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.
