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:
