Stephanie’s Deal by Jennifer Brock

This serial is a spinoff from my holiday story, Nancy’s Patterson’s Criss-Crossed Christmas Pageant. The first couple of episodes overlap the timeline of that story, but from a different point of view. Later chapters will continue showing what happens to Stephanie, for as long as she exists.

Episode 1

It seemed like “You aren’t living up to your potential” was Steven’s mother’s favorite phrase. Any time his older sister Michelle would bring home a B on her report card, the parents were always “Good job, honey!” But if Steven got a B, they were all “Try harder next time.” While it was true that he could get B’s without trying much at all, it wasn’t fair! Just once, he’d like to be the favorite!

Then that stupid baby wouldn’t shut up at the stupid Christmas pageant rehearsal, and suddenly Mrs. Patterson was switching all the parts around, and before anyone could protest, the girls had the boys’ parts and the boys had the girls’ parts. It was nuts! He wasn’t very happy at all to be an angel.

But the worst part, the worst part, was when busybody Michelle home from her fancy college saw his pageant flyer on the kitchen counter, and started laughing at him. She claimed that the paper said he needed to wear a bra and panties and other girlie underwear stuff under his angel dress, but she wouldn’t show it to him. She said it would be nice to have a little sister again, and the memories all came rushing back.

When Michelle was nine and Steven was three, she used to dress him up in her old clothes (or maybe it was doll dresses) and say he was “her little sister Stephanie.” She made him have tea parties with her, where he’s have to refer to one of her dolls as his baby, and Michelle would have one of hers, and they’d talk about stupid girl things. Or they’d play with her Barbie dollhouse, and Steven always had to be Skipper, he was never Ken. And one time she actually made him go outside in a dress to learn to play hopscotch. Mom never stopped her; she was just happy to see her kids playing together. But there was nothing Steven could do about it.

Michelle asked their mother, “When you go shopping for Stephanie’s panties, can I come with?” Mom read the note and giggled a little and said Michelle could tag along, but Steven had to go himself as well. Michelle didn’t let it go and said, “Come on, Stephanie, it will be fun!” He tried to make her stop but she just got worse. On the way to the mall she said stuff like, “Gee, Stephanie, why are you so down? The day a girl gets her first bra is supposed to be a happy one.”

Mom didn’t make her stop teasing, and even joined in accidentally. She said, “The paper said a bra was optional. We’ll try on a slip in the changing room, and see if she needs a bra to make it hang better.”

Steven did his best to try to be invisible, and hope that the humiliation got over quickly. Mom led them straight to the girls’ underwear section, accompanied by a half a million “Stephanie’s” from Michelle. She grabbed a four-pack of medium size white panties, and handed it to him while she held up white lacy slips against him to figure out what size, and picked out a couple of them and then found another rack where it was like they’d separated the top part of the slip from the bottom part and she took some of those, and then she picked out three or four different bras and got some white pantyhose.

Then came the really embarrassing part, when she found a store clerk and said that she needed to go into a changing room with her son to try on some lingerie, but she didn’t know whether to use the men’s or women’s rooms. The clerk seemed to take a moment to keep from chuckling and said that the ladies’ changing rooms would be fine. Mom also checked that it would be okay to open Steven’s package of panties in the changing room, as long as she promised to purchase them.

The only saving grace was that Michelle waited outside the changing area. His mother had Steven strip completely naked, and then she handed him a pair of panties to put on. They weren’t very different from his usual underwear; they just had a thinner waistband and no flap in the front. But when he put them on, they came to a different place on his body than usual, and it felt weird. Mom said they fit perfectly, except for the little bulge that seemed out of place. Even though Steven was already blushing, he turned a deeper shade of red.

