Sissy for Sister Ch. 02

Author's Note: This is a fictional story about a brother and sister relationship featuring gentle female domination over a crossdressing brother with gay sex and chastity. Since each chapter may contain content that falls under different categories, please refer to the 'Story Tags' tab under 'Story Info' for a list of categories this chapter includes.

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Myles tossed and turned in bed. His mind was on fire. He knew he was dreaming, but lacked the strength to awaken. His dream would go on undisturbed. It was a scenario like so many he'd experienced for real, and so many more he'd imagined. Dressed in black negligee and wearing a rose gold coloured wig, in his Rose Gold persona, locked in chastity, 'Rose' sucked another boy's cock while he sat in a powerful position, watching a boy pound a girl on the TV.

His name was James. He was Myles' 'jerk buddy', and the only person who knew that Myles was Rose Gold. They played a lot of masturbation games together, roulette games that decided what they would watch and how the winner would punish the loser. Myles almost never won, so James frequently got to have his way with Rose. And sometimes, just for good measure, James would measure both their penises and humiliate James for having such a small one. And use that as a pretence to fuck Rose.

Rose felt her orgasm coming. She toyed with and prodded at the cage, and felt like she would blow her load soon. It was an odd sensation, she had never cum from cageplay, nor from anal sex. Myles had only ever cum from direct stimulation to his penis--'her clitty' in his Rose Gold persona.

That had changed, however, with Sienna teasing Myles to an orgasm.

Myles awoke tossing and turning to the fire in his loins. His erection tented the quilt. He threw it off and gazed upon himself. Last night was for the first time in over a year that he wore boy's pyjamas.

He had thought it wise sleep as Myles for a few days while he adjusted so he could avoid any awkward, life-changing, disastrous surprises. But not being able to see his hard-on through his sheer nightgown felt unusual.

Laying his head back against his pillow, Myles pulled his trousers down past his dick and wrapped his fingers around it. A couple of strokes later an image popped into his head; of Sienna speared on Damien's cock. He tried to replace his former bully with himself, or James or someone else entirely, but both Damien and Sienna looked his way and laughed at him. He desperately imagined his sister being brought to an earth-shattering climax.

So he shook the vision from his imagination. He got out of bed, put on his Rose Gold wig, and called James.

"Hey Myles, what's up?"

"I-It's Rose... I miss you."

"It's only been a few days, and I told you on Wednesday we'll see each other again. I think I could come to see you for a few days before Christmas if you'd like."

"That would be nice. Would we play games?"

"Sure will. I'll even give you a handicap so you have a fair chance to top me for a change."

"Really?" I'd certainly appreciate the generosity... I'd make sure to repay you somehow."

"I can think of a couple things I'd like..." James lilted. Rose giggled.

"But how am I going to cope in the meantime?" She begged.

"Play a few roulettes. I know you love them. Find a guy and let him have his way with you. If you're really so horny then put on your cage right now and channel all of that energy towards your date."

"Put on my chastity cage?" Her heart pounded, she needed to cum.

"Sure. Put it on now regardless of whether the roulette says you should be chaste or not."

"O-Okay."

"Gotta go. Speak to you soon, yeah?"

"Yeah. Bye. I miss you."

They hung up and Rose returned to her suitcase. She collected her chastity cage, and began to tremble. She loved the thing and felt terrified of it at the same time. Putting her fate in someone else's hands, or the hands of a cold dice roll for a roulette game that would determine how long she had to be caged for felt so exhilarating. It was a micro chastity cage not even two inches from the base ring to the tip of the cage. It had a snug fit that Rose could not escape from. It had an internal locking bolt and a pair of two keys. Rose slid the bolt out and the cage collapsed into two halves. She slid the base ring on and gave it a tug, to get comfortable. She had no idea how long she'd have to be caged for. Then she slid the cage itself over the top and once more adjusted the fit, before sliding the bolt back in and sealing herself with a twist of the key.

Feeling the heat rising within her, she stripped off her pyjamas and carried a dildo to her bed, she sat up against the headboard and snapped a selfie, making sure to get her whole, feminine body, the cage and the dildo. She posted it on her Rose Gold account, and made sure to get changed before heading downstairs.

"Bad news, big bro: Mum said she won't be able to make it today. She doesn't know when she'll be home now."

Sad news to greet him with, with a matching expression plastered on Sienna's cute face. But she managed to smile up at him after that. She sat at the table eating a bowl of cereal. She was dressed in warm Christmas-themed pyjamas. There was nothing particularly sexy about anything she did, but his dick tensed in its cage regardless. He prayed a silent 'thank you' to James for suggesting the cage, and then got a bowl for himself.

Myles phone kept beeping as the first responses to Rose's post came in.

"Looks like you're really blowing up." Sienna commented. Myles sat down across from her and checked his phone at an angle she couldn't see the screen. Many comments were supportive, a lot of her fans loved seeing Rose in chastity, and some were suggestions for more sex tapes. Rose also had a few more subscribers including one called 'Bussy_Breaker_5599'. She had become really popular and was making a lot of money. Myles would soon be able to pay off his university fees on Rose's income alone.

"It's just a group chat." Myles lied. He put his phone on silent and placed it face down on the table. "Had a good sleep?"

"Like a baby." Sienna replied. "I haven't slept that well since before you left. I'm glad you're back."

"Me too."

Sienna finished her bowl and carried it over to the dishwasher. She glanced back over her shoulder while she loaded it away.

"Hey, I thought you should know something. I didn't mean what I said last night. I got carried away. Damien didn't... You know... Take my virginity."

"So you're still a...?"

