Sissy for Sister Ch. 09

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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A week had passed since Myles had kissed Sienna and earned himself an absolute minimum of one week before he could cum again. Fortunately, Sienna was not going to make him wait any longer. It was the final day Myles and Sienna had with James. The following morning, he was due to return home. Myles and Sienna wanted to see him off at the airport, and had booked two nights in the countryside and had a full day planned, including sledding, a movie, dinner and a romantic ride under the stars on a reindeer-drawn carriage. Out here, with little traffic to invade their ears with the rough sounds of engines and horns, a clear forecast and little light pollution to hide away their view of the stars, the night was due to be a perfect one.

Sienna had told Myles that she and James wanted to spend the day with Rose. But she didn't make Rose wear the bell around her clitty, and go without panties. To go sledding, Sienna had let her dress in warm gear and thick leggings.

But that didn't mean she hadn't let Rose go without a little gift from her. Rose wore her prostate massager, waiting for Sienna and James to come down so they could go out. Sienna had told Rose that she needed James' help to get ready, so Rose sat in front of the fireplace in the lobby of the bed and breakfast, watching the logs crackle and burn, involuntarily twitching to the buzzing inside her and wishing that she was instead in the room with her sister and best friend, her eyes to the floor while she listened to them have sex. That's what they were doing, she was certain of it.

Rose was in for a day of teasing like no other. Back in the room, before she was sent out, Sienna pulled her leggings and her panties down, loosened her up with lube and slowly inserted the prostate massager. And then she turned it on and sent Rose on her way with one single message:

"I'm going to let you cum for being such a good boy recently. But you're still only allowed to have one. Tell me if you cream your panties and I'll turn down the vibrator to go easy on you. But if you don't want to cum during the day, James and I will spit roast you tonight. Your choice."

Rose sat, desperately wanting to feel Sienna's dildo inside her, along with James' cock, but she didn't know how much more of this she could take. She hated the sly smile on Sienna's face when she acted like enduring a whole day of this pleasure would be no big deal.

"How do we look?" Sienna's voice brought Rose back into the room, and she gazed round just barely holding back an orgasm. Her whole body tensed and she edged. So little of Rose's mind had the resistance left to hold that edge back. So much of her wanted to give in and have an easier day, but she wanted that reward for enduring this. That tiny part of her mind won out and she brought herself back from the edge, shuddering while she did. Her panties were already full of pre-cum.

Rose stared at them for a moment longer. Sienna looked so beautiful in her big waterproof coat and leggings that matched her own, and James looked so handsome with his hair styled back over and a clean shave.

"D-Did you...?" Rose couldn't finish her question, but Sienna understood.

"Yes." She answered. "Did you?"

"N-No. I almost did. I want to hold on for you, Miss Sienna."

"I know how you feel, Rose." James added. "If it helps, I have it pretty hard too, having to stare at two beautiful girls all day. It's pretty much on par with waterboarding."

Rose tried to force a smile, but the weaponised pleasure concentrated against her prostate simply broke her.

"...You arsehole..."

What should have been a fun time sledding that gave Rose a chance to ignore the massager buzzing against her prostate increased the pleasure she felt. Every bump and bounce on the ride down buried it inside her further and as it rubbed against her prostate it increased everything she felt. Simply sliding down a hill became the most difficult teasing she'd ever endured.

Already driven mad with pleasure, Rose imagined herself getting railed by every sexy woman she saw and every handsome man. She almost felt like they were all staring at her, thinking the same thing as she was.

Touring the village after lunch, Rose seemed to trail behind Sienna and James. Her little sister approached her and snuggled up against her as they walked.

"You know, you don't have to suffer like this. It's already been three hours. But you've still got about eight more to go. You can cum. I told you that. You can." Sienna then led Rose over to the side of the street and pinned her up against the wall and whispered so softly into her ear:

"Go on, just give in. Cum for me."

Rose started squirming. She hated just how little power she had to resist her cruel little sister. Just those words and she lost control. She felt herself spiralling towards that orgasm. Her clitty shook violently in its cage. And her arse shook on her prostate massager.

"Cum like a shameless little slave."

