Jack and Jill by Trudy

Melvin led a rather low key existence until
he was asked by his friend Trudy to become
Jill to her being Jack for a Halloween party.

But for Melvin, this wasn't just fling...

it was the role of a lifetime!

Jack & Jill by Trudy

Part 1

By Jessica C
Copyright © 2013 Jessica C
All Rights Reserved.


Image Credits: Title Pictures purchased and licensed for publishing from

123rf.com. The models in these images in no way supports nor conveys the issues and situations brought up within the story. The models use within this work is solely for the representation of looks of the main characters of this particular story. ~Sephrena

Part 1: The Same But Different
Chapter 1
I am the same person I’ve always been but different from six months ago. My name was Melvin then, Mel for short and it still is Mel, but not quite the same. I work in the large grocery store in our town, More for Less-Super Grocer. I've worked here for the past two years and this past Halloween changed things for me. You see workers are encouraged next week to come in costumes that do not .hinder their work.

Trudy, a high school girl from the next town over, has worked as long as I have. She is very pretty and we get along really well. I would like to go out with her, but that's wishful thinking or so I thought.

Last spring I got up the nerve and did ask her out for a date but I was embarrassed when she almost laughed in my face. She was caught unaware and out of respect for me, she swallowed her laughter. “I’m sorry Mel, I was thinking of something else and you caught me by surprise. That is very cute of you, but we work so closely together. I’ve come to think of you as a brother. I’m sorry but the image of dating my brother isn’t very appealing for a date.”

The past year I have been working at the bakery area and it's counter. Somehow we also have responsibility for greeting cards and the cosmetics area as well. Doris the bakery manager doesn’t like boys working her counter and relating to her customers. When the store manager told her the owner wanted her workers to try the various cosmetic products. She agreed, hoping it would help in getting rid of me. Doris is a no-frills kind of woman and she doesn’t like ideas where she doesn’t have a say.

She already has me working in the cosmetic area knowing I would be teased about it. She hoped I would ask to transfer to another area. It does bother me, in particular when John a classmate from school, says things like, “I can’t decide which I think is cuter: you being a bakery girl or the cosmetic lady?” Another time he said, “You know a dress would be a bit more feminine and would probably help sales.” When it started getting to me, I asked Trudy's help, she agreed to help me in trying and commenting on the various cosmetics I was asked to try. While Trudy had her laughs as did I, she’s been supportive and respects me for putting up with it.

While I act like I don’t like it, the part I don’t like was being teased. Deep down I like learning how to apply and use makeup. I never told anyone, but I have secretly been trying on girl clothes since I was nine. I blame that all on my mother.


When I was eight, I had a tree-hut my dad built for my brother and me. It was to be just for us boys, but the neighbor girl, Jamie, complained that I wouldn’t let her into our fort. Well, that's another story… Once I invited her to go up when she was wearing a skirt and my mom caught me looking up to see her underpants. Mom came up with an old dress of my sister and a pair of panties. I had to change up in the hut while Jamie waited at the bottom of the ladder to watch me come down. I had to play with Jamie for the rest of the afternoon as Melanie.

No one knows I like to dress as a girl, but several times when Trudy and I test the makeup she has me put on a blouse, wear barrettes or jewelry. That was so I would see how cosmetics could compliment a girl’s clothes and accessories or just the opposite be bad for her.


Today, Trudy came over to talk to me before she punched in for work. “Hey Mel, I want to ask you something in preparation for Halloween and work next week.”

“So what’s the question?”

“It’s about Halloween at work; let me know when you when you take your break and I will take mine…”

Doris interrupts, “Why don’t you ask him now? I’ll probably need to okay it too.” Trudy looks at her wondering if Doris already knew. Doris says, “I heard you talking to Rosie, I was outside the women’s room,” Doris confessed and smiled as Trudy relaxed; it did the opposite for me. We walk to the opposite end of the counter.

“Mel, would you be willing to be Jill with Jack from the nursery rhyme with me?” It is too simple to be true.

