Danielle delighted in flopping down on the couch to play video games while hearing the clink of dishes in the kitchen. There had been countless occasions where she had done the lion's share of the chores while Darren played video games and it felt just for the tables to be turned like this.
When Darren came back into the living room, she looked at him at once, smiling. Darren, however, looked downright miserable, tugging even now at the skirt of his dress in a vain attempt to hide his frilly panties.
“Something wrong?” She asked cheekily. He did not answer. “Don’t you feel pretty in your new dress?” Unsure of how to respond, he simply muttered something under his breath. “Maybe you’d like me to do your hair?” Darren squirmed a bit. The terms of the bet were that he only had to do what she said. There was nothing about inviting more torment.
“No” he whispered before clearing his throat. “No thanks.” Danielle reveled in his abrupt meekness. Darren might never learn it, but Danielle had been inspired to put him in a dress by April Kent, the older sister of one of Darren's friends, Max. As April had delighted in telling Danielle, Max had spent the last four Friday evenings following along with a series of DVDs aimed at teaching young girls ballet. Even in a pink leotard, tights, and a tutu, Max had been defiant from what April had told her, so Danielle was a bit taken aback by how dramatic of a transformation Darren had gone through in the last hour.
“Is the kitchen all set?” She asked. Darren nodded. “You know, Darren, just because you're in a dress doesn't mean your voice doesn't work.” She snapped her fingers. “Since you've got to do whatever I say, for the rest of the night, you need to answer all of my questions with complete sentences. Understand?”
“Yes, uh, Dani.” Darren said. She smiled and nodded approvingly.
“Is the kitchen all set?”
“Yes, Dani.”
“Let's go check, just to be sure.” She said. She figured that, unless it was ridiculously subpar, she had too many chores for him to do to have him spend all evening cleaning the kitchen. “Oh, but real quick.” She turned him around so that his back was to her and she zipped the dress up. She could not help but giggle as he gasped, the bodice of the dress tightening around him. “Can't believe you went that long unzipped, Darren!” She exclaimed. “Now you're really sealed in.” She smiled as Darren reached behind him, only able to brush the zipper with the tips of his fingers. He realized that he would be stuck in the dress until Dani released him.
Darren yelped as Dani seized an opportunity and yanked his skirt up, exposing his panties fully.
“I see Darren's panties!” She teased in sing-song, smirking as he fussily pushed his skirt back down. “Sorry, it's one of those things boys always do to girls, so I figured I'd return the favor.”
“I never did that.”
“Well, I so rarely wore dresses.” Dani replied matter-of-factly. “Let's go inspect your handiwork in the kitchen, hmm?”
Perhaps inspired by fear of being forced into something even worse, Darren had done an actually decent job in the kitchen and Dani allowed him to see how impressed she was. “Not bad, little” she paused. “Little sister doesn't sound right. You're not a girl, are you?”
“No" He said, his relief apparent on his face.
“But you're dressed like a six year old girl, so you can't really be my twin brother.” She thought out loud. “Ah ha! I think we'll go with my little princess. How's that sound?”
“Um… isn't there something else we could go with?”
“I think princess works.” Dani replied with a smirk. “Now, enough dilly-dallying. You've got laundry to do.”
“I do?” Dani nodded and, taking his hand, lead him toward the laundry room.
“We’ll make it easy and have you start with just your own.” She said. “Next time, you’ll do mine and mom’s too.” She giggled as his cheeks turned pink at that. “She and I have done your laundry a lot. It’s about time you return the favor.” She opened the washing machine for him. “First things first, put your clothes in here. I brought them downstairs for you, but I won’t do that next time.”
“Next time?”
“Yep. I’m going to bring it up to mom, but I think it’d be good for you to become the official laundry boy of the family.” She saw his face and added “obviously the title will need some work.” She turned to leave him to his task. “Come find me in the living room once you've got the washer going.”
Returning to the couch, she started yet another game of Soul Contract. Now that her secret was out, she delighted in playing the game and knocking another one of Darren's high scores from the list.
