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

Trudy, a high school girl from the next town over, works at the store as well. She was very pretty, while I would love to go out with her, it was wishful thinking or so I thought. Last spring I got up the nerve and asked her out for a date. 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.”

For the past few months, I have been working at the Bakery counter and somehow we also have responsibility for greeting cards as well as the cosmetics area. 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 wanted her workers to try the various cosmetic products and comment. She agreed partly in hopes of getting rid of me. Doris, a no-frills kind of woman, doesn’t like ideas where she doesn’t have a say.

However, she already had me working in the cosmetic area knowing I would be teased about it. She hoped I would ask to transfer to another area. It did bother me, in particular, John a classmate from school works here. He said things like, “I can’t decide which I think is cuter: you being a bakery girl or the 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 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 was supportive and respected me for putting up with the hassle.

While I acted like I didn’t like it; the part I didn’t like was being teased. Deep down I enjoyed learning how to apply and use makeup. I couldn’t tell anyone, but I had secretly been trying on girl clothes since I was nine. I blamed 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's another story… Once I invited her to go up the fort ladder 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 knew I'd like to dress as a girl, but several times when Trudy and I tested the makeup she had me put on a blouse, wear barrettes, or jewelry. It was so I would see how cosmetics could compliment a girl’s clothes and accessories or detract from her appearance.

This day, 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?”

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

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

“Mel, would you be willing for us to be Jill and Jack from the nursery rhyme together?”

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

“Halloween is on 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 Halloween dance and I wanted you to come with me. You want 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, both will 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 covering 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 wanted to show Trudy off at my school. I didn’t have many dates. Including this one, it would be my second.

Trudy asked, “Would you be able to get your store discount in purchasing the cosmetics we 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 would 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. I did 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 was not sure why Jack needed makeup other than she’s wanted me to portray a younger person. When I was ready to go on my break, Doris handed me a makeup list from Trudy that I was to purchase. Some, like the lip gloss and eyeshadow, were definitely for her. I suspected the concealer and foundation could be for me. I am 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, nail polish, and eyeshadow. I selected what I thought would be extra cute on Trudy. After I work out my deal with Doris, got the regular and bakery girl discount, and paid for it all, I took it over to Trudy to check when she’s on break. She complimented my selection after she finished her break.

I called 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 asked, “I would like Dad to be part of the discussion as well.” That was so I didn’t get in over my head and have no support. Somehow I often end up on the short end of the stick. Simple things somehow become more complicated than I imagined

Mom said, “Unfortunately your Father has an early job to get going on. Halloween cosmetics and costumes are not his real 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.

“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 had met us at the door and 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 think your son will need your blessing and both of us to help him.” I’m puzzled as Trudy seems to be making this more complicated than was necessary.

Mom says, “It sounds like a cute idea; the only twist I could imagine would be for you two to be playing opposite roles than might be expected.” Mom looked at Trudy and then at me. She checked my bag of cosmetics and smiled all the more. “Trudy, I think you are the only person who could have gotten Mel to agree to do this.”

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

Sara quickly came down and Mom told 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 had a big smile.

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

“‘Melanie’ that was what I called her earlier tonight; I thought I was being original. Why did 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 think his delicate features will lend to his looks of being a girl, but I need to know what clothes we have and what we need to get yet. Plus, I was hoping you would allow Mel to get her hair done so she looks like a pretty young girl?”

I finally got 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 needed 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 clumsy 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 would make a darling couple if you’re Jill,” Trudy said.

“Plus we already agreed 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 would 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 needed 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 many outfits, bras, and panties.”

Sara spoke, “A girl’s first bra is special Mel, plus the bras and panties should be your own. I don’t want you wearing stuff like that of mine. My brother in my panties, eew, 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 were worried about what we might say. Relax, I suspect it is something you feel a need to try. We will support that.”

Mom said, “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 couldn’t believe we were heading up to her room to do this.

“Hurry brother and take off your clothes while I get what you need to wear.” I was standing there like a deer in headlights until 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 took off my clothes.

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

I said, “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 and as she clasped 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 very different. Now let’s go downstairs.” I didn’t want to go and yet I did. I put up a little fuss. Mom looked up and Trudy stood and turns around. Her smile indicated she agreed with Sara.

“I have no trouble seeing how cute you will be as Jill.” Mom spoke, “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 would be cute.

Trudy looked down, “Melanie needs to shave her legs before we go shopping tomorrow.” Finally, everyone was satisfied and Trudy finally went home, having told 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 would have a pretty girl picking me up at school.

I still had five pages to read for homework. I fought to stay awake for the last two pages. Finally, I took a shower and got ready for bed. Mom came 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 said.

“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 didn’t realize that I was ready to cry until Mom took me into her arms and I cried on her shoulder; I’m too old for this. I liked how soft she felt; I wished I could feel like that.

I didn’t remember mom leaving, my falling asleep, or who turned out the light. I needed to hurry and get ready for school. I took a shower and used Sara’s Silksense to shave my legs and under my arms. I wasn't very hairy so I was very surprised at how different my legs felt. I started to put on my jeans but switched over to some dress slacks as the jeans were rough on my legs. When I finally dressed I went down to the kitchen to grab some juice and something to eat.

I couldn’t get over how different my legs felt. Sara saw me gliding my hand over my legs. “Does it feel that different,” she asked? Mom turned to see what she was talking about and I drew my hands back. Sara said, “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 face as Mom said, “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 did I realized I was already 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. …Had 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 besides being smooth like your legs? Please get your slacks back on.”

Mom and Sara got back to what they were doing, except for a word here and a bit of teasing there. Just before we were to leave for school Sara said, “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 said she would do it, but I took the bottle and did them myself. I was sure Sara saw things right away, but it was the third period at school when Sandy, my science lab partner saw them and giggled.

“Oh no, I’m going to be the laughing stock of the school,” I explain to Sandy as we worked 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 said we could use the back room and that we needed to use the fume hood.” I remained quiet but I was embarrassed as Sandy took her purse and we went 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 get you to relax and talk.”

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

“That was okay in fourth grade, maybe being Jill will be good for you.” Sandy was about finished with my nails when Deb came looking for Sandy. “Hey Deb, I know how to get Mel to talk?” Deb pauses like she’s really not interested until Sandy joked, “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 took a close look and then looked at my lips and eyes for other makeup. “Here let me get your eyelashes.” She had 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 said. 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 said, “You might as well let her do it properly, you know she always gets her way.”

I’m kind of lucky; Deb was true to her word and did them very lightly.

Story to be continued…