Sissy for Sister Ch. 01

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.

"We should get a picture. Where's my phone?" She kept fumbling, and then slapped her forehead. "Bollocks, I left it in the car. Can you take the pic?"

"Sure." Myles replied. He lifted his phone and absentmindedly unlocked it. Appearing on the screen, an inappropriate image stopped his heart; a video paused on a frame of a chaste femboy taking a dildo up her arse, her face hidden away off-camera. Across the top of the screen, the name of the user read 'Rose Gold' and the website name 'DigiHoles' accompanied it--a portmanteau of Digital and Onaholes.

"Huh?" Sienna muttered. Myles quickly double tapped the lock button, and his camera replaced the image.

"It's okay," He convinced himself. "All boys look at porn. Sienna won't think it's that weird."

So he chose not to say anything, and the two smiled for their selfie.

"Send it to me later, okay?" Sienna asked. Myles nodded his assent. Sienna remained by his side. Myles gazed out the window for a moment, but his attention turned back to his sister. She seemed embroiled in some waking slumber, her eyes faced downwards, just one thought rattling around in an otherwise empty head.

"Hey, do you think we can see our house from here?" He asked her with a smile. She just nodded but didn't change her expression at all.

"I don't know... Maybe..." Sienna paused. A bit of her told her not to go through with it, but if she was to suffer another heartbreak, she needed consolation. She needed answers.

"Myles, do you hate me?"

"What? No! How could you ask that?!"

"We used to spend so much time together..."

"Yeah..."

"You pushed me away. I tried to become the girl I thought you wanted me to be, but no matter what I did, you just ignored me. And then you left for university and you never even called or text."

"I'm sorry I ignored you, Sienna. But you know that if you needed anything you could have called me. I would have answered."

"You're my big brother! Of course I needed you! I needed you so many damn times! And I called! But you didn't pick up, so don't lie to me...!"

He shamefully hung his head. That was the answer she didn't want. She whimpered a little and the anger just died. Replaced with disappointment.

"When you left, I felt so lonely. So I bought a puppy. His name was Charlie."

Myles looked sideways, where he could just see a little of her head drooped like his was. He feared what her next line would be.

"Sienna, you don't have to..."

"Charlie got ran over. I bawled my eyes out and you couldn't even be arsed to pick up your fucking phone!"

She began to cry, and so Myles held her and his little sister sobbed into his shoulder.

"I'm sorry. I am so, so sorry. I thought I was helping you by ignoring you, so that I wouldn't hurt you. I see now that I actually hurt you by ignoring you. If I had just made some sacrifices, I could have taken much better care of you."

He fell silent then, thinking about his own life. He held so many secrets from everyone he knew at university. In the end, he'd sacrificed so much more than if he had just stayed. He sighed, held his sister's hand and got onto his knees.

"Listen to me, Sienna. I pledge that from now on, things will be different. I won't ignore you anymore. I won't run away. And you better never get tired of seeing this face, because I'm never leaving your side."

"But what about when university starts back up?"

"Yeah, about that. I'm not going back. I barely made it through last year. I can't handle it, the work is too tough for me. I'm done. That's why I came back now."

"You really mean it?"

"I do."

"Thank you, Myles." She kissed his cheek, and he stood up and took his seat again. Sienna's second heartbreak had also been averted, so long as Myles could stick to his words, and not run away again.

Driving back home, Myles couldn't stop thinking about Rose Gold. He knew her by another name, his own name. He was Rose Gold. He'd created the persona and started dressing as a girl, dicking himself on camera in a chastity cage to make money. And he'd made quite a lot. So much that stopping now felt impossible.

Rose Gold had been born out of one desire alone; to help Myles satisfy his sexual urges and distract him from his massive crush on his own sister. He'd had a crush on her for a long time, pushed her away to try and silence the voices urging him to make a move on her. That hadn't worked, so he tried something more drastic. Rose Gold was the end result of all those attempts to channel his sexual energy in some other direction; a femboy who had been fucked dozens of times by a dozen boys. Often with her own little 'clitty' locked in a tiny chastity cage.