The next thing to go on was the white pantyhose, which his mother called “tights.” She said that they were just like Batman wears, so he shouldn’t have a problem with them. Of course Batman didn’t wear panties under his, so it wasn’t a fair comparison, but at least she was trying. They kind of went on like pants, but slower. It was obvious why they were called tights; Mom showed him how he had to stretch them out as he pulled them up. When they were in place, she had him do this weird dance to get them to sit right in the crotch. He did not feel at all like Batman — Batgirl, maybe.

And it only got girlier. Mom had him raise his arms and pulled a silky slip over his head and then tugged at the lace hem to try to see how it sat on him. She looked at him from a couple different angles, clucked her tongue, and then said the words he feared most, “You’re going to need a bra with this.” She pulled the slip off over his head and then went to her small stack of bras. The first one she tried was almost like a tank top, only it stopped in the middle of his chest with a really tight band, and the straps were very thin. It was uncomfortable, but he really had nothing to compare it to. Mom pulled the slip back over his head and looked at it, then shook her head. She said he needed one with more definite cups.

The next one she tried had a couple of triangles on the front where the boobs would go. Unlike the last one, it went on frontwards. He put his arms through the straps, and she wrapped the band around and hooked it in back, then played with the little buckles on the straps. It fit better than the last one, and he made the mistake of telling his mother it was more comfortable. She brightened up and told him that she was glad he was getting into it. It might have been comfortable, but it looked funny. There was a pleat in the middle of each triangle that wanted to be filled with something he just didn’t have. His mother seemed to agree when she saw the slip over it.

The third one was even more like a real bra. It had white lace panels on its rounded cups, and once she had settled it into place, Steven saw that the cups had some padding in them. It looked like he had real boobs, and when the slip came down it seemed even more like they belonged there. His mother fluffed his hair and said that he really looked like a real girl. She told him not to take anything off and made him wait in the booth while she handed the things she didn’t want to the attendant.

When she came back, she had Michelle with her. “You look really cute, Stephanie.” She made him spin around so she could see the back. “It’s too bad we’re not buying you a dress to go over that, or you could wear it out of the store.”

Mom actually did want him to keep the tights on since they’d be going shoe shopping next, so he had to leave the panties on, too. She did take off his slip, though, and he put his pants on to avoid feeling too embarrassed. Mom asked him if he was forgetting something, and pointed at his bra. He tried reaching around behind his back, but he couldn’t figure out how to unfasten it.

Michelle took his hands. “Come here, Sis. I can show you how to unhook that. But you know, if you leave it on you’ll look like a girl even in your jeans and shirt. Maybe it would be easier for you to go shopping for girls’ shoes if the shoe guy thought you were a girl. What do you say, Stephanie?”

Steven looked at his mother and she just shrugged, saying that Michelle had a point. Against his better judgment, Steven kept the bra on and his mother cut the tag off so she could pay for it. Steven put his shirt back on and it looked weird with the little bumps sticking out, but he did admit that he seemed girlish.

Michelle stopped him from exiting, saying that there were three things that would make Stephanie perfect. First, she took the plastic headband off of her own head and then put it on her new little sister, which instantly made his hairstyle feminine. Second, she had him make a little kissy mouth and she pulled a tube of lip gloss out of her purse and brushed some on his lips. The third thing was really mortifying. She said that little girls didn’t have lumps in the front of her pants, and he needed to open his jeans and reach down into his panties and push his thing back between his legs. He didn’t quite understand what she meant, so she reached in there and did it herself. That earned her a shocked look from Mom, but she did agree that Stephanie looked much better.

Confident in his disguise, Steven didn’t feel quite so self-conscious as they stood at the cashier to pay for his girls’ underwear. When they left the store he thanked his sister for her help, and she gave him a little hug. It was weird — normally they couldn’t stand each other. It was like Michelle liked him better as a girl.

The shoe store was halfway down the mall. Since they wanted white shoes, which were out of season, they had to go to a specialty store. Mom said she wasn’t sure if her daughter’s feet had grown any, and Stephanie happily sat in the chair while the shoe man measured her foot. He asked what kind of shoes they were looking for and when she pulled the paper out of her purse to double check, Stephanie’s cover was blown.

