Sissy for Sister

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.

---

Sienna had been watching Myles sleep; watching him struggle and strain. It had been a restless night. One he'd wished for, one where he and Sienna slept in the same bed. He was naked, while she wore pyjamas, and he was in his chastity cage, and Sienna had sought to tease him from the very beginning.

He'd had naughty dreams all night, the way she rubbed up against him and pressed her thigh against his chastity cage. She looked so sweet, but a smirk was fighting desperately to creep onto her face.

"Did you sleep well?"

"I-I..." Myles didn't know what to say. There didn't appear to be a good answer. "Thank you for letting me sleep with you, Miss Sienna."

Myles sighed then, that was all he could think to say.

"I can always make room in my bed for my favourite sissy toy. So long as you're good."

A pained groan escaped him. Intense teasing and a restless night didn't seem like a reward, yet he wanted it. He wanted to be teased relentlessly by her. It aroused him as much as it confused him.

Sienna rolled onto her side, and leaned forwards towards her drawers. She pressed her butt into his thigh. She was smirking, not that Myles could see, but figured she would be. He knew that she was exaggerating her movements; that she didn't need to lean so far. Sienna grabbed a wand vibrator from her drawers and laid back, holding it in the air to show her brother.

"We have to go pick up our tree today." She moaned. "But I'd love to just lounge around in bed all day playing with my wand."

Still, Sienna remained. A couple of moments passed, and a smirk crept onto her face.

"But I suppose, if you really want to listen, I'd be willing to play with it for your sake."

It was clear that she wanted him to beg. He didn't even want to go buy the tree so early, he certainly didn't mind if she played with herself, but he didn't want to stay and listen to her. To get even more horny than he already was. And to beg for that torture...

Myles thought for a moment and explored the outside of his cage with his hand. He had never practised orgasm control and it had only been a few days since Sienna had last let him cum, yet he had never felt so horny.

"Miss Sienna..."

"Yes, sissy toy?"

"P-Please masturbate with your wand and let your slave listen to you cum."

"I could... I don't know... Do you really want me to?" She asked. She sounded unsure, but she beamed from cheek to cheek. The message was loud and clear.

"Yes, Miss Sienna. I'm begging you to let me listen to you masturbate. My dick is far too small to ever satisfy you so this is the only way you can cum with me. Please let me listen to you orgasm so that I can be reminded of how pathetic I am."

"I suppose since you asked nicely." Sienna giggled then, and kissed Myles on the cheek. Her lips lingered by his ear. "Good boy." She added.

Sienna pulled the covers back and turned on the wand. Myles wondered how exactly she was going to do this, and whether he would be told to avert his eyes, but was relieved to see Sienna just press the wand up against her cleft of Venus.

She shuffled on the bed and moaned softly. She pressed her head up against Myles and shut her eyes. Slowly, Sienna circled her clitoris with the wand, rapidly easing and applying more pressure. The girl was clearly an expert, and Myles wondered how long it might be before he got to feel her orgasm. His caged cock began to leak.

Soon enough, Myles had his answer. Sienna began to shake, her hips lifted and she began involuntarily humping the wand. Her soft moans became more forceful until she was roaring with pleasure--her lips so soft and inviting and her open mouth sewn together with saliva so lewd--she shook through an awesome orgasm.

As she came down from that climax, she opened her eyes, looked up at Myles through loose strands of hair clinging to her forehead and smiled sweetly.

"I was only planning on teasing you once... But now I want more..." There was a flash of some unknown look on her face to cut up her gaze of genuine happiness, comfort and love. Her hand explored Myles and found the pre-cum dribbling down the bars of his chastity cage. She brought her now wet fingers up to her mouth and licked them clean. And smiled at him again.

"A bit of a reward for you..." She hummed. Her hand with the wand lingered near her crotch, and the emotion passed from her face. She looked vacant for a moment. And sighed. "I shouldn't waste time on another one. Come on, it's time to get up."

And that flash of emotion became clear. Myles had to beg her again.

"W-Wait, Miss Sienna. Please give yourself another orgasm to tease me more. The more aroused I am, the better I can serve as you since it's the only thing I'm good for."

"Oh, that's so pathetic... Good boy. But I wonder how many I could make you beg for before you just can't take it anymore. Fortunately for you, we won't have time today. I want to get down to the tree farm before all the good ones are taken. This really will be the last time now. You'd better make sure I remember when I want a third one."

"Will do, Miss Sienna."

After a second orgasm, a wet patch started to fade in on her panties, and Sienna sent Myles out to get breakfast ready so she could change clothes. After breakfast, she let him get changed but handed him his prostate manager and confided that she was wearing her vibrator as well.

