Jack and Jill by Trudy - 5 - Becoming Jack and Jill

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Jack and Jill by Trudy
5 - Becoming Jack and Jill

By Jessica C

The Halloween treat is about to be changed…
Mel became Jill at Trudy’s request
But Melvin becomes entangled with Melanie

Come eight o’clock, Trudy comes up with the idea of skipping around the store hand in hand. Half way around I trip not use to the heels. Trudy decides to fall down beside me. Trudy, “Jill, sit against the cola display.” Three little girls come over and Jack pulled out a book, “Would you like Jill read you a story.” Sure enough the book is “Jack and Jill” and the girls sit down perfectly behaved and listen as I begin to read. Two more children are seated by the end of the story. Two other mothers and children come as we finish and we read the story once more. Three more parents are now hoping we will read the story one more time.

Trudy speaks up, “We’re going to fall down over by the bakery counter. So if it is okay we will read to them there?” Trudy compliments me on how I kept my legs together and folded to the side. Over by the bakery Jack falls down first and I tumble as Jack takes away any dignity I had.

Jack reads the story the first time, and Doris treats each of the children each to half of a black and white cookie. A diabetic boy is given a buttered roll instead. When we get up having read the story two more times, Mrs. Kendral, the wife of the store owner, is there to greet us.

“I would like to invite you girls over to our house for dinner Sunday if your parents will allow you to come.”

Trudy answers, “I think our parents were hoping for this to come to an end Saturday, but a one day extension probably won’t be too long.”

I hesitated to ask, “Mrs. Kendral as you probably know I’m not a girl; would I need to come dressed as Jill?”

“Yes Mr. Greene, I know you’re not, but I would like you come as Jill if you would. I will like to take some pictures then if it is okay?” I curtsy and Trudy bows as we say “Yes, Mrs. Kendral,” pending our parents approval. Mrs. Kendral takes a picture now. “I must say, you both look and act exceptionally well. I’ve heard that Jill’s outfits change every day is that true?”

Trudy speaks up, “Yes, we’re treating her like a regular girl; and you know the same outfit won’t do,” she giggles. …Mrs. Kendral smiles, “Who’s we?”

“O, her Mom, sister and now my mom helps and girls at both schools have taken interest in Jill.” Trudy and Mrs. Kendral walk away talking and I get back to work behind the counter.

Come time to leave at 9:00 p.m., Doris asks me to resupply the cosmetics. Posted there are pictures of me as Jill, Rosie as a Gypsy, two princesses and two Twilight girls. Doris has lists of some of the makeup from each. If I hadn’t learned much working the cosmetic area, I had not have realized we were having a favorable impact on the costumers. A lot has been bought even tonight.


Derek comes to give me a ride home, as had my Mom and my Grandma is with her. I was not expecting my grandmother to see me dressed as Jill. Grandma has a poker face as she speaks, “I wanted to come and see my new granddaughter come Halloween.”

“Why am I the one who is out of the loop? This is so embarrassing.” Mom takes a picture just in case I wondered if I turned red with embarrassment.

Derek wants to take me out for ice cream. Mom giggles, “It’s a school night so no more than a half hour.” I try to give mom an expression to say ‘No’. Trudy said she will join us, so I am surprised when we are given a booth that Derek scoots in behind me. Surprised is one thing, uncomfortable is another. Derek takes a picture, he says is for his younger brother. “Squirt says, you doing this, has broken the ice for him and others. He’s going to be Princess Leia tomorrow.”

I start to say… Derek interrupts, “I know you’re not like him, but he thinks otherwise and if it gives him courage, I am thankful. Someone has even asked if I will dance with you, but I want to make sure it won’t embarrass you?” I don’t have the nerve to tell a 250 pound knight ‘No’.

When Trudy gets up to use the restroom, our waitress realizes I need to use the restroom as well. “My girlfriend Traci will go with you if that would help.” Traci quickly comes over, she checks the restroom after Trudy and then waves me in. “I wouldn’t have known if Elaine hadn’t told me. You make a very convincing girl.” We continue to talk. “I really like your leggings; you have the legs for them. I just wish you hadn’t worn the skirt, though it does look part of the outfit.” She smiles as I come out, properly done up and she is amused by my comfort in touching up my makeup and hair. “Way to go girl.” I thank her and offer to pick up her bill but she says ‘No’.

We’re home at 10:10 and for some reason I kiss Derek on the cheek and say thanks. Nana pulls me into the kitchen as I come through the door. I am compelled to do the girly things of turning 360o, and letting grandmother fuss over my skirt, sweater and how well I look in leggings. She moves over and I am to sit next to her. She gives me a hug and visits speaking to me as Melanie.

