Darren fumed as he sat on the couch, the memories of last night and that very morning still fresh in his mind. As if it had not been enough for Dani to send him to the bathroom still in the sissy outfit and pigtails, he came back to find that she had laid out clothes for him.
“I’m not wearing those.” He assumed the briefs were under the shirt, grateful that Dani had at least not put them out on display.
“Well,” Dani said, accurately sensing he was still upset about his change in underwear. “I’ll let you choose. You can stay in your panties and wear a dress or you can be a boy for the day.” She left unsaid that he would be back in a dress the moment mom left for work that afternoon. Dani knew she could not turn him into a little girl in just a week, but she was bound and determined to see how close she could get. If Max Kent could become his sister’s pretty ballerina, Darren would be her little princess. She knew it.
“Dani!”
“Shh, mom’s sleeping, remember?”
“Well, she should know what you’re doing.”
“What am I doing?” Dani asked. “All I see is you wearing my old nightie.”
“But” he sputtered, but he knew she was right. He was so indignant and flustered that he did not even notice that she had hanged the dress from last night in his closet until later that morning. Even then, he left it, knowing that Dani would just make him put it back. Did she really have photos like she had said? How had she taken them? For a moment, he imagined a bunch of hidden cameras around the house, like in one of his comic books. He scoffed. A thirteen year old girl did not have the money for those. She was probably lying about photos. He would find out somehow.
Dani sat on her bed while her brother fumed downstairs, thoroughly pleased with herself. She still had not decided on a name for her little princess project, but she knew it would come. There was something so fun about calling him her little princess.
“Which dress should my little princess wear tonight?” Once he accepted that he was a princess now and would never be a boy again, she would switch to simply calling him her little sister. After all, what else would you call a child who went to bed nice and early dressed in a nightie and hugging a doll? She nearly fell into a fit of giggles as she excitedly looked forward to the day when that became Darren’s normal.
For the next couple days, Dani and Darren fell into a routine of sorts. Once their mom left, Dani ran a bath for Darren and then laid out an outfit for the boy to wear. He could not believe that she always seemed to find a different dress for him to wear, but the threat of all his friends learning about the growing store of photos kept him from resisting too much. During the day, Darren tried to get a moment to tell his mom about what Dani did to him each and every night, but Dani always seemed to be there. He attempted to at least drop hints, but his mom just smiled and complimented them on finally being mature enough to get along without a babysitter. Dani knew the truth though.
As tempted as Dani was to push Darren further, she forced herself to hold back. Sure, she sometimes worried that they might plateau, but it was not like things were getting all that stagnant. Darren blushed and sighed when she presented him with his outfit for the evening, but she had noticed that he was less resistant to playing with his doll Emily, the only activity other than chores she allowed him to do, for now. Still, she felt a desire to push him, but knew it would come with time. As she watched clips of Max doing ballet, she had to remind herself that he had started weeks before Darren had. Patience. That was the key.
Besides, she had had a lot of success in a very short period of time. Darren wore dresses, panties, and nighties. His boxers were gone. The baths that had replaced showers for him were an area rife with potential for making him into the little princess she so desperately wanted. She just needed an excuse to take over his baths and then he would realize that dresses were nothing compared to a proper little princess bath. Still, that could wait. For now.
It was the afternoon of the fourth day that Dani decided that it was time to try to move things forward. Making sure Darren was not hiding in his room and could hear, she asked mom quite openly about the arrangement.
“Mom, after your overnight shifts are done, will I still be babysitting Darren every night?”
“Babysit?” Darren exclaimed, hazel eyes all but flashing.
“Darren, sweetie, inside voice.” Mom said. “You’re not really babysitting him, you know.”
“Aren’t I?” Dani asked. “I’m making sure he cleans up, stays out of trouble. It’s really the same as when I babysit Cayden Denborough.” She yearned to remind her mom that she had even admitted it was basically babysitting just a few days earlier.
“Well,”
“Mom, she’s not babysitting me!”
“True, but she’s been in charge the last few days, hasn’t she?”
“Yeah, but”
“And this is the first time I’ve heard either of you yell in the last few days, so it seems like it’s working.”
“But, mom, she” Darren searched for the words to explain that he had spent the last three nights in dresses and girl clothes without humiliating himself in the process. “She makes me go to bed early.” He finally managed.
“What time?” Mom asked.
“A lot later than I put Cayden Denborough to bed.” Dani played it off as a joke with a chuckle, but as far as she was concerned, Darren had just earned himself the same seven PM bedtime as the preschooler for as long as she was in charge. Little princesses like Darren needed their beauty sleep, after all.
“Here’s the deal, Darren. I want you to keep track of everything Dani does that you feel is abusing her power. And no, that does not include making you help with chores or making you shower. It’s nice to not have to hold my breath when you walk by. Tomorrow, you can tell me and we’ll discuss things.” Dani tried to conceal her concern. Could the game be up? Mom might not see things the same way she did. Sure, she did not have to say she was making her brother into her little princess plaything, but she would have to explain some things. “But, for tonight, Dani is in charge. Understand?”
“I can”
“No arguments, mister.” Mom said, completely missing that Darren already had a long list of perceived slights. “I’m going to shower and then leave for work. You two behave tonight, okay? You’ve been doing so well that I hope we don’t have to change anything.” She turned to leave, eyeing her kids. “And I better not hear any arguing while I’m getting ready for work.”
Betty Pearl's Sissy Stories 20.1
Topic: Dani's Little Sister (Read 38751 times)
