Mom Satisfied My Curiosity About Cross Dressing

From an early age I loved to be dressed in girl's clothes and pretend I was a girl. The first time it happened, it was a babysitter who fixed me up in her little sister's clothes. 

I was always sneaking into my mom's room and playing with her things. There came a time when I was 12 and 13 years old when my mom's
underwear, dresses and shoes fit me perfectly.

My mom was an executive secretary for a company president and she always dressed very well.

Mom was working late a lot in those days and I was often alone at home after school. There was no one else in the house. My parents were
divorced and I was the only child. Whenever I could I would get dressed up in mom's things and go around the house. I started putting on nail polish and make-up and her jewelry. I adored walking around in her high heels wearing a tight skirt with a girdle and nylons.

Before long, mom caught me all dressed up and she wasn't happy about it. She made me promise that I wouldn't do it again. But, of course, I did. And she caught me again, and again and again. Mom got very upset every time. She started punishing me by holding back my allowance and insisting that
I stay indoors and study.

I was then in the 7th and 8th grades and I was the smallest boy in my class. I was deathly afraid that my secret love for girly clothes and things
would be revealed, and mom knew this.

At one point, she decided to take me to see a psychologist. It was a woman and she met with mom first and
then gave me some tests and talked with me. I remember her asking me if I wanted to be a girl. I said no. 
She asked me why I liked to wear my mom's clothes. I said I was just curious about mom's clothes.

About a week later I got caught again wearing a dress that mom had just bought to wear to a wedding.
To make matters worse, I had trouble with the zipper, and damaged the dress when I took it off. She was furious.

The dress was repaired and she wore it to the wedding, but I was really in the doghouse after that.

Not long after that, she caught me again. One Saturday, mom pretended she was going shopping for the whole day
and I was to be at home, practicing for my piano lessons and doing homework and chores. Of course, the minute mom
left, I was in her bedroom getting into her things again. But, she came back about two hours later and caught dressed to
the nines, wearing make-up and nail polish and even some of her expensive perfume.

This time, she didn't get angry. She just smiled and went about her business in the house and left me alone. Late that afternoon, she had me take off
her things and clean up my face and nails and get back into my boy clothes.

Two weeks later, it was Halloween on a Saturday. That morning, Mom took me with her to the beauty salon where she had her hair
done. I had been there with her a few other times. But this time, I was the one who was going to get the works. The beauty salon
ladies fixed me up with a nice wig, did my make-up and put polish on my fingernails and my toenails.

Mom had brought along a suitcase with a set of underwear and one of her own skirt suit business outfits. When the ladies were done
with me, she took into a back room at the salon and gisfieot me dressed up as a lady complete with a bra and falsies. I had a ladies' mid-length
coat, high heels, a big handbag and kid gloves, and a cute little hat pinned to my wig. I was 14 years old at the time, but when mom was done with me, I looked like a young woman in her late teens or early 20s.

"Today, you are going to be my daughter," she told me.

Mom was dressed up too in a similar outfit and she had gotten her hair and nails done that morning as well.. 
She took me out to lunch at a nice restaurant and then we went shopping in the afternoon and she bought me
some dresses and underwear of my own that I could wear at home.

That evening I wore a Cinderella costume and mom dressed as a witch and we went to see a movie together.

After this time, mom allowed me to dress at home as I pleased in my girl's outfits, or in some of her things that
she didn't need any longer.

I've been dressing as a woman whenever possible now for nearly 70 years.


Sissylips Sissylips
9 Responses Dec 21, 2010

Such a great story and a really great mom.

You make me jealious,i wish I had a mother like your's.

Wonderful story !

Thank You very much for your letter it brought back many painful memories (70+ years). I wish my mother had acknowledged my crossdressiing, it would have helped tremendously. Thank You

Great story and glad your mom had a change of attitude to become supportive of your desire to wear female clothes.

Loved the story, and I was happy to read that your mom evetually was ok with your crossdressing. Some mothers are particularly good dressers and have elaborate wardrobes. Something a crossdressing son would not be able to resist. I always wonder how mothers deal with those pesky erections that are unavoidable, yet highly noticeable, when they help dress their sons. I know most mom's ignore them. A few mother's, however, opt to provide their sons with relief.

Wonderful story. I really enjoyed the read. My Mom knew the first time that I dressed. She didn't take me shopping but to my surprize she bought duplicates to what I had stolen in my size.

Very nice story. I am glad that your mom changed her attitude and while I'm sure you had a great relationship with her up till then, I imagine it improved greatly after she accepted you for what you are. Congrats!

Lucky for you Mum came around in the end, it must have been wonderful when she did, I am glad that you have had a wonderful life of crossdressing.<br />
<br />
Love Kathy