My First Time.
It was a cold, wet day. My school was on one of those boring rainy day schedules. Then, at lunch time, on the way to the cafeteria, the worst thing that could possibly happen, did.
I slipped and fell, (I was pushed by Eddie Richardson, the school bully) and I was covered with mud.
Being only nine years old at the time, I wasn't allowed to go home without an adult signing me out. The secretary, Mrs. White, called my mom. With both my parents at work, my mom called Mrs. Brumble. Betty Brumble had been my babysitter for about 2 years and I would go to her house, which was only 4 houses down from mine, every day after school until my dad came home. My mom went to college after work to study nursing. Betty was divorced and had two daughters. Amy who was eight and Denise who was eleven.
"No problem Judy, I think we can figure something out". This was the only part of the conversation I heard when Mrs. Brumble called my mom to tell her I needed a change of clothes and I had forgotten my key. "Well Dennis, I guess we'll play it by ear."
Betty handed me a towel and had me strip in the service porch and told me to go take a bath while she washed my clothes. She also told me that I would have to spend the whole evening because my dad had to work till midnight and my mom would be at school till ten. I was a bit apprehensive at first but she assured me she wouldn't look.
When I finished by bath, (In record time) My clothes were still in the washer. Betty told me I could go sit in the girls room in a towel and watch TV until my clothes were done. Amy and Denise wouldn't be home for another half hour at least so I had nothing to worry about.
Famous last words...
I was sitting there in my towel watching Gilligan's Island when Denise came in. She had not talked to her mom before she went to her room. Betty came in right behind her and told her what was happening. Then she went to check my cloths.
Denise was a bit older than me but we had learned to play together without too much fighting. I guess we got along best when we were teasing Amy. Denise then went to her closet and got out one of her dresses and held it out...
"You can wear this till your clothes are ready" she snickered.
"Very funny" I replied, my face already turning red.
"I dare you" she said.
A dare is something anyone is allowed to ignore without the fear of loosing face and Ignore her is what I did.
"I double dare you" she challenged.
Now a double dare is a little different from a dare. A kid who has been double dared has to make at least a small gesture toward accepting the dare, however, still does not have to go all the way.
I grabbed the dress and held it in my hand on my lap but continued to watch TV still ignoring the dare.
"I triple dare you" she sounded.
Well, there it was. The dare of dares. No kid could resist a triple dare and still be considered for membership in the human race.
"Turn around" I ordered.
When she turned around, I stood up, dropped my towel and slipped on the dress.
"There" I said.
Denise turned around and immediately started laughing at me and pointing her finger.
"All right, all right," I said, "Turn around again"
"No" was her reply and with that, I was stuck.
I grabbed my towel and started toward the door when Betty and Amy came in. Their mouths fell open and for a moment, they were speechless.
"Don't you look adorable" Betty finally said.
After I explained what happened, she asked me if I ever wear girls clothes at home. I had never even so much as tried on my sisters panties.
"Does that dress feel good on you?" she asked.
I sort of blushed and that was answer enough for her. She said I could stay dressed as a girl all evening if I wanted. At the coaxing of Denise and Amy I agreed and at that Betty went to Amy's dresser and after she had Denise and Amy leave the room, handed me a pair of light yellow panties. They were the kind that had several rows of lacy ruffles. After I slipped them on, Betty told me that Denise's dress was to big on me and that it was meant for an older girl any way. She slipped the dress off me and went to the closet leaving me standing there in the panties. She came out of the closet with a dress that more fit the occasion, she said. It was a yellow party dress that had several layers of built in petty coats. The skirt was short and the petty coats made it stick out so you could just barley see the bottom row of ruffles on the panties. "Something is missing" she said. After a moment she went back to the dresser and got out a pair of white "little girl" tights with little pink flowers on them. I had to take off the panties to put them on. Next came a pair of Amy's shoes. They were shiny red with a single strap across the top.
Becky left the room for a few minutes and returned with a little blond wig. She said it was Denise's from an old Halloween costume. She placed it on my head and then brushed it so the bangs were just above my eyes. It had a kind of a "Barbara Ann" look.
"All done" she said "You look just like a little girl. I think we'll call you Jennifer"
She led me to the door and down the hall to the living room where Denise and Amy were waiting. She had them close there eyes until I walked into the middle of the room.
