Sissy for Sister Ch. 03

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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"Sie--..." Rose was about to call out her sister's name in surprise, but she bit her tongue and managed to keep that name in her mouth. But Sienna giggled.

"Sienna...?" She rhetorically asked. "My brother Myles said that he doesn't know you personally. But you live locally and you clearly know who I am. So, how do you know him? Is he your boyfriend?"

Rose felt it a way out, so she nodded eagerly.

"That's right. He's my boyfriend. We were at university together."

"Now you've followed him across the country to be with him. And yet here you are having sex with another man. You're a naughty sissy, Rose. But judging by your profile on DigiHoles, you do this sort of thing all the time, and Myles knows all about it. In fact, I don't think I've seen a single video of the two of you together. Is it just that he feels too shy to be caught on camera? Or maybe you've never even let him have sex with you."

"He's never had sex with me." Rose admitted. She cursed herself. She knew that she should have said he did, but the truth--albeit an odd truth to admit--slipped out.

"I suspected that might be the case. If Myles is only allowed to enjoy the videos of you getting fucked by other men then my friend Harry here can help the three of us make a really good video for your boyfriend's enjoyment."

Rose looked towards her sister with terror in her eyes, but Sienna simply smirked. She'd been fucked in chastity by strangers lots of times--some whose names she never learned--and filmed it for strangers to enjoy a great percentage of those times. And one time, she'd even got fucked alongside a real girl. She planned for Sienna to watch the video. But to have her watch the show live was much worse. To get fucked in front of the girl she had a huge crush on and somehow cuck Myles--herself--at the same time was a strange situation to wrap her head around. It was simply too much. She was convinced she couldn't go through with it.

"W-What will be doing?" Rose nervously asked.

"We can do a little bit of cock worship." Harry answered.

"Then Harry can stretch your bussy with toys until you can fit his cock."

"And then I can really make you scream."

"Come on, Rose." Sienna teased. "You came all this way dressed like a pretty girl to have sex with some guy, you can't back out now and retain your dignity, so you may as well make a good video out of it."

Blushing like mad, Rose nodded and Sienna reached for her phone on the table. Harry picked it up first and handed it to her.

"Okay, first I want to get some footage of you doing a striptease."

Harry stepped to the side of the room and fiddled with a remote. Music flooded the room then from two speakers either side of his TV. Rose felt a burning in her cheeks, Sienna and Harry had clearly planned all of this in advance. And she was playing right into their hands.

Sienna held up the phone and Harry joined behind the camera while Rose started dancing sensually. She'd had a bit of experience dancing as a girl. In the club on a couple dates with boys from university. And this wouldn't be the first time she'd performed a striptease. As she swayed her hips and ran her hands up her body she watched Sienna run her tongue across her top lip hungrily. Sienna hadn't even realise what she