Stephanie's Deal - Episode 5

Printer-friendly version
Nintendo Wii dressed in pink
     
Stephanie’s Deal

by Jennifer Brock

Eleven-year-old Steven Brooks is being punished over his Christmas vacation by having to dress as a girl. In this installment, Stephanie learns about formal wear, breasts, and boys who wear dresses.

Episode 5

“Wake up, Little Sis!”

Steven was awakened by his sister gently shaking him and talking in his ear, or more correctly Stephanie was, since she realized she was still wearing a nightgown and panties. She blinked a couple of times while trying to remember how to wake up as a girl. “Michelle? Is something wrong? What’s happening?”

“We’ve got to get an early start. Go take your bath and I’ll pick you out something to wear.” She noticed that Michelle was already fully dressed kind of nicely in a soft purple dress that came down past her knees. Stephanie wondered why she was in such a hurry, but did as she was told.

The bath did feel really nice, and it was good to take off the tape that kept her boy parts in place; it had been on for two days straight and was getting very uncomfortable. She wanted to have a nice long, relaxing soak in the tub, but she didn’t want to risk her sister barging in and telling her to go faster. She just took as long as necessary to get everything clean.

When she finished and returned to her room in her bathrobe, Michelle was still waiting. Stephanie really didn’t like having to get dressed in front of her sister, but they were both supposed to be girls, so she couldn’t really complain. She had her dress in her new pink panties with the hearts on them, one of her white padded bras, a pair of tan pantyhose (which made her feel grown up and a little sexy), and a full slip. Then Michelle helped her put on a pale green dress that zipped up in the back, and had her slip into her Mary Janes.

Michelle did her little fishing line trick to take out Stephanie’s hoop earrings, which really were more comfortable to sleep in now that she thought about it. She put in the new pink dangly ones that Aunt Jeannie had made. Stephanie thought they looked cute in the mirror, but it took a while to get used to their rattling. Michelle clipped her new necklace behind her neck, and Stephanie put on her new watch. Her sister smiled approvingly when she grabbed her purse on the way out without being told to.

They got their coats and waved a quick goodbye to Mom, and hit the road in Michelle’s car. She finally explained where they were going. “There’s a place in Wallace that has wholesale formals, and hopefully we’ll be able to find dresses there.”

“We’re already wearing dresses. Why do we need more?”

“We’re expected at your little friend’s fancy tea party at 2:00. Knowing her mother, I’m guessing this is the kind of tea party you need to get really dressed up for. You have a bunch of dresses, but none of them are formal. In a pinch I could probably just wear my prom gown from last year, but it shows a little more skin that I’d be comfortable with at a preteen’s party, so it would be nice if we can find something for me, too.”

“Why do we have to go so far? There’s no place in town that sells pretty dresses?”

“Big department stores would only have formal dresses around prom season, and then probably not in your size. Our only other local option would be a little specialty shop, but they really don’t have any stock on hand. You’ll see when you get fitted for your bridesmaid dress; she’ll probably go to a bunch of different bridal shops until she’s satisfied, and then she’ll be picking out colors and styles. She might want you to come along to try something on before she picks it. Now that would just be a sample, not an actual dress. Once she picks a style and color, they’d order your dress and then wait a few weeks for it to come in. And when they have the dress, you’ll have to go back and try it on, and they’ll measure you for alterations, and when the alterations are done, you’ll have to go back.”

“Wow. How do you know all this? You were never in a wedding!”

“Gee thanks for reminding me that you get to be a bridesmaid before me, Little Sis. I’m not exactly sure where I learned about buying bridal wear. It’s just something girls pick up.”

“I thought I’d only have to be a bridesmaid for a couple hours at a wedding, but I have to go dress shopping three times?”

“Um, Honey, weddings are pretty much an all-day thing for the wedding party. You’ve got to get all dressed up somewhere, and then get to the ceremony early, and then stand in a receiving line until the last guest leaves, and then maybe go somewhere for pictures before the reception, and you’re expected to stay through the whole reception. And that’s just on the wedding day. There’s also going to be a rehearsal some time before the wedding, which usually comes with a rehearsal dinner, so that’s pretty much a whole evening. And as a bridesmaid, you can be expected to get invited to the bridal shower, which is usually a few hours on a weekend afternoon. You’re lucky you’re young enough that you’re probably exempt from the Bachelorette party. Danny mentioned something about the wedding party taking a ballroom dancing class, but I’m not sure if he was joking. “

“Oh my gosh. I didn’t realize. I thought I was just volunteering for a couple hours; that’s all Jack’s wedding was. Why didn’t anybody tell me before I said yes?”

