Jack and Jill by Trudy - 2 - Ahead of Schedule

Printer-friendly version
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 2

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 2: Ahead of Schedule
 
Chapter 4
 
 
The rest of the day goes well until the last period when I’m to have gym and remember I have white panties on. I decide to take my books to my locker making me late for gym. Hopefully all of the guys are already changed and out of the locker room. I’m nervous but doing well until I catch one foot on my pant leg and tumble to the floor having hit the lockers making a loud noise. I’m up quickly and have my pants off. When I begin pulling down the panty is when Derek begins walking by and sees me.

Derek is 6’ 5” and at least 250 pounds; unfortunately, he’s in gym class because he is recuperating from a football injury. “Hey, man be careful, you shouldn’t wear them on gym day. You shouldn’t look for trouble but if it comes looking for you let me know.” Derek pauses, “My little brother is like you, so I kinda understand.”

“I’m not like that. It’s just that last night I tried on a Halloween costume and I forgot to take them off,” I tell him.

Derek says, “You had plenty of time to change, so you must like them some. But that’s all right, just don’t lie to me.” I finish changing and get out to the gym. Coach, our instructor, has me running because I’m late.

Finally, school is over and I'm outside the school when Trudy beeps her horn to get my attention. I’m glad she also got the attention of other guys as well. Someone calls out, “Where have you been hiding her Mel?” I just smile and wave back. As we drive off Trudy teases me, “You should ask him along, we probably could find a cute outfit for her as well.”

I say, “I don’t think so he’s a guy.”

Trudy interrupts, “So that is not stopping you. How was your day at school?” She giggles as I explain about Sandy noticing the nail polish I missed. When I tell her about my panties and Derek, Trudy loses control and giggles so bad she pulls over. We finally make it to my house.

-<-0->-

I run into the house and upstairs saying, “I need to take a shower and change.”

While I’m in the shower Mom calls in and says, “I've laid out an outfit for you. If you need help, I'm sure one of us will like to help you.” I simply say thanks and don’t think anything of it. That is until I’m back in my room and see the outfit. It’s one of my sister’s old outfits that she doesn’t wear anymore. It’s nice enough, I’ve even worn it before. There is masking tape over my clothes drawers and at my closet. “Mom, I can’t do this! It is bad enough looking for girl clothes.”

She says and others agree, “It will be harder to explain why Melvin has to try on a bra or a dress.” The next thing I know is Sara is in my room. She takes me to her room and helps me to get dressed. This time she has me put on pantyhose and pick out a pair of her shoes to wear.

I pick out a pair of navy blue flats but she comes back with a pair of blue two-inch heels. She gets her way. She calls up Trudy and has me sit near her makeup table. They are doing my makeup and hair. Then Trudy stops and holds an ice cube to one ear. Sara had her ears pierced at Claire’s so it isn’t until I’m poked with the needle and the first earring is in, I realize what is happening. Sara is in front of me checking the pierced ear to mark my left ear. “While Trudy's still holding the ice to this ear?” Sarah smiles as Trudy pokes in a second hole and puts in another earring. This one is a small ring.

Sara smiles as I relax and cooperate with having my left ear pierced twice. Sara encourages me, “Close your eyes Melanie and if you don’t see yourself before you go you can stay home.” I close my eyes and the thought of a picture I drew two years ago came to mind. It was my dream picture if I could be a girl.

I felt Sara and Trudy at work and heard Trudy say, “I hope he doesn’t take out what you just gave him. Do you know what he likes?”

“Nope, I just like how he’s turning out and I hope he will too.” After just two minutes of keeping my eyes closed, I’m getting restless. Sara helps me stand and says “We are ready. Count to three slowly and then open your eyes.”

“One, two, three” and I open my eyes. “Thanks for being so patient, I hope you like the new Melanie,” Trudy says. I wonder what she means until I see the transformation and look at the clock. It is forty-five minutes after we started and Mom has purses in her hand.

