Sissy for Sister Ch. 06

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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Rose opened wide for the man's cum to mess up her makeup. One long groan indicated he was ready and a single thick jet of cum ran across Rose's face. She opened wide and tried to catch the next on her tongue. The man, straddling her chest in the back of Sienna's car, slapped his cock down on her tongue, and another jet fired. He managed a couple more, leaving Rose looking so indignant. Just an easy fuck. Sienna, recording from the front seat, loved every second of this video.

The teen shut off the video, and tossed the phone onto the back seat with Rose.

"Okay, sissy toy. You stay here and let his cum dry on your face. I hear it's good for the skin."

"Your turn next, girly." The man proclaimed.

"I'm not some cheap whore you can fuck in a car. You better make me feel really good."

"You don't have to worry about that." The man told her, as the two got out of the car, leaving an exhausted Rose to wait for her sister to emasculate her yet again.

She lay there with a big smile on her face. She loved this. Two weeks had passed since she'd come home. None of this was the life she expected, but it was better than she could have ever hoped for. It wasn't perfect, and after recent troubles, Sienna seemed intimidated to try anything new. But even in a wounded state their relationship was a lot of fun.

Sienna eventually returned and drove the two home. The man's cum had dried on Rose's face, but Sienna smirked knowing it was there, and that she wouldn't even let her sissy have a shower to clean it off that until the next day.

Rose followed Sienna into the house, and needed no order. She began to strip down to her girly undies. Sienna watched her in a dress, and waited with an offer on her tongue.

"That man came so much on you, and then again in me. Does he ever tire? If you ask me nicely, I might let you wear my panties. I'm absolutely gushing his cum into them."

"Yes, please, Miss Sienna. I want that. I need that. I'll be the best slave you could ever hope for if you let me wear your panties."

"Okay. That's enough."

Sienna slid her panties down her legs, but made sure not to let Rose sneak a peek at her worn red pussy bruised from all the annihilation it experienced. She brought over those soiled plain white panties. Rose took off her own panties and slid on her sister's. Immediately, she began adding her own pre-cum to the sexy concoction below.

"Good boy. I might reward you later. But I have to go back to work now."

Rose saw her out and changed out of her wig and back into her Myles persona. Myles kept those soiled panties on, but wandered the house doing miscellaneous chores. His heart raced thinking about how his sister might let him cum. He hoped that she would. He felt so horny.

She'd been teasing him recently. She'd let him get close, she let him edge, but not cum on the sound of her voice or her soft moans getting fucked by real men. The last time she had let him cum was at the tree farm in front of Mr Tate about a week prior. Truthfully, Myles didn't know why it upset him so much to stealthily cum in front of an unknowing spectator. In the week since it had happened, Myles had slipped further and further into the control of his devious little sister. Each day that passed sapped his will to deny her perverted wishes for him--and now he looked back fondly on that day at the tree farm. But he couldn't admit that to her. No matter how badly it harmed their relationship.

Burdened with those unpleasant thoughts and his own arousal, Myles needed something to distract himself. And after half an hour around the house by himself, his prayers were answered by a knock on the door. Sienna had left him a robe and granted him permission to use it in the event of unexpected visitors. Myles threw on the robe, pulled open the door and his face lit up.

"James! You're here."

"Hey, Myles!"

James tried to step inside the house but found Myles in his way, throwing himself into James' arms.

"You have missed me haven't you?"

"I missed you a lot. These last couple weeks have been pretty difficult."

James wrapped his arms around Myles too, lifted him and put him down a little further into the house, and closed the door.

"You smell pretty bad." Myles told him.

"You know you love it." James teased. He didn't need to say anything more. His thin eyes and killer smirk gave away what situation he referred to: A time when they were jerking off together and James tormented Myles until he sniffed his armpit, and lost their game immediately.

"Shut up." Myles blushed. "You better not say that sort of thing when my sister gets back."

"Don't worry. I'd never out you to your own family. I bet she doesn't know anything about Rose Gold or your addiction to my cock.

"Fuck off... But you're wrong about Sienna. It's complicated. I can tell you anything, right?"

"Anything."

"I had a crush on her since we were little even though I knew it was wrong. And it turns out she felt the same way about me. We're sort of in a relationship now. She's my domme and she holds my chastity keys now."