It was a short drive out of town past the Christmas market. Sienna focused on the road for the most part. Myles could feel her tense up as they got past the safety of the town's boundaries. But she looked cute when she focused, bit on her tongue and letting it part those soft lips of hers. She noticed he was staring at her, and she smiled.

"What?" For once she sounded a little embarrassed.

"I was just thinking how cute you look right now, Miss Sienna."

"That's a coincidence. I was just thinking how cute you look riding dick." She replied. Thinking about it clearly then, Myles nodded his head. He should have seen that one coming, he told himself. But now he had Sienna talking, she didn't seem keen to be quiet again.

"Last year, Mum wasn't here to come pick up the tree either. Obviously, a sweet little girl like me couldn't manage to get the tree on the car all by myself. So I guilt-tripped Uncle Rab into helping me buy one. As much fun as I had with him, I think today is going to be much better."

Myles hoped so too. To make up for the time he'd missed. The time he'd abandoned her outright, and the time he'd ignored her to run from his feelings.

There weren't many customers at the farm at that early time of day. And there were many spots free in the car park. They pulled in and Sienna seemed to relax. She smirked upon getting the car straight first try. She didn't hesitate to rush out the car and circle it to make sure. She practically jumped in the air throwing her fist to the sky.

"Yes!" She called out. Myles watched her from by the door on his side. He slammed it closed.

"Good job, Miss Sienna."

"It is, isn't it?"

"Are you afraid of driving outside of town?"

"I haven't had much experience yet. But I'm glad you're here with me. You make me feel safe."

Myles smiled at her. That was the sort of line every guy wanted to hear from his girlfriend. Even an incestuous sissy loved hearing it from his domme sister. Sienna looked so pleased with herself she decided to give herself a reward, and fiddled with her phone. Their vibrators sprung to life, and Myles felt such a pressure in his loins already. Sienna hurried to him and hugged his arm tightly.

"Tell me when you get close, Myles."

Sienna rushed around the car and led her brother into the tree farm. There was still a great selection of trees cut and ready to be wrapped. Sienna seemed stumped what to pick. Though she knew how to decorate the tree well, picking one was another matter. Her Mum had always bought what her daughter picked, but Sienna did appreciate the suggestions of her Mum and her big brother.

So after they had seen them all, Myles pointed one out.

"How about that one?"

"Don't you think it's a little short and thin and limp and... I don't know, pathetic?" Her sly smirk told him what she was talking about. He gulped. It quickly became clear how she was planning on entertaining herself. "What about that one over there?"

She led him over and she stood beside it. Her posture, with her arms pulled in and held under her breasts, the way she leaned in to it, it was like she was with a man who towered over her, who made her feel protected in his frame. Myles almost whimpered. He couldn't believe he was being cucked by a damn Christmas tree.

"If you like that one..." He moaned.

"Perhaps it's a bit more than a girl like me can handle. I mean, it's a lot of wood."

Sienna giggled at the sight of his struggling face.

"Oh, come on, sissy toy, this is just sad. Don't finish yet."

"A-Alright." It was certainly tough, but it sounded like she planned on letting him cum, and that gave him what strength he needed.

Pointing out more flaws with the trees he suggested, Sienna found reasons to press up against him, bend over in front of him, and stretch once or twice to lift her jumper and show him her cute toned stomach.

The hardest part was when she bent over in front of him and pressed her arse against his cage. She moaned softly while she did it, and Myles couldn't help but press against her harder while his dick drooled for her. She looked up at him but didn't stand up, the arch to her back was so irresistible, and that naughty face she made only threatened to finish him right there and then.

She mouthed a warning at him, and he felt weak in the knees. He could barely stand, but felt that warning loud and clear. If he came, there would be consequences. But, Myles questioned whether he could tolerate this, or whether it was just too much. He barely noticed when Sienna sauntered back over to the first tree.

"You were right the first time." She lilted. "This tree is perfect. Let's get it."

Only when she waved him over, did he notice what was going on. Sienna watched him with a smirk as he struggled to make his way to her.

"You can't last much longer, can you?" She asked. There was very little playfulness in her voice. Myles shook his head to answer. And Sienna withdrew her phone.

"I'll turn it down for now. But I want to keep you riding that edge. When the buzzing goes back to full, cum for me, okay?"

"O-Okay." He nervously answered. 'How long would she force him to ride the edge', he questioned, but did not think it wise to ask her. In just a moment, Sienna had also dragged the owner of the tree farm over to buy the tree in question.

"Good morning, sweetie." The man said. He knew Sienna by name, since she and her mother had been coming for years.

"Good morning, Mr Tate. We'd like..."

"Aren't you going to introduce me, Sienna?" He cut her off. "Is this your boyfriend?"

