Pam and I... The Early Years

I came upon a photo today that brought back memories of my youth. In fact, my earliest memories that I can fully remember involve my sister and me dressing in her clothes, thus beginning my crossdressing experiences that continued to today.

Pam is 8 years older than me. So, when we were growing up she was always babysitting me to give my mother a break or when our parents went out.

My earliest memories were of Pam and me riding our ponies and playing out in the pastures and wooded timbers of our horse farm. I idolized my older sister and was always doing whatever she asked just to make her happy. As early as age four I remember getting some hand-me-down clothing of hers, usually pants or shorts, maybe a shirt, but especially a cowgirl brown leather skirt with matching fringe vest. Thinking back now, I am surprised that, given our age difference, those items were still around when I got to the size to fit into them. I loved that outfit and wore it many times when we played, even outside when riding ponies. There weren’t many kids either of our ages around most of the time, so we played together often.

I also remember during those early babysitting times, when we were alone in the house, Pam would practice putting make-up on me or styling my hair into cute little girly styles. I was her own real-life Barbie doll. I loved the attention she gave me as well. There were many times that our mother saw this, but she thought it was great that we were getting along and not fighting.

The remember that both my mother and Pam were really into dressing nicely. They often wore dresses, even just around the house. When I was six, my sister had several cancan petticoats, like those worn with the poodle skirts. I fell in love with those and stoled one out of her room one day when she was gone and hid it in a big box in the basement. I would sneak down there and put it on every day, then stash it away when someone came down the stairs. Pam discovered it missing one day and a frantic search was afoot to find it. No one thought to ask me if I knew where it was, and I probably would have lied if asked. When it was discovered, everyone knew that it had to be me because there was no other reason for it being hidden in a box in the basement. My punishment was that I was told not to go into Pam’s room without permission.

Soon after that incident is when Pam dressed me up fully for the first time. She was alone with me for the evening and called me into her room. She had been cleaning out dresser drawers and had several items of clothing laying on her bed.

“Let’s play dress up,” she announced and had me strip out of my clothes. Even though I was almost seven, I was not embarrassed about her seeing me naked because she had given me baths as long as I could remember.

As she put a bra on me she said, “This was my first bra, before I had boobies to put in it. You can have it, if you want.”

I remember being so excited about receiving that bra, and continued getting fully dressed up, complete with girdle, stockings, a petticoat, and dress. She then did my make-up and put bows in my hair. I was really surprised at how much I looked like a girl. What I remember most was both of us standing there in her room wearing identical underwear, just like in this picture.

We were so involved in our playing that we didn’t hear our parents come home. They walked in the door and immediately saw me. Dad just about flipped out, I could tell by his expression that he was not happy seeing me dresses as a girl, but he didn’t say anything, just walked back to his bedroom. Mom had me stand up and turn around so she could see how I looked. I remember her saying that I looked very cute, and how happy I was to hear that.

“We couldn’t find any shoes that would fit him, Mom,” Pam announced.

“He doesn’t need any as long as he is staying in the house, but he should at least wear slippers so he doesn’t get a run in those stockings,” is all Mom replied.

I had no plans to ever leave the house and no one ever suggested it either. Pam and I repeated the dress-up games several times over the next two years, but I never left the house. Then, when she turned sixteen, she started dating and didn’t have much time for her little brother anymore. My dressing continued, but only when I was alone. Mom only saw me dressed as a girl a few times, Dad only that once. But the seeds were planted and have continued with me.

Fortunately, I met Linda who turned out to be very supportive of my crossdressing. We started dating in high school and have been together ever since. On our honeymoon, she gave me my own sexy nightgown to wear as her way of saying that she expected Beverly to be a part of this marriage.

And the rest, as they say, is history.