Myles could only keep his cool for so long. He wheeled his suitcase into the house, and parked it by the stairs. Sienna followed him inside, and put up her coat. Then, she began to take off her Christmas jumper.

"It's nice but it's super itchy." She announced. Myles stood with jaw agape at the beautiful figure stood before him. His little sister, dressed in a tight T-shirt revealing the incredible figure she had developed.

She smiled at him, and let out a giggle.

"Got something to say?"

"Umm... N-No..."

"Then do you want to... Myles!" She noticed it before he did, the erection tenting his trousers. She turned away and shielded her eyes with her hand.

"Shit... Sorry."

"It's okay. Been a long flight, right?" Sienna asked him. As if offering him a reasonable explanation.

"I'll go upstairs and put my things away."

"Or..." Sienna mumbled. Myles stopped at the base of the steps, a hand now firmly around the handle of the suitcase. Sienna's heart pounded like mad. She felt mad. "It might be lonely taking care of it by yourself... I could give you a hand if you take a seat."

Myles felt himself walking over despite his mind crying out not to. He wanted his sister, he wanted to love her and make her his girlfriend. But it was a forbidden fruit--and that was why the sweet scent of its juice enticed him so. He could not have her. He knew that. But he walked over regardless. And sat beside her.

The eyes of the two siblings met, they each blushed and glanced away. At opposite ends of the settee, they felt so distant. Sienna nervously shuffled closer. She carefully placed her hand down on her brother's thigh.

"Sienna, you don't have to..."

"It'll be a 'welcome home' present, to show you how much I care." She interrupted. Myles nodded cautiously.

"Okay."

Myles moved his own hand down his stomach to the hem of his T-shirt, lifted it and then slipped his thumb under the elasticated rim of his trousers. He pulled them down, exposing his smooth, shaved pelvis, and the very base of his penis. He hesitated to reveal anymore. But Sienna stroked up his thigh, and her hand briefly brushed Myles' as she slipped her hand down into his trousers and felt her brother's dick for the first time. She tried to keep a frown off of her face, mapping out the size with exploratory touches, and realising that her brother just didn't measure up to other boys.

Still, her touches felt incredible, and Myles lay back against the settee, enjoying her simple teasing. He had never enjoyed the touch of a girl, and had very little experience of someone else touching his penis at all, usually made to take care of his own pleasure after satisfying other boys as Rose Gold.

Now, Sienna pulled his cock from his trousers and Myles let his trousers rest underneath his balls. This felt unreal, Myles and Sienna met eyes again, and Sienna flashed a cute little smile at her big brother. But she felt almost humiliated playing with a dick this small.

She began to stroke him, having to only use two fingers and a thumb so she could have any shaft to stroke at all. Myles began to tense immediately, and the feeling of humiliation grew in Sienna. They'd barely begun, and she felt a tightness building in his dick that heralded his looming orgasm.

Not wanting this to be over so soon, Sienna slowed her hand and then lifted it from her brother's dick. She snuggled into him and began unzipping her skinny jeans, Myles' heart beat so hard she could hear it, and the question whether she was about to have sex with him crossed his mind, but he dismissed it out of hand. Sienna slipped her hand under her panties and began to stroke herself. She leaned against her brother, close enough that he could feel her breath as she gazed into his eyes. He wanted to kiss her, he wanted it more than anything else.

And he felt ready to do it if she gave him any indication that's what she wanted too.

Sienna took her brother's dick again and began to stroke, in unison with her fingers probing her wet pussy and her thumb massaging her clitoris.

"Mmm, this feels good. Does it feel good for you too?"

"Yeah, it fucking does." Myles moaned back.

