Jack and Jill by Trudy - 4 – Becoming a Student and Sister

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Jack and Jill by Trudy
4 – Becoming a Student and Sister

By Jessica C

“Sense and Sensibility” is reading better tonight: I have more empathy for the woman but I know it can’t be from just wearing a skirt. I didn’t hear Sara come in or know she is here in my room till she starts brushing my hair. “Do you realize your speech is noticeably better?” she asks.

We visit, she feels I am more relaxed despite my saying I am uncomfortable. I tell her I am thinking of going to school in femme. “I don’t want to worry about my hair and all the transformations after school.”

She says, “If you do, you should wear something different from your Halloween costume until Thursday.” It makes sense and she leaves to figure out what I could wear. When she comes back she has two outfits but first suggests I have the breast forms glued so I can sleep in them. She tells me, “It will be a different experience.” I am sure she is teasing since they are soft, how could it be any different. I went to bed at 11:15 and come midnight, I tried to have Sara help me to take them off. She wouldn’t, “I told you it would be an experience now let me sleep.” So I had to learn to sleep differently.

Sara wakes me at 5:30 saying, “Rise and shine girly! It is going to take longer to get ready for school today.” Mom pokes her head in later, surprised and upset that I didn’t ask her permission. Sara and I are walking into school before she chuckles, “You forgot to get a permission slip for gym didn’t you?” She knew and didn’t tell me. I text home, Mom, I need a note to get out of gym class.” But Mom texts back, “You need to get permission from your counselor or the school nurse.”

I am glad I have a reasonable outfit on. I decide on asking Ms. Braun my counselor. She sends a note to my first class that I will be late. “Mel, tell me why you are dressed as you are?” She calls my mother and it is agreed by them I will make a five paper report on my experience; to make up for my missing gym.

I ask, “What if I’d want to agree something else?” Ms. Braun responds, “I am not asking I am telling you, you have already come dressed as a girl and without permission. What I am asking is appropriate for your actions. You will be having the experience anyway.” Mrs. Braun is real good, most students, me included, do not argue with her. I need to sign an agreement as Melanie and Melvin.

I am given an excuse for being late to Ms. Roberts’ class. Ms. Roberts smiles and asks, “Melanie please introduce yourself and explain what you are doing. Class this is Melanie’s first day with us.” The class claps and says hi like I am a new student. This is more embarrassing than I thought possible.

She asks me to explain how my life is different as a female student. She gives me permission to wait until Friday to address the class with my response. She already knows about the report. I am relieved but not home free. She asks for two girls to be my chaperones. Three classmates including Sandy volunteer to help me. I am surprised by their help and how nice they are to me. Don’t worry, not all my classmates are so friendly like that including some other girls.

I eat lunch with a group of girls and they force me into the girl’s room to check my makeup. They giggle as I use the toilet and they praise me as they know I am sitting down.

Erica has done something to set her eyes off which I like and I ask about it. She has time so she does it to me which was not my intention. It is not glitter but her eyes are luminescent. Sara sees me and wonders.

I plan to ride home with Sara until I get called out of class. Mom says, she had come to take me to have my hair done. I tell her, “I don’t want to go to the barbers looking like this.”

“That is good because your appointment is at Carol’s salon.” I don’t think I want that either. Carol was a neighbor years ago and she is happy to see me come through the doors. “It has been a long time since you wished you were a little girl and could sit up here and get your hair done.”

I had forgotten about when my mom would bring me along. She was right; I did wish she would do my hair. Several times she would have me sit on my mother’s lap or in the chair and she would brush my hair out.

I whispered to myself, “Twice you used lipstick.”

Thought it wasn’t loud enough to be heard, but Carol says, “It was more like a half dozen times, but you were a pretty boy. Now look, how you have blossomed.” I begin to tear, Carol hands me a tissue, “Hey that’s all right, you’re not the first pretty boy to sit there.”

“Let’s give you a perm of loose curls that will work well for Jill and Melanie both.” Carol checks my purse and finds the fingernail polish to redo my nails while my hair is drying. Mom has left me, so Carol felt free to take her conversation wherever she wants. That included: if I have dated other boys; would I like to be a girl for a weekend; and why I thought Trudy chose me. I had not thought of any of those ideas, but the question of why Trudy chose me especially intrigues me.


It is 3:30 when Carol is brushing my hair do out; it is a childhood dream, come true. But should I be wanting it? The truth is I do, but I have trouble accepting this for me. I don’t realize how much I am smiling until. Carol says, “Mel until I hear otherwise, how happy you are about this? Don’t feel pressed, it is for you alone to share.” I want to give Carol a hug and kiss. Without me asking she shows me how to give a kiss while wearing makeup. She smiles, when I ask, “How did you know?”