"Ladies" said Becky, "I would like to present to you, for the first time, your new sister, Jennifer"
When the girls opened their eye's all they could do is stare. All Amy could say was "She's Pretty!" "She sure is!" Denise replied.
They had me do a spin in the middle of the room and then Becky led me to the full length mirror in her room. When I opened my eyes, I did not know the cute little girl in the mirror. I would be the cutest girl in my class if were to go to school this way, I thought. The feeling I got from seeing myself dressed that way for the first time was a feeling I never felt before. I looked and felt like a little girl.
Becky than announced that we were going out for dinner. I was self conscious and said I didn't want to go because my friends might see me and recognize me. Becky said that was nonsense. I looked nothing like Dennis and that even if we were to run into anyone I know, they would never recognize me. I could get to the car from inside the house and wouldn't even have to go out side. There was nothing to worry about.
We were sitting in the booth at the restaurant waiting for our food when Mrs. White, from my school saw us and came over to talk to Becky.
"Hi Mrs. Brumble"
"Hello Mrs. White, how are you this evening"
"Oh fine, my husband had a lodge meeting and I decided I didn't want to cook. I see the girls are out with you tonight, Hi Girls"
Amy and Denise replied, I turned my head.
"And who is this pretty little girl" Mrs. White inquired.
"Oh, this is my niece, Jennifer."
"She looks familiar. She doesn't go to Robertson does she"
"No, she lives out in the valley."
"Wait a minute, why, I know you. Mrs. Brumble, he looks adorable. Does his parents know about this."
"Know, why, a.. No." Becky seemed embarrassed.
"Don't worry, your secret's safe with me. I dressed my two boy's in dresses till they were 12. Whenever John was away on business that is, they loved it. And I think it gave them an understanding of women that most men don't have."
"I know what you mean, My ex sure didn't have that understanding"
"Maybe one of these days Jennifer would like to visit our school. I could arrange it so she wouldn't be in Dennis' class and I'm sure Dennis could be excused for a day."
"Wouldn't he be recognized?"
"No, to tell you the truth, I really wasn't sure myself."
Mrs White said good night and left the restaurant. We finished our meal and started home. Since it was Friday night, Becky thought it would be fun to go to the show at the mall. She called my mom, who was home getting ready to go to school and asked if she minded and that I could spend the night. Mom agreed.
When we got to the mall, we had some time to kill before the movie and we went walking through the mall. Then Becky said that I would need something to wear to bed that night and we should pick it out now. We went to the large department store in the mall and then to the girls department. Becky picked out a pink baby doll outfit and led me to a changing room where I tried it on. The top was pink and frilly with lots of lace. The panties had plenty of ruffles. That's when I told Becky that I sometimes wet the bed. She said not to worry about it, Amy has the same problem.
After the movie we went straight home and were told to get ready for bed. Amy and Denise got ready first and then let me go into the room to change. When I came out in my baby doll, Becky told me and Amy to go to her room. In Becky's room, Amy went over to the bed and laid on her back, she slipped her panties off. Becky came in and told me to do the same thing. I complied.
She went to her closet and brought out a bag. She then said that little girls who wet the bed had to have the right protection. I knew exactly what she was talking about. Diapers. My mother would make me wear them the night after I would wet the bed. Becky took out the cloth diapers and powdered Amy first. Then lifter her legs and slipped the diaper under her and pined it on. Then she powdered me and pinned my diaper on. She took my panties off the floor and handed both Amy and me a pair of pink rubber lined panties with lots of ruffles. Amy told me the rule was, If we woke up in wet diapers in the morning, we had to call Becky and not take them off ourselves. I slept like a baby girl,and never wet the bed again.
Jennifer would be visiting Becky's house quite often for the rest of the school year.
Jennifer's Day at School
"Mrs. White told me there would be no problem with Jennifer visiting school today Dennis" Becky said as she greeted me at her door that morning. She had talked to Mrs. White only the day before to make sure everything would go smooth. I had pretended to be sick that morning which caused my mom to phone the school to say she was keeping me home. She had then called Becky to see if she could babysit me all day so she could go to work. "No Problem" Becky had told her..."I would be happy to watch him for you Judy. Just go to work and don't worry about him. He'll be all right".