I’m stunned, but no one understands. I yell, “How did you know?” as I ran to my room. I’m looking for my old drawing pad. It’s under my bed near the night table. I draw to relax at night. They have no trouble finding the drawing as Sara, Mom and Trudy come into my room.

Sara asks, “Know what?” I just turned the sketch pad toward them, “This is Melanie.” Sara is giggling, “O wow! I swear I didn’t know, but it is you.” Melanie was already there in my head.
 
Chapter 5
 
 
It is a cool October day as we step out to go to the car. “This is weird and I’m still uncomfortable going with you three.” The air hits my legs and then up my skirt. I am no longer tired from my day at school. The cold air wakes me up completely.

Sara tells me as I open the car door, “Remember to smooth out your skirt from behind and underneath as you sit down. Keep your legs together as you turn and bring them into the car.” It is like my movements are choreographed with her talking.

Trudy speaks, “Pull the seat belt around and try to have the shoulder strap go between your breasts.” It sounds simple enough but for a rookie, it takes a little effort and for a boy, it seems odd to be doing this at all.

Mom turns to look back at me, “Well, how is it that you have a girl picture of yourself and neither Sara nor I knew it?”

Without hesitation, Sara says, “I didn’t Mom; it’s just how she turned out when we brought the girl forward.”

“Let Mel …speak for...” I could tell Mom is struggling about using pronouns.

I tell her, “Mom that was from two years ago when I was getting teased so much as the other guys grew taller. I just wanted to hide sometimes. Mel is so bland people don’t even notice me; so I drew a girl that I thought I could be and who people would look at.”

Mom asks, “So you’re comfortable as Melanie?”

“No, but it is weird Mom. I don’t know how, but Melanie is comfortable.” Sara pats the top of my hand to comfort me.

Trudy pulls into the parking lot of a nice restaurant near the River Glen Mall. “We need to eat so my first treat is dinner then we shop,” Mom says as she lights from the car. I usually would be ravenous by now but my appetite can only take in half of my order. Instead of pushing vegetables aside, now their tastes sweet and tart, are what I desire.

No one asks as they recognize they're the tastes of this girl. Nor did they complain when I followed them into the lady’s room to do what is needed, wash and touch up my makeup as needed. As I walk out it hits me that I am walking out of the women’s restroom and I blush in embarrassment. Mom gives me a hug, “I wondered why you were so cool. So how do you feel about being one of the girls?”

-<-0->-

We are soon at River Glen Mall and start out with the more expensive department store and some women shops around it. We see a number of outfits and dresses that would be nice but apart from getting measured and several pairs of panties it is all window shopping. I thought it is all to be window shopping but I sense that is not the general expectation.

We walk past a department store that Sara says is good for everyday stuff and find ourselves at Macy’s. With measurements in hand, we are at the bras. I am embarrassed as Claudette a very attractive young saleswoman arrives to help us. Someone must have said something as she comments, “It will be my pleasure to help you, but you’re too cute to remain a tomboy.”

Trudy explains we're going to be Jack and Jill for Halloween as well as a couple of costume dances. Claudette giggles, “I hope she will be Jill most of the time. It should be cute with all the attention the boys will be giving her.” She looks at the two bras picked out for me to try and she pulls out a lacy bra, “I think you should try this one if you are willing to be a bit daring and showy. It is very comfortable and not expensive. It would not be fair if I didn’t suggest we buy it.” Sarah takes and holds it up to me, “Woo, woo, this will be great with a blouse a few buttons short.”

I expect Mom to save me from further humiliation; it doesn’t happen. Trudy comes carrying a cotton blouse with a skirt to go with it. “Don’t worry Melanie we’re just asking you to try things right now.” Going into a woman’s dressing room raises my anxiety level higher than it already is. Mom wants to come into help me but gives way to Sara while I want neither.

Sara has one of the panties, explaining it will put me in the mood. “The mood it will put me in could be a problem.” There is laughter outside the changing room, “Don’t listen so closely!” Not waiting for me to resist Sara unbuttons and undoes the zipper on my skirt. I’m taking off my blouse, then the bra. I see myself in the mirror. Seeing the girl in the mirror with her new bra showing in all its glory would be exciting if they weren’t mine. They’re still very exciting and beautiful. I can only dream it is really me.