“Laundry going, princess?” She asked, typing her name into the #2 spot when Darren came shuffling into the room.
“Yes.” He muttered through somewhat gritted teeth. “Can I play my game now?” She smiled at him and pointed to the high scores. The highest his name appeared now was fifth.
“I've been thinking, Darren.” She said, seeing his eyes almost well up with tears. “Since you're not the best at Soul Contract, maybe we should find you something else to play.” She nodded to a pink plastic tub she had gotten out when he had been cleaning the kitchen. Darren opened it and groaned to see a doll in the bin. She grinned. “Since I'm better than you at a boy game.” Her voice made it very clear that she thought it was ridiculous to even think of video games as a boy thing. “I figured you'll be better than me at dolls.”
“What do I do?” He asked.
“Play with her. Brush her hair, feed her her bottle. It's all in the bin there for you, Darren. There's even a few different dresses. Make sure she tries on each one and decide which is best for her.” Darren stood up to sit on the couch, but Dani had other ideas. “It'll probably be easier to sit on the floor.”
“How long do I have to do this?”
“At least until you're done with the laundry.” Dani said. “But if you do get bored, I can teach you other alternatives to video games. We can go outside and you can jump rope or play hopscotch.” She grinned. “We could even try to find the old baby carriage I had for my dolls and we could go for a walk around the block. I believe it's in the garage somewhere.”
She caught Darren staring at the television as she played his game a few times, but she quietly reminded him to play with his doll each time. Remembering one of her goals for the night, she surreptitiously snuck a few photos of Darren brushing his doll’s hair, careful to keep her cell phone a secret from her brother.
Smiling fondly, she looked at him. Darren was always the first to mention that he had been born fifteen minutes before Danielle, but for as long as she could remember, she had always thought of Darren as her little brother. She also suspected that their mom thought of him as younger than her. Looking at him now, she knew that there was no way he would ever be anything but her younger sibling. Even after he returned to boy clothes, she had taken away his mature underwear and she had resolved that baths would replace showers for him. If she could come up with a way to make it clear that she was only doing it because he was too little to bathe himself, she planned to start giving him his baths, just like she had done with little Cayden Denborough. Perhaps bath toys? She liked the idea of Darren having to play with mermaid Barbies in the tub each and every night.
After a while, they heard the washer beep, indicating that it was done. Darren remained on the floor, absentmindedly brushing the doll's hair. Dani looked at him expectantly for a moment and only then did Darren stand up, giving Dani quite the generous view of his frilly panties.
“I see Paris, I see France” Dani said in sing-song. Darren glared at her. “I figured since your panties are so fancy, you want me to look at them.” She said with a shrug. Darren's face became a deep red between embarrassment and anger. “Tell me what you're wearing under your dress, Darren.” She said with a grin.
“No.”
“C'mon. You know the bet.”
“Haven't I done enough?” He growled.
“Darren, Darren, Darren.” She said. “You've spent countless hours sitting on this couch, not lifting a finger. One night of doing a few chores isn't going to kill you.”
“Look at how I'm dressed!”
“How are you dressed? Tell me what you're wearing and I'll leave you alone to go put the laundry in the dryer.” Darren stared down at his feet. “Complete sentences, remember. I'm wearing” she gestured for him to follow her example.
“I'm wearing a dress?”
“And what's underneath?”
“I'm wearing shoes.” He pointed to his Mary Janes. “And socks.”
“They're called Mary Janes, but go on. What else are you wearing?”
“I've got underwear on.”
“Are they boxers? Boxer briefs? Tighty whities?”
“They're panties.” He said, barely above a whisper.
“That's my princess!” She cooed. “Go rotate the laundry now and hurry back. Your dolly misses you!” She listened to him growl, quickly snapping a few pictures of him and his bouncing dress as he stomped away. Should she send them to April now or wait? She could not decide. “I need some more of Darren and his dolly.” She mused to herself.
