My younger sister was one of those girls who thought that she could do anything. One day we were playing with six other kids and we got into a argument about who could run the fastest. With her being just a girl and me being the man. I was fourteen and she was eleven. I bet her I could out run her to the lamp post about a block away. She did not take me up on it at first, but went to talk with the other two girls and came back and said okay but the bet will be the loser does what ever the winner says no matter what. I knew I was not going to lose so I quickly agreed. She then added no excuses. That was because I always find an excuse if I lose at anything or did I should say. Still confident I agreed.
We were at the starting line and Billy counted to three and off we went with me in the lead by a small bit. Just as we were about twenty feet from the post I fell because of a crack in the concrete sidewalk. She blew by and began to dance with joy. I was crying because my knee was scuffed. They all came to me and helped me and I was soon okay with my pain.
As we walked back to the front of out house Billy ask what was the bet? I quickly looked at him as I was hoping no one would remember that part. My little sister came over and said well I know you fell and got hurt so I might forget the bet. I was so happy but missed the part about "might", she then said but my girlfriends and I are tired of your always trying to be the leader and making us other kids do what you want. So the loser that being you will be our baby for the day. I said how can I be a baby I am to big? She told me to come to Sue's house. We all went there and her mother was there but was doing some things and said we could go to the basement to play out of her way. I suddenly remembered a few days ago that in a Tom and Jerry cartoon how the little girl made Tom dress like a baby and do everything she said and that the other cats peeked in the window and saw him and he was degraded. I started saying I would not do it and everyone said I had promised not to dodge the punishment for losing. I ran out of the basement. For a couple of days none of my friends would speak to me. I got real lonely with no one to play with.
In a few days hi knew I had to do the punishment or not have my friends. I told my sister I would do it if she insisted with the hopes she would say no. The next day was Saturday and she told me that all the ones who were the race would be at Sue's house at ten and told, em to be there. I was beside myself waiting for the clock to do it's thing. When I got to the basement they were all there. I looked at a pile of things on the couch and knew it was my wardrobe for the day. I even saw a stack of diapers, some pink plastic panties and other baby things. I had to go in the bathroom and take off all my clothes and put on the first diaper and come out. It was hard to get a diaper on myself but I soon got it on and swallowed hard and opened the door. They all began to laugh and point at my diaper. It took the girls no time to get started putting the pink plastic panties on me as I lay on a mat on the floor. Then they put a very short dress on me they tied my hands behind me so I could not do anything for my self. I had to lay on Sue's lap and suck a baby bottle. The baby bottle tasted funny and I soon learned why. My eyes got big and Sue said it is working. I tried to run but it only made me let go sooner. I was so humiliated all the kids were laughing at me historically. Sue said now what do we do and my sister asked if Sue's fifteen years old sister Tina was home. Sue said oh yes and she went to the bottom step and called for her sister. This was a girl I masturbated thinking about kissing and stuff now she was going to be changing my diaper.
She came down and said oh look at the pretty baby. She asked what her name was and I wonder who she meant and Sue came to my side and said this is Sissy Baby isn't she cute. Tina removed my diaper and wiped me clean and said what a cute little baby I was then she tickled my chin and kissed my cheek. I hoped she would then leave but she went to the couch and watched as I was humiliated by the other kids. Sue said they did not have any other plastic panties and Tina offered a pair of her's. She went to her room and returned with a really frilly pair of pink panties, Sue put them on me and I started cursing and saying I was not a baby and they had to turn me loose. Tina said what a bad baby I was and pulled me over her lap and pulled down the panties and diaper and spanked me until I was crying. She ask if I was going to be a good little girl and I said yes through sobs. She put my diaper back in place and pulled hr panties over the diaper. They spent the day humiliating me with all sorts of baby stuff. When the day was done I was released and made a vow to not be so mean to the others or they would tell everyone about my "baby day".
About two weeks later I was going to the ball field to see if anyone was there and as I passed Sue's house her sister Tina was on the porch. Tina told me to come up on the porch. She asked me if I had enjoyed being a baby and I said no. She said did you like wearing my pretty panties? I blushed and she said you did didn't you I looked away but she took my chin and pulled my face around and said don't be shy tell me the truth. I felt like crying but said "yes". She smiled and ask if I would like to wear them again? I went blank, she said if you do just get up and follow me otherwise go about you business. I slowly followed her into her house. She gave me a Coke and we sat on her couch in that basement as she asked me questions that I was embarrassed to answer but could not refuse in my mind I had to answer her because I liked her. She said if I ask her she would let me wear her panties. I thought about how I had dreams of wearing her panties but never thought I would. I told her I wanted to, she lead me to her room on the second floor and opened a drawer that was full of panties all colors and materials. My mind went crazy and my penis gave me away, she noticed the little bulge in my pants and touch the front of my pants with her finger and smiled. She said "pick a pair" I looked deep into the drawer for a long minute and picked up a baby blue pair with lace on the back of them. Tina said you can have them, She took them and put them in my pocket and said go home and come back with them on next Tuesday. She also said don't wash them or you will be spanked. I said okay and she kissed me on the cheek.