"Hmm..." James thought it over. But the smile on Myles' face won him over. "If that's what you want then I'm happy for you."

"Thank you. Look what she's making me wear." Myles took off his sister's robe and showed James the panties he was wearing, soiled and stinking. James reached out and toyed with Myles' cage through the fabric, leaving the slave to moan and gently thrust his hips.

James lifted his hand, and stuffed his fingers into Myles' mouth.

"So I take it I've lost my jerk buddy. Oh well, you weren't very good at it anyway. Can I still fuck you? Will your domme allow that?"

"She will. In fact, she'll want to watch and take a turn with you afterwards."

"I'll have to make sure to save my energy for her as well then, assuming she's sexy."

"I bet you two will get along. How long are you staying?" Myles asked.

"I can stay a few nights. Maybe a week. Unless you get sick of me before then. More than enough time to steal your darling sister away from you."

"I forgot how annoying you are." Myles playfully jabbed.

"This place is nice. You said your family is rich but I never expected it to be this nice."

"Thanks. I suppose you'll see my room later. Sienna's too, maybe."

"I plan on getting really familiar with them. Now before I get settled in, how about you take me out for a drink?"

"That would be nice. I'll get dressed."

After a couple of drinks, James couldn't get it down, and needed Myles to offer a hand. Or an arsehole. James got him back home, and bent him over the island counter in the kitchen. Panties around one ankle. James had his own trousers and boxer shorts by around his own ankles and he pounded away. Rough. Just like Myles loved it. Myles moaned in Rose's voice. Loud and eager.

"Harder! Faster"! I've missed this cock!" Myles cried out.

"And I've missed this bussy." He gasped out. He felt close. He heard a car arrive, and then someone approach the door. He tried to time it right, and came inside Myles just as the door opened. And Myles cried out in pleasure.

Sienna dropped her bag!

"Wh--?! Myles, you scared the shit out of me!" She cried out. Her eyes turned to the figure mounting him. "Who's this?!"

James withdrew his cock from Myles, and the boy just about slid off of the counter. He still leaned against it, exhausted and hoping to catch his breath.

"This is my best friend James from uni. And a dickhead who thinks it's funny to make me scream in front of my sister."

"It was funny." He answered.

"It was hot." Sienna corrected. "It's never a bad thing to fulfil your role in life as a wet hole for real men. Hi, I'm Sienna. It's nice to meet you."

"Nice to meet you too." James quickly pulled up his trousers, and Sienna drew her tongue across her lip.

"You don't have to do that for my sake. Your dick is really quite handsome."

"Never had any complaints from Myles. Maybe you and my dick can get better acquainted later on." James answered.

Myles groaned to that, and felt pre-cum escape him. This had been a mistake, he felt even hornier now, and didn't think it was possible to be this aroused without orgasming imminently.

Sienna picked up her bag and headed over to the two boys.

"If any of this broke, you're going to get punished, sissy toy."

"Sorry, Miss Sienna."

"You will be. And to think, I was going to cook you a nice dinner for being such a good slave recently."

"How about you let me help? I'm pretty handy in the kitchen." James told her. "Myles never complains no matter what I feed him."

"Oh that's so nice. You two seem like really good..." Sienna saw his shit-eating grin and her voice trailed off. "That was a joke, wasn't it? I don't get it... Oh... Now I do."

"You arse." Myles moaned. He finally felt the strength return to his legs, and he pulled up his sister's panties.

"So maybe I'm not all that good. But I wasn't kidding about helping you. We can get to know each other better and I can treat my best friend to a good meal."

"You're sweet." Sienna approached him and felt small in his frame. She could already tell she was going to like him. He exuded a certain masculine air. In but a moment she realised its source. "You just arrived today, didn't you?"

"Yeah. Maybe I should get a shower first."

"What a coincidence. I was just thinking that after a hard, sweaty day at work, I should get one too. Maybe we should shower together." Sienna flirted. Myles watched helplessly as James kissed her on the lips, and she led him away upstairs.

