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.
