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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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 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.

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.

I am sorry that I missed this wonderful story of your first venture out into the world with silky panties cradling your widdle dragon and a sissy slip and dress swishing around your bare legs sending sensations up to the brain and every nerve ending in your body tingled with fear and excitement. Gad!

Even now, after a dozen or so years in girlish clothes, I wonder why fear and embarrassment are still a secret part of my feminine enjoyment. I guess only those of us who have walked both sides of the path can truly appreciate these feelings.

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

I've always found sales ladies to be very helpful - especially with bra fitting



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.