I try on the panty of satin and lace panty, I'm glad it might have enough substance to hold my excitement. Sara has me put my arms through the straps of the bra and to lean forward to place my breasts in the cups of the bra as the sales girl suggests. The breast forms have a jiggle to them and I swear they are real. Sara sees my face and comments as I guide my hands and arms around my back to get it properly hooked. “Some boy I know has too much experience in doing this,” she says.

“Not me, I usually do it from the front and bring it around,” I said too much again.

“Thanks for the confirmation Melanie,” Sara again succeeds in making me uncomfortable. She has me put on the skirt before asking, “Trudy, she needs Claudette’s help in adjusting the bra straps.”

The knock on the door is Claudette and she discretely comes in and Sara steps out. “Wow, I hope you aren’t offended but you are a young cutie.” She shows me how to adjust the straps and there is nothing complicated about it. She runs her finger under the straps to make sure they are just right, neither too loose nor too tight or if a strap is twisted. She touches the bottom of the cups, showing me the support and fullness of the cups. Then lightly has me lightly touch the tips of the bra, “Do you think that leaves enough room for growth?”

I never thought about breasts growing and while mine won’t I’m anxious to know more, “How much might I expect my breasts to grow, say in six months to a year?”

“It is hard to get an idea of what can happen, but like you are at a small B cup but with the next spurt, you could easily be filling a B cup over-flowing. If it’s okay,” she has her hands on her blouse buttons opening the top, “Last spring I was barely a small C, now look. I’m college age and they have finally blossomed,” she’s all smiles. “Go ahead and look, I won’t force you but if you want you could touch but nothing more please.”

It is Melanie, not Melvin, who is gasping, not with sexual thoughts but a girl’s wishful thinking. “Here now, let’s see how you are with the blouse on? Try it with these buttons open, knowing you can button up more for your comfort. I don’t think you would want to open up anymore, even without trying you could get a bad reputation. It is important how a girl presents herself and is better to leave some things to the imagination. Your presentation of yourself shows how beautiful you are while calling for respect from those around to you.”

She begins to open the door, “Take your purse and show yourself to your mother and the others. Girls, not boys are a better measure of how you look generally.” Claudette steps out and then holds the door open. I forget to take a good look in the mirror, but Trudy has me by the hand. “O Girl this is a knockout, you are definitely sweet.” I find Mom to see her expression, and Sara is next to her motioning with her hand to twirl around. I oblige her but with just two-inch heels on I need to go onto my toes and not my heels.

I twirled fast enough that I felt my skirt lift a bit. A little three-year-old is being taken with us, her mom has something for her to try on. “Look, mommy, how pretty her legs are; does she know her panties are showing?” I can’t help but giggle. I look to my Mom, “It’s the taller boys I worry about.” She begins to giggle.

“So how do all of you feel about the bra and outfit? She can easily do up two buttons and easily be as pretty.” Mom’s hand goes under the blouse as she is feeling the bra strap.

“Mom, I’m not Sara.” She looks up, touches my hair and pushing it back a little.

“No, you are Mel-anie, my younger daughter.” Touché, I like the sound of it, half wishing it were true. She touches the hem on the skirt, “Do not worry it is in very good taste.”

“Thanks, Mom.” Sara takes me by the hand to a full-length mirror. Standing in front of the mirror and making a good observation of how I look like a pretty girl. I’m wondering why as Melvin I am doing this or enjoying this one single bit.

“Are you comfortable with that being one outfit?” Trudy asks. I am not surprised we are more than window shopping, “Yes I like the outfit.”

