I was watching a talk show on TV featuring Jenny Jones called “Sugar, a day in my heels!” It’s about wives and girlfriends who dress their men up as girls and take them shopping, and one who spends the whole day as a waitress.
This brings back memories of my childhood experience when I was sixteen years old. My sister and I were arguing about whether it was harder to be a boy or a girl. I said of course it’s easy for girls, they have easy jobs, dating doesn’t cost anything, and the only thing they need to do is get better looking.
My eighteen year old sister says that boys never have to do housework, let alone work in a restaurant and pinch asses and fondle boobs like she does. Boys get to hang out all day, and even though they have to pay for the girls when they take them out, the girls have to pay for it too. They have to go to a lot of trouble to dress up, and they have to kiss the boys on the mouth and more.
So in the end, as you may have guessed, we decided to race and I’m going to be a girl for a day.
Wearing her clothes wasn’t a challenge, as we were all about the same size and the clothes fit, even her shoes. The hardest part was learning to walk in high heels and to hold my hands and feet like a girl. I had to learn how to sit in a dress so I didn’t get naked, how to use the girls’ restroom, and how to wink. I promised to be a girl on Saturdays, to wait tables at the restaurant with my sister, and to go on date nights together. I also promised to let her do my makeup on Friday nights, and she made me shave my legs chest and armpit hair and perm my long hair into little waves.
When I was dressed in women’s clothes she began to teach me the mannerisms of a girl, and she purposely made me wear her shortest skirts and highest heels for me to practise in, until she felt that I could wear any of her dresses and cope without difficulty with every awkward scene she could think of. The most surprising thing about the whole process was that when I was dressed I didn’t look like a boy in a girl’s dress, but a saucy young girl, perfectly capable of walking down the street in the daytime, and even my mother wasn’t the one who could tell at a glance that it was me in a dress and not my sister’s female companion.
I tried my best to learn everything they taught me, to prove to them that it wasn’t hard to be a girl, but a boy. But was that all? I must admit that gradually I began to wonder.
My mom thought she’d help my sister with my teenage grooming lessons too, and talked to me about boys and sex like a mother and daughter. She also decided she wanted an early quiz, so she took my sister and me out for ice cream. Because of my curly hair, they thought I’d be better suited for seven-quarter length pants, though I still had to walk in heels, only slightly lower than I’d practiced.
We arrived at the ice cream parlor and I felt a little shy as I stood at the counter and asked for ice cream. To my surprise, no one pointed at me or stared at me in a different way than they did at the other girls. I felt a couple of young guys looking at my sister and I, but didn’t see that I was a boy, and they even whistled at us. I blushed a little, but had a feeling of triumph: I could actually be attractive to them.
My mom noticed my blush and told me that being whistled at by boys was part of a girl’s daily life and that if I was a girl for a few more days I would get used to it because I did look like a pretty girl. Upon hearing this, my face reddened even more instead.
After ice cream, we went back home. I put on one of my sister’s doll pajamas. They wore my curly hair to give me a taste of what kind of discomfort a girl has to put up with in order to dress up.
The next morning I woke up and was grabbed to do women’s chores. Mom always thought that men and women had their own business, so I never did chores, but today I was a girl and had to do my share.
After doing my chores, I put on the clothes I had made for entertaining and accompanied my sister to the restaurant. My sister introduced me to the owner and told him about the bet between us. He was happy that I was working for him, especially on this busiest day.
They simply told me how to entertain and what I was going to do.
I picked up a couple of menus in one piece with my sister, then I was assigned a couple of tables and I was left to tend to them alone for the rest of the day.
Work was pretty fun, no one knew I was male except for the three of us. I was still taken aback though and did let out a scream, it was the first time a male customer pinched my ass when I walked by the counter. I didn’t know what to do, so I just calmed myself down and kept working ignoring him. The harassment continued throughout the shift, and I guess by the time I got close to the end of the shift I had adapted to it, and was even a little disappointed when I passed them without anyone pinching me.
When I got out of the door and went home, I was exhausted. I rushed to the shower thinking the day was finally over, but when I got out, my sister reminded me that I had to get ready for my date tonight. We had to go out for dinner and then dance.
Not only is it a staycation, but just getting ready now makes me think it’s not going to be easy. I have to put on makeup, a tuxedo and heels, and all sorts of little bits and pieces, and finally I have to do my hair. The girl always has to do a lot to get ready to stop, she shows me how to do it but doesn’t help me personally at all.
I tried so many times to get my makeup to look decent. On the date, the boy she got didn’t have the slightest idea that we weren’t sisters and that I was under 18. My sister gave me her school badge so that I could get into clubs. We felt that they wouldn’t notice that we had exactly the same names, they would probably look at the birthdays, but even if the birthdays were the same, they should still think we were twins. We looked so much alike that we could totally be twins.
The boys picked us up and dropped us off at the best restaurant in town. The dinner was very good and the boys were great, they were easy to talk to and we had a lot of places to talk about. We got into the night club easily, my boys loved to dance and were not turned away. I felt as if I had been dancing on the floor all night and I was overjoyed.
Toward the end of the day, the boys suggested going out for a stroll. They drove us to Evening Lake and found a very secluded spot. It was beautiful there and I was glad we could stay in the car and not have to walk in heels. The boys were very gentlemanly and didn’t force themselves on us, I did have to compromise by letting him snuggle and kiss me lightly, but he did only what he could ask for on a first date.
We went back to the house after being there for an hour or two and they dropped us off at the door, kissed us on the lips and said goodnight. Mom had been waiting for us, she wanted to know everything about the date.
My sister didn’t give any details, and when I was asked how I felt about being a girl for a day, I admitted that it was better to be a boy. Being a girl was too much work and I was glad I didn’t have to be a girl for another day, I still liked being a boy again.