Carol has called for my mother and is waiting for her to pick me up and pay the bill. But I have calculated what she has done, the bill with tip and expecting I forgot something. I made out my own check. Since I hardly buy anything I know it is covered. Carol smiles “Are you sure?” She knows my pride is on the line and accepts my check with no argument.


Mom gets me home and there is enough time to make a good change. Sara comes into check my hairdo and gives me a gentle hug. She helps me to get out of my school outfit and to change into the light blue skirt. I didn’t measure it but I know the petticoats and skirt aren’t shorter than yesterday. While they are a reasonable length if you are a girl who knows how to wear that length, I’m not her.

My panty has ruffles on the outside. Mom points out the pink ruffled panty and petticoat match very well and it would be difficult to say where one started and the other ended. I was to have pigtails but that is out with the new perm.

When Trudy arrives she insists I have a bit more rouge on my cheeks and it does lend to the Jill motif. Tonight my toenails are showing in all their painted glory. Again Jack’s outfit is simple and Trudy makes the cutest picturesque boy-girl.

We get to our parking spot at work and as we get out there is a small crowd to greet us. Our little town paper is out to get some photos. I hear a classmate Stacy telling my friend Jeff, “See, that’s what I would like you to do for me sometime.”

My white pantyhose set off the pink petticoat and compliments my blue skirt and white top. Trudy puts a large bonnet on me and a Dutch-boy hat on her.

As we enter the store, Tom is smiling and shaking his head at me while asking us to take our time going around the store three times. “Tomorrow, I’m having you two greet customers until 7:00 p.m.” Tom calls me aside and says, “You have Friday night off to go to your dance; please tell your mother thanks.”

I’m upset because my mother asked without me knowing and I try to tell the manager. “Tom, I want it changed back.”

“Your mother and friends are too important to the store. You will go to the dance and like it. You will not want to play sick.”

One little girl says, “You are both pretty girls, but which of you is the most beautiful girl?”

I respond “Trudy is because she is playing a boy but she still looks as pretty as me.” Trudy whispered, “I would have been very upset if you told her you weren’t a girl. I thank you very much for the compliment.”

The little girl says, “Jack should give Jill a pretend kiss even though she’s really a girl.” Trudy kisses me on the cheek as it would be against store policy to do more. The store has their top baker take some pictures of us, saying she has some ideas for special cakes.

Trudy is enjoying herself, the fact is this is all her idea, but constantly she thanks me for cooperating so well. A good number of girls from our two schools parade through the store. During the second time around I am pinched in the rear, Trudy tells me I need to stop responding to what they are doing. I pick up dropped handkerchiefs, purses and lipsticks and rarely ever show my panties. I can’t really tell if I did or not.


Come six o’clock when I go back to the bakery for work, I have over a dozen girls, between then and 9:00, asking me for help with makeup. Doris is all too pleased to send me over to help. The girls are surprised that I give them good advice and suggestions to them. A grocery store usually does not expect to do a major business in cosmetics, but this week we will do a brisk business if tonight is an indication.

Rose Bianca, a cashier and classmate, is the first to have the idea of getting tampons and having me sign the box. “To Rosie, From Jill on the Hill”. Word spreads fast and a dozen girls come into the store and buy various products for me to sign. Tom makes me go up by the cash registers to sign them after they are bought.

Tonight, it is Sandy and her boyfriend who come to give me a ride home. Kenny is surprised that Sandy wants to ride in the back with me. But Kenny is an old friend and we both know I am not competition, no fear.


When I get home Mom has a warm bubble bath waiting for me. She allows me to get in the bath and below the bubbles before she comes in. I am uncomfortable because my breasts show. ‘I know they aren’t real’ but I’m still uncomfortable with that.

Mom and I visit, while I insist this is nothing only for Halloween, I thank my Mom for all she’s been doing and what it cost. She compliments me for paying Carol for my permanent. She shows me on her smart phone the many pictures sent to her tonight. We share a lot of girl talk including the paper Ms Braun is having me do.

Against my wishes, my Mom has me sit up so she can wash my back. It is then and drying off that I realize the bath oil is very nice for my skin. The soap I use on my face is also a woman’s facial soap. Mom uses a cotton swab around my pierced ears, for the first time there is no sting.

When I get ready for bed, I stay up to finish “Sense and Sensibility”. The last ten pages I read lying on my bed. Sara pokes in her head and asks, “Are you enjoying my comforter and sheets?” I had not noticed but Mom had switched them in place of mine. My sister is not going without as she has two more sets befitting a girl’s desire to keep things fresh and attractive.

She remarks about my new hairdo and I ask to brush her hair, her usual 100 strokes. My sister is a natural strawberry blonde and very pretty.

