CAKED IN MAKEUP
Dear Auntie Helga,
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I am writing this story to share my experiences in girls' clothing starting at age 14 (I
am now 22). Before I begin, I would just like to say how much I appreciate Petticoat
Discipline Quarterly and all of its contributors. It's nice to know that there are other
men out there who share the same interest.
Throughout my early teenage years in junior high, I was quite the class clown. However,
the girls in my class must have found something about my sense of humor appalling. By the
time 8th grade began I had already gone through a handful of girlfriends. The problem was
that almost every relationship didn't end too well. Today when I look back, I realize
how disrespectful and arrogant I was to each of them. There was only one girl who had the
patience to put up with me, and her name was Kate.
It was some time shortly before summer recess had started that I had my first run in with
petticoat discipline. Kate had invited me over her house on a Friday night to hang out
with her and a good friend who was also in our class, Jackie. Secretly, I had been looking
forward to the evening all throughout the day, but when I arrived at her front door I
tried to play it off cool.
When I rang the doorbell, Kate's older sister opened it. I walked inside the house and the
first thing I saw were Kate, Kate's mom, and Jackie surrounding me. They all began to
giggle but quickly stopped, and after saying hello, the girls led me up into Kate's room
where we sat down and began to chat. I didn't really think much of the awkward incident
until suddenly I felt Kate grab my arms. Next thing I knew, Jackie was tying them up to
the back of my chair. I tried to resist, thinking it was some sort of game, but I wasn't
strong enough to break the bond. As a 14 year old boy, I found it devastating I had been
beaten by 2 girls. Little did I know I would need to get used to it over time.
Jackie began telling me of their plans. "Michael, you are such a sissy. You think you are
the most masculine, macho thing, don't you. Well we are going to show you what you
really are. Not a teenage boy, but a teenage girl."
Her words began to ring through my head. I couldn't let them do this to me, but I was tied
up and I knew there was no way out. I began to blush violet red and my eyes welled up with
While I pleaded for them to cut the rope, Kate started browsing her wardrobes and pulled
out dress after dress and skirt after skirt. She laid out a total of 10 different complete
outfits upon her bed. I stared on in disbelief while Jackie was playing with my long,
brown hair, telling me how much of a pretty girl I will make. The first thing they did was
straighten my hair. Then they gave me a manicure and pedicure with hot pink nail polish.
Next they applied all the facial make up. Thick red lipstick, pink blush and eye shadow,
and heavy black mascara. They held a mirror up in front of my face, and as I looked at
myself I realized that if a stranger had to guess, the chances were a hundred to one that
they would say I was a girl.
"What should we name her?" Kate asked, "How about Michelle?"
"I love it!" Jackie yelled.
"Michelle, pose for your picture. We know that all of the girls at school are going to be
dying to see our new friend."
I sat there hopelessly, caked in makeup. I couldn't even smile until the girls slapped me
across the face and forced me to make the most girlish gestures.
"You are so cute!" The girls whispered into my ear.
As if it weren't enough, I still had to dress in the 10 different outfits Kate had
picked out for me. The first one was a tight pink tank, pink tights, a jean skirt that was
only long enough to cover up my butt, and a lacy red bra with matching panties. Then they
put my hair into pigtails.
"Come on Michelle, the fashion show is about to begin!"
They then finally released me from the chair and led me downstairs, knowing I had no place to run dressed how I was. But as I entered their basement, I was in a state of shock. All of my past girl friends were there! They began to burst into laughter at first glance. I felt totally humiliated. Each girl had known about this ahead of time, and they each also brought their own outfit for me to wear from home. I knew that if I didn't play along, the pictures would surface. So, when they told me to twirl, I twirled. When they told me to strut, I had no choice but to strut. By midnight, I had gone through at least a total of 20 different outfits as Michelle, and the girls had given me no less than 5 makeovers. I had never expected it to get that extreme.
When they ran out of ideas of what to do, they invited me to their slumber party.
"Please Michelle; it will be so much fun. We can hang out all of tomorrow too!"
I eventually gave in and called my mom, who had no idea that on the other end, her son was actually a daughter.
We spent the remained of the night doing each other's nails and talking about boys. When
morning came, all of the girls left except for Kate and Jackie. They told me that Kate's
mom had made special plans for us, but that they were a surprise for me. Kate let me
shower in her bathroom, and when I got out they redid my hair, makeup, and gave me new
clothing, this time even stuffing my bra. We hopped into the car and before long we were
in the city mall. I couldn't believe I was in public! The first place we stopped at was
the spa. Kate's mom told the ladies working there that I was a sissy boy who's dream
was to be a little girl. They chuckled but were very understanding about it, and even
called me by Michelle. The stop after was the hair salon, where Kate convinced me to get
bangs. Last but not least, we went shopping. I had to try on even more outfits than the
When the day was over, Kate asked me if I liked it better as Michelle or Michael. I
couldn't believe my mouth, but I honestly responded Michelle. I pinky swore to Kate that I
would be Michelle for every following weekend throughout the summer. She hugged me and
said she couldn't wait for the next week. Now I share an apartment with Kate. I hope you enjoyed
the story of my first experience as a girl, and I hope to write to you again in the
Your Girl Michelle
Thank you for your letter Michelle. What a delightful introduction to
the softer side. You must have been terrible to those poor girls, but of course being the smarter sex,
they must have known you would come around soon enough, and you did.