Mom speaks to tell Claudette, to write it up but hold it. “She might choose to wear it home; I would like her father see it.” I continue picking out with help two outfits and one dress. The dress is a mini-dress and if I like it, Trudy wants me to wear it to her dance. I try the last bra and I like it as well as the dress, but not necessarily them together. Mom agrees, “I think that bra is very nice but more for everyday use; like when you’re Jill at the store.” I think that is where the mini denim skirt might come in, but I hold out for one not so plain. Claudette pulls out one with a lot of pretty stitchery and design that takes it up a notch.

“I can see with this skirt Jack and Jill going up the hill; I just wish Trudy that you were Jill.”

Claudette begins to laugh, “She really does have an image problem doesn’t she?”

Now Trudy and Sara are giggling out loud. “You wouldn’t believe the extent of Melanie’s image problem.”
 
Chapter 6
 
 
Mom pays for my clothes as well as buying a blouse Sara likes. We’re walking past some stores when Mom guides me into a shop, Second Skin Intimates. My mother asks a saleswoman, “Do you have some nice sleep shirts for young women?” I’m wearing the first outfit I tried on, so the woman smiles. “Is this to be her first time with some special pieces of sleepwear?”

“I’m just window shopping I’d like to see my sister try what she likes.”

“There is enough to go around young lady; your Mom has you in tow right now, and says you are the one I get to help.” We reach the section and I wish I could stop from looking but I can’t. It looks like satin but I’m not sure. It has buttons in the front but not all the way down. Three colors and styles are selected to try. I like the style of the light blue one with buttons down the front but I like the deep plum color. There is a loose set of shorts that goes with pink lace and satin top and wide straps that Sara talks me into trying. And I am now at a quandary of which to get.

Mom solves the problem saying I am getting both, “But Mom I don’t even need one, I’m Melvin at home.”

“Shush and I will explain later young lady.” She giggles as I feel close to my first paddling as a girl.

We’re on our way out and Sara, Trudy and I look into a shoe store window. “See Melanie that wedge heel that is the kind of heel you need for work.” I see the heel she’s pointing at and I look further into the store and see a beige and blue shoe with a sandal heel on a display inside the store. “Mom, could I just look at that pair of shoes?”

She asks what I see and I point, “That is a very nice looking shoe, I like your taste.” She and I stroll in and look. “ It is a very smart looking shoe, the heel is 2  ½”. “A girl could manage that for four hours, but I don’t think you would be able to do it?”

“I don’t like you saying what I can’t do, especially since I haven’t even tried it.”

Mom says, “One, I would be surprised if it the price of $37.95 is correct. Those shoes don’t start under $80 unless they are on sale. Even then you would be lucky to get 15% off.”

Melanie asks, “What if I’m willing to pay for it with my own money?”

“You just are stubborn enough to try and prove a point. I say go ahead if it is your money.” My foot is narrow and small for a boy. But I am worried because I haven’t taken care of them as Sara does.

The salesperson measures my feet but continues to stare after she says I have an 8 regular. “I can bring out the shoes and you could try them to see if they fit. But you either need a good pedicure and have our mother help you learn how to care for your feet.”

Mom speaks up, “I have shown you and haven’t I told you to take better care of your feet?” She whispers to Sara and Sara walks out of the store and out of sight. Mom walks off with our salesperson and points to the price of the shoes. The woman points to another price sign as well as a price on the box.”

Harriet brings over the shoes and points to the price on the box. “I am sorry young lady but this pair costs $87.95 and that is on sale from its regular price of $109.95.” It is a very good everyday shoe and the only one I could recommend to a young woman planning to work in them.”

I naively ask, “Why would anyone pay that price for an ordinary everyday shoe?”

“One, it caught your eye because it is not ordinary and I suggest you just try it. That is the only way you might realize its value.” Trudy has found a similar pair yet distinctive enough that she is trying it.

“Wow! Sara, you need to try this,” Trudy’s talking to my sister.

I have on my pair; I stand and see the side view in the mirror. My legs now have shaped more like a girl. “Mom, I love them but that is a lot of money.”

Mom smiles, “If you will split the cost of the clothes; I will go halves on the shoes.”

“It would be cheaper for me to just pay for the shoes.” Harriet tells Trudy, “If she buys her shoes. I would let each of you have your shoes for $80.00 a pair?”

