. Of course, I pleaded to stay in the car.  It would be fair to say my face burned with embarrassment for the next few hours. We stopped in several stores and my mother bought me what seemed like an entire wardrobe of clothes. I could not bear to look at the sales clerks as they rung up everything from dresses, skirts and blouses, to panties, makeup and jewelry. I can't remember if it was then, but I also remember when she bought my a training bra with the assistance of the sales lady.  I remember that my knees shook with embarrassment.  Over time, I learned to enjoy my trips shopping with my mother.
kayleew2000 kayleew2000 18-21 18 Responses Mar 25, 2012

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Hi Kaylee, Your story is so fascinating. Thanks for sharing. It sounds like you have had an interesting journey. I'm sure it's a little strange to have actually lived the life so many people here fantasize about. No doubt, the reality is more complex than the fantasy. Most importantly it sounds like you are peace with the person you now are. May you get all the Jimmy Choos your heart desires! Xoxo Sandy

Hi Sandy,
Actually, that is an amazing observation. I have often wondered about those who have dreamed of being raised as girls. Would they really find a life in skirts and dresses even for a few months as enjoyable as the fantasy they dreamed.

Some might but I think that would only happen with a kid who was TG. I think for many the concept it intriguing but the reality would not have been as fun.

I believe for CD's we wanted someone to see us for who we are and guide us along. The reality is we learned to navigate the world and hide the girly side we knew would be seen and judged.

I totally agree. I wonder how the world would turn out if all boys were given an opportunity for a few weeks to see life through the eyes of a girl.

I think a more gender neutral or gender fluid society would be much better than what we have today. Too much stigma is attached to what a boy or girl is supposed to be and do. Humans are much more complex than we allow for and we box people into roles and responsibilities that they might not choose of given the choice.

Viva LA revolution

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A bond between a mother and son is always great, but a bond between mother and daughter is always greater. Being a girly girl with a mother, you get to enjoy life so much better together. Instead of sitting in the waiting room when your mother gets her perm and her nails painted, you get to join in and get all dolled up together. Life is so much better as a girl.

It's funny ...my mom and sister almost never did girly things together when we were growing up which is probably why I was chosen to fill that role.

Hi Kaylee, it's funny, even though my upbringing was not like yours, I had a similar situation with my mom and sister. In lots of subtle ways, my mom communicated to me that she thought that somehow God or Nature or whomever played a practical joke - that son and daughter had somehow been switched. It wasn't that she was taking me for manis and pedis (lol I wish) but it was more like the way she talked to me. Like, "Sandy, YOU understand what I'm saying, because you're like ME." Of course, how could I not be flattered that she felt that way. And anyway, she was right.

Yes, a bond between mother and son is great, between mother and daughter greater, but I would argue, between mother and sissy or femme or TG son, is the greatest. Because he is like her, and she is sharing her feminine world with him, not be accident of birth (ie genetic daughter) but by choice. He is saying, "I know I am supposed to be like Daddy, but I CHOOSE to be like you." And in spite of how society might judge, she welcomes him with open arms. That is so special!

Based on all those I have heard from on EP, I would bet for every "girlish"-boy and supportive mother there are thousands more who have been forced to carry their unfulfilled dreams through life. I don't know if it is always a closer bond between mother and a girlish-son, but it certainly was so in our family. Being raised in a single parent home with my step-sister, I became the girly-girl my mother always dreamed of the more my older sister walked her own "tom-boyish" path. My new life came at a time I was desperate to bond with my new family and being raised as one of the girls just brought us all that much closer together.

Yes, I'm sure you're right - lots of people leading lives of quiet desperation. But, two encouraging trends - 1. The internet has been a lifesaver for making people realize they are not alone, and 2. I think our society in general is becoming much more tolerant of these issues, and hopefully that will encourage more mothers to embrace their sons who are feminine.

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I wish that my mother had done something similar for me when I was a child

Wow that is an amazing experience for an 8 year old. With where I am now, it all sounds like it would be such a wonderful experience. In fact I fantasize about such things. But to have it really happen at such a young age, it must have produced all kinds of conflicted and confusing feelings. I'm interested to read more and see how it progressed from there. Thanks for sharing it. Bethann

You are welcome, Bethann. Conflicts and confusion were pretty common events through my life although I also learned to accept and enjoy. Along with acceptance I am now learning to find where I fit in the social aspect of my world.