"No! Absolutely not!" Sienna cut her brother off. "But I've never done it with Damien. I just thought it would be hotter to talk about him fucking me than some guy you don't even know."

"Why are you telling me this?" Myles asked. As hot and bothered as it had made him, he didn't really want to think about his sister getting railed by anyone. Even in his fantasies, he never thought about actually fucking his sister, just kissing and touching her and licking her to orgasm before she'd suck him off.

"Because I thought I should come clean about my own love life before I asked about yours."

Myles gulped hard. There was no way he could answer honestly about all the things he'd done; the humiliating situations, the cross-dressing and chastity. Even just about the toys he owned. But he figured he knew the first question she would ask:

"Do you have a girlfriend?"

"No." He answered her. Her face twisted to one of sympathy.

"I bet now that you're back all the girls will look at you like a gallant soldier returning from war. You'll forever be my hero."

"Thanks." He answered. She looked so adorable in his eyes.

"But to be honest, I thought maybe you did have a girlfriend: Rose Gold."

Struggling to keep a calm outward appearance, Myles felt his heart racing. He slowly shook his head as to not lose control.

"N-No... I don't actually know who she is."

"So she's just some femboy on the internet you like?"

"Like? Yeah. I mean, no. It's just that... She was... Recommended to me by a friend. I only just subscribed, I have no idea if I'll resub next month."

"That's a shame." Sienna sat down at the TV and began flicking through the channels. "I subscribed to her on DigiHoles last night and looked through her catalogue. I had a lot of fun watching her get fucked. I hoped we could watch her together and play sometime."

"P-Play?! You mean like last night?!"

"Obviously. I'm not saying we should play a board game while we watch her. Promise me you'll watch a few more of her videos before you make up your mind about her."

"I promise."

He silently promised more than that. He promised Sienna would always have more content to enjoy. After breakfast, he found an excuse to go upstairs and get cracking to play a roulette and set up his next date.

That day, Rose played a roulette to decide who she would let fuck her, how, for how long, where and what she would wear. Then she went on another date the following day. And another after that. Unknowingly, Sienna kept teasing Myles with a pair of jeans that made her arse look incredible, or by walking barefoot around the house, or by cooing to films with a purr that sounded remarkably similar to those she made when he watched her cum.

So Rose got fucked in lingerie at some guy's house. She got fucked dressed as a maid in Sienna's room while she was at work. And she sucked some guy off late at night in a movie theatre.

It just made her hornier and hornier. None of those guys had been able to make her cum in her cage no matter what they did to her. She sat in her room trembling at her laptop looking for the next roulette to play; that would instruct her how to fuck her next date.

While she was looking, a message came through on her dating app. It was only one of many, but this one gave her cause to have more than a quick glance down to her phone. Yet, she didn't realise why at first. The username 'Bussy_Breaker_5599' seemed somehow familiar to her.

The opening line of the conversation told her exactly where she had heard the name:

"Are you Rose Gold?"

"Yes." Rose cautiously replied. She didn't know if it was wise to reveal that, and risk her location getting leaked to her followers, but this fan may have already figured it out anyway. She had set her username to Rose, and the rose gold hair in her profile picture was a big clue for those in the know.

"I love your DigiHoles videos. Wanna meet?"

Rose typed out a reply that would let this guy down gently, but hesitated to hit send. Her eyes glanced back up to her laptop, and she looked again for a roulette to play. Perhaps it would be fate that she'd be his. Judging by his profile picture, he was a blonde man, rather handsome. Knowing that he made videos, he might have been more willing to let her make one with him.

She rolled a roulette and the man came up unlucky. For who she would fuck, the roulette told her she'd have to pick 'someone younger' than her. This man was most certainly older than she was. Yet, still her hand hovered over the send button. Rose bit her bottom lip and thought to herself that there was no harm in seeing someone else while she set up her next roulette date.

So she deleted her response, and typed out another.

"I'm in Watwick at the moment. Where do you want to meet?"

"Could you come to my house? I'll send you the address."

The address came through, and Rose stood to grab her sexiest lingerie and a dress to put over it.

"I'll be over in an hour." She replied.

"Looking forward to it, sissy toy."

Rose's eyes kept meeting the taxi driver's staring at her in the rear view mirror. She fidgeted with her purse to keep her hands busy. She wondered if the taxi driver wanted something extra from her, and fantasies of him drilling her little arsehole ran through her mind. Her lust was driving her crazy, she hoped the time would soon come when it would feel right to take off her chastity cage and reward herself with a powerful orgasm to her little clit.

Until that day, the lust she wore openly would continue to entice men like this one, who could not tell that the beautiful young woman he had in the back of his car was actually a dirty, cock-addicted femboy.

They arrived at their destination and Rose handed over the fare. She got out and went to knock on the door. The man opened the door and Rose smiled up at him. She felt so small in his presence. He was a fine specimen of a man, someone worthy of punishing her tight sissy arse for the sin of being so weak and submissive.

This man, who Rose only knew by his username 'Bussy_Breaker_5599', led her inside and shut the door behind her.

"You look exactly how I expected you to look."

"Did you think I would catfish you?" Rose asked. She giggled a little but did want an answer. She was confused what exactly he was talking about.

"I have a confession to make. I haven't been talking to you at all. I don't even have that hook-up app. I didn't set up this date."

"You didn't...? Then who did?"

"Someone who wanted to lure you here. She's behind you."

"Hello, Rose Gold." A girl's voice called out calmly from behind Rose. It sounded familiar. Too familiar. She knew precisely whose voice that was. And the prospect of facing her dressed as Rose terrified her. But still, she turned slowly, to face Sienna. A sly smile was plastered on Sienna's face. If Rose wanted to get out of this one intact, she needed to think fast.