Mom says, “I have already laid out your stuff for tomorrow in Sara’s room as well as your night clothes. Nana will use your room tonight. Your Grandmother wants to see Jill already for Halloween.”

“My young lady, you have a fair wardrobe and selection of makeup for just a few days. Are you sure this is not a change in lifestyle?” Nana giggled, but I was afraid she was being somewhat serious.

“Why does everyone say that?”

“Mom, Mrs. Kendral has invited Trudy and me to dinner Sunday as Jack and Jill. We need your permission but it would be okay with me if you say ‘No’. And I wished you had said ‘No’ to Derek.”

“If you already said ‘Yes’ to her you have my permission. Did you say, ‘Yes’?”

“You know I did, but you need to help me.”

“It is just one more day and if you didn’t want to do it you should have spoken for yourself. It would put your father and his business in a bad position to say ‘no’ afterwards. Your Father doesn’t mind being here for you; if he loses customers because of you being a girl, he will handle that.”

Grandma asks, “Can I do your nails if they are to be different for tomorrow?”

We agreed that I would shower and get ready for bed first. It took more time to take off my makeup and cleanse my face as it was more elaborate than the other days. Sara tells me to shampoo and condition my hair as well and she will roll my curls so I won’t damage them as I sleep.

I did as told and I am sitting downstairs in my camisole and pants with Sara rolling my hair and Grandma doing my nails. Since I deny being a girl, Grandma is talking to Sara and Mom about me. They’re done in thirty minutes as I work on my report as we talk. I proofread and print it off my report before I go to sleep. Getting to sleep with rollers in my hair and Halloween to be officially here in the morning, sleep is not easy. Sara tells me Melanie was talking in her sleep. Sleeping with rollers in my hair is among a number of new experiences I have being a girl.


Today’s outfit is simple enough the light blue cotton skirt with straps crisscrossed in the back and straight down the front. “Mom, this isn’t the skirt I am to wear! The petticoat and skirt are too short. The cotton blouse is pretty but opens too far down in front.”

I am thankful for little favors like the pantyhose being the same color all the way up and I have learned how to kneel down in short skirts. Grandma does not allow me to take my makeup and do it away from her. A boy doesn’t necessarily see it as a compliment when his grandma compliments his ability to do her makeup, yet she won’t let him do it without her help.

Sara has her computer on in the kitchen with a camera connection to Trudy, so we can see each other as we are ready for school. A friend’s sister stops over to give me a ride to school saying it is her turn. I wanted to date her that was my initial reason to become her brother’s friend. Her brother is now wearing her cheerleading uniform. Steve says, “There are probably more crossovers today than normal. And most are seriously attired in good femme style due to the help of a girlfriend or sisters and classmates.”

Word is that one second floor girls’ room is reserved for girls like us. Sandy and Deb however tell me the rule is for others not me. Mrs. Roberts is amused when I hand in my report in a day early. “Mel, I’m not sure which one I am addressing, but if I get my wish I will see Melanie here tomorrow and next week. Melvin doesn’t usually have his reports on time or legible let alone a day early.”

“I assure you it is just a coincidence that I am dressed as Jill, I already had it done.” I’m not getting as much extra attention today as everyone is in costume. With my luck the day does not go smoothly. I am called to the office shortly after lunch. The library has received two copies of the Courier News, with me featured on the front page of the area news. I am misquoted, “Saying the school wouldn’t have the nerve to allow me to wear the weighted pregnancy bump harness.”

Ms. Braun greets me, “You should not have publicly challenged the school like that.” The Principal calls us both into his office, “Young Greene, we have an excellent high school health program. I have just talked to the Superintendent on the phone and he is asking you and your parents to attend Monday’s School Board Meeting.”

I say, “You can’t take the reporter’s word over mine?”

“I have already confirmed that she talked with you on this very subject.”

“Yes, but she has it wrong.” Plus I didn’t say “Two weeks or two months I’m almost half way through a two week challenge. I think this week has taught me all I need to know.”

The Principal is trying to hold his cool but I know he’s steaming. “I for one think you are the one greatly mistaken. How long do you think a good challenge of changing the weights and the size of the bump would take to give you a good experience?”

“Mr. Lawrence, I have an Aunt due in February, if you want I would be willing to follow in her shoes and make a report but I don’t think a guy can do justice to such a report in two weeks. Especially during the busy time of year we are coming into.”

Principal Lawrence, “Do you think you and your Aunt are close enough that between now and her delivery in February you could come close enough to do it justice?”

“Principal Lawrence, I just want to get through Halloween and not talk about this now, but sure we’re close.”