Trudy smiles, “That settles it, she and I are both buying a pair.” Sara found a pair like mine beige with a red leather stripe. She is buying a size seven and Trudy has a 6 ½ size shoe. I have a debit card for emergencies, and since I never use it, I have mom’s permission to buy my shoes with it.

I am good and tired as we walk toward the mall exit. Mom’s lagging behind and the others have stopped with her. Finally, I ask, “What now, I am tired and still have some homework. Plus I need to take care of my feet, which should be all but impossible.”

“Go in this store and tell them your name.” It is one of those small shops with a row of chairs and tables for women having their fingernails done. Teshi takes me behind a screen, “Would you please take your pantyhose off. Then please come to my table, please. You can put your pantyhose in this bag for your convenience.”

I am going to say no, but Teshi is already walking away. Trudy is nearby, “I can show you how to do it simply.” I walk behind the screen and soon come out and go to Teshi. She has me place my feet in some warm goop. I am not sure if it is a wax, oil or what, I’m just surprised that in a strange way it feels good.

I get to pick the polish to be applied. I choose a red medium dark and Teshi says, “It is a very nice color, especially good for you.” She sees I resist having my hands done for some reason. “Please, I would like to do your fingernails to make them nicer for you. If we use this light pink tint it will not be seen by others, and it will be very good in protecting your nails.” So now my fingers are in a similar solution and after five minutes she begins to work on my fingers while massaging my hands. “You have not been kind to your hands but they are very nice and will become beautiful.”

Sara is rubbing my shoulders and neck to get me relaxed and to stay awake. Teshi is soon done with one hand and working on the other. Another girl is helping with my right foot. Pealing of the waxy goo, I see some improvement as I watch her work on the cuticles of each toe. Areas on my feet that were dry or rough peel away with no tearing or bleeding. The excess cuticle areas are cut away with very small scissors.

Teshi finishes my other hand and starts cutting my toenails, shaping them with emery boards. She files, feels for bumps or roughness and uses finer boards as she nears finishing. Each toe coats so nicely, but after she finishes one toe she puts a cotton ball between the toes. She makes sure the first coat is really dry before starting a second coat. I like my fingernails and while the pink tint is clear it is a gloss and with the shaping of the nails, I enjoy seeing them as Melanie’s. I’m now waiting for my toes to be good and dry before we leave.

Though, I was getting tired before they started to work on my fingers and toes I had no trouble staying awake to see how things are done. Teshi gives me a coupon that is good any time in November for 40% off whatever I have done and it could include one friend.

-<-0->-

Once in the car, Sara invites me to lay my head in her lap. I say, “No”, but my head is in her lap by the first traffic light. I fall asleep listening to the other girls. Once we’re home they say they talked to me I answered most of their questions.

Right now I don’t care, but even without much makeup I find getting ready for bed to be a chore. Since Sara is helping me I kind of enjoy taking off my makeup and moisturizing my skin. Sara pushes me into the shower telling me to shampoo my hair really well if I want any semblance of boy’s hair. Melanie’s nightshirt is out for me.

I am ready for bed; when Mom calls me downstairs and without thinking I run down to see what she wants. Mom and Dad are sitting in the den when I show up. Mom smiles and Dad looks at me, “I thought Halloween is next Thursday.” Dad shakes his head and then pulls me to him. “You know we love you very much.” He gives me a kiss on the cheek, “Go say goodnight to your mother.”
 
 
To Be Continued...
 
 

Please share a comment, or acknowledge if you enjoyed the story. You are welcome to write directly to the writer as well. I respond to most of the compliments and letters to me the author. ~Jessica

 

up
178 users have voted.
If you liked this post, you can leave a comment and/or a kudos! Click the "Thumbs Up!" button above to leave a Kudos

Comments

Good continuation

This was still good, and I like seeing Melanie's journey continue. But I will say I preferred the first part. I think a big part of that is because the rest of the cast largely fell away in this part. Sara, Trudy, and Harriet all blended together without distinction. Part of that was necessity, since you were concentrating on Mel, but I still missed those voices.