“I’m sorry, Kiddo. I guess we thought you knew. It is a really nice thing you’re doing for Grace and Matt, so just keep that in mind.”

“So even after my contract is out, I’m going to have to be Stephanie at least six more times?”

“Looks like it. More if that dance thing is real.”

“Oh, crud.”

“Would that be so bad? It seems like you’re having fun being a girl.”

“It’s not too bad, but I’d rather be myself.”

“Well anyway, that’s how formal dresses usually work. But where we’re going today is a place that sells last year’s dresses at the price the little bridal shop would pay, so we save a bunch of money, but their selection is likely to be limited, particularly for stuff for girls your age, since I don’t think it’s pageant season. We’re going early in case we have to try somewhere else and still get back in time.”

Michelle surprised her by stopping along the way to drive through a Donut Barn to get some breakfast. She even bought Stephanie a cup of coffee. It made her feel very grown up, eating a bagel and drinking a coffee while sitting in a car wearing pantyhose, on her way to go clothes shopping without Mom. It was really pretty cool. When she finished her bagel, she flipped down the visor and fixed her lip gloss, then she turned the radio up and just grooved along with the music for a while.

Michelle just laughed and pretended to be shocked that she’d “created a monster.” She handed Stephanie the little piece of paper that had their directions on it. She’d never been to the place herself and just had some friends get their prom dresses there. She wanted to be able to check with Stephanie for their next turns so that they didn’t get lost. Stephanie liked having the responsibility. It was weird that this was the same sister she was so sure was out to get her only the day before.

They found the place without any wrong turns, and the girls shared a high five. Then Michelle showed her sister how to get in touch with her inner supermodel and do a fierce strut into the store.

They went looking for Stephanie’s dress first. Fortunately, there were indeed a couple rows in a section labeled “Teens and Tweens.” There was a moment of panic when neither of them knew her size, but then Michelle checked the tag on the dress Stephanie was wearing, and learned she was a size 8. But formal sizes are all over the place, so she looked for anything from 7 to 9. They weren’t in any kind of order, so they had to search through the whole rack.

Michelle took one rack and sent Stephanie to look through the other one. She told her to make sure it had the right kind of top — she needed one she could wear her bra under, so she had to avoid halters or spaghetti straps. It kind of creeped Michelle out how many sexy dresses there were in little girl sizes. She showed Stephanie the kind of bodice they were looking for, and that the frillier the dress, the better. They needed the kind of thing her little eight-year-old friend Robin (secretly a boy named Bobby) probably imagined that a lady at a fancy tea party would wear.

They found six potentials, and went to the changing room. The first one was blue and covered in shiny little sequins. It was too small, even though it was a 9. The second one was white and fit okay, but it had a very plain line to it. It looked classy, but not really fancy. Michelle said she thought it was a dress for an upscale flower girl. The third one was a bright red that almost perfectly matched her fingernails, but the big puffy shoulders were made of this netting stuff that really itched, and reminded Stephanie of the bag they sell onions in at the grocery store.

The fourth one also didn’t fit, which was a shame because it was a very pretty pink with tiny beads sewn in patterns all over. The fifth one looked incredible and fit very nice. It was white, and had rows of billowing ruffles. Michelle said that it was probably another flower girl, or maybe a communion dress. But she worried that a white dress might not work; you’re only supposed to wear white in the spring. She also thought it might make her look a little too much like a bride.

But the last one they tried was it! It was a pretty pink sleeveless dress with a big wide skirt that had layers of things under it to make it stick out like a real princess dress. There were patterns of white lace all over. Michelle pointed out that the color matched perfectly some of the beads in her jewelry. It was a little loose in the bust, but she said they could just stuff Stephanie’s bra a little more and the dress would fit better. Michelle thought it was probably a Quinceaá±era dress, made for celebrating a Mexican girl’s fifteenth birthday. A short Mexican girl, if it fit Stephanie so well. It was pretty cool thinking that she was wearing a dress designed for an older girl; it just added to the generally grown up feeling of the day.