“Well then I will let you go and seek to get a recommendation ready for when you meet with the school board.”

“Then I’m not in trouble and am free to go?”

“No. You are not in trouble; I like your ideas. Ms Braun has a note inviting you and your parents to the Board meeting. Take it and you are free to go.”

My stomach is in knots and I need to quickly go to the restroom before I make a mess. Several girls giggle when they see me come out of a stall. “Was it that much of an emergency that you couldn’t make it upstairs?” I apologize and said it was, describing my blight much to their amusement.

Word is out that I have agreed to something with Principal Lawrence.


Today of all days I have to walk home. It is cool and damp and I have Goosebumbs all over and I am turning blue by the time I get home. Mom too is upset about my remarks in the paper and not surprised about the meeting with the School Board. “Mom, I met with Principal Lawrence. He too was very upset but he cooled down and we reached a good understanding by the time I left. I will only have to do a report with Aunt Marti’s help.”

“Well, you need to get ready for Trudy to pick you up. She asks for your makeup to be a little brighter for work today. She also asked, if I thought a little padding would be out of line. So I suggest you put on a fresh blouse, do your makeup for evening wear and I will be in with the lift pads in a moment.” I’m running on automatic pilot, not wanting any more arguments.

I ask for Grandma’s help with makeup, but she gives me over to Sara. Sara makes sure I wash my upper body right, making sure I don’t scrub like a guy or use my old soap. Patting myself dry she smiles and leaves me to finish on my own. I used my girl’s deodorant and lightly use powder so I don’t chaff.

Luckily, I call Sara back as I am already putting in the pads wrong in my bra. Sara says, “Since you have breast forms you might not notice how that actually feels; other women will see it and wonder why you don’t?” I pay attention so not to make the same mistake in the future. Sara compliments, “You do pay close attention, I will credit you that.”

The blouse I put on is a shimmering pink, “Sara, I can’t see this Jill carrying a pail of water?” I move and then I see my mid-section showing. “Sara, this blouse way is too small, I can’t wear this.”

“It is not short that is part of its design. Just be glad you look good in it, most boys couldn’t carry that off. But you have a pretty mid-section girly.”

“No boy, including me, should hear something like that. Mom will not let me go out like this.”

“Let me ask you a question Mel, what do you do when Deb or some other attractive girl wears one like it around you?”

“That’s not the point; I’m a red-blooded boy.”

Sara waits tapping her foot, “Okay, just look at it that way when...” She smiles, “This Halloween you like a red-blooded girl out to tease the red-blooded boys.” I turn red and feel a little nauseous. Trudy and Mom are behind me and I hear them giggle. Mom says, “That settles that, now take your purse and get to work.” Before I could speak, Mom says, “No buts, just shake your hips and get going.”

I slide my hands behind and under my skirt to sit in the car properly. “My Mel, you have come a long way this week. I appreciate what you have done and I am looking forward to the dances tomorrow and Saturday. Do you think the guys and girls at your school will be cool about me being with you?”

When we get out of Trudy’s car, she pulls out a white basket with a white bow made of tooling. Then she kneels and asks, “Will you marry me?” Then I am caught in one of those girls looking times with her staring until I answer. I’m in, “Yes!” I find myself jumping up and down, hugging Jack and playing the part. I pause and Sara’s puts a veil on me that trails down my body to the back of my knees.

Rosie and others are inside congratulating Jack and Jill as a forever couple. “Jill, you need to call your parents to make sure they approve.”

I call home, I get Mom but she gives me over to Dad. “Dad, is it okay if I marry Trudy?”

“Who’s this, where is my daughter Jill?” I answered again this time Mel, no Jill. I give the phone to Trudy so I can get my voice back and take the phone back. “Hi Daddy, Jack just asked me to marry him and I said, ‘Yes’.”

Dad keeps his composure, “I know dear, he asked for your mother’s and my approval the other night. This must be a real treat for the two of you.”

The Store Manager is asking us to please walk around the store so we can greet customers as they come in. We help to hand out candy to Trick or Treaters coming into the store. We’re also asked to read the Jack and Jill story for several groups of children as well as asked to reenact the story.

I am asked again and again about the newspaper story and causing trouble for the school. Tom calls me aside, “Mel you need to respond constructively so there is no fallout here at the store.”

“For Tom and everyone who is asking: I just want to assure you I talked with Mr. Lawrence our Principal. I apologized and will meet with the school board and I have agreed to co-operate with them. If my Aunt agrees I will follow in her for a better understanding maybe until she has her baby in February.” Everyone including Tom voices their approval by clapping.