"Don't tease her like that, Sienna." James warned. Focusing on his voice, Rose managed to hold on momentarily. It would only take another word from Sienna to make her fire her load so hard. But instead, Sienna giggled.

"Okay, okay. I won't cheat." She teased. As she turned away, though, she brushed her hand off of Rose's chastity cage, earning another whimper. The slave just about fell to her knees sobbing. But she held on, and didn't cum. Sienna giggled and she and James continued on ahead, to let Rose pick herself back up at her own pace.

Rose couldn't pay attention to the movie at all. It was a small movie theatre. Only one screen. Only a few dozen seats. Small and cosy to suit the village. It was some action flick with a handsome lead actor that Rose couldn't stop fantasising about. The way he'd overpower her, force her onto the bed, toss her over, pull up her dress and have his way with her.

Rose edged every few minutes. She kept her eye on the time. But there was still so long to go before they'd get back into that bed and breakfast and she could get her sister's strap-on inside her. She longed for the strength to endure, but she didn't know if she could manage it.

During dinner, she had a little bit of a reprieve. The restaurant was rather quiet, so Sienna did her the favour of turning the vibrator speed down. Rose struggled to small talk her way through, her voice weak and shaky, stuttering and repeating herself and losing track of the conversation constantly, she was clearly a wreck. James felt really bad for Rose when Sienna asked to go to the restroom together once dinner was over. He could only imagine that they would come back with news that Rose had failed to hold on long enough.

But in that restroom, Rose stood leaned against the sinks barely managing to hold herself up. She panted and softly moaned. She didn't care if anyone was in there with them, she could barely hold on.

"You've only got about two hours left. I am so proud of you for making it this long. I was going to tease you and make you cum, but actually, I find myself rooting for you. But you're not going to do it. You know that, right? As soon as we leave, I'm going to turn the vibrator back up and... You just won't be able to hold on."

"I'll hold on. I-I p-promise." She barely managed to say.

"You didn't get to cum at all this week, sissy toy. And you have to remember that I own your clitty. Any orgasm could be your last. So why not enjoy each one like it will be your last. Don't try to hold on and fail. Just let yourself cum and enjoy it."

"Y-Yes, Miss Sienna."

"Don't 'Yes, Miss Sienna' me; it's not an order. Just a suggestion." Sienna applied a fresh coat of lipstick and made kissy faces in her reflection. "You could do with a fresh coat as well. You must have been drooling all over yourself all day."

Seeing that Rose was in no state to handle a delicate task like putting on her own lipstick, Sienna did it for her, and led her sissy outside the restroom. Sienna let James 'pay' for the meal, but really, it was Rose who actually had to. She followed her sister and her best friend outside, where she was promised a shameful, sad end to her hours of teasing.

Stood away from the doors of the restaurant, under a thick blanket of clouds and the heavy buzzing of a streetlight in the car park, Sienna took out her phone and turned on the screen. She looked to be going intentionally slowly, even hesitating to do what she needed to.

"Rose, please tell me that you want to fail this and just enjoy your orgasm."

"Yes, Miss..."

"Only if you want to." James interjected. Rose looked at him with innocent eyes, she looked so weak and really needed help. She could barely manage, every bit of will had been sapped from her, and even at the best of times she couldn't resister her owner.

But Rose managed a face of a little confidence, yet felt her knees wobble.

"Please, Miss Sienna. Make me cum shamefully."

And then Sienna sighed. And the phone hung lazily by her side.

"You don't really want to cum now, do you? Myles, listen to me: Just give in. You're going to cum when I turn it up. If you don't try to enjoy this, I'm going to feel like a really shitty person. You don't want to make me feel that way, do you?"

James leaned down to Sienna, and whispered something into her ear. And she nodded.

"Okay, sissy toy. If you beg me, I won't turn it up."

Rose opened her mouth to let the desperate, shameful words roll off her tongue and beg for her sister to take it easy on her, but no words came. She remembered her promise to Sienna, and wanted to make her sister happy. It was obvious Sienna was only giving her this opportunity as a compromise to make Rose happy, at the expense of her own. Rose couldn't allow that, so she promised herself that she would always put Sienna's happiness before her own, and find strength in her love of submitting to her little sister. Because she did love it, more than anything else in the whole world. She forever wanted to be dominated by her little sister; sweet and innocent and cruel and devious all at the same time.