“What’s in it for me?” I ask. Which is out of character from me, but Trudy seems ready for the question.

“Halloween is Thursday next week and your school has a costume dance that I would go to with you on Friday. Saturday, our school has a bigger costume dance and I would like you to come with me. You wanted us to go out on a date, this will be two dance dates in two nights.” I already figured it out and was very happy with the idea.

“It would be unlikely we both can get one of those nights off, getting both would be next to impossible,” I said.

Trudy spoke, “I shared my idea with Tom, the store manager; he liked the idea saying it was funny and cute. He already said we can have Saturday off and he would see about Friday night but made no promises. Tom’s pretty fair, I expect we will get the time off with giving this much notice.”

I’d rather have Friday for the sure day-off since I want to show Trudy off at my school. I don’t have many dates. Including this one, it would be my second.

Trudy says, “You should even be able to get your store and department discounts in purchasing our cosmetics.”

I said, “You already can do that with your discount,” Though the department manager often marked another 5% off for girls in our department.

Doris broke back in, “I would make you a deal with the cosmetics like I would with the other Bakery girls. Just agree and you two get to work!”

“Okay, I agree I also agreed to purchase whatever cosmetics we need here. I do it for plays; I might as well do it for Halloween.”


A half hour later another worker gave me a note from Trudy. “Let me give you a ride home after work, I want to make sure things are okay with your mother.”

I’m not sure why Jack needed makeup other than if she wanted me to portray a younger boy. When I'm ready to go on my break, Doris hands me a makeup list from Trudy that I am to purchase. Some, like the lip gloss and eyeshadow, are definitely for her. I suspected the concealer and foundation could be for me. I was happy with her choices knowing they will not show much. Hopefully, they wouldn’t show at all.

It took my entire break to select everything as it took time to decide on the blush, the nail polish, and eyeshadow. After I work out my deal with Doris and get the regular discount I paid for it all. I took it over to Trudy to check when she went on her break. She complimented my selection as she came by after she finished her break.

I call home, “Mom my friend Trudy would like to stop after work tonight to visit with you about Halloween next week. Is it okay if she comes in when she gives me a ride home?” Mom agrees and then I ask, “I would like Dad to be part of the discussion as well.” That was so I didn’t get in over my head and no have support.

Mom, unfortunately, said, “Your Father has an early job to get going on. Halloween cosmetics and costumes are not high on his interest anyway.”

The store was busy and time passed quickly and Trudy encouraged me to punch out so we could go talk to my mother.
Chapter 2
Mom greets us at the door, “Hi Trudy, it is nice to finally meet the famous Trudy that Mel raves about. So what's important that you needed my help or approval?” Mom had met took Trudy to visit in the dining room.

Trudy spoke first, “Mrs. Greene, I asked Mel to be Jack and Jill with me with a twist. I thought your son would need your blessing and both of us would need to help him.” I’m puzzled as Trudy seems to be making it more complicated than necessary.

Mom said, “It sounds like a very cute idea; the only twist I could imagine would be for you two to be playing opposite roles that might be expected.” Mom looked to Trudy and then to me. She checks my bag of cosmetics and smiles some more. “Trudy, I think you're probably the only person who could get Mel to agree to do this.”

Mom calls upstairs, “Sara come down here and hear what your little brother is doing for Halloween.”

Sara is quickly down and Mom tells her, “Trudy asked your brother to be Jill with her being Jack from the old nursery rhyme.”

I try to speak up, but Trudy cuts in, “I asked him tonight and he already has bought this makeup to help him get the look.” She hands the bag of cosmetics to Sara and Sara looks in and soon has a big smile.

Sara cuts into the conversation, “I have a light blue skirt with big straps that button to a bib-like front. And I have some petticoats to help it flare out. I think it would be darling on Melanie.”

“Melanie! That is what I called her earlier tonight; I thought I was being original. Why do you call him Melanie?”

Mom said, “We can talk about that another time. What do you need from us to help make things work?”

