Sissy for Sister Ch. 04

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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Over the next couple days, Sienna got more information out of Myles about Rose and her lifestyle. And she took a look at all the sissy stuff he had brought back home with him.

He had so few boy clothes, and she made sure to keep him naked or in girl's lingerie whenever they were due to be at home alone. There was still no word on when their Mum would get home.

As Myles wrapped up his first week back home, Sienna came down in a sexy Christmas dress; red with white ruffles at the edging, long sleeves but only half way down her legs, kept warm by white pantyhose and matching boots. She also wore a Christmas hat.

"Sissy toy. Look what I bought. I noticed you have an outfit just like this one. Go put it on, we're going to go buy new decorations for Christmas. I think we should put them up tomorrow."

"Sounds good, Miss Sienna. I'll be back shortly."

Sienna smirked to herself as her brother rushed upstairs. Perhaps what Sienna was looking forwards to the most--what she most wanted to decorate, was Rose herself.

Downtown, Sienna pulled into parking spot and reached into her bag.

"One last thing. This is for you."

She handed Rose a prostate massager. Quite a large one at that. Rose trembled as she took it.

"It's operated by app. Does it excite you to know your cruel little sister will have control over you in public?"

"Yes, Miss Sienna."

"Good boy. Go ahead and put it in now."

Sienna leaned over with a bottle of lube, and gave a squirt onto the prostate massager. Rose glanced around and hoped no one would see her lift up her dress, pull her panties to the side and slip the massager in. She hated that her devious sister had waited until now to make her put it in, but the rest of her thoughts were scrambled when it immediately gave her a little taste of future torment, and she shivered with anticipation.

"I'm wearing one too." Sienna chirped. "I'm wearing one in my pussy. They're a pair. When yours buzzes mine does too. Let's go."

Rose felt the stares she and Sienna were getting as they walked into the shopping centre. Rose tugged on Sienna's sleeve, and leaned in as much as possible.

"Miss Sienna, don't you find it a bit embarrassing to be wearing the same outfit?"

"It is a little, isn't it? Take off your dress."

"W-What?!"

"It's simple: If you take off your dress we won't be wearing the same outfit."

"I can't. Everyone will see my clitty." Rose's panicked tone made her louder than she wanted to be, but she still stuck close to her little sis.

"You pointed out the problem, yet you're scared of the solution. Well, it can't be helped. You'll just have to do a punishment instead. I'll let you keep your dress, but you better not hesitate to do your punishment."

"I won't. I promise."

"If you do, I really will make you take off your dress. And I won't let you cum for a year."

Rose nodded her assent, and braced herself for what was to come. The thought of being denied an orgasm for a whole year was worse than any punishment Sienna could concoct. That was what Rose told herself. Because if Sienna was crueller than that... That wasn't worth thinking about.

The first store they went into was like stepping into Santa's workshop itself. The magic radiated off of every bauble and every garland running across the ceiling. Numerous decorated Christmas trees proudly towering over the aisles called to Sienna. She gasped with pure joy taking in the sights. Soon enough, her eyes were drawn to two little girls dancing to the Christmas classics blasting over the speakers.

"Come on." Sienna cheered. She rushed off into the store, and Rose felt the vibrator buzz. It really had found the perfect angle to tease her the most.

When Rose caught up to Sienna she had already put some odd bits and pieces in a trolley. She leaned over the trolley as she pushed it, seductively raising the back of her dress--the rim of her panties under her pantyhose were just out of view.

"We'll need to buy a tree tomorrow morning." Sienna told him. It seemed an obvious thing to say, they had bought a real tree every year for as long as Rose could remember. Sure, she had her issues with real trees dropping their needles in the living room, but she loved going with Sienna and her Mum to pick one up as children. It was a family tradition she had hated giving up for all the years she and Sienna had a strained relationship.

"It'll just be the two of us, this year." Rose suggested. Sienna nodded.

"True. I haven't heard anything from Mum. But that's okay, we'll make our own fun tomorrow as well."

Sienna didn't make it easy for Rose. She held the phone against the trolley handles, and her thumb ran up and down, sending pleasurable vibrations through the air and into Rose's arse. The pulsing, always faster and slower moments apart forced Rose's knees to buckle and quiver. She forced her lips down into her shoulder to moan softly. And but moments later, that wasn't good enough. She felt her clit slobbering into her panties. Sienna was clearly affected by hers too, but she leaned against the trolley and pushed slowly, rather enjoying the sensations. In control of the app, she went at the speed she could handle without taking into consideration what Rose could, or rather couldn't, endure.

Sienna collected all sorts of odd things, but Rose had learned not to question it. Her little sister always took control when it came to decorating the tree, and it always looked fantastic.