Now seemed like the perfect opportunity to do as she had promised and be a man.

"No, Miss Sienna. You're not going to abandon your original plan. Turn it up."

"B-But you'll...?" After the shock, Sienna composed herself. Rose looked so weak, but determined not to fail. There was a quiet resolve in her eyes. Compassion, fuelled by love. Sienna smiled and lifted her phone.

"Good luck." James told her.

"Yeah, good luck, sissy toy. We're both rooting for you."

Sienna turned the vibrator to max, and Rose moaned aloud and once again fell to her knees. She moaned and moaned and Sienna could only watch and hope she could pull back from that looming edge. Even James felt tight in the chest. After a couple of minutes, Rose picked herself up off the ground.

"Miss Sienna... I can do it." She couldn't even open both eyes, but she was just to say holding on. "You give me the strength to be your perfect slave. I will never let you down. I love you."

"Good boy..." Sienna's voice cracked. A couple tears ran down her cheeks. "I love you too. So much."

Sienna wiped her face clean and ran to Rose and hugged her tightly, forgetting just how much more agonising that made it on the poor slave.

The three enjoyed that horse-drawn carriage ride. The clouds parted to reveal the starlight. And what a beauty that sky was. It was a fairy-tale ending. Sienna felt like the luckiest girl in the world, and maybe she was right. She, Rose and James all had everything they ever wanted, together on that night. The three snuggled together looking up towards the night sky and toured the historic village for the most unforgettable hour of their whole lives.

When they got into their room at the bed and breakfast, Rose didn't hesitate to strip down to her bra and panties. Sienna hurried to get her phone out and turned off her prostate massager. Rose pulled forwards her panties to prove that, though they'd looked like she'd gone for a swim, there was no cum inside them, and her balls were still full and swollen behind her cage.

James approached Rose and pulled her chin upwards and kissed her deeply while Sienna prepared. She stripped down to her panties and her bra, and stepped into her strap-on. She pulled it up and fastened it tight, and then moved back towards Rose. She swung her hips and slapped Rose's cage with the dildo a few times.

"Look at this obscene little clit." She grasped her own rubber phallus. "This is what a dick is supposed to look like. Or like this." Sienna gave the signal to James, and he exposed his own as well. "Go on, sissy toy, work your magic."

Rose got down to her knees to worship both of the cocks in front of her. Stroking James' while sucking Sienna's got a giggle from the girl.

"Good boy. Don't go too hard on James and make him cum, I want a big goodbye present from him."

When Rose did take James' cock into her mouth, she went slow and steady, opting to slowly deep throat him and really show off her skills. Each deep throat, she held for two seconds. And all without gagging. The smile on Sienna's face was huge and she just wanted to grab James and feel him on top of her right away, but her sissy needed her attention. She deserved every bit of it.

James backed up and sat on the edge of the bed and Rose followed to keep sucking his beautiful dick. She knelt on the floor while Sienna approached from behind. When Sienna tried to pull the prostate massager from Rose's arse, every muscle fought back against her. So much that Sienna didn't think she could do it.

"Sissy toy, I'm going to need you to relax." She pulled again and again Rose's butt rejected her stealing away its toy. Her arousal flared with each little rub against her prostate. "James, do you have a crowbar?"

"You need to make her less horny."

"Yeah, I figured. Okay, here goes. Don't be upset about this Rose, you're not being punished. It's just pragmatic."

Sienna grasped the plug, and pulled as far as she could. Rose still eagerly serviced James, everything else had melted away in her brain. She was just a pair of holes to be railed for the pleasure of others. But that all froze when she felt a sharp slap against her balls. She cried in pain despite James' dick in her mouth.

"Woah, get that out. I don't want you biting off my dick."

The saliva clinging between Rose's slutty mouth and James' cock looked incredible. Rose just wanted to lick it all up. But suddenly, there was another, even harder strike to her worthless little balls. A third. And a fourth that just about reduced Rose to tears.