Michelle thought they ought to look for some shoes for Stephanie, too. There was a shelf of “pageant shoes” not far from where they’d found her dress, and Michelle picked out a pair of sandals that were made of a see-through plastic that reminded her of Cinderella’s glass slippers. They had high heels, like a whole two inches or so, and felt kind of weird on Stephanie’s feet. But they made her feel like a real lady, so she’d get used to the weirdness.

With Stephanie settled, they next had to pick out a dress for her sister. Michelle thought it would be nice if her dress also matched her earrings from Aunt Jeannie, so they went looking at purple ones. She popped an earring out and handed it to her little sister, so they could split up and look on different racks. She told Stephanie that she usually took a size 7 in juniors’ or 8 in ladies’ sizes. The whole size thing was kind of confusing, so she had to explain that younger women used odd number sizes and older women used even number sizes, because their styles of clothing were different. But in formal gowns there wasn’t as much difference; a dress designed for a fancy grown lady might work for her.

She wanted Stephanie to come with her into the changing room to help zip her up as well as to give an opinion. Stephanie had to leave her dress and shoes with the attendant so no one else would buy them. It was kind of uncomfortable for her when Michelle stripped down to her underwear to try on dresses, and a major shock when she even took her bra off to try on a backless halter-style gown. Stephanie tried not to stare, but her sister’s chest really was pretty.

She ended up going with that halter dress. It was a shiny silky material, and had rows of ruffles around the skirt, which was just as puffy as Stephanie’s. Just to be matching, Michelle also got herself a pair of transparent pageant shoes, although her heels were a little higher. She also found a cute little handbag for each of them, pretty drawstring bags covered in glittery white rhinestones. Michelle didn’t even flinch when the cashier said they needed to pay more than a hundred dollars for all of it, and just handed over her credit card. Stephanie wished she’d be that cool when she was her sister’s age.

They got back in the car and headed home, but stopped on the way at the store to buy some makeup for Stephanie. Michelle said that she wanted to give her a really glamorous look for the fancy party, and it wouldn’t be safe to share hers so they needed to get all new stuff.

They got home with plenty of time to spare. There was going to be food at the tea party, so they only had a quick bite for lunch. Mom wanted to see what they’d bought, but Michelle made her wait until they got all dressed up. She went to her room and got these funny looking little football-shaped things for Stephanie to stuff her bra with. It was kind of weird seeing her reflection with what looked like real boobs, realer than with just her bra padding. Then she put on her new dress, and it really did look better with more on top.

Michelle wrapped a towel around her shoulders to keep makeup from getting on her pretty dress, and fastened it with a safety pin. She pulled Stephanie’s hair off her face with a headband, and then she started putting all of Stephanie’s new makeup on her face. She started by using this paint-like stuff all over to make her skin flawless. Then she drew around her eyes with a special pen, and then brushed heavy mascara on her eyelashes. Stephanie had to close her eyes while Michelle attacked her with a scary-looking eyelash curler.

Michelle used three different colors of eyeshadow on her, so she had to keep her eyes closed for a while, and they felt different when she opened them again. Michelle then dusted her cheeks with blush powder, and finished off by putting lipstick on her top lip and telling her to rub her lips together. Then she had to kiss a tissue to blot. After waiting a little, she then put some lipgloss on top of her lipstick. She sprinkled some sparkly glitter stuff all over and then unpinned the towel. A spray of cologne, and she was done. A look in the mirror showed a girl who was maybe thirteen, looking very sophisticated. She thanked her sister for making her so pretty.

Stephanie then got to watch her sister go through the same process. She had a special bra to wear under her halter, so at least she didn’t have to see her topless again for very long. She helped her sister fasten the towel and handed her things when she needed them. It was really fascinating watching her transform herself from just naturally cute to really glamorously beautiful.

They went downstairs and struck poses for Mom to take their pictures. She told them they both looked really pretty, and couldn’t get over how much older Stephanie seemed. Mom did have a couple pointers for her on how to walk and stand in her heels, and it really made her conscious of her boobs when she stood up straight. Even after practicing sitting down in the big puffy skirt, it still took a couple tries to get into the car.

She gave one last check of her makeup in the mirror before stepping out to walk up to Robin’s door. Stephanie rang the doorbell, and she could hear voices from inside the house. The door swung open, and there was her friend, in a white dress with little bows all over, a pretty hat with little flowers on it behind her head, and cute lace gloves on her hands.