Sienna wasn't used to long showers, but James knew them well. She leaned against the glass, her back bent and her arse pointed out, James was quickly becoming familiar with her soft pussy. He grasped her long black and red hair in his hand pulled her head back so she could look up into him, her eyes filled with ecstasy. She looked perfect. She was the most beautiful girl he had ever fucked. They once again kissed while he finished himself inside of her.

They emerged from the bathroom to find Myles knelt drenched in his own pre-cum.

"I can see why you like him so much, Myles. I'm going to start dinner now."

James stood in the bathroom doorway while Sienna headed downstairs. Myles stood up and looked up to his friend. His eyes looked moist too, the arousal just about killing him.

"That was incredible. I can't get enough of your sister."

Myles whimpered, a little more pre-cum drooling from his caged dick.

"Please fuck her well."

"I will... I already did. Come on. We should help your sister in the kitchen."

Sienna thought to tease her brother over dinner by giving James the position as the head of the table, and seating her and her brother adjacent to him and across from each other. She frequently raised her foot and rubbed James' cock through his trousers with her barefoot, and less frequently she raised her other foot to tap at Myles' cage. The movements of both boys told the other when she was playing with one, and as they finished, she pressed her back hard into her chair and played with both at the same time.

"So what is the deal with you two? The way I understand it, Myles was your little sissy fucktoy?"

"That about sums it up. He would pretend that he just wanted to jerk off with me, but I'd catch him staring at my dick as we stroked."

Myles blushed hard.

"Th-That's not true! Tell her you're kidding."

"That's so cute." Sienna mewed. Myles blush turned into a solid crimson from cheek to cheek.

"It's not true."

"He actually won our jerk off games twice. We would use a roulette to decide what to watch and what the winner got to do to the loser usually. The first time Myles won he was so excited and then all he got to do was cum on my cock. The second time, though, I had to suck him off."

"I didn't realise Myles had ever received a blowjob. It's actually kind of hot, but I bet he came really quickly."

"He came within a minute."

"What do you expect?" Myles voice cracked. "I had been masturbating. I told you to give me a moment to cool down."

"Yeah." Sienna giggled. "That wasn't fair James. You needed to let him cool down so he could last the whole minute. What I want to know, sissy toy, is how you managed to act so much more like a man those two times."

"I spent the whole morning masturbating until it was a struggle to even keep it up."

"That's right. Both times he won his cock felt really soft even when he came. And the time he got to splooge on my cock, he dribbled just one droplet."

"He emptied the tank? Sounds like cheating to me, but so hot. Myles, go run one of those roulettes, I want to play with James."

"You have no chance of beating me." He boasted, "I've cum twice since I got here."

"So have I." She boasted back, thinking of her two incredible orgasms in the shower with James.

"You're a girl. I bet that'll only make you cum quicker next time."

"But you'll go easy on a cute little girl like me, won't you? Maybe you'll let me and Myles be a tag team. Think you can beat two of us?"

Myles perked up from the other end of the room while he connected his laptop to the TV. Sienna had promised he would not get to masturbate anymore and he was under no illusion she might have mercy on him and forgot this one--her most important rule. But to lose at all, she'd need to let him cum somehow, and he wanted that, he wanted to lose the game, no matter what it meant James could do to Sienna.

It was a rather simple roulette game, they roll for porn to watch and roll how to masturbate to it. The first to cum loses and rolls a losers punishment. The winner rolls a winner's reward. The punishments were different things to do with his cum or to wear for the rest of the day. The rewards were different ways the winner could cum on the loser.

Sienna began giggling loudly and Myles glanced over. James had scooped her up into his arms and he carried her over to the settee sat her down. Then he sat next to her. Myles remained near the laptop plugged into the TV.

"Got something good for us?" Sienna asked.

"Y-Yeah. Do you like the look of this one, Miss Sienna?"

"I have no clue what I'm looking at. Let's see..."

"It looks good." James told her. She smiled and nodded energetically.

"If you say so. Let's do it."

Myles rolled for the categories all at once. James laughed reading the first result; what porn they would watch. Myles winced and Sienna needed them to point it out to her.

"Trap porn." James cheered.

