My mom and sis had caught me wearing their clothes a few times and my mom made the remark one day after catching me again. She said, “the next time, I’m going to dress you up all the way”, “you’ll see what it feels like to be a girl.”
Sis had caught me a few times wearing her clothes after that. And each time I would beg her not to tell mom.
And of course, sis would always come up with a compromise. She told me If I would help her with some things around the house, she would keep it our little secret.
Time went on and I was still sneaking and trying on her clothes when she wasn’t home. I always tried to put everything back so she would not notice. And I thot I was getting good at this too. Neither mom nor sis had said anything about my dressing for a few months.
Then one day after school I came home and sis was already home. As I opened the door, sis ask me to come to her room. As I entered, I saw on her bed was some lingerie and some other clothes. I ask in a very timid voice, “what’s..a what’s going on?” She said she knew I was still getting into her things, but she just didn’t say anything. She didn’t want to upset mom. So, today she went to a department store after school and purchased some clothes and wanted me to try them on.
Sis said, in a stern voice,” take off your school uniform! “ Now, I’m going to help you on with the dress. Put your arms up and I’ll pull it over your head. Now, I know you saw the petticoat on my bed when you came in. It’s short just like mine, Come on! step into it and pull it up under your dress.”
“Well now, I think you’re starting to look like a girl, Come over here and let me put some makeup on you. And let’s fix your hair a little. Now we’re going to go into the living room, sit down and wait till mom gets home to see what a nice sweet girl you turned out to be.”
I pleaded and begged hoping sis would not do this to me. I said, “please don’t tell mom, I’ll do anything for you, please sis”. “Sis said anything?”. Hmmm… sis thought for a moment and said “every day after school I want you to put on this outfit and do all of my chores. And if I ever catch you not dressed up, then mom and all your friends will know all about it.
Everything was going great, I would get home from school and put on my dress. Then I’d walk down to the community boxes and get our mail. When sis came home, she would inspect me to make sure I was dressed right. She would always giggle a little and shake her head at me. She’d say,” I just can’t believe you actually enjoy wearing that stuff!”
Sis said I’m going to have to learn how to walk in my dresses and heels. And also how to fluff my dress up before sitting down like a girl. She took a few minutes every day to show me something. She did sit me down one Saturday and showed me how to apply my makeup a little better. And she would always remark how I have become a wonderful sister to her.
She would check to see if her work was done as she ask. Sis didn’t want mom to be dissatisfied at all. Since she was supposed to be doing it anyways.
One day after school, I got dressed and started washing the clothes. I heard the door open. I yelled out, “Sis, I’m in the laundry room”, The door opened slowly, I spun around and there was my mom. I could see she was shocked and her smile on her face went to a confused look, then she said in a giggling voice, “well!, I guess you’ve been busy dressing up again, haven’t you now!. “And that dress!, It looks so sweet on you!”
I explained that sis caught me again in her things and dressed me this way. She didn’t say anything for a few minutes. Then said, ” Well, sis is in charge of you, so you better do as she says or you will have to answer to me as well.
Mom said, Hurry and get finished up in there, then go to your room. I will talk to sis when she comes home.
Later in my room, I heard mom and sis in the kitchen talking and giggling. Sometimes they would let out a loud laugh, but I couldn’t make out what they were saying.
Finally, they called me for supper. As I came in, mom handed me an apron and said “get over there and start serving the food.” I didn’t know what was going on, but I got everything over to the table and went to sit down.
Mom said, “Oh! No!, you don’t sit here with us. This table is for grown-up people. When you are finished serving us, you can take your plate to the back porch and eat. We don’t want to look at sissy’s while we eat. Sis said look she’s starting to cry, Mom looked up and said “no wonder you want to wear a dress.” “take those sissy tears outside please!”
When they finished, they called for me and told me to clean up everything in the kitchen, then come into the living room.
As I walked in mom and sis giggled and told me to sit down. Mom watched as I put my hands under my rear and smoothed out my dress as I sit down. She said, “OMG! I guess you are a sissy girl, aren’t you!” With that said, they both started laughing again.
Mom said that she would leave a list for sis of things for me to do around the house. Then said, she wanted me up at 5 am. “you’ll cook me breakfast, clean up and start your cleaning. There will be no more sleeping in for the summer. And if I didn’t get up, I would get paddled.
Mom said when sis got home from summer school, she was going to take me shopping for some more summer dresses and lingerie. “And if she doesn’t behave, sis has her permission to paddle me when they get home.”
Mom said,” you are going to learn how sissy girls live and act for the next two months of summer. I hope you enjoy yourself.”