"I'll let you in on a secret Mum doesn't know: Your little sister isn't a virgin anymore." She felt Myles nearing the edge from that statement alone. So she slowed, and decided to watch the hairs on the back of his neck stand on edge when she whispered into his ear: "I've been practising my dirty talk and I want to try it out. I bet I can make you cum with my voice alone. Do you want that? Do you want me to tease you to cum without any help from my hand? Or do you want your little sister to make you cum in her hand?"

His breathing was strained and heavy. Sienna could tell what he would choose, but she wanted to hear him say it, to admit how pathetic he was.

"Make me cum with your voice." He begged her.

"Good boy." She whispered back. One by one she unwrapped her fingers around his cock, and left it pulsating and straining up into the air. "Okay now, no touching, no matter how badly you want to. I promise it'll feel really good when you cum."

Sienna stood up and pulled up her shirt, revealing her toned and sexy body underneath. Her bra, a plain white bra, formed an incredible bust. From this position, Myles could spy the rim of her panties, but next she pulled down her jeans to show him the rest. Slender and shapely legs, underneath cute banana pattern panties.

She climbed atop the settee, straddled her brother and placed her hands either side of his head, she lowered herself towards him so that their lips were almost touching, but not a single part of them did touch. Her eyes were filled with lust. And so were his.

"I bet you want to see more, don't you?" One hand slithered from the settee, first onto Myles' cheek, and then down his chin, over his neck down his chest, to his belt, and then lifted and moved over to her own panties. She slipped the hand back inside and massaged herself again. She moaned softly and smiled at her brother.

"Your ex-bully, Damien, he got to see it all. His eyes got to explore every curve and every bump. But that's not all he got to do. He got to put his dick inside, and explore the insides of my warm, tight, wet pussy as well. He got to feel the warmth of my boobs against his face as he rammed my pussy with his big cock again and again and again. He was so rough with me, your little sister, he treated me like a cum rag, just a piece of meat to stick his dick in to relieve himself. He fucked me hard and ordered me to scream his name when I came. And wrapped in his big arms, I felt so submissive and I screamed his name extra loud: 'Aah! Damien! I'm cumming!'"

Myles tried desperately to stifle a pained gasp escaping his lips. He was humping the air a little, his small dick was quivering. Sienna knew he couldn't take much more of her teasing. She felt it was time to step it up and end this.

"He made me cum so many times, every thrust felt like he'd break me. He wanted to claim me as his prize, but from the very moment I saw him naked, I knew that I was his. He owned me that day, he claimed my virginity."

Sienna's tale even excited her. And she felt her climax come shattering in. She moaned hard as her pussy spattered into her hand, and as Myles' cock erupted with semen. He fired his cum all over himself, on his shirt and even onto his own face, humiliating himself. He was left visibly shaking, as Sienna struggled to hold herself up, her legs shaking like his. She pulled her hand out her panties and began stroking his chest through his shirt.

"Good boy. I bet that felt good, huh?"

"Y-Yes..." He barely answered.

"You can go get a shower in a minute to clean yourself up, but I'm glad you gave yourself a bukkake, it makes it easier for our last part. Close your eyes, big brother, and take a big breath in through your nose."

She did it with him, and took a lungful of that smell. The potent smell of Myles' cum, it was unmistakable. Sienna hummed with love for it.

"And breathe out through your mouth. Good boy. It's the smell of a job well done. You love it too, don't you?" Sienna climbed off of Myles, and put her clothes back on. Myles stuffed his cock back into his trousers, and contemplated whether he was supposed to answer that last question. The answer was yes, but he felt embarrassed to tell her that, especially considering the state of his face. He didn't want to say yes, and would prefer to lie, but it didn't really feel like she wanted an answer, so telling her that he didn't love the smell of cum might seem a tad suspicious. On the other hand, if he didn't say anything, she might realise that he did. He sighed internally, and chose not to say anything. The moment had passed, now it would be awkward no matter what.