“We’re going to keep things nice and simple tonight.” Dani said almost as soon as mom had left. Darren wondered for a moment if she was concerned about him getting to report to mom about everything she did. “Once you’re in your dress and panties, we’re going to play a board game.”
“I’m not wearing a dress!”
“Mom even told you I’m in charge, Darren. I know you heard that.”
“Yeah, and”
“And I know you’ll tattle to her about everything I do. A big boy wouldn’t, but we’ve already established that you’re a little princess and little princesses tell mommy everything, just like good little girls should.” She loved how confused he looked. It was definitely a gambit he had not expected. “Now, march that cute little butt upstairs and put on the dress and panties I set out for you.” She smiled as Darren shuffled off. Sure, he would probably tell mom some things, but she knew he would never reveal everything.
Dani busied herself with setting up the board game, delighted that Darren would be coming downstairs any moment now. The board game she had chosen for them was nothing but princesses and glitter. She had gone through quite the princess phase in kindergarten and she was glad mom held on to everything so that they had it for Darren’s princess phase.
Dani looked at the board before her and realized it had been some time since she had sent her little princess upstairs to put on his dress. It was so rare for him to show defiance; she was unsure if she should even think about punishing him or simply reminding him what he was supposed to be doing.
Trusting that Darren would do the right thing, she slowly walked toward the stairs, hoping to see him coming in the dress she had picked out for him. She knew that, by the time his closet was filled, he would start picking out dresses for himself. The fact that he would be her little princess was a foregone conclusion in her mind.
Dani did not even knock on the door to his room. She did not see any need to. Being twins, they saw each other naked quite frequently until mom decided it was time for them to start doing things separately. Sure, they were growing up, but Dani had gotten top marks in her health class. Darren did not have anything she did not know about.
“What’s taking so long?” She asked, seeing him sitting on his bed. He had successfully taken off his shirt, but he was sitting there in his shorts, reading a comic book. She smiled a bit to see a white waistband peeking out of his shorts, but that was not really the point.
“Oh, I got distracted.” She did not have her mom’s gift for immediately knowing when Darren lied.
“Silly me. I forgot that my little princess gets distracted so very easily.” Darren’s cheeks turned a bit rosy. Dani wondered if she could replicate that with makeup. “You’ve wasted so much time, I think it’s time to put on your dress so we can start having fun.” Darren glanced over at the blue dress she had left out for him, matching panties right on top with more lace and frills than he was accustomed to even over the last few days.
“I… but…” he obviously had assumed that Dani would not dare put him in a dress with him reporting to mom. “I” maybe she just wanted one last hurrah. That must have been it, Darren thought. Maybe she was hoping she could humiliate him into silence. Those panties, how he hated the girly word, were even girlier than any of the others he had worn. He was going to tell mom everything, even if the thought of doing so embarrassed him. After all, he was fifteen minutes older than Dani and that made her his little sister. She was certainly as annoying as little sisters he saw on TV! But no, he would tell mom everything, even if she teased him about his little sister turning him into a sissy. He would put on the dress one last time, but he was not going to make it easy. “I don’t want to.”
“I’ve kept your secret, Darren.”
“What secret?”
“About how you’re actually my little princess.” She smiled as his face moved past pink and turned red. “I’ve been very nice about letting you play pretend as a boy during the day, but we both know you’re my little princess and my little princess needs to be in dresses as much as possible.”
“Dani, stop.”
“Darren, it’s been three days of dresses, panties, being the good little princess I know you want to be. What’s so different about today?”
“I” he did not have an answer.
“I figured you’d be eager to put on a dress, so you could tell mom all about it tomorrow.” Dani said. Darren studied her again. Why was she so excited about him revealing everything she had done to him? It confused him more than anything else about the last few days. Was she trying to make him not want to tell? That had to be. Well, he was going to tell, no matter what. “Please put on your dress, Darren. The game’s all set up downstairs and I really want to play.”
“What game is it?”
“I’ll only answer that question after you’re in your dress.” She replied, turning to leave the room. Darren groaned. That could not be good.
All the same, the boy was sitting in front of the sparkly pink game board in a blue dress not that different from Cinderella’s from the Disney movie. He looked like a princess who had been cursed to have a boy’s head atop her shoulders. Dani admired him, but then tsked. “Who’s missing, Darren?”
“I don’t know.” Everything was so confusing today.
“Where is Emily? Go get her right now.” She wondered if Darren was even conscious of how he held his dress down as he got up off of the floor. This was only his fourth day in dresses and he navigated them far better than she probably would. She nodded to herself. He was a little princess, after all.
By the time Darren had returned with Emily in his arms, Dani had dreamed up a variety of hairstyles for her brother. After all, he could not keep his current short hairdo if he was to be her little princess.
“How do we play this game?” Darren asked hollowly as he sat down. Dani noticed that he placed Emily in his lap, but said nothing.
“It’s simple. We draw a card, read it aloud, and move to that space on the board.”
“So it’s like Candyland?”