“White Mary Janes or ballet flats? Oh! You must be one of those angel boys from Second Baptist. Getting in a little practice being a girl, are you? You’re not the only one. There was a pretty little thing in here earlier that you never would have expected wasn’t what she appeared.”

Steven was crushed. Of course if there was only one store that sold the right kind of shoes, they’d already know about the pageant. Michelle must have figured it out or something and used it to trick him so she could dress him as a girl, just like when they were little. He wanted to rip the stupid girl stuff off and run out of there, but it was under his clothes and being naked in the mall would be even worse. He squeezed his hand into a fist and tried not to give her the satisfaction of seeing him cry.

Mom made him walk around a little in the shoes. They had more heel than he was used to, so it felt weird, but she thought they’d work just fine. Michelle winked and said “Looking good, Sis! Put a little more hip into it and you’ll drive all the boys crazy.”

When they got home he went into his room and tried to take off all the stupid girl stuff, but he couldn’t get his bra off and had to call his mother to help. She was busy and sent his sister instead. How could she be so insensitive? Didn’t she realize what Michelle had done to him? For her part, Michelle also played it cool, acting as though she hadn’t tried to trick him. She showed him how the bra hooks worked, and placed his hands for him where he’d be able to do it himself. She’d brought in his slip and the rest of his panties, and cleared a space in his top drawer for all his new special clothes. Steven just wanted to be left alone. She patted him on the head and took her headband with her. He’d forgotten that he was even wearing it.

That wasn’t all he’d forgotten. At dinner that night his father was giving Steven a weird look, and finally asked him if he was wearing lipstick. Michelle corrected him that it was lip gloss, and they all explained about the pageant and the mall and pretending to be Stephanie. Dad thought it was funny, and asked if he could see his new daughter, so after dinner Steven was once more dressed by his mother and sister in his full regalia. He said that Stephanie was very pretty, and made her give her Daddy a kiss on the cheek before sending her away.

The rest of the week was more or less normal, except that Michelle kept calling him Stephanie. By Friday even Mom was tired of it and made her stop. That night, while his father was out at his monthly poker game and his mother and sister were out finishing their Christmas shopping, Steven took advantage of being left home alone.

He knew Michelle was the favorite, but he needed to know whether his parents cared about him at all. There was only one Christmas present he’d asked them for, and if they really loved him they would have bought it. He knew his mother usually hid the presents in her bedroom closet, but when he peeked in there he was foiled. The presents were already wrapped. But he had a solution to that problem as well. There was one box that could have been his treasure, and it was indeed addressed “To Steven from Mom and Dad.” He got a knife from the kitchen and very carefully cut through the tape at the end of the box, and very gently unwrapped the box enough that he could see that this present was in fact the Nintendo Wii he’d asked for. His parents did care after all!

He was doing his little happy dance when suddenly the bedroom door opened and there was his mother. “Steven Thomas Brooks! What are you doing in my closet?” She saw the partially unwrapped present and turned red. “Go. To. Your. Room. Now, Mister!”
Steven slunk off to his room while his mother continued to yell at the back of his head.
“When your father gets home, we’ll discuss your punishment. I’d come home to get my wallet out of my other coat, but there’s no way I’m going to leave you alone now. I’ll call your sister and see if she can get a ride from someone else. You’ve been very inconsiderate, young man.”

His parents had never given him severe punishments before, but he’d never really done anything as obviously wrong either. He sat in his room fearing what would happen for a couple hours or so when the door opened and his father told him to go to the dining room for a family meeting. He did not look happy.

