Jack and Jill by Trudy - 1 The Same But Different

Jack and Jill by Trudy - 1
The Same But Different

By Jessica C

Reposted from four years ago... In Nov 2013 it was ten days late for Halloween.

I am the same person I’ve always been but different from six months ago. My name is Melvin, Mel for short and I work in the large grocery store in our town, More for Less-Super Grocer. I’ve worked here for the past two years. Halloween is coming up and workers are encouraged next week to come in costume.

Trudy, a high school girl from the next town over, works at the store as well. She is very pretty, while I would like to go out with her, it is 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 inspiring for a date.”

The past year I have been working at the Bakery counter and somehow we also have responsibility for greeting cards and the cosmetics area as well. Doris the bakery manager doesn’t really like boys working her counter and relating to her customers. So when the store manager told her the owner wants her workers to try the various cosmetic products, she agrees partly in hopes of getting rid of me. Doris is a no-frills kind of woman; she doesn’t like ideas where she doesn’t have a say.

However, she already has me working in the cosmetic area knowing I will be teased about it. She hopes I will ask to transfer to another area. It does bother me, in particular, John a classmate from school works here. He says things like, “I can’t decide which I think is cuter: you being a bakery girl or a cosmetic lady?” Another time, “You surprise me a dress would be a bit more feminine and could probably help sales.” When it started getting to me, I ask Trudy’s help, she agrees to help me in trying and commenting on the various cosmetics I’m asked to try. While Trudy has her laughs as do I, she’s supportive and respects me for putting up with it.

While I act like I don’t like it; the part I don’t like is being teased. Deep down I like learning how to apply and use makeup. I can’t tell anyone, but I have secretly been trying on girl clothes since I was nine. I blame it 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. But that is 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 Sara 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 also 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 so I would see how cosmetics could compliment a girl’s clothes and accessories or just the opposite is bad.

Today Trudy comes over to talk to me before she punches 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. “I heard you talking to Rosie, I was outside the women’s room,” Doris confesses. Doris smiles and Trudy relaxes; it did the opposite for me. We walk to the opposite end of the counter.

“Mel, would you be willing to be Jill and Jack from the nursery rhyme with me?”

It is too simple to be true. “What’s in it for me?” I ask. That is out of character from me, but Trudy seems ready for the question.

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

“It is unlikely we both can get one of those nights off, both will be next to impossible,” I say.

Trudy spoke, “I shared my idea with Tom (store manager); he likes the idea saying it is funny and cute. He already says 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 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 said, “You will now be able to get your store discount in purchasing the cosmetics we’ll need.”

“You already can do that with your discount,” I respond, though Doris, my department manager often marks another 5% off for girls in our department.

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

“Okay, I agree I will agree 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. “I will give you a ride home after work, so I can make sure things are okay with your mother.”

I’m not sure why Jack needs makeup other than she’s wanting me to portray a younger person. When I am 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, is definitely for her. I suspect the concealer and foundation could be for me. I am happy with her choices knowing they will not show much. Hopefully, they won’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. I selected what I thought would be extra cute on Trudy. After I work out my deal with Doris, get the regular discount and paid for it all, I took it over to Trudy to check when she’s on break. She compliments my selection as she finishes her break.

I call home and “Mom my friend Trudy would like to stop after work tonight to visit with you about Halloween next week. Is it okay if she stops 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 is so I don’t get in over my head and no have support. Somehow I often end up on the short end of the stick; simple things somehow become more complicated than I imagined

Mom says, “Unfortunately your Father has an early job to get going on; Halloween cosmetics and costumes are not his real interest anyway.”

The store is busy and time passes quickly and Trudy encourages me to punch out so we can go talk to my mother.


“Hi Trudy, it is nice to finally meet the famous Trudy that Mel raves about. So what is up that you desire my help or approval?” Mom has met us at the door and takes Trudy to visit in the dining room.

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

“It sounds like a cute idea; the only twist I could imagine would be for you two to be playing opposite roles that might be expected.” Mom looks at Trudy and then to me. She checks my bag of cosmetics and smiles all the more. “Trudy, I think you are the only person who could have gotten 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 is asking 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 speaks again, “I think his delicate features will lend to his looks like a girl, but I need to know what clothes we have and what we need to get yet. Plus, I’m hoping 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 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 guy being a tart. 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 body we will make a darling couple if you’re Jill,” Trudy says.

“Plus we already agree we will go to each school’s costume dance. The store wants some workers like us to begin wearing our costumes 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 will be great. I suspect some stores might balk at him trying on a bra or making sure an outfit fits or not. Hopefully, by the end of the weekend, we can decide what we still want to get and figure out what kind of budget we are working with and the 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 speaks, “A girl’s first bra is special Mel, plus the bras and panties should be your own. I don’t want you wearing my stuff like that. My brother in my panties, eeew, I don’t think so.”

Mom speaks up, “Mel, you agreed to this, you called me if we can meet tonight and have already paid some forty dollars for what looks like at least sixty dollars of cosmetics. I suspect you are worried about what we might say. Relax, I suspect it is something you feel a need to try and we will 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 takes my hand; I don’t believe she is leading up to her room to do this.

“Hurry brother and take off your clothes while I get what you need to wear.” I am just standing there like a deer in headlights until Sara threatens 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.

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

“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.”

I’m wearing the panties as Sara held the bra for me to put my arms in as she clasps the back. “Don’t worry I won’t tell them how cooperative you are 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 and Trudy stands and turns around. Her smile indicates she agrees with Sara

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

Trudy looks down, “Melanie needs to shave her legs before we go shopping tomorrow.” Finally, everyone is satisfied and Trudy finally goes home, telling me, “I should be outside of your school five minutes early so don’t take your time and look for me outside your school.” That brings a smile to my face thinking I will have a pretty girl picking me up at school.


I still have ten pages to read for homework. I am fighting to stay awake for the last two pages. Finally, I take a shower and get ready for bed. Mom comes in to check on me. “So Mel you’ve had a very busy day today. Are you more excited or nervous about going shopping tomorrow?”

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

“You didn’t hold your ground and speak up requesting a change. I think you must really want to give it a try. Plus I think it will be a good experience for you. Try not to be too eager or too nervous.” I don’t realize why I am ready to cry until Mom takes me into her arms and I cry on her shoulder; I’m too old for this. I like how soft she feels; I wish I could feel like that.

I don’t remember falling asleep, Mom leaving or who turned out the light. I need to hurry and get ready for school. I take a shower and use Sara’s Silksense to shave my legs and under my arms. I am not very hairy so I am very surprised how different my legs feel. I start to put on my jeans but switch over to some dress slacks as the jeans were rough on my legs. When I am 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.”

“I didn’t, I’m not even sure if I can go through with it, so there!”

“Sara, what made you think Mel shaved his legs?” Mom asks. “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 are becoming a young woman and I am not sure how comfortable I am about this. …Have you and Trudy been planning this?”

“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? 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 there. 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 science 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 but that we need to 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.

Story to be continued…

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