Trudy spoke again, “I thought his delicate features would lend to his look. But I need to know what clothes we have and what we need to get yet. Plus, I hoped you would allow Mel to get her hair done so she looks like a pretty young girl?”

I finally get to speak up, “Don’t I have a say in this? I think things are moving too fast; I should have more of a say.”

Trudy says, “Yes you have a say, you need to agree with things or it won’t work. But we are the ones who know what it takes to be a girl and you don’t. Like you can wear a nice outfit, but can you walk around like Jill or will you look like a clumsy guy being a nerd. That would take away from the whole idea.”

“I think it would be better if I’m Jack and you were Jill. Things would be a whole lot easier.”

“But the point of Halloween is to pretend and with your long hair, nice legs, and slim body we would make a darling couple if you’re Jill," Trudy said.

“Plus we already agreed we would go to each school’s costume dance. The store would like some workers like us to begin wearing our costumes on Monday or Tuesday next week. Neither of us works tomorrow so I thought I could take you to do some shopping. Mrs. G if you could come that would be great. I suspect some stores might balk at him trying on a bra or making sure an outfit fitted or not. Hopefully, by the end of the weekend, we could decide what we still want to get and figure out what kind of budget we are working with and what alterations we need to make.”

Mel, “Woe, I’ve already purchased over forty dollars of cosmetics. I don’t plan to pay for a number of outfits, bras, and panties.”

Sara spoke up, “A girl’s first bra is special Mel, plus the bras and panties need to be your own. I don’t want you wearing any of my stuff like that. My brother in my panties, eeew, I don’t think so.”

Mom spoke up, “Mel, you agreed to this, you called me, if we could meet tonight and you have already paid some forty dollars for what looks like at least sixty dollars of cosmetics. I suspect you are worried about what we or others might say. Well, relax, I suspect it was something you felt a need to try and we support that.”

“Sara if the blue skirt is easy to get to why don’t you take your brother and let him try it on. Then the two of you come back down here.” Sara took my hand; I don’t believe she's leading up to her room to do this.

“Hurry brother and take off your clothes while I get what you need to wear.” I was just standing there till Sara threatened me. "You better get those clothes off now! You don’t want me undressing you!”

I said, “You wouldn’t.” But seeing her eyes, I quickly take off my clothes down to my underpants.

“Turn around, when you take off your underpants and put these on. You won’t want boy underpants on under these clothes.”

I told her, “I don’t want to dress like a girl!”

“Tell someone who cares. Have you ever tried this one on?”

“I don’t think so. Oops, what did you say?"

"Yes, you know darn well what I said and don't deny the possibility."


I was pulling the smooth panties as Sara held the bra for me to put my arms in and she clasped the back. “Don’t worry I won’t tell them how cooperative you're being. Now step into the skirt and help pull it up. Wait let’s get a white blouse on you. Now the straps and see how cute you look?”

“I look like a boy in a dress,” I’m disappointed.

“Don’t worry, it is a good fit, once you have the petticoats, makeup on, your hair brushed out and some breasts; you will look much different. Now let’s go downstairs.” I don’t want to go and yet I do. I put up a little fuss. Mom looks up as Trudy stood and turned me around. Her smile indicated she agrees with Sara

“I have no trouble seeing how cute you will be as Jill.” Mom speaks, “Trudy please paint her nails, Sara or I could brush out your hair so we can get a quick idea.” The three women see enough to say I'd be cute.

Trudy looks down, “Melanie needs to shave her legs before we go shopping tomorrow.” Everyone's satisfied and Trudy goes home. She says, “You should be outside of your school five minutes early so don’t take your time. Please look for me outside your school.” That brought a smile to my face thinking I would have pretty Trudy picking me up at school.
Chapter 3
I still have ten pages to read for homework. I fought to stay awake for the last two pages. I take a shower and get ready for bed. Mom checks on me. “So Mel you’ve had a very busy day today. Are you more excited or nervous about going shopping tomorrow?”