As Darren moved his laundry from the washer to the dryer, his mind reeled. He squirmed in place every time he felt the dress brush against his cotton-clad bottom, his Mary Janes clicking on the linoleum of the laundry room. How had Danielle done this? How had she so completely gotten the upper hand? The fact that she soundly beat him at Soul Contract was not even as important as how quickly she had turned him from a thirteen year old boy to a… whatever he was now. It was obvious that she had planned this all in advance, but he could not even comprehend how it had happened. Who would have helped her? He shuddered as he wondered for a moment if their mom was a part of this. Could that be possible? No, there was no way. She loved her son. She would never want him to become a sissy or whatever. He clenched his jaw. It was clear what he needed to do. He needed to march back out to the living room and assert his masculinity!
Starting the dryer, he did just that, marching as authoritative as he could with the skirt of the dress bouncing with each and every step. When he reached the living room, however, he stopped and stared at his sister, waiting to be acknowledged.
“Your dolly missed you, Darren. I tried to tell her you'll be right back, but I think she got scared anyway.”
“Look” Darren said, trying to resummon the nerve he had built up in the laundry room. “Hasn't this gone far enough?”
“Nope.” She said so quickly that it took him aback. “The bet was loser does whatever the winner says for the whole night. If you'd won, there's no way you'd let me quit this early.”
“But”
“Sit down and play with your dolly. What's her name anyway?”
“I dunno.”
“Well, ask her.” Darren, a bit confused, picked up the doll and, feeling quite foolish, asked her her name. “Hold her to your ear so she can whisper it.” Danielle instructed, surreptitiously taking a few photos of Darren complying. “Well?”
“Emily” Danielle smiled.
“That’s a pretty name. See? Told you you’re a natural at dolls.”
“I’m a boy though.” He mumbled, still holding the doll.
“I know you are.” Danielle said. “It’s not going to hurt you to play dolls one night.” Or every night, she added mentally. “Besides, you can either play with Emily or I can find more chores for you to do. Which will it be?” Darren did not respond, other than picking up the toy bottle and feeding it to Emily. Danielle smiled, idly wondering if they had an old baby bottle somewhere that she could make Darren use.
They fell into peaceful tranquility until the dryer finished and Darren rose, taking more care not to flash Danielle, much to her delight. She followed him upstairs and watched as he put his clothes away in his dresser. Normally, he would just leave them in the basket, but she refused to allow it. As he put the last of his t-shirts away, she smiled at him.
“Run downstairs and grab Emily, then meet me back here.”
“Why?”
“Don’t waste time asking silly questions. You’ll find out soon enough.”
“But”
“Enough! If you want to take your dress off, don’t say another word.” Despite the questions that he still had, Darren silently obeyed and Danielle hurried to her room to grab what she needed for the next phase of her plan. By the time Darren had returned from downstairs, she was back in his room with just what she needed on his bed behind her. “Did you apologize to Emily for leaving her down there?”
“No.”
“You need to.” She nodded approvingly. “Now, let’s get your dress off and your nightie on.”
“Nightie?”
“The night’s not over yet.” She observed, walking around behind him and unzipping his dress down his back as he looked at the pink nightgown she had put on his bed. “Which means you still have to do what I say.” His unhappiness was evident, but he remained silent, glad to remove the dress, even if it left him in just his panties. “Leave your panties on, Darren. You can wait until morning to put your tighty whities back on.”
“But you said”
“C’mon, Darren.” She interjected. “You’re a smart boy. Surely by now, you’ve realized that this isn’t going to just stop at the end of the night? I’ve got you under my control. Permanently.”
“What do you mean?”
“Don't worry about it.” She said, reaching over and patting the pouting boy on the top of his head. “Let's get that dress off so you can get ready for beddy byes.”
“No!” Darren exclaimed, pushing her away.
“You want to stay in your dress?” Danielle was genuinely surprised.
“No, I want you to stop this. It’s gone too far.”
“Has not. You agreed to the bet.”
“But I didn’t know how far you’d take it.”
“Trust me,” Danielle said, thinking of Max and Abby. “I could’ve taken things a lot further.”
“Well, I’ve had enough.” Darren exclaimed angrily. “I’m taking this dress off!”