"It's okay. It's okay." James told her. "Just look up. Keep staring into my eyes. You're really beautiful tonight. You are so stunning."

His voice and kind words helped Rose endure two more hard slaps to the balls. Finally, Sienna managed to get the plug out. She licked it clean for James to watch. James stroked Rose's hair back over her ear, and then eased her lips down onto his cock again. Sienna got on all fours and put her tongue to Rose's arse.

Exploring Rose's insides tasted incredible, and Sienna felt intoxicated by it. The questions that pierced her mind such as 'why have I never done this before now?' made her kick herself for her foolishness. She laid on her belly and tasted Rose for far longer than originally anticipated. When Rose's areshole was just a mess of red lipstick smears and dripping with Sienna's saliva, Sienna finally got back up onto her knees, and pressed her warm body up against Rose's slender back, and pushed her dildo inside.

"Fuck, I could get addicted to the taste of your tight little butt, Rose."

Sienna slid her dildo into Rose's saliva-lubed arse easily. Immediately, Rose's well-trained body responded and she leaned forwards into James' cock, curving her back to give her little sister a better angle of penetration. Grasping Rose's small crotch, she could feel her brother's balls tighten with each thrust. Sienna could feel how close Rose was to blowing her eager load.

Even after those hard slaps to her poor balls, Rose was close already. After a whole day of teasing, she wanted to be fucked senseless. Sienna pounded away into Rose, while James held the back of her head and guided her up and down his pole. Rose began to moan, and James took charge.

"About to cum?" He asked. Rose nodded at him while sucking his cock, her big eyes pleading to make it feel really, really good. He wanted her to have a good one, but she was the only one who could make it any better now. "Okay, can you try to ride the edge for fifteen seconds this time?"

As horny as she was, fifteen seconds felt like a lifetime. Each passed painfully slowly, and her little sister didn't relent. Each second was filled with three long slaps against her arse with that fat dildo she wore.

Rose reached that fifteen second mark and moaned loud again.

"What about another fifteen?" Sienna teased her with. Rose, it seemed, could do nothing but groan. Sienna let off the speed a little and leaned in to press their bodies together, and whispered seductively into her sissy brother's ear:

"If you manage it, I'll encourage you."

With that, Sienna sped up again, as fast as she could, actually managing to reach a speed of two hundred thrusts per minute. With each and every thrust, Rose's caged cock sputtered pre-cum, mixed with her cum, through a painful and ruined orgasm that lasted the whole fifteen seconds. But since she achieved her goal in a sense, Sienna leaned in again, and gave Rose her final reward.

"Good boy. Your submission makes me wetter than any boy has ever made me." She said them quietly. Those words were not for James' ears, but for Rose alone. And that made the femboy so very happy. She finally let go and felt her ruin turn into a glorious full anal orgasm. As she fired her load, her entire body shuddered and James thrust his entire cock down her throat to keep her still. It lasted almost a minute and Rose had left a big pool of cum on the floor, and had milked her balls entirely. She collapsed into her pool of cum, with barely the strength to move from the spot. Sienna stood and slipped off the dildo.

"You look so pathetic laying in your own cum. I love it. But now that my sissy toy with her little baby dick has had her fun, it's time for the grown-ups to play. Just stay there until we're done, okay, Rose?"

Sienna threw herself into James' arms with as much passion as she could muster. This boy, who she'd come to care for so much in just over a week, she was greatly disappointed would have to leave so soon.

James unhooked Sienna's bra and tossed it from the bed, threw her to her back and began kissing her neck, down her chest, over her breasts, and down her tummy. She cooed.

"James." She asked, stroking his hair. "You will come again, won't you?"

Reaching her crotch, James pulled down her panties, and slid them all the way down her slender legs and sent them in the same direction as her bra. He climbed in between her knees and lined up his cock. He came in for another kiss as he entered her wet and warm pussy.

"I'll come for the whole Easter break." He promised. She giggled and they kept kissing.

Rose could only follow the instructions she had been given, laying in her own stinky cum, listening to Sienna get fucked by a man she was falling in love with, as she became hornier and hornier to undo the amazing reward she had just received. And as she lay there, she simply beamed the biggest grin. It truly had been an amazing day.