Wednesday morning I wake as Sara or Mom is leaving my room. Another outfit is lying on the end of the bed for today at school. Along with getting ready I have removed my nail polish. I removed the polish from my toes but I was uncomfortable to put it back on. I did a nice job of shaping and repainting my fingernails. They’re now a pretty rose pink as is Trudy’s instructions for Wednesday.

Sara calls the harvest gold skirt, a pencil skirt with a soft sweater blouse without sleeves and another long sleeve cardigan sweater with roses to wear over it. I’ve seen plenty of classmates wear them looking very nice, but they were all girls.

Sara checks on me and takes the time to do my toes, leaving me with cotton balls between my toes as they set. It takes me twice as long as Sara to make-up my face, but it is still quicker than yesterday.

When I go down for breakfast Mom says, “I thought you might dress as a girl again today.”

I say, “You should know you put out the outfit.”

“That was your sister, but neither of us said you had to wear it. Sara just agreed to provide you with a nice outfit if you should choose to wear one. We figured you could pick out your own boy clothes if that was what you want.”

Dad is sitting drinking his coffee, when I moaned, “Dad?”

He said, “You’re looking way too pretty to get any sympathy out of me.”

He said, “A girl name Sandy called saying she and Deb will pick you up for school, unless she hears you are coming as Mel. I told her you would be ready.”

“See, you did set me up to go as a girl.”

Mom is offended, “Sara just came down and I asked her how you were dressing. She told me she had just polished your toes and you were again a pretty girl. Yes I did tell Sandy, but I am offended by you acting like an immature boy.”

Mom says, “You are sending so many mixed signals and you seem to blame being a cute girl on others instead of taking credit for it. If you want you can turn around and get dressed as Mel and I will give you a note for being late. But I’ll also want you to call Trudy and say it is all over you can’t take it anymore.”

“Mom, I didn’t mean that. I plan to go to school as Melanie.”

Dad spoke, “Mel, we are not obligating you to choose how you are going to live. But we do want you to stop trying to have what you are doing both ways. You are taking the joy for being Melanie, and making it more of a responsibility. We know this is a lot for a young man, but we are trying to support you in having this experience. We love you very much, though this isn’t easy for us.”

Mom hugs me, “We love Mel, but we are falling in love with Melanie, even if it is just our brave son trying a dream on for size. We want you to be proud and enjoy what you are daring to do as well.”

“Thanks and Mom you know the outfit I’m to wear to work tonight. I think I need something else.”

“Your sister and I think the same and she has a dark blue skirt that is short but will work both with your leggings and that pink sweater. You will not only be cute but Sara says you will be very much in fashion.”

I am using my computer to begin my report on Austen’s book. ‘Do the choices of Elinor and Marianne make sense? Does the young Austen’s inexperience show up in the book, or decisions one makes in life don’t always make sense in accord with the feelings and thoughts of others. One of Austen’s strengths is to take the road less traveled.’

Sandy snuck in and was reading by draft; “You know Melanie I don’t think Mel wouldn't have come close to considering this.” I’m stunned and shutdown my computer quickly under the guise of hurriedly going with them.

Deb remarks as we are riding to school, “Are you trying to portray yourself as an ordinary girl going to school? If you are, you can join our group. That is if you can keep up with the girl talk.”

“I think Sara is making sure I don’t get in trouble.” “Or asked on a date,” Deb adds, “unfortunately you appear to be a cute junior girl.”

I am surprised that I am receiving compliments from Deb, but I welcome the idea of being able to walk in the company of a group of girls. “Vice Principal Branch told me you are only to be using the girls’ restroom in emergencies.” But I told him, to a girl being clean before and after lunch and fixing our makeup will be considered an emergency. He threw up his hands, knowing we’re comfortable enough with you.”

We are walking into our classroom when Deb asks, “What are you to Derek that he’s watching to make sure nothing bad will happen to you? You’re not a secret girlfriend are you?”

I giggle as I say “No.”

A number of girls comment on my hair and ask where it was done; while others ask, if I dress myself and do my own makeup. I don’t respond to questions about how I manage my breasts. I eat another light meal and Sandy asks “How much weight are you am seeking to lose?” She guesses I have lost three pounds and is upset that I am not tracking my weight loss.

I have chorus again today and the choir director puts me back in with the girls. He says “Melanie your vocal range has significantly increased as well as your ability to stay on key and to sing clearly. Would you mind singing in the girl chorus for the Variety Show in two weeks?”

“No, I am not going to be dressing as a girl after Halloween?”