“Good. Let me help you.” Darren’s anger deflated somewhat.
“No, I mean I’m taking it off and not putting that on.” He pointed at the nightgown.
“I’m not letting you run around in just your panties.”
“Why are you not listening to me!” He growled.
“I am! You’re just not listening to reason!”
“I’m not wearing girl clothes anymore!” Danielle stepped back and smiled at him. Her behavior was so strange that he stopped and stared at her. “What?”
“Let’s just say you’ll regret it if you don’t put that nightgown on.”
“What are you talking about?” Danielle only smiled and mimed zipping her lips. If she played her cards right, he would put on the nightgown and her cell phone would remain a secret. Darren growled, but knew his sister to know all too well that she would not tell him whatever she was talking about until she wanted to. She was the absolute best at keeping secrets.
He reached behind himself to try and unzip the dress, but he could not get his arms to twist enough to grasp it. He grabbed the skirt and tried to pull the dress over his head. Danielle took a risk and snapped a few photos of him with the dress over his head and his pantied bottom completely exposed. “Need some help?” She asked with a smile as he tried to resituate the dress.
“Yeah.” He begrudgingly muttered. He turned his back to her and she reached out for the zipper, but stopped.
“Promise you’ll put your nightie on?”
“I promise.” He softly said.
“What do you promise, Darren?”
“To put it on.”
“I think Emily would be very sad if you don’t.” Darren scoffed.
“She’s just”
“Treading on thin ice there, Darren.” Danielle interrupted. “You’ve been doing so well, playing with Emily all night.”
“So?”
“So I thought you loved her. You haven’t even asked to play Soul Contract in a while.” Darren grumbled, but did not respond. “Promise Emily that you’ll put your nightgown on right away after I unzip your dress.” Darren’s conflicting emotions were written all over his face.
“I promise, Emily.” He mumbled. Danielle grinned.
“Good boy.” She summarily unzipped the dress and pulled it over his head, snickering once again when she set eyes on her brother’s far more feminine panties. She realized with no small amount of regret that she should have replaced his boxers and boxer briefs with panties, not tighty whities. Then again, this was only the first night of a whole week of overnight shifts for their mom. She could not help but imagine just how far she could take Darren by the end of the week. For now, though, she would be satisfied with getting him into a nightie and sending him to bed. “Ready for your nightgown?” She asked.
“I guess.” The alternative, after all, was standing around in a frilly white pair of panties, which did not strike him as particularly appealing. Taking up the nightgown, he pulled it over his head. Once Danielle went to bed, he would be able to take it off, right?
“Hmm” Danielle said, looking him over. The pink nightgown fell further down his body than the dress had, completely covering his panties. The lace collar and lace fringe around the bubble sleeves did more than enough to emphasize the juvenile feminineness of the garment. “It suits you even more than your dress did.” Danielle remarked.
“You haven’t worn these in years.”
“True, but you should start.”
“No.” Rolling her eyes, Danielle walked over to his bed and pulled back the covers.
“Hop in.”
“What?”
“It’s bedtime.”
“Is not!”
“Is so.” She replied.
“I’m not going to bed.”
“Well, brush your teeth and use the bathroom first, but it’s bedtime.”
“It’s too early.”
“I don’t want to hear it.” She dropped into what she called her babysitter voice and her tone matched their mom’s stern voice enough that she could see that it was having an effect on her brother. “You have five minutes to brush your teeth, use the bathroom, and get back here or else.”
“Or else what?”
“Like I said, you won’t like what happens.” Remaining vague seemed like it would be more effective than specifying what she would do. “March, mister.” To her delight, Darren begrudgingly complied. Glancing at the clock beside his bed, she gave him five minutes.
Four minutes later, however, she left his room and went to the upstairs bathroom, only to find it empty. Had he gone downstairs? It seemed unlikely, but where else could he have gone? She went down the stairs to find her wayward brother.
Betty Pearl's Sissy Stories 20.1
Topic: Dani's Little Sister (Read 38697 times)
