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My Mother and My Crossdressing

I will readily admit that I am quite vain, which means I could spend hours and hours at a time looking at pictures of myself dressed as a woman. And while I think I generally present the image of a demure, conservative cross dresser, I just love to take pictures of myself in a bra, lingerie, or a racy thong with thigh high stockings.

crossdressing a black thong and lacey stockingsSo what does this have to do with my mother? When I first began taking pictures of myself dressed as a woman in 2009, I distinctly remember flinching on multiple occasions the first time I would view a new photo shoot because I saw my mother in many of my pictures and not me. And I vividly remember the biggest jump came when I looked at a set of pictures where I was dressed in a very short red dress, a black thong from Victoria's Secret, lacey black thigh-high stockings, and black high-heels. The reason this photo shoot made me jump was because I just couldn't picture my mother ever wearing that kind of outfit; yet, there she was before my very eyes...or so I thought for a split second.

The reason I know that my mother would have never dressed in such an outfit is because I went through every inch of her closet and drawers all throughout my youth and memorized everything she owned. The raciest pair of panties she ever owned were plain, black panties with plenty of material to cover her up. I say "owned" because she didn't wear these as part of her every day collection of underwear. They hung from a hangar in a closet with a very conservative black nightie hidden by one of my father's large button down shirts, obviously the outfit she wore at my father's request when they would make love.

But the purpose of this entry is certainly not to talk about my mother's underwear collection as that would prove to be a very short, boring entry. Rather, I just wanted to reflect on a few occasions growing up where my mother discovered things that gave her obvious hints that I loved to cross dress because a lot of the correspondence that I get from readers of my diary who tell their stories focuses on experiences they had with their own mothers, especially those times when their mothers discovered their secrets. Also, all of the pictures I post on this page are the ones that most resemble my mother.

cross dressing in my mother's clothesAs I relate on my cross dressing history page, some of the earliest memories of my life regard incidents of cross dressing. I talk about that first bra I borrowed from my mother and then also several incidents of wearing my sister's panties as a small child. And while I vividly remember sneaking those items and wearing them as often as I came across them, I have no memory of putting any bras or panties back in the drawer where I found them. There is no doubt that my mother came across these bras and panties and restored them to their rightful owners. But, I suspect she wasn't overly concerned by this writing it off as a childish phase because how often do you see a little boy wearing fingernail or toenail polish? All boys like their nails painted, and they ask their mothers to do it.

I suspect by about the second or third grade, I was rational enough to realize that stealing my sister's panties and wearing them to school posed some danger, both in getting caught at school and in getting caught at home. So while I did stop the practice of wearing panties to school, a few years later I developed a new practice: staying home from school and wearing panties.

Both of my parents worked, so on days when I felt sick and would stay home from school, I would be there by myself lying on my parents' bed (I guess that was a privilege of being sick) and watch TV. My parents both worked close to home, and one of them would always come home during their lunch hour to make lunch for me and check on my overall well-being, and once I realized that this was the routine, I quickly understood that I had two windows during those sick days when I could cross dress.

It unfortunately never occurred to me to pretend to be sick so I could stay home and cross dress, but on those days when I had a sore throat or a sick stomach and it was determined that I would stay home from school, the routine worked like this:

- Go into my parents room with my blanket and lie on their bed
- Wait for the last person to leave the house
- Jump off the bed and dress into a bra and panties, pantyhose, and a blouse and skirt combination from my mother's closet
- Cross dress until just before lunchtime where I would put every thing back and change back into my own pajamas
- Wait for a parent to come home for lunch
- Wait for the parent to leave and then raid my mother's closet again until my first sibling came home from school

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A girl and a flower garden

Signs of a Girl

Challenges of being a girl 24/7

Quiet Picnic as a Girl

Why My Bra and Panties Rarely Match

Dimensions of being a girl

Pantyhose here and there

Connecting with my cross dressing roots

My slip is showing

Crossdressing and Halloween

Sunday Morning Walks in a Dress



My Biggest "What If?"

Mornings as a Girl

My Mother and My Crossdressing

Motherly Feelings While Crossdressed

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