“It hasn’t been Halloween yet this week, nor will it be Friday, but you’ve been granted permission to dress the way you are from Monday through Friday. If you are Melanie Friday, I think you should be Melanie in the Variety Show.” The other girls’ applause and the guys hooting did nothing for my cause. Several girls talk, “We believe Mel is not capable of such a transformation.” They and others speculate other possibilities. Word is out that Melanie wears different outfits in portraying Jill. The burning question is how she will be dressed when she goes to work today.

I did meet my first opposition and bullying as three boys bump me into a wall, some lockers and finally one trips me. Mack is caught by Derek as he stopped to tease me while I was on the floor. “Derek no! I thank you for stopping him but you can’t hurt him; remember the second guy gets the foul called on him.” It is a football expression pertaining to the rule breaker getting away with a foul as the second party gets charged with the foul if he responds in kind.

Mack’s feet were off the floor before Derek puts him down. Derek fakes a misstep and drives his elbow into Mack. Mack complains but someone professes to see it as a trip, thus no foul.

I am now standing as Sandy asks, “Derek will you dance with Melanie Friday night?” His reply is a whisper that I can’t hear, but Sandy smiles upon hearing it.

After school I am heading to Deb’s car with Sandy when Derek offers me a ride. Mel/Melanie is uncomfortable with the idea. Sandy says, “It is the least you can do for your knight in shining armor.” Derek has a pick-up but it is nicely kept, has power and handles well as Derek says and demonstrates. He is also a gentleman as he gets out and would have opened the door if I had waited.


Mom greets me and asks about my chaperone. Mom’s upset upon hearing about the trouble with three guys. Mom walks with me to my room and shows me the skirt lying out with the rest of my stuff for tonight. Along with the outfit is a new Secret deodorant, “That is another thing a girl does not usually share. If you don’t mind I want to see my new little girl change? I know you are not so little, but you are my youngest as well as new from the girl perspective.”

I amuse my Mom as long as I can turn away at times. I kind of like being her little girl. There is a shower cap for my quick shower as well as a large wrap as I dry off. Using Satinsense my legs are hair free and feeling wonderful. My panties are a powder blue and my leggings are a mixture of pink, white, blue and grey. There is a pattern that works well in making a girl’s legs look slim while accenting their shape. While the blue skirt is long enough the material is light and moves with any and every movement or breeze.

I need to use my pretty bra as the neckline or the sweater would show off my bra. There is just a hint of cleavage unless I bow forward a little. Mom has me take out my hoops and in their place are teardrop dangles. My eye makeup is light and bright but not too bright. My face looks like a younger Jill. “You can be glad this is like a costume, because if it wasn’t with guys like the young hulk who brought you home, you would be staying home.”

I smile and contain my giggle. “You don’t mean that?”

“Look in the mirror and consider yourself the Mom of the young woman you see?” I like what I see and it causes me to get excited. I spray lightly with a perfume Sara had left and walk into the spray. “That better not be the one that changes with your body heat?” I didn’t know there are fragrances like that.


Mom drives me to work and lets me off at Trudy’s car. The leggings protect my legs from the cold but I can feel the breeze and my skirt’s lively movement. Mom has her smartphone on video format. Somehow she is also getting pictures. There are two yellow baby ducks in the pail of water tonight. Trudy puts pink and yellow barrettes in my hair before we go in.

Tom has a special in-store sales flyer we are to give out. It is designed to get lookers tempted to buy something and from what we see it often works. We are handing out Kisses to young children, but on our second trip around the store I broke open a bag of sugar-free candies. I remembered from last year a few diabetic children we weren’t ready for.

Trudy smiles, she sees a little boy looking at the sugar-free candy. “What kind do you like?” The boy points to three kinds and Trudy takes it to a cashier, “Rosie, I’ll give you the money if you give me a paid sticker.” A deal is made and the boy and his mommy were very happy.

“Let’s go greet, I can do for many of those.”

A Courier News reporter comes and wants some pictures and information. We buy some time saying she needs permission from Tom the store Manager. We know he left for a late dinner. She takes some pictures and gets her story from customers and other workers. When Rosie goes on her break, she tells me the reporter spoke with my mother for a short time. I am relatively sure my Mom would be discrete, but I am somewhat nervous by the number of people she asks.

Trudy tells the reporter, “I came up with the idea last year after a boy in my school had to wear one of those weighted pregnancy bumps for a week last year.”

The reporter asks me, “In the spirit of school rivalries would you do that for two weeks?”

“This is enough for me and luckily I haven’t been asked?”

“Now I’ve asked, but if it needs to be official, I hope your School Board will read tomorrow’s article?” With that the reporter is ready to leave and things return to my strange Halloween normal.

“You can ask but I don’t think the School Board would allow me to do it even if there was to be pressure from the public.”

Story is to be continued…

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