Stephanie told Robin she looked very pretty, and Robin was just awestruck. Her mother, in a really nice frilly yellow dress, came up behind her and had to remind her to invite her guests in. Robin remembered she was trying to be the hostess, and showed the newcomers into the sunroom.

Michelle had a brief conversation with Mrs. Perrone. She told her that she had a lovely home, and said that she was glad she guessed correctly what a “Pretty Dress Tea Party” meant, but she apologized for forgetting to get hats and gloves for the proper tea party look. She asked that Michelle please call her Kendra, and said that the sisters looked perfectly lovely, and didn’t need any more accessories.

The other guests had already arrived. Nine-year-old Tina (who was secretly a boy named Justin) was wearing a pretty pink dress that wasn’t quite as fancy as Stephanie’s, but she got extra credit because her baby sister Rachel and her mother Kelly were wearing identical dresses. They all told each other how pretty they were, and blushes of appreciation circled the room.

Most of them wanted to say that Stephanie was the most beautiful, but she demurred and said that Robin was much prettier. The smile she got in return proved it. The mothers asked where they got their pretty dresses, and Michelle told the story of their morning’s adventure. Kendra asked for the address of the place, and she said she had it written down in the car, and asked to be reminded when they were leaving.

Robin and her mother got up to get the refreshments, and came back wheeling an antique tea cart into the room. Kendra poured tea from a beautiful old teapot into cups, and Robin passed them out. The younger girls took their tea with plenty of milk and sugar, but it was in fact real tea.

Robin also set out a couple of trays of little triangular sandwiches with the crust cut off. She explained that they’d researched tea parties but instead of something snooty like watercress or cucumber sandwiches, they’d made some with jam like one of the books did, but also some with both peanut butter and jam.

Stephanie said that was a very smart decision, and nibbled at a sandwich. It was actually pretty good, although it was tricky trying not to laugh at Robin taking big boyish bites of her sandwich while wearing lace gloves.

Tina pointed out that Rachel wasn’t allowed to go near peanut butter, and her mother wasn’t supposed to have any either, so she made sure the tray nearest her family only had jam sandwiches. Kelly said they were yummy even with just jam, and Stephanie couldn’t tell whether she was just trying to be nice.

I guess she realized that everyone else was eating, because Rachel made a noise that meant she was hungry. Without any embarrassment, Kelly just unbuttoned the top of her dress and brought out a breast for Rachel to suck on. Stephanie tried to be polite and not look.

Robin, however, was almost staring. She asked, “Does that hurt?”

Her mother tried to shush her, and whispered, “Honey! It’s not good manners to ask something like that.”

Kelly laughed. “No, that’s ok. She’s just curious. No, Robin, it doesn’t hurt. Maybe in a few months when she starts getting teeth it might pinch a little. It only gets uncomfortable if she keeps sucking after I’m out of milk, but she’s not that hungry usually.”

Robin was still fascinated. “That’s just, so cool. Is it milk just like milk from a cow is milk?”

“Well, yes and no. It isn’t quite as white as cow milk, and the taste is different.”

Tina chimed in. “Yeah, it’s kind of sweeter.”

It was Kendra’s turn to be shocked. “You’ve tasted it? You mean…”

Tina’s explanation calmed her down. “So that Daddy and I can help with the feeding, sometimes she uses this machine that pumps her milk into bottles. And I spilled once and tasted it. It was good.”

Robin sighed. “It’s too bad we’ll never be able to feed our babies like that.”

Michelle decided to join the conversation. “Don’t be so sure. Even boys have nipples. If a doctor gave you the right hormones, they could be made to give milk.”

Robin was interested. “Really? Boys can have boobs?”

“Well, hormones can make boys grow boobs, too. But I’m not sure if you have to have boobs before you can make milk.”

Tina looked confused. “Why would a boy want boobs?”

Michelle answered, “Well, sometimes a boy will realize that he’s really a girl inside, so when he’s old enough he can go to a doctor and get hormones and operations and things to make him look like a girl, and sometimes he’ll even go all the way and get the boy things in his underpants rearranged into girl things.”

Robin was getting excited. “They can do that? Really?”

“It’s not perfect. She may look exactly like a girl, but she still can’t grow a baby of her own inside. Science can’t make those parts yet.”

Robin was a little dejected. “So I could make milk for a baby, but I couldn’t be a mommy. That’s not fair.”