Denise and Amy were sitting in the kitchen eating breakfast and Becky had set a place for me also. During breakfast Becky told me that she had picked out the perfect outfit for Jennifer to wear for her first visit to Robertson Elementary School. I couldn't wait.
After breakfast Becky had me go to the girls room and wait for her. When she came in, she told me to take my clothes off. I was standing there naked when she had Amy and Denise come into the room to help her get me dressed. I was embarrassed to have the two girls see me nude for the first time since but Becky told them to pretend I was their sister and ignore the difference. Becky then left the room and returned with several boxes that were wrapped in pink wrapping paper.
"Here is Jennifer's new outfit" she said, handing me the boxes. The first box I unwrapped contained several pair of little girl's panties. There were lacy pink ones with ruffles, yellow ones with pink hearts and flowers and white ones with wide lace trim. I put on the pink ones with the ruffles. I then opened another box which contained a layered white petty coat. Amy held it up over my head and slipped it on me and Denise pulled the layers into place. The third box contained several dresses for different occasions. One was a yellow satin party dress with lots of little tassels on it. Another one was more of a Jumper. It was maroon and had shoulder straps with buttons that were covered with red ribbons. It was meant to be worn with a white pull over blouse. The third dress was the one Becky wanted me to wear to school. It was red taffeta and had little heart sequins. Becky slipped the dress over my head and Amy and Denise helped adjust the skirt over the layers of the petty coat. The dress came to just about even with my knees. My socks were pink with lace trim and my shoes were red with tassels to match my dress. The last box had several little girl wigs, all blond. Becky placed one over my head and adjusted it so it would not come off during school.
"All done" She said, and pushed me out to arms length to look at her handy work. "You should have been born a girl." She said. I blushed.
We pulled up to the school about fifteen minutes before the bell rang and before I got out, Becky reached in her purse and took out a compact that contained red rouge. She brushed each side of my face and said rosy red cheeks would make me even more adorable. Amy and Denise walked with us to the office where we were met by Mrs. White. There were several other teachers there along with the Principal, Mr. Gundridge.
I was introduced as Jennifer, Denise and Amy's cousin and as planned, no one suspected a thing. We had pulled it off. I was taken to Ms. Pierce's room and introduced to the class.
During the first recess I was invited to play hop-scotch with Amy and two other girls. At one point as I was playing, I slipped and fell forward. The skirt of my dress and my frilly petty coats flew up over my back exposing my ruffled panties. The other girls thought my panties were very pretty. I noticed some of the boys who were playing nearby stopped to look and my panties also. This was common for boys to want to see a little girls panties. I kind of felt flattered. This was my first experience of how a young girl could get boys to do her bidding. Just give them a look at your panties.
After lunch, several boys approached me and wanted to play with me. A couple of them were in Dennis' class and I thought if they every found out who Jennifer really was, I would never hear the end of it.
During the after noon recess I was playing with a ball with some of the other girls. When the ball was kicked across the playground to where the fifth and sixth graders were playing. I had to go chase it. When I got to where the ball was, I got the scare of my life. My sister, who was a sixth grader picked up the ball. She asked my name. "Jennifer" I said in my best girl voice. "Jennifer" she said. "Well Jennifer, you little girls are not supposed to cross the line or you will get in trouble". I told her I was only visiting the school and didn't know the rules. She tossed me the big rubber ball and as I turned around, she yelled "Dennis". My first urge was to turn around but I caught myself and continued. That was close, I thought. I was relieved that the day was almost over. But I was enjoying being a little school girl for a day.
After school Becky met Denise, Amy and me at the gate and as we walked to the car, Becky asked how Jennifer did in school today. After giving her an account of the day, she said she had a big surprise for me when we get home.
I walked in the house and was told to go to the girls room and take my dress and petticoats off. I was sitting on the bed in my panties when Becky came in. She went to the closet and opened it. She then told me that while I was in school, she had gone shopping and had bought me an entire new wardrobe. There were blouses, pants, panties, babydoll nighties, dresses, slips, petticoats, and shoes. Becky had separated all Jennifer's new clothes to one side of the closet and had put a name tag on the top. I was told that any time I wanted to come over, even on the weekends and dress up, I could. I did.
As time went on, Jennifer was invited back to school on several occasions. She always wore the prettiest things to school and as she got older, won the attention of several boys who had developed crushes on her.
Stay tuned for "Sweet Sixteen, Jennifer's First Date".