When they got out the shop, Sienna quickly pulled Rose to the side. She pulled a bright red ribbon out of the bag, and ripped it from its packaging.

"Come on, tie your hair into a ponytail with this."

Sienna tied ribbons around her twin buns. But she held one last piece of ribbon as she rummaged through her bag a second time. She revealed a little bell, and kept it in her palm. She picked up her bags and without a word headed over to the restrooms.

"Take these." She told Rose. Rose tried to take the bags, but she quickly realised Sienna was trying to hand her the items in her hands. The ribbon and the bell. "Tie that around your base ring so the bell is at the top. I want to hear you jingle when you walk."

"O-Okay, Miss Sienna." Rose hurried into the girl's restroom and into a stall to fasten the ribbon in place. She returned just a minute later, beet red. A quiet ringing accompanied her.

"I-It wouldn't jingle, so I had to take off my... My panties..." Her lip quivered. Sienna burst into a fit of giggles.

"I'm going to make you pick up so many things off the bottom shelf in the next shop."

Sienna gave her sissy sister a little buzz for good measure, and Rose whimpered softly, feeling her clitty dribble even more pre-cum. She hoped it would drip down onto the floor but instead felt it staining the fabric on the inside of her dress.

Rose hurried after her sister, jingling as she went. Rose didn't even realise where they were going. It was only when her sister stopped to check out a necklace that she realised they had gone into a clothing store. A big glass case separated them from fine silver and gold jewellery.

Another buzz rocked Rose, and she again struggled against the pleasure. A stain began to appear at the bottom of the dress behind her exposed clitty.

"Some ladies wear their slave's chastity key openly." She announced loudly, lost in thought. Rose hurriedly looked around frantically.

"Not so loud...! I mean: Not so loud, Miss Sienna."

"Almost earned yourself a second punishment there, sissy toy. Now, I'm thinking I should wear it on a silver necklace. What do you think?"

"The key is silver coloured. I think silver is the best choice too."

"Well done, you passed the test; never disagree with your Mistress." Sienna turned away from the glass case and spied one of the young women working on the shop floor. "See her over there? She's really pretty."

"Yes, Miss Sienna. She is. But she's not nearly as pretty as you."

Sienna adjusted her glasses.

"Cute. But I'm not fishing for compliments. I just wanted to tell you that I don't know who she is."

"Right?"

"I have no idea who she is. I don't know her name. I don't think I've ever seen her before."

"Yeah, I get it." Rose cautiously answered. She was sure this was going somewhere, but she didn't know where.

"Tell her I want to buy one of these necklaces. And explain that it's for your chastity key."

"W-What?!"

"I'm not going to repeat myself so you can pretend to have some dignity. This is your punishment. Go on."

Rose walked slowly across the shop floor, accompanied by the bell ringing against her chastity cage. Each step felt like a march through lava. She felt like she could drop dead any second. She almost wanted to. If her clitty wasn't drooling like mad, she could have. But the humiliation felt incredible.

"Umm, miss? My..." She realised that she couldn't say sister, and a big smile drew across her face. "My g-g-girlfriend wants to buy a necklace for my... For my chastity cage key..." Rose got redder and redder, and a smirk briefly appeared on the girl's face before she sucked in her lips and held them between her teeth. "Could you please open the cabinet?"

"Mmhmm." The shop girl nodded and quickly turned away from Rose, the smile returning only once her face was entirely hidden from the chaste femboy.

"Is that your girlfriend?" The shop girl asked aloud, nearing Sienna. Sienna turned to them, and pulled an expression that told Rose she was in trouble.

"Y-Yes." Rose answered. The buzzing came hard now, and didn't stop. Rose's clitty sputtered into her dress, widening that wet patch. An orgasm felt close.

"Hey, it's that one." Sienna pointed through the glass, and waited just a moment. "Did Rose tell you what it's for?"

"Yes." The shop girl could barely hold back her laughter.

"This is the key." Sienna flashed it. "Do you think that necklace would go well with it? I'd show you the cage as well but Rose would bawl her eyes out."

The shop girl almost choked on her tongue and couldn't hold back her smile any longer. She put her hand over her mouth to stop herself from laughing aloud, and then stroked her face to pretend to think.

"I think that one would look nice." The chain the girl pointed to looked finer and more delicate. Sienna hummed aloud, and nodded.

"You're right. I'll take that one."

The shop girl collected it and made sure to walk ahead of the siblings back to the counter. Rose could barely walk in a straight line, she stumbled and stopped and pained gasps escaped her lips. Sienna was going red from her own vibrator, but knowing Sienna was having fun too didn't make this any less embarrassing for Rose. They reached the counter and the buzzing cut off right before Rose felt like she'd hit the point of no return and cum to her sister's great ire.