Tina looked at her friend. “Do you really want to be a girl for real real? This isn’t just a game?”

Robin shrugged. “I don’t know. Maybe.”

Michelle interrupted, “You know, sometimes a boy doesn’t feel like a girl inside, and knows he’s a boy but likes dressing up like a girl. There’s a student at my college who’s like that.”

Stephanie cocked her ear. “Is that what gave you the idea to dress me up?”

“No, I don’t know her that well. I hadn’t even thought about her until now.”

Robin looked over and asked, “Would you want to be a girl, Stephanie?”

She felt the weight of being a tie breaker, and tried to find a diplomatic answer. “Well, it’s fun wearing pretty dresses and glamorous makeup sometimes, but I don’t know whether being a girl all the time would be as fun. It’s like, would you really want to live at Disneyland and let the rides and characters be boring everyday things, or is it better to only have one week a year to look forward to? But it would probably be easier doing some things if you were an actual girl.”

Robin’s mother was really uncomfortable with where the discussion was going, and decided it was time to serve the cake. It was a really scrumptious four-layer chocolate cake with creamy fudge frosting. It did an excellent job of filling everyone’s mouths and changing the subject of the conversation to how delicious the dessert was.

Stephanie asked if it was from a bakery, and Kendra said she’d made it from scratch. Stephanie asked for the recipe, and Michelle explained that her little sister had discovered the joy of cooking for her family. Kelly talked about how Tina had been a godsend around the house ever since the baby was born, even before she was playing at being a girl. There was nothing that would keep a boy from cooking or cleaning.

Eventually, the party wound down and it was time to go. Michelle went to get the info for the formals store for Robin’s mother, and Stephanie said her goodbyes. She knelt down and gave Robin a little hug as they were leaving. “Tina and her little sister look really sweet together. And Michelle here has usually been pretty cool to her little sister. I think it would be really awesome to have a little sister of my own, so I’d like to know if you want the job. What do you think? Would you want to be my official little sister?”

Robin smiled broadly and squeezed tighter. “Really? That would be great!”

“Okay, then. It’s official. If you ever need someone to talk to, you can call me, for whatever. I’ll be there for you.” She gave her a kiss on the cheek and went out to the car with her other sister.

up
126 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

Awwwww

This is such a sweet and sugary story. I love stories this sweet, it makes me wish my muse could write stuff like this *sniff* I'm stuck with an evil muse though, she only likes writing horror, pooh T_T

 

    I just got to be me :D

 

I know who I am, I am me, and I like me ^^
Transgender, Gamer, Little, Princess, Therian and proud :D

She took the best title

Chelsea took the best title -- "Awwww".

I've been following this one and "Oscar Night" and have to say that I really admire your writing.
They're both good stories and are written well.

Kaleigh

Stephanie's Deal-5

Looks as if there just might be a few of the boys that might want to be girls here. I must admit that this story is going further than I thought it would at first. Will be interesting to see what happens next.
May Your Light Forever Shine

    Stanman
May Your Light Forever Shine

stephanie deal#5

wow relly good and i want to see a lot more dont stop now ,
love n hugs awalys
[email protected]

mr charlles r purcell
verry good story i wood love to see a lot more of this all i can say is wow verry good thanks for shareing

I don't know whether I like this ...

Jezzi Stewart's picture

... or Oscar Night better. Congrats on two great stories, Jennifer. I hope the ballroom dancing classes are a go. It will be interesting to see, when Steve's time as Stephanie 24/7 is up, how he/she balances both roles as things progress toward the wedding.

"All the world really is a stage, darlings, so strut your stuff, have fun, and give the public a good show!" Miss Jezzi Belle at the end of each show

BE a lady!

This episode...

...is where this series really takes off for me. :-) Before this, you've shown Stephanie/Steven enjoying activities as a girl, and even aspects of being a girl. This is where she seems to pull that all together and admit that the whole package of >being< a girl might be a good thing. I really liked that analogy comparing it to the Mousy Park. It seems to show the appeal, as well as a bit of fear at how much of an appeal it is (fear that it might become less appealing if overindulged). We've also seen her relationships with her family change from suspicion to understanding, and in this they begin to really blossom.
Overall, a very nice episode. :-) Thank you!

-Liz

Successor to the LToC
Formerly known as "momonoimoto"