When Steven entered the dining room, he saw three angry faces. As soon as he sat down, his father started the speech. “We are very disappointed in you. Your mother showed me what you did, and not only have you cut everyone’s plans short tonight, but you might have ruined our Christmas. We didn’t raise you to be an unappreciative brat, and I hope you understand the magnitude of what you have done.” Steven only nodded. “Now, my opinion was that unappreciative brats shouldn’t get expensive presents that their fathers had to wait in freezing lines to buy for them, so I suggested that your punishment should be that we return your presents to the store, so that maybe they could be bought for some other kid, who deserves them. But your mother doesn’t think that would be enough.”

She spoke up, “Just not having something wouldn’t be a strong enough reminder. I wanted to come up with a punishment where you’d have to constantly think about what you’ve done and realize that you’ve completely lost our trust. I brainstormed to come up with something, but then your sister suggested something that made sense to me. She saw how annoyed you were with her calling you Stephanie and how irritated you were at dressing up like a girl, so her proposal is that you become Stephanie full-time.”

Steven didn’t understand what she was saying, and his face made that clear. Michelle stepped into the conversation, and slid a piece of paper across the table to him. “Here’s the deal: from now until you have to go back to school, you’ll have to dress in girl clothes, act in a completely girlish manner, and answer to the name Stephanie. But more than that, you can’t whine or complain or refuse to do anything a real girl would do. This paper makes it official. If you sign here, it means you agree to dress and act as a proper young lady, cheerfully and without complaint, until your school resumes classes and you can go back to being Steven. If you don’t take this deal, we go with Dad’s idea, and your cool new videogame goes back to the store, which is a shame because I was looking forward to kicking your butt at it. It also goes back if at any point you try to back out of the deal, or don’t uphold your end. Furthermore, if Steven’s not here on Christmas, neither will his presents, so they won’t come out of the closet until he’s back. Do you understand this deal?”

Steven nodded. “I think so. Either I become a girl for a week and a half, or I lose all my presents? And if I try and mess up I lose all my presents anyway?” He understood correctly. So he was being challenged. The only way he could earn back their trust would be to take this deal and put his everything into being the best girl he could be. It was weird, but it wouldn’t be for very long, and since he had to be a girl for the pageant anyway, that was one day that would take care of itself. He picked up the pen and signed his name on the paper.

Mom stood up. “Okay, Stephanie. The first thing you need to do is get rid of all your boy clothes. There’s a stack of plastic storage totes in the living room that I usually use for storing my winter clothes. Bring them to your room. Take off what you’re wearing now and put them in the laundry. Since I don’t want you running around naked, put on a pair of panties and your slip. It will have to serve as your nightgown for tonight. Then I want you to empty you bureau and your closet into the totes, with the only exception being the new things we bought you on Monday. Leave the full totes in the hallway, and your father will take them down to the basement. When all Steven’s clothes are out of your room, I want you to go to bed. I’m going out now to a store that’s having an all-night sale, so you’ll have something to wear. Do you understand?”

Steven took a moment to think about how a proper young lady would respond. He folded his hands in his lap. “Yes, Mother. I can do that. Thank you for going out so late to buy me some new clothes. I will try to do my best to deserve them. May I please be excused?”

His mother was in a bit of shock over the drastic change in his manner, so it took her a while to answer. She dismissed her child and Stephanie thanked her and slipped into the living room to go about her chores. Still furious from Steven’s transgression, she drove her older daughter off to the store to get some things for her younger one. She hoped that this whole thing wouldn’t be a mistake.

Steven had only been told to wear a slip and panties, but he put on his bra, too. He thought it would make Stephanie feel more girlish. He knew that the only way this was going to work would be if he put every effort into becoming Stephanie, to make her as real as possible. He started throwing his clothes into the totes, but then she realized that that was not the way a proper young lady would put away clothes. She dumped everything out on her bed and then carefully folded each item before placing it neatly in the tote. After dismantling Steven’s entire wardrobe, she was exhausted. Even though she was very nervous about what challenges the next morning would bring, she fell asleep almost immediately upon climbing under the covers. She just hoped that Stephanie lived up to her potential.