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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Late November in the UK brought cold wind and the first snow of winter. Sienna stood looking out across the long airport longing for it to land against all odds and every weather report trying to dash her dreams. She needed this miracle to make up for a lousy year filled with heartbreak that might have had one left in store for her.
Sienna awaited her brother Myles, returning from university at the other end of the country. She didn't have to wait long before something in the corner of her eyes drew her wistful gaze from the windows to a young man hauling along a heavy suitcase.
"Myles! You're home!" Sienna rushed up and hugged him. Myles felt speechless, the little sister he left one and a half years ago seemed unrecognisable to him now. Somewhere between seventeen and nineteen, Sienna had one final growth spurt; not up, but out. She boasted a curvier figure now, a completely new wardrobe, a pair of glasses, and dyed hair.
"Sienna?!" He had to beg. She giggled and did a twirl.
"How do I look?"
"You look good. Really good."
"Thanks. I don't really like my glasses, though. I couldn't find a pair that doesn't make my face look fat."
"They're fine. I didn't even know you needed them."
Sienna's expression quickly faded. And she just hesitated, avoiding eye contact. She gulped hard, and worked a smile back on to her face. She grabbed her brother by the arm and held on tight as she led him to the car.
"Yeah, I need them to drive. I've just been wearing them all the time though..."
They continued making small talk as they headed out of the airport. Sienna's feet dug hard into slush, yet she no longer concerned herself with that. She had avoided one potential heartbreak, but the shadow of another loomed over her.
Getting into the car, Myles couldn't take his eyes off of his little sister. She adjusted the mirrors, and then huffed in frustration. Her glasses had fogged over. She took them off to clean them, and a lock of hair fell in front of her face. Myles leaned in and brushed it back for her.
"This is fancy." She'd dyed her natural brown hair black, and put in red highlights on the underside of her hair. She'd tied her hair into double buns, and had a messy fringe. Seeing stands of red and black intertwined through the buns looked cute, and those big glasses completed the look.
"Hey, the Christmas fair is in town. Do you want to go see it? It would give us time to catch up. Mum said she won't be back until tomorrow anyway, so there's no rush to get home..."
"Yeah, that sounds nice."
Sienna started the engine and they pulled out of the car park. Apprehension filled her. Though she was a friendly and outgoing young lady, she wasn't the most charismatic person, and she felt a need to charm her brother, like he was just some stranger. But she couldn't even focus on that right now when the road required her full attention, especially in this weather.
They had a connection once--when they were children. But it had long since evaporated, lost to the wind.
Growing up, Myles had always strived to be the perfect brother to his little sister Sienna. It had always just been the two of them for as long as Myles could remember. They lived with their Mum, but had no clue who their father was. She didn't talk about their father. He was alive, he sent enough money that their mother didn't even have to work, but she worked anyway. Drowned herself in work, actually.
The two had long since given up trying to solve that mystery. And to this day, they know nothing about him. Their home life was lonely, but they had plenty of money and an unbreakable bond.
As teenagers, though, they began to grow apart. Myles had his friends and they always wanted to ride their bikes off into the countryside and spend the day finding adventure. Sienna cut her hair short, hid her body behind baggy hoodies and tried to chase after them, but day after day they escaped her. Eventually, she gave up on her intentional tomboy phase and found her own friends to pass the days with.
Days tuned to weeks. Weeks turned to months. And inside jokes turned to spiritless pleasantries in the hallway. Myles went off to university a few years later, and didn't even text his little sister.
But he thought about her. Every day. While she cried at night, lamenting what they had lost and wondered, hopelessly, why they had grown so distant, Myles struggled to sleep each night with the weight of why he had pushed her away.
By the time they reached the Christmas fair in the car, the snow had stopped falling and already turned to puddles lining the streets and roads. With the amount of traffic around, the pair had to park a few streets over. So Sienna snuggled into her brother's arm, and the two walked those dark streets to the fair.
As they neared, it was impossible not to crack a smile at the ambiance. The lights, sounds and smells. A grand carousel, decorated with lights and gold trimmings stood tall as the centrepiece for the fair, surrounded by stalls, trees and tall decorations. People dressed for the occasion in Christmas hats, thick jumpers and long coats wandered the area. A group of children ran past Myles and Sienna, and the girl cooed.
"Remember when we used to come here as kids?"
"I remember. You were always so cute in those fur boots you had with the fluffy things."
"You mean bobbles? Or pompoms, if you prefer."
"Yeah, those."
"How could you not remember the name?"
"I don't know. I don't memorise the names of girl's clothing." He lied. He wanted her to believe he knew nothing about girls' clothes, when the truth of the matter was that he had a rich knowledge of all things girly.
"We haven't been here together for a long time." Sienna mumbled. She looked so sad, and this time, she really struggled to force a smile back on her face. "Hey, I'll treat you to a gingerbread man. Wait right here." She rushed off into the crowd, and Myles turned his eyes upwards to the ride sticking out past the bright lights of the stalls. He nodded to himself firmly, if Sienna would treat him to a gingerbread man, then he'd treat her to a ride on the observation wheel. It wasn't a huge wheel, but from the top they'd be able to see all of the fair and so much of Watwick.
Once Sienna got back with their treats, Myles took her onto the wheel, and the cart began to lift them into the air.
Sienna hopped onto her brother's side of the cart, and fumbled at her pockets.