“Exactly! Like I said, we’re keeping it simple tonight. No video games, no fighting. We’re just going to play this game, have some dinner, things like that.”
“I’m still going to tell mom about what you’ve done.” He gestured to his dress. Dani smiled and nodded. Her brother had no subtlety. He always said exactly what he was thinking. That was what made it so easy to manipulate him.
“Of course. I bet you will.” She said. “Let’s play. You go first.” She smiled to herself. The rules stated that the youngest princess go first and that was Darren to a t. “Take the card, read it out loud, and do what it says.”
“You’re the prima ballerina in the Sparkle Soirée. P-pirow? Huh?” Dani took the card from him and nodded knowingly.
“It’s pirouette, Darren. It’s a spin ballerinas do. Though how you’re supposed to pirouette to the next purple space, I don’t know. Here, read it out loud again.”
“You’re the prima ballerina of the Sparkle Soirée. Pirouette to the next purple space.” Dani watched as he moved and then took the next card.
“The Powder Puff Pixies have declared you their guest of honor. Enjoy a feast at their hollow at the next yellow space.”
“Ugh, your nails need time to dry. Skip your turn.” Darren read aloud. Dani smiled.
“When me and Abby used to play this game as kids, we’d always shake our hands to dry our nails and then admire them, any time that card came up.” Darren clearly did not know what to do with that information as Dani demonstrated. “Well, go on.”
“It’s your turn.”
“You haven’t dried your nails yet, Darren.” Darren sighed and gave a halfhearted attempt, knowing all too well that Sarah would probably make him do it again. To his surprise, she just smiled and drew her card. He soon knew why. Every other card seemed to involve his nails needing to dry. Each and every time, Dani would look at him expectantly. By the time they were nearing the end, Darren found himself starting to do it even before Dani realized what the card was. Nefarious.
After the game finally ended with Darren being declared the princess of the game as the winner, Dani allowed him to watch TV while she made dinner, as long as he kept Emily in his lap, brushing her hair with at least a little effort.
After dinner, Darren did the dishes, despite whining about there being a million of them. Why did Dani always use every pot and pan in the kitchen whenever she made dinner? Despite his fussing, the dishes were done in no time and he even wiped the table while Dani sat and supervised, loving to see her brother hurrying around in his dress. By the time he was done, it was quarter to seven. Dani stood up and smiled at him.
“Alright, my sweet little princess, time for bed.”
“What?”
“Well, I figured I have less time to torture you if you go to bed nice and early.”
“I am not going to bed!”
“Think of it this way, Darren.” She said. “You can either go to bed now like a good little princess or I can figure out something else to help you feel more like the little princess you are.”
“Like what?” He did not want to call her bluff, but his male ego forced him to.
“Well, we could paint your nails. Not your fingernails, but your toenails so mom doesn't find out, as long as you wear socks.” Seeing that he was still not budging, she kneeled down and reached for one of his ankles as if she was going to start right then and there. She frowned at his leg hair. That would have to go, but how? She wondered if she had any tights still upstairs.
“I'll go to bed.” Darren mumbled. Dani grinned.
“Let's go get you into your nightie and I can do your hair, okay?” Darren sighed and nodded. Dani had to hide her delight at seeing him pick up Emily, but then wondered why she did. “That's my little princess! Emily goes with you everywhere, doesn't she?” Darren blushed and followed her up to his room.
Once Darren was in his nightgown and pigtails, Dani smiled as he started to get into bed with her even saying to. She almost wanted to let him go to bed, but knew it was ridiculous to put her twin brother to bed at this hour, even if he was rapidly becoming her little princess.
“I don't think you need to go to bed quite yet.”
“But” Darren bit back his words. There was no way to finish that sentence that made him sound like the young man he knew he was.
“Seven o’clock will be your bedtime when you behave like a bratty boy.” Dani said. “When you behave like my little princess, you can stay up later.” Darren knew exactly what she was doing, but how could he fight it? Calling her out on it would surely be deemed bratty boy behavior. “Well? Do you want to stay up or go to bed?”
“I want to stay up.”
“Then you had better ask nicely, don't you think?”
“May I please stay up?” It was the most polite Darren had been in a long time and Dani almost agreed right then and there, but she knew she had to push her little princess a bit more.
“Little princesses say pretty please, Darren.”
“Pretty please?” He said, only rolling his eyes a bit. It was good enough. She nodded.
“Alright, but remember, when I say it's bedtime for my little princess, that means it's bedtime. As my little princess, you need lots and lots of beauty sleep.” Darren had no idea how much time he had bought himself, so he sat down on the living room floor almost immediately and played with Emily without a fuss. It amazed Danielle that the brother who had loved Soul Contract just four days ago now did not seem to mind sitting on the floor in a dress or nightie, brushing a doll's hair and changing her dresses. Dani wondered if, deep down, he really was a sissy. Not that it mattered, really. He would be one whether or not he had been one already.
Betty Pearl's Sissy Stories 20.1
Topic: Dani's Little Sister (Read 37611 times)