I can imagine some mental anguish of being a boy dressing as a girl. Then secretly enjoy the Loving attention you are receiving your mother and wanting her approval. ;-)

That's a good comment, Angie. I think that pretty well sums up my life from 8 to 14 or so.

I imagine that first trip out must have been a bit nerve wracking. i know I would not have been happy about it.

Nerve wracking? ...yes. Was I unhappy at first? ...probably. Embarrassing? ...certainly. But it did not take long to discover the excitement of strolling through the malls shopping with my sister and mother. Through the years we looked forward to our little shopping excursions almost every weekend.

That is awesome. I never got along with my parents and sisters enough to even consider the idea of knowing I like more feminine stuff let alone be completely open about it. Still don't and have no intention of letting them in on it as they are some of the most judgmental people I know

Do you ever wear jeans or trousers kayleew x

Almost never growing up but I did get a pair or two to wear in the winter and I still have a couple pair now. They are cute with plenty of bling on the pockets.

What a lucky girl you are!

Did you get a pair of heels that first day out shopping?

Funny... I don't exactly remember what kind of shoes we bought during those first few shopping trips. I remember wearing small heels some of the time in the early years but mostly they were wedgies or low heel shoes with colorful designs and bows. The first pair of actual "high heels" that I remember were a birthday present when I was about 12. I had to dress up to go to a wedding for a friend of my mother's. They were red open-toe pumps with a cute bow over the toes. I felt so grown up. Before that I just played around in my mom's heels, and of course, now I have at least 25 or 30 pairs of heels in my closet. If I could afford it, I would probably have twice that many ... :-)

What did you wear to the wedding you spoke of? How high were your heels then?

The heels were black sandals with a pink trimmed black bow. They were only about 2 1/2 inches or so ...but not wedgies. They were my first thin heels and I felt like I was walking on my toes all day. I wore a simple short black sequin dress with a black thin string bow in back. It also had a handful of pink heart-shaped sequins scattered all over and a thin pink high-waist belt. I loved that dress and talked my mom into letting me wear it on special occasions. I so miss those innocent days of dressing up in pretty clothes.

OMG that sounds simply beautiful, Kaylee! I assume that you also wore stockings. Did your mom help you get dressed for the wedding? Since I am physically challenged my mother had to help me most of the time to get dressed. She was a stickler about my appearance and my femininity. Guess that's why I ask so many questions about stupid stuff. I, too attended weddings and other events as a girl. First wedding I attended as a girl was when I was 9. Mother and I wore matching pale yellow long dresses with matching pumps. That was the first time that I wore a two inch heel and did fairly well walking. Did your mom dress you often? Mine did only because she knew I was a girl really inside. Would love to hear more about your experiences as a girl..

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I really do believe if more parents did this theirs sons would love and cherish the experiences for the rest of their lives.

Lucky you being in such good family!

It took me a few years, but I finally did learn to appreciate how wonderful they were to me.

Being embarrassed is part of the reason it is so remember-able!!

I look back on those first trips out in public with a sense of humor although, I remember them being very traumatic andembarrassng.

Thats the experience all wish we had. To be our mothers little girl.

Wonderful Kay<br />
I've always found sales ladies to be very helpful - especially with bra fitting<br />
Hugs<br />
Sammi

at that age never fear the sales people selling you girls clothing and such, unless you are alone, I find when I accompany the sales people relax and enjoy it.

Of course, those fears were some years ago. I think i learned like most girls how wonderful shopping for clothes can be.

my mother allways take me out as girl

Like I've said numerous times OUR MOMs know us so well, she sees the little girl in all of us boys, unfortunately only a few are brave enough to assist us in bringing her all the way forward.

I went from resenting my Mother to learning to how wonderful life could be. I suspect i was most fortunate to be home-schooled and not have to deal with the cruelty of narrow-minded highschool boys. Although I had not purposely sought a feminine lifestyle, I learned to love being part of the secret inner circle living only with my sister and mother.