Sienna blushed and furiously shook her head--which upset Myles a little--but he understood the need to keep up appearances with the owner who clearly had a good memory.

"This is Myles, my brother. You remember him, don't you?"

"Oh, yes: Myles! I haven't seen you in what... Four years?"

"I think so." Myles answered. He was focusing too much on the gentle, yet unmistakable buzzing in his arse. But though he didn't have the energy to spare to do the maths, four years sounded about right as the time Myles had avoided Sienna for.

With that reintroduction out of the way, Mr Tate turned back to Sienna.

"So which tree would you like, darling?"

"This one, please."

"Good choice. Are you and your brother going to be able to get it to the car by yourselves?"

"I can handle it." Myles answered, feeling like he had to. And when he did, the buzzing went on full blast. Sienna covered her chin and mouth with her hand, to cover a little of her flush and stifle any moans she made. While Myles could barely control himself. He had been told to cum when this happened, but trying to stealthily cum in front of someone else felt so humiliating. And so wrong. Yet, any resistance Myles might have once been able to front against Sienna had been wiped away by the position of authority she held over him. He simply lacked the strength to resist her now. And so, he let his body shake as he came.

He whimpered as he filled his boxers with his thin, watery semen. Mr Tate kept glancing over, but Sienna did well to distract him. She made a few comments, then handed over the cash. Mr Tate watched the red-faced Myles as he headed away past one of the rows of trees. Sienna kept her eyes off of Myles, staring at the tree they had bought. Myles slowly approached, and her smile grew wider despite her desperate attempts to keep a plain look.

And so she couldn't hold it in. She giggled hard at his expense. Myles felt like he was about to cry. But Sienna didn't look at him.

"Come on, sissy toy. You wouldn't make a little girl like me carry this tree to the car, would you?"

"N-No, Miss Sienna." Myles wrapped the tree and carried it to the car. Myles strapped it to the roof while Sienna sat inside and toyed with their vibrators. She enjoyed herself and rubbed her clitoris through her trousers trying to achieve another orgasm, though only served to tease herself instead. She regretted trying it at all and vowed to take it out on her slave.

Myles climbed into the car after her and she smiled at him.

"All done?"

Myles nodded and watched Sienna check her mirrors and adjust her glasses. She brushed her fringe aside and fruitlessly tried to tighten her hair buns without having to redo them. Again, she didn't notice the tears welling in Myles' eyes.

"That was so funny. Did you enjoy it?" She asked. Myles watched her, a small and weak part of him demanded that he ask her to look at him, to get the answer for herself, but he couldn't. So he simply nodded.

"Y-Yes, Miss Sienna."

He decided to be quiet and suffer through it, hoping that if he didn't say anything, it would get better in future. Sienna fired the engine, and pulled out of the spot. Giving the road her full attention on the way back, she didn't sense Myles watching her again, but her mind began to wander regardless. And she noticed something, something that didn't sit right the whole journey.

When they arrived, she twisted the key and sat still. She glanced over at her brother. He sat with one elbow on the ridge beside the window, and cradled his forehead with his hand. The positioning hid his eyes from Sienna, and he stared sideways out the window, barely moving. She sunk into her chair a little, and spoke with the softest voice she could manage.

"Myles? Are you okay?"

"Yes, Miss Sienna."

"It's just that you didn't say a word to me on the way back."

"Sorry, Miss Sienna. I was deep in thought." Still, he didn't turn his head to look at her.

"Are you sure that's all it is?"

"Yes. I'm okay."

He opened the car door and got out, shut it and rushed into the house. He quickly undressed and ran into the downstairs bathroom. By that time, Sienna still hadn't left the car. But she did slowly. She locked it and headed in and over to the bathroom. Inside, she could hear Myles sobbing. She knocked, and the sounds inside stopped.

"I went too far today. I'm sorry. I got carried away. I promise that it won't happen again." Yet, she recalled saying something like that the day prior. A look of worry spread across her face. "I'm going to be a good Mistress." She added. But she struggled to believe those words herself as she tried to convince Myles of them.

He didn't reply. So Sienna simply took a step away from the door. He needed space, and she figured she could bring in the tree on her own. By the time she made it back inside the house, Myles had escaped to his room. Sienna made dinner that day as way of an apology, and by then, he had managed to stem his tears and put on a brave face, and changed the subject whenever Sienna broached the topic of what happened at the tree farm.

It felt tense and they both knew that neither could be happy if they didn't know what the other wanted or expected from this relationship. Those rules that Sienna laid out when she offered Myles to become her slave seemed to have slipped away from them. And renegotiating their agreement, while so simple in concept, seemed so hard to even bring up in practise. Yet, it was clear that if they didn't so something, their relationship was cruising along to heartbreak, and neither could bring themselves to change course.