I was 13 years old when I wore my first bra. Here's how it came about:
I lived with my family at the end of a quiet residential street with a large
wooded area beyond. Across the street lived a girl named Kay, just a few
months older than me. We had played together for years. There were no
other children near our age on our street at the time. We were both the only
children in our families.
When we were younger, she liked to have all-girl tea parties. Since there
were no other girls in the neighbourhood, she told me I would have to be
a girl or leave. While I protested weakly, I was happy to wear the dress
she presented me. She also liked to put nail polish on me and sometimes
even some of her mother's clip-on earrings.
As we got older the tea parties stopped, but she continued to treat me in
many ways as her girlfriend rather than the boy across the street. She
was an early developer as compared to most of the girls her age. I would
be visiting her as she was ironing clothes. She would show me her bras,
initially training bras, but then regular ones as she carefully ironed them
(old days, right?).
One day she told me she would show me how to iron. She insisted my ironing
included her bras. She would ask me which ones I thought the prettiest. (Hard
to say, as they were all white at the time.)
Then came the weekend when the youth group at our church was planning a
Halloween masquerade party. Kay decided that I would go as a girl, and she
would go as a boy. I reluctantly agreed (sure), and it was game on.
The party was several weeks away, and Kay busied herself trying to decide what
I would wear. We spent many after-school afternoons with me trying on various
dresses or skirt and blouse combinations. And to make it a real as possible, she
insisted that I should wear a bra and panties underneath. So she placed a white
bra over my chest and hooked it tightly in the back. I told her it felt really funny.
She assured me my sensation was normal, and that I needed to practice wearing
it to get used to it. So I wore a bra home that night. My mother thought it was
quite funny. My father said nothing.
Now this was the late Fifties, and many proper young ladies were wearing panty
girdles. About a week before the party, Kay decided that I would wear one, with
light tan stockings attached to the garter clips.
My final costume consisted of bra and panty girdle with stockings, a white slip and
knee-length black flowered dress, and a pair of Kay's mother's high heels (only two
inches or so).
The look was completed with carefully applied make-up, clip-on earrings, bracelet
and necklace, and a dime-store blonde wig.
Kay wore one of my dark suits, white shirt and tie, with her hair up and under a
fedora hat, and dime-store beard and mustache. Nobody knew who we were, and we
won the best costume prizes.
Oh, and Kay told me at the end of the evening that the bra and panty girdle were mine
to keep. She would ask me from time to time if i were still wearing them. Of course!
Over the years, I did a lot more ironing for Kay and helped her do her house-
cleaning chores. Ah, the early making of a maid.
We went our separate ways after high school, and I have seen her only a few times since.
But I have many pleasant memories of the girly things we did together over the years.
Fondly remembering the old days,
Maid Ruth Ann