I said, “Mom, I was excited about doing something with Trudy. I didn’t intend to be Jill.”

Mom said with a little annoyance in her voice, “If that was true, you didn’t hold your ground or speak up requesting a change. I think you must really want to give it a try. Plus I think it could be a good experience for you. Try not to be too eager or too nervous.” I didn’t realize I was ready to cry until Mom took me into her arms and I cried on her shoulder. I liked how soft she feels; I wished I could feel like that.

I don’t remember falling asleep, Mom leaving or who turned out the light. I woke up and needed to hurry and get ready for school. I took a shower and use Sara’s Silksense to shave my legs and under my arms. I was not very hairy so I was very surprised at how different my legs felt. I start to put on my jeans but switch over to some dress slacks as the jeans are rough on my legs. When I'm finally dressed I go down to the kitchen to grab some juice and something to eat.

I can’t get over how different my legs feel. Sara sees me gliding my hand over my legs. “Does it feel that different,” she asks? Mom turns to see what she is talking about and I draw my hands back. Sara, “Mom, I think Mel has already begun her transformation.”

Indignantly I said, “I didn’t, I’m not even sure I can go through with it, so there.”

“Sara, what made you think Mel shaved his legs?” Mom asked. “And Mel why are you wearing your dress slacks?” Panic must be registering on my as Mom says, “Mel stand up and drop your pants.”

“But Mom that would be embarrassing, last night was bad enough!” I stood up and started for my room.

“Stop and drop them; your Dad has already left.” As I do I realize I’m wearing panties, how embarrassing. The room goes silent and then Mom speaks again, “Now, I’m the one who is not so comfortable. It looks like you became a young woman and I am not sure how comfortable I am about this. …Have you and Trudy been planning this for a while?”

“No, I needed a shower this morning and Sara’s shaving gel was there…” I said.

Sara interrupts, “So what excuse do you have for the panties beside being smooth like your legs? And please get your slacks back on.”

Mom and Sara go back to what they are doing, with the exception of a word here and a bit of teasing. Just before we’re to leave for school Sara says, “Is Melanie going to school with you?” I see her gazing at my hands and notice my nails are still polished.

“O *__, do you have some polish remover,” Sara says she would do it, but I took the bottle and did them myself. I am sure Sara saw things right away, but it was the third period at school when Sandy, my lab partner sees them and giggles.

“O no, I’m going to be the laughing stock of the school,” I explain to Sandy as we work on our project.

“I would help you get the rest of the nail polish off but we girls usually do it in the girls’ room, we can’t work on makeup or do our nails in class.” We were done our project ten minutes early. Without my knowing Sandy spoke to the teacher. “Mr. Barstow says we can use the back room and use the fume hood.” I remain quiet but I’m still embarrassed as Sandy takes her purse and we go back to the back room.


“You know Mel at least now you are talking to me, I guess it takes me seeing the girl side for you to relax and talk.”

I smile, “I’m not sure what to say to girls other than joking around.”

"That is okay in fourth grade, maybe being Jill will be good for you.” Sandy is about finished with my nails when Deb comes looking for Sandy. “Hey Deb, I know how to get Mel talking?” Deb pauses like she’s really not interested until Sandy jokes, “We just need to treat him like one of the girls. It’s a secret for now but he’s going to be Jill like in ‘Jack and Jill’ for Halloween. She forgot to take her nail polish completely off and I caught it.”

Deb takes a close look and then looks at my lips and eyes for other makeup. “Here let me get your eyelashes.” She has her mascara in hand. “Don’t worry, I will just do each lightly and with your lashes, no one will notice.”

“Most girls in the school have noticed your eyelashes and would die to have them,” Sandy says. I didn’t think most girls knew I existed.

I didn’t want my lashes done but Deb doesn’t take ‘No’ for an answer. Sandy says, “You might as well let her do it properly, you know she always gets her way.”

I’m kind of lucky; Deb is true to her word and does them very lightly.
To Be Continued...

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