Dressing Up For The First Time

I was always interested in women's clothing. I don't know what it was but it just made me wonder what it was like to be a girl. When i was 15 i finally gave into my curiosity and wanted to browse my sisters clothes. I went into my sisters room when the house was empty and opened up her closet. I saw all of her nice shirts, blouses and dresses, i looked around pulling some stuff out and eventually made my way to her dresser and saw all the panties and bras. I wanted so badly to try on a whole outfit but i was terrified of getting caught. Then i got an idea. I picked out the clothes i wanted to try on (a purple tank top with short shorts and a padded purple bra with a lacy thong) and went to my room, locked the door then striped down and started to put on the thong and bra. It felt so good to be wearing them, it just felt right but something was off, i needed boobs. I stuffed the bra with socks and then it looked right. Then i put on the shorts witch were even shorter on me and the tank top. I looked in the mirror. My body looked good and my face need some work. I went back to my sisters room and grabbed her razor, shaving gel, and her make up bag. I went to my bathroom and took off everything and shaved off all hair below my neck. I never realized how good my legs and *** looked now that all the hair was gone. I put back on all the clothes witch felt even better now that my skin was silky smooth, then went to my mirror to apply the blush, eye liner, lipstick, eye shadow, and mascara. I went back to my sisters room and got her blonde wig and came back and put it on. I looked amazing, no one would be able to tell that i was a boy. I spent the rest of the day in the clothes. I started doing my nails, looking at clothes online and taking cute pictures of myself in the mirror. When it started to get near the time my parents got home i went back to my sisters room to put everything back. I was heartbroken that i had to take off everything, but i did and i put everything in the room back to the way it was. At least once a week i would dress up in different clothes, but the time after this was when i really discovered how fun it was to cross dress.
Part 2 of this story is up, go to my profile to read it
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16 Responses Oct 10, 2012

Love to see your pix. Ur profile pic is awesome

Aww I love "First time dressing up" stories like this. I can relate to that gut wrenching feeling that comes when you're forced to go back to being a boy cuz of the people you live with. Don't worry chica, when you're able to live as a girl 24/7 things will be easier.

it seems to me a great story

hey you should add and message me :)

mmmmmm wonderful thank you for sharing.

Fabulous sweetie

Thank you so much for sharing this :)

although i dont believe in same sex marriage, i dont believe its anyones fault that they are gay. if thats the way you are im sure your parents will accept you. thats all i have to say about that. but your not a girl im just pointing that out your a boy

you do realize that not all cross dressers are gay?

I did pretty much the same thing when I was 13- 14. I found some of my mom's old clothes in the basement and put some on. I quit doing it a few years alter, because I became manlier and I probably don't look good in clothing designed for the opposite sex. I actually posted a pic of me in a bra after a buddy dared me to do it, on Facebook less than a year ago. I wasn't doing it to be gay, but just as a joke. someone shared this pic and I was bullied for it. They found out it was me. I threatened one of those people with bodily harm, and I was lucky I didn't get in trouble. my high school had a fun day where students dressed up as the opposite sex, and I PARTICIPATED ONCE. I felt weird doing that and look back at it with embarrassment. I didn't have the kind of personality to be doing that, as other people didn't stand out too much when they dress like that. Even though I have done this at home, I am not someone who should of been doing that at school as some people suspected me of being gay or bi In middle school and always denied it. I mainly like the opposite sex and have a thing for transgender people. I have very little to no desire to be a transexual though.

Your really pretty! www.cheapsneakercn.com

I have been crossing for about 40 some years, and when i was younger I had wore my moms and sister clothes. I had got caught and my mom ask if i waz a ferry did not aprove.I wish I had come out of the closet lot of sooner. Now at 51 I still crossderss and I buy my own clothing, makeup. I take everything off so my wife wont find out as she dont even aprove of it. I wish I had known about the help and support groups a lot of sooner

You're absolutely gorgeous.

sounds like a very interesting beginning, look forward to hearing more - maybe with someone else who dresses or what happened when you got caught and what did you have to do then ?
Can you reinvent the original outfit ? love to see pics of that (to go along with the story)

I started teh same way when i was 12 with my sisters clothes. I was 15 before as well before i started shaving my legs and tummy!

I started with sisters clothes as well.
I would look forward to nights in high school when I knew she and parents would be gone.
I'd run into her room right away and pick an outfit to wear.

Hey babe,

Your story reminds me of my times home alone between 12-23 before I finally moved out. Please dress as much as you can and whenever you can, never letting an opportunity pass. You'll be happier for it! Have fun!!!