Love Wearing Mommy's Clothes

Well it all started really young. I don't quite remember the very first time fully dressing up as a girl, because at the age of 5 I was taking my mothers pantyhose and putting them on. Later as i got a little older, around 8 to 12 is when I would then finally get the chance to fully dress up. This is a story of my most vivid first experience dressing up. I was around 11 years old and my mother had been living in this one bedroom apartment at the apartment complex where she worked. As being a kid my mother gave me the bedroom, while she slept on a bed where the dinning room should have been. With me having the bedroom my mother didn't have anywhere to hang her dresses, so my clothes were put in drawers and she would use my closets for her dresses and high heels. At night when my mother was asleep I would sneak over to her and go into her drawers of her chest. I would take a few different color pantyhose (beige, tan, black, navy, white), I then would take a bra, panties and her white teddy she had. (my favorite) I then go back into the room with my acquired items not shutting the door for it made to much noise. I would put her teddy on stuffing the breast area with my underwear or socks, I then go into the closet and find an outfit to wear. I would usually go with either with a black skirt with a leopard print blouse or her black dress that had a belt attached or her black and white poka-dotted dress. Depending on my choice I would then pick the pantyhose color that went best and then put the clothes on. While dressed and easily able to be caught if my mother woke up, I would go to the bathroom and apply her make up. Usually I would just apply lipstick and a little blush for i wasn't experienced in applying make up. I would then put on a wig my mother had for some reason and then would go back to my room and find the high heels I wanted to wear. I then would walk around my room and act as femininely as possible. On a few occasions my mother would wake up to go the bathroom and i would take off the wig and would jump in bed and hide under my covers not to be scene. On one occasion I recall vividly of when I was dressed in the teddy, with the black skirt and leopard print blouse, make up and wig and some a black pair of high heels with black pantyhose walking around my room when my mother had woke up to use the bathroom. As I was walking around my room dressed up unaware that my mother was awake, she walked in on me and was quite passive in asking me what I was doing and telling to take off her clothes and go to sleep. I never did get in trouble but I would continue to secretly dress up every time I had visitation with my Mom since my Dad had custody of me. There would be a few times my Mom would catch me with her things but never dressed again. I sure do miss those days of wearing my Mothers clothes and feeling sexy or like Mommy secret little princess.
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7 Responses Jul 13, 2010

I am happy for you that your mother took this in stride. When I was caught, I received a different reaction, but it turned out to be a fairy tale dream for the most part. My cross-dressing days began when I was five or so also and blossomed into who I am today. So much happened that I just had to write a book about it. If you like to read, then you may want to look up (Google) "He's my Little Girl" by M.A. Damien.
You are off to a good start. Even if you don't dress up again, never let this past experience upset you in any way. Most (if not all men), tried to dress up in female attire whether whole or in part at least once in their lifetime. There are skeletons in everyone's closet.

Hi, I have had the same sort of experience. My Mum did not like it at all. That didn't stop me. See my profile for more. Hugs amietv

Great story...!!!...;-)

I like to wear Silksarees,Silkskirts ,petticoat,silkyblouse. <br />
I will wear silkskirts,silksarees petticoat,silkyblouse.<br />
<br />
I began to wear Girl's Dress , my age of 7 (seven) years old. I will take silksarees,silkyblouse,petticoat,silkskirts from my sister's collections. <br />
I enjoyed with silksarees,silkskirts,silkblouses severaltimes.


I get from your story your mom wanted you to become a sissyboy. I'd be willing to bet she would have got you your own little girl dresses and would have raised you to be more girly.

Wow, thats the spirit... snaked, took the dress... And your Mom is very calm i think.. "she walked in on me and was quite passive in asking me what I was doing and telling to take off her clothes and go to sleep." :D