Darren peeked out of his sister’s room. He was fairly certain he had heard her go downstairs, but what if it was just a trick? He tiptoed back toward his bedroom, but thought better of it. When Danielle inevitably came back upstairs, it seemed obvious that she would check his room first. Where could he hide? Her room seemed obvious. With Danielle downstairs, he was stuck on just this floor. He looked around, trying to ignore his growing anxiety. He was trapped.
Darren went into his room and locked the door before immediately yanking the nightgown over his head, quickly followed by the panties. He hurried over to his dresser, but then he heard the sound of the lock turning. He yelped and tried to hurry, but the sudden reminder that Danielle had replaced his underwear with white briefs made him pause just enough for him to still be standing there when she successfully got in.
“Don’t even think about it.” She was all business, not even blinking at her brother’s nudity. She marched right over to him and, grabbing his wrist, yanked him over to the bed. Darren could not help but marvel at her strength as she yanked him over her lap and immediately began to spank him. “You do not do that!” She said, punctuating it with spanks.
“Stop!” He yelled, tears already falling down his cheeks. Neither of them had been spanked in years and it was the combination of the pain and the embarrassment of his sister spanking him that caused Darren to break down so quickly.
“Promise to be good.” Danielle said, pausing to allow him to speak.
“I promise. Ow!” She had smacked his bottom again, just to drive home his obedience.
“Promise to be a good little boy.”
“I promise!” He yelped as she struck his bottom again.
“Say the full promise.”
“I promise to be a good little boy.” Darren wailed, tears practically pouring down his cheeks.
“And what do good little boys do?” She asked softly. Darren had to stop crying just to hear her.
“Um… wear” he sniffled. “Wear that stuff?”
“Here's what you're going to do, Darren.” She said. “Stand up and face me.” He quickly complied, his hands cupped over his privates. “You are going to put on your panties and your nightgown. Repeat.”
“I'm gonna put on my panties and nightgown.” The boy mumbled.
“Then you're going to get into bed and kiss your dolly Emily good night. Repeat.”
“Then I'm going to get into bed and kiss Emily good night.” He sniffled again. She could tell he was on the verge of tears.
“Go on and do it.” She said gently. She sat there on his bed, watching as he complied completely with her instructions. She knew that he had probably not brushed his teeth, so she stopped him as he went toward the bed. Handing him Emily, she smiled as he kissed the doll's forehead. “Let's go brush your teeth first. Bring Emily so she can be sure you did it.”
She made sure he hugged Emily to his chest with one arm before taking her brother by his free hand and leading him to the bathroom. She smiled as she saw him look at his reflection in horror.
“You're right. You're missing something.” She pulled open a drawer and pulled out two hair ties. “Hold still.” With a practiced hand, she styled his hair into two pigtails, each held in place by a hair tie. Darren stared at this reflection wide-eyed. “Not done yet.” She said. The pigtails were hilariously short, but she had just the idea to dress them up a bit. Taking two lengths of pink ribbon, she tied a bow over each of the hair ties. Darren looked away from his reflection, too embarrassed to even meet his own gaze.
Danielle stood there, enjoying her brother's abject submission as he brushed his teeth with the doll still against his chest. Satisfied, she took his hand and led him back to his bedroom. Docile as a lamb, he got into bed and she pulled the covers over him, tucking him in snugly.
“I expect to come in here in the morning to find you still in your nightie and panties with Emily in your arms.” She said, looking down at her brother.
“But” Danielle continued as if he had not interrupted.
“If you don’t, every single picture I snuck of you playing with Emily in your pretty dress will become public.”
“What pictures?”
“Trust me,” she said with a grin. “There are a lot of them.” She reveled in his shock for a moment. “Don't worry. I don't think I got any of you in your nightie. A boy's nightie should be kept private, don't you think?” Darren's expression was impossible to read, but she thought she saw the faintest glimmer of gratitude or relief. She smiled and left him to his bed. “If you're a naughty little boy and try to get out of bed, I'll have to use the baby monitor.” She cautioned. “And, of course, your friends will know all about how you spent the evening.” She turned off the light. “Nighty night, little brother.”
* * *
As Nicole got home, she stifled a yawn. The house seemed quiet, but that was on account of it being five-thirty AM. Danielle was an early riser, but not this early. She breathed a sigh of tired relief as she stepped out of her shoes and walked up the stairs in her stocking feet. She knew her kids were thirteen, but she still felt a maternal urge to peek in on them. Coming to Danielle’s door, she gently eased it open and poked her head in. There was Danielle, sleeping peacefully. In the twilight of the room, it almost looked like she was wearing one of Darren’s basketball jerseys and shorts. Dismissing it as a trick of her overtired mind, Nicole closed the door and softly tiptoed down the hall to Darren’s room.
She reached out for the knob, but stopped herself. Danielle and Darren were too old for her to be peeking in on them while they were sleeping. She needed to give them their independence. If something had gone wrong, she would get the full report from Danielle. She had not gotten a single frantic call or even a text, so surely the evening went off without a hitch? Then again, no news might not be good news in this case.
She placed her ear to the closed door and heard the deep, even breaths of her sleeping son. Good. He was in there, at least. Placated, she walked to her own room, none the wiser that, in his sleep, Darren had kicked off the blankets and was lying there, fully exposed in a little girl’s nightgown. He still hugged Emily to his chest and his hair remained in ribbon-bound pigtails. All of that would remain a secret from Nicole, at least for now.
Betty Pearl's Sissy Stories 20.1
Topic: Dani's Little Sister (Read 38917 times)
