Monday, August 23, 2010

How it all started

I started trying on my mother's panties when I was 11 years old. I would sneak into my parent’s room, when they were out and go through my mother's underwear drawer. I quickly found her secret stash of "sexy panties" that she kept at the bottom of her drawer. I loved the feel of them next to my body and how they looked on me. They looked so much better than the “tighty whities” that I had for underwear. Lol

I quickly graduated to trying on my mother's bra's, nylons, shoes and clothes. I even started putting on makeup when time allowed. That was always quite the experience because I tended to have a heavy hand when it came to applying makeup, so I looked like a badly made up trollop.

I was always very careful to put things back exactly as I found them, but I am sure my mother must have suspected I was messing with her stuff, especially after I broke her eyeliner pencil one time, but she never said a word.

Actually my mother was an unwilling participant (or was she really a willing accomplice??) in my desire to explore dressing as a woman. When I was in grade six I insisted that I go dressed up as a woman to school for Halloween. So she put an outfit together, a skirt with a jacket and a blouse, a pair of pumps, pantyhose, a bra and a pair of my own underwear. No sexy ones from her secret stash.  She fixed my hair up, and even put some make up on me and sent me off to school.

I was in heaven! I thought I looked amazing and secretly wished I could go to school dressed as a girly every day. I received lots of compliments on my costume, so many in fact that I decided to dress up as a woman for Halloween in grade seven and eight as well. Lol Don’t get the wrong idea, there was lots of clandestine dressing up sessions in between official Halloween outings. But I really looked forward to those sanctioned days when I could go out in public dressed as a girl, even though I was supposed to be in a Halloween costume.

By the time Halloween in grade eight rolled around when my mother asked me what I wanted to go to school and I said same as last year, she actually said “no”. When I asked why not, she said “that my feet were too big to wear her shoes, and that my legs were too hairy to wear nylons.” Damn puberty!!! Well she was right about the shoes, I knew they did not fit, but I still knew her clothes fit, they were a little shorter on me than her, but they still fit. Her suggestion was to dress up as a hobo and leave it at that.

I was heart-broken, devastated, I had already picked out the dress and jewellery I wanted to wear. Lol!! After much sulking and complaining, and you let me dress up last year comments, she finally relented. But she made me work for it and put up little challenges and roadblocks along the way in order to thwart me.

For instance she made me phone one of her friends to ask if I could borrow a pair of shoes to wear. Then there was the hair on the leg thing. Not that I had a lot of hair, it was just starting to grow, but she insisted that the hair had to go, or I had to go dressed up to school as a hobo.

So the night before Halloween, she had me put on a pair of gym shorts (they were much shorter than the ones the kids wear today) and she took me into the bathroom; pulled out her electric razor and showed me how to use it. She then rolled up the gym shorts slightly and said “I was to shave my legs up to the rolled up hem. That way when the hair started growing back it would look normal.” Kind of like my leg hair was growing in for the first time. I also had a little under arm hair she said had to go as well. I looked at her and said ‘OK” and went to work.

I had secretly wanted to shave my legs since the hair on my legs had started growing in. Now I had the blessing of my mother to get rid of it!! After about thirty minutes or so, she came back in and checked on my progress. I thought I was pretty much done, but she felt my legs, said “there was still hair on them”, grabbed the razor and finished up the job. She then rubbed baby oil on them and off to bed I went happy as a clam.

The next morning, she had a surprise for me; she had borrowed a wig, from a friend for me to wear, and she had laid out a full complement of woman’s undergarments for me, including panties!!! She said, “If you want to dress like a woman, you have to look like a woman, and that means from the top of your head, right down to your shoes, and underwear. Now go put your panties on and come back and I will help you get dressed.”

Anyway, I came back with my panties on, and she helped me get dressed. She even stuffed my bra for me, so that I had some cleavage. Next came the wig and make-up and of course pictures. I got lots of “doesn’t my little girl look pretty” comments from her, still trying to stop me. But I kept looking in the mirror saying to myself yes, I do look pretty. Lol. She gave me a purse to carry my keys and put some money in and off I walked to school.

If you have not figured it out yet, my mother kept trying to humiliate me into not going dressed as a girl. Whenever she did not want me to do something, she would use humiliation to bring me back in line. This time it back fired on her though, because everything she used to try and humiliate me, was what I wanted. So I won this round, but she would use this against me for years to come.

Also, for whatever reason me dressing up as a woman as a thirteen year old, was not as acceptable as when I was eleven or twelve. Maybe she thought I would get teased or maybe she knew I was wearing her stuff and she was not home, but could not bring it up. Who knows, but I certainly did not get teased that day at school for my costume, but I did get some weird looks the next day when I showed up in gym class with my shaved legs.

Actually that year, I kind of freaked out my teacher. I think me dressed up as a girl for the whole day was making him uncomfortable; he came over and quietly asked me if I wanted to change into something else. I said no I was perfectly fine. He then suggested that I take off the dress and wear my gym clothes that I had on underneath the dress, and then when it was time for the party I could put the dress back on. I politely said to him that I was not wearing gym shorts under my dress but was wearing a bra, a slip, panties and pantyhose. His face went beet red and he walked away.

He actually brought it up with my parents at a teacher parent interview a couple of weeks later. He said that he thought it was inappropriate for a 13 year old boy to be wearing woman’s undergarments to school, even if it was Halloween. He felt I should have been wearing shorts under the dress, not woman’s underwear. My mom just shrugged and said it was my decision and she had done everything she could think of to stop me.

The thing was that dressing up secretly behind my parents back, or dressing up as a woman for Halloween was never a sexual thing for me. Oh I will admit that as I hit puberty, putting on a pair of panties gave me an erection, and I became sexually aroused, but after a while the erection went away and I just enjoyed the feeling of clothes and looking at the transformation in the mirror.

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