Sienna made Rose pay for the chain, and then attached the key right there at the counter, and put the necklace on around her neck.

"How do I look?" She asked Rose. Rose hesitated to answer. The shop girl had made sure to float away like a leaf on the wind, just before her laughter escaped from her. Rose and Sienna stood staring into each other's eyes, listening to that maniacal laughter. Eventually, Rose winced but cast those sounds aside and forced a smile onto her face. She nodded for her sister.

"You look great. I like that you've decided to wear my key openly."

"When we're together and you're dressed like that, no one will even suspect it's yours. That's if they even know what it's for to begin with. At least it's one for an integrated lock and not just a padlock. What's even the point in wearing a key like that?"

"Umm, Miss Sienna. The exit is this way." Rose whined. Sienna was walking while she rambled, but headed further into the shop.

"Yeah, we have more things to buy. Come on."

"B-But..." Rose glanced over to the shop girl, who now stood whispering into the ear of her co-worker. Rose blushed and turned away just as the co-worker glanced at her.

"But what? Choose your next words carefully, sissy toy."

"But nothing? I'm sorry, Miss Sienna."

Rose had to follow her Mistress back into the shop, and pretend that the girls in the shop weren't all quickly learning about her situation. She felt eyes on her, but Sienna was only after one more thing. A necklace for Rose herself. She found what she was looking for, a leather choker mounted with a steel love heart.

"I'll make you wear this. When you do, it'll be a reminder of who owns you."

"Yes, Miss Sienna."

"Good, you're learning. Now, should I get it in black or white?" She mumbled. "Black goes with everything. Come on."

Again, Sienna made Rose pay for it, but to the sissy's surprise, Sienna didn't actually hand it over. She put it in her bag, and led Rose out of the shop.

"Come on, we still have a lot of decorations to purchase."

They were out for hours, and got lunch in between shops. Sienna was true to her word, and made Rose collect a lot of things from the bottom shelves of numerous shops. Every time, Rose had to crouch in a matter she was certain wouldn't make her clitty peek out under the dress, and every time Sienna stepped closer and pressed her foot up against Rose's clitty from behind.

Humiliation aside, Rose enjoyed their day. With a little bit of flirting, it felt like they were a real couple, and she felt reminded why she cared for Sienna so much. It didn't matter that other men got to fuck Sienna while she was denied; they didn't get to do this. Sure, the fact that Rose had become a cuck didn't go over her head, but she loved this arrangement, and she promised herself that she would do whatever it took to make Sienna happy, no matter how humiliating.

When they finally made it back home, Rose put their bags down by the door, and took Sienna's coat. She came back to the sight of Sienna holding the choker she had bought.

"I kept this until now because I didn't think it would be fair to make you put this on without a few words first. This choker is your collar. And that means it's a promise that I own you. Is there anything you'd like to say to me?"

"Yes. I'm never going to abandon you ever again, Miss Sienna. To me, that's what I'll choose this collar to represent. I am yours, forever. B-Because... I love you."

Sienna's body language changed. She seemed less dominating. More caring. More loving. More like a teen girl with sweetness in her eyes.

"You idiot. I know you love me. You didn't need to make me all flustered by saying it. But, I guess it wouldn't be fair if I didn't tell you that I love you too. I told myself for so long that you hated me, that it's why you stopped wanting to spend any time with me. And it hurt extra hard because I loved you more than just as a sister even though I knew it was wrong. But you avoided me because you loved me too, didn't you?"

"Yes. I'm sorry I hurt you, but I will spend my whole life trying to put it right. Starting with this." He put his hand around hers, and held the collar too. She smirked.

"Thank you... Okay, enough stalling. Strip off completely and kneel down."

Rose did as Sienna asked, taking off the wig and returning as Myles. So it was Myles who kneeled, naked save for the cage now adorned with a ribbon and a bell.

Sienna fastened the very girly choker around his neck and allowed him to stand. She kissed him on the cheek.

"I'm sorry I was so tough on you today. I got carried away. I know I need to be more sensitive to your needs."

Myles wanted to protest. He wanted to tell her that he enjoyed it. That it was the perfect amount of humiliation. Bringing him up to that point he didn't think he could handle, without crossing his limits. And that he never would have been strong enough to humiliate himself like that, and he loved her all the more for it. But the words wouldn't come. Sienna began to walk away.

"Now come on, I need to cum after all that teasing, so we're going to watch a romantic movie and I'm going to cum, but you're not allowed to. Got it? If you cum, I'll make you really wish you hadn't."