Again, it was still enjoyable, with a fair amount of wish fulfillment in the story, but nicely done. I still hope to see a bit more variety in the reactions to Mel.

titania.jpg

Titania

Lord, what fools these mortals be!

See what I can do...

Titania ...about voices & characters fading away. It is a good thought to check for coming stories as well.

hug with a pat on the back,
JessieC

Jessica E. Connors

Jessica Connors

Me thinks . . .

Hypatia Littlewings's picture

that the family already suspects something.

*grin*
~Hypatia >i< ..:::

Family knows

The family knows but does Mel know herself?

Family a few steps a head..

I think Becky Anne is going on good intuition; is it denial or something else that keeps Mel from recognizing Melanie? Maybe just maybe is it...?

Thanks for fairy power on this.

Jessie

Jessica E. Connors

Jessica Connors

Me thinks . . .

you think very well. Thanks for reading and commenting. I does me well.
Give you a hug Hypatia, yet careful not to damage your wings.

JessieC

Jessica E. Connors

Jessica Connors

Thank you, so much,

Love the story,beautifully written----our boy is finding herself at last!

ALISON

Boy is finding herself...

Alison, One of the loves for me is friends like her sister and friend loving Melanie as they help bring her along. Though neither see where the story might go.
I hope you love the story because you see love in it.

Hugs, JessieC

Jessica E. Connors

Jessica Connors

I love it too...

Andrea Lena's picture

...that turn of phrase is so cute; the boy is finding herself... And yes...it's important for me to know that friends and family don't know where this is all going but they are there for Mel none the less! Yay Love!!!!

  

To be alive is to be vulnerable. Madeleine L'Engle
Love, Andrea Lena

They are there for Mel none the less...

Yes, the thought that others are supportive; as Melanie may be emerging in life they are supportive for Mel anie even with the unknown. I suspect some hope it is just a passing experience, hopefully they will continue to be there if it becomes lasting; hopefully Melanie will sometime claim her life if it is to be.

Appreciate you thoughts ^_^.
Hugs, JessieC

Jessica E. Connors

Jessica Connors

Mel's accepts he feels good...

...at being Jill, but is not accepting being Melanie. Mel did not expect to be Jill this many times; yet he decides to go to school as such.

Good to hear from you Desiree

Love with hugs, JessieC

Jessica E. Connors

Jessica Connors

Hmmm....

Mel drew a picture of himself as though he were a girl years prior? Ok this changes things a little, becoming Melanie may not be such a stretch after all. Once the cats out of the bag I doubt it possible to put her back! Nice Jess! Keep'em comin' hon. Loving Hugs, Talia

Ok this changes things...

Thanks Talia... Was it alright to wait to show the past, I am glad you see it and commented as such. You again connected dots drawn on a three dimensional surface.

Loving hugs Girl, JessieC

Jessica E. Connors

Jessica Connors

Mel

Renee_Heart2's picture

Is becoming a real young lady & she likes it. I think she REALLY does want to be a girl & have a big sister & Trudy I think might be a lesbian as she likes Mel as a girl, but I could be wrong. I hope Mel's mom & dad DO let her be the girl she is meant to be full time.

How it all started when he was 9 & now a halloween party that Mel's friend Trudy dreams up & now she is coming out of her tomboy phase & becoming a REAL woman.

Look forward to the next chapter of this GREAT story.

Love Samantha Renee Heart

Linkage through time... and events

...How it all started when he was 9 & now a Halloween party that Mel's friend Trudy dreams up Thanks Samantha While the thread between Trudy and Melanie won't surface immediately the potential strangely if it comes will probably surprise Trudy the most.

Appreciate the comments.

Hugs pretty sister, JessieC

Jessica E. Connors

Jessica Connors

I am still quite liking this story.

WillowD's picture

I am wondering, though, if Trudy is going to become more than a coworker, i.e. friend or girlfriend, of Mel's.