Jack gives me a kiss on the cheek whispering, “Will there be little Jack and Jill coming?”

I shake my head over how everything seems to take a life of its own. “I am enjoying doing this with you as I hope you are doing.”

“Mel, this is turning out to be way more fun than I ever imagined. I am especially proud how you have gone along with it. I don’t think any girl could find a guy more cooperative. I think this will be remembered for a long time and never, ever duplicated.” This time she kisses me on the lips. I only wish I had time to savor it. Maybe I shouldn’t be surprised as she kisses me again. This time it is with even more affection.

More than a half dozen parents mostly moms thank us for remember their children who need something gluten or sugar free. Each time Trudy gives Jill the credit. I don’t know how or why, but three moms got together and presented me with a gift “To be opened later”.


Come a little before 7:00 we are sent to the downtown to represent the store in the Halloween Parade. Even with the sandal heels I am not happy about walking in the three block parade as it will also be another 3 ½ blocks back. I’ve never seen this many people turn out to walk or see the Halloween Parade.

On our way back, Carol of the Women’s Towne Shoppe presents each of us with a gift. “If it is not the right size you can exchange your gift but there are no refunds.” When we got back to the store Tom quickly says, “You can’t accept gifts as a store employee.”

Trudy shot back, “They’re probably womyn’s clothing so do you want it or you can to tell Ms. Carol Brandt she needs to take it back. But I wouldn’t be surprised if she checks for us at DHS’s dance to see if we’re wearing them. We also got candy as ‘Trick or Treaters, do you want our candy.” Tom quickly backs off and graciously made an exception.

“Do you really think Carol would expect something like that?” I ask after Tom left.

“I’m sure of it; she approached me yesterday for sizes, so I knew Tom couldn’t use it.”

“You know what she gave me don’t you? Please tell me,” I said emphatically.

“It is something you can wear tomorrow and I am sure she expects you too.” She teases but wouldn’t tell me anything more. I wish I could get upset with her, but I can’t. Even when we go to the Pizza Tower after work she slaps my hand when I try to open the gift, “Not until I drop you at your house.”

There is a good size group of us, mostly girls. If we were guys we would need to order atleast two more pizzas. Several girls have Trudy and I sign a copy the newspaper article. Another three girls buy a paper at the counter and again we sign their copies. Sandy has me kiss her copy before I sign it. As we leave, someone comments how well I participated in the girl talk.

Trudy remembers the envelope, “To be opened later.” The other girls are as anxious as we are. Trudy opens it, “Sweet, it’s for two free facials.” I respond, “Just what I need.”

Sandy whispers, “Try it before you knock it.”

It is after 10:30 p.m. when I get home but Trudy still taps her car horn as I get out. I was planning to hid the gifts before going in the house. Sara came too quickly to the door so I couldn’t do it. She sees the gift and drags me to the nook where Mom and Grandma are waiting.

Sara sits next to Grandma and I have to stand and open the gift. My nails let me slide my fingers under the paper and open the gift without tearing the wrapping as well as take care of the ribbon and bow. “I’m glad it is too small to be an outfit.”

My smile turns to surprise when I find a pretty red dress. Mom checks the size and holds it in front of me. “Not too many junior boys can wear a size eight. Please go and change into it; I want to make sure it fits.” Mom blocks my attempt to sit down and she turns me and gives me a pat on my bottom to get going.

It is a pretty red dress and it is neither too short nor too sexy, though it is sexy enough. There is a short half-slip out on my bed to wear with the dress. Sara comes in and checks the dress and slip. “Melanie, the hem of the slip should be an inch above the hem of you dress.” She loosens the dress and has me hold it as she scoots up my slip and makes sure it is even all the way around. She zips up the back and smoothes the skirt.

When we go back out to my parents and Grandma, I twirl so they can see it better. Mom remarks, “Only a daughter who is happy with how she looks does that.”

I’m surprised to see Dad. “I hear you are to wear that dress to school. You will need to write a thank you to Carol and the store, do you hear me?” I confirmed hearing his request.

I go back to my room as I have history and math homework to get done. Mom comes in and tells me, “You need to take off the dress before you resume your studies young lady.” To my mind, a guy doesn’t worry about things like that. “I am very proud of you Mel. I hope you appreciate how special people are treating you. Do you agree how pretty the dress is on you?”

Alone with Mom I feel comfortable telling her, “Thanks Mom; it is kind of nice since I am doing this that I feel like a pretty girl. But please let that be just between you and me.” Mom remarks about it being our mother/daughter secret. I studied, as well as took off my makeup and showered and went to bed just before 1:00 a.m. As a boy I could have been to bed much earlier if only…

To be continued

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