"I know just the little trap we can watch!" She replied with an eagerness to her voice. She and James shared a laugh. Myles opened a new tab and logged in to DigiHoles. He loaded a video to play a video he made back at the university where two men spit-roasted Rose and switched back to the roulette. Myles looked along to the next roll; James and Sienna were to masturbate each other. Sienna, looking down to James' big hands, looked pleased to see that option.

"I'm going to keep my panties on so Myles can't try and sneak a peek. Just put your hand under. Sissy toy, I need you behind me. I want you to hold me for emotional support."

"Yes, Miss Sienna." He returned to the video and hit play, and then he and Sienna got into position, she wrapped her fingers around James' hard cock, and he slipped his fingers down her panties. Myles could only hold her waist and enjoy the feeling of her soft cotton panties. He felt thankful she let him do this, it was the most he had ever gotten from her.

Sienna was entirely engrossed in the video within moments. James glanced to his cock and smirked. She was so captivated she wasn't even stroking, but he wasn't going to warn her of that. He expertly fingered her and rubbed her clit at the same time, and the way she was shaking, it felt incredible.

"Miss Sienna, you need to focus." Myles warned her. Sienna's eyes flashed and the life returned to her.

"Right." She answered. Her delicate hand began frantically rubbing up and down that long shaft.

"Just give in." James mocked. "I can tell you won't last much longer." He didn't turn his eyes away from the screen, but Sienna didn't realise it. She wanted to give him a tough look but she couldn't pull her gaze from her femboy brother having the time of his life in a video she felt was perfect in every way except his unsightly tiny erection. But it didn't take much to imagine him in chastity instead. It wasn't as if those boys were letting him touch himself. He struggled against one pinning him down by his dainty wrists and stuffing his dick down Rose's throat.

"No way. I'm going to win no matter what."

"Really? Is that why your glasses are steaming up?"

"They're not... Argh... You're really irritating."

James decided to finish her off. He stuffed two fingers into her and explored her insides. She moaned hard and the occasional spasm told both of them it was over. She could only last a few more moments before she squirted into her panties. She collapsed into Myles' embrace and smiled a big vacant grin up at him.

"Did I win?" She sounded exhausted suddenly, Myles could only shake his head softly. "We're a team, aren't we? Promise me you'll win."

"I-I... I promise."

"Good boy... You'll get punished if you don't." James held Sienna forwards so Myles could get off the settee and go and pause the video. He nervously swapped back to the roulette and rolled for Sienna's punishment. She was to smear her cum on her face. Since James had a handful of it already, he took off her glasses and smeared it for her. She made an 'eww' sound while he did. She didn't understand why it was happening, but she sprang back to life. Myles feared getting an additional punishment of Sienna's choosing, but he still secretly wanted to lose, so he could cum.

"Reroll porn category and way to masturbate while you're there. Let's change things up a bit." James told him. Myles hit to reroll. It was oral POV, and, coincidentally, the guy with the bigger dick would suck the guy with the smaller dick while jerking his own.

Myles loved the idea of getting his little cock sucked, but reminded himself of the cage. He selected a video on the internet and returned to the settee. Sienna stood and let Myles sit close to his best friend. She noticed he trembled in anticipation.

"Ready?" James asked.

"Yes. I am so ready for this."

James began to lean over, but Sienna cried out.

"Stop! Myles hasn't cum in a while so we're already at a disadvantage. I'm not going to let you get away with not having to watch the video."

"The rules are the rules." James warned her.

"I know... What I'm saying is..." She sighed, and neared her brother. She knelt down in front of him and his heart beat faster. "Does this excite you, you little sissy toy pervert? I'll suck your dick in your cage."

"Thank you, Miss Sienna. I'll try to get even hornier and more frustrated for you."

"Good boy."

Sienna worked her magic, lapping all over his caged cock. Each lick sent electricity coursing through his veins. Every little sensation was multiplied by a thousand times. He squealed like a girl for every millimetre of flesh she could touch. Myles could only shift his attention from the video, a sweet blonde girl sucking a big dick, to his tiny cock in his cage getting teased by his adorable sister. As his mind scrambled, his imagination filled in the rest, and soon he was seeing his little sister sucking that big dick on screen. And it was the thought of getting cucked that sent him over the edge. He felt himself falling through time and space, as a jet of his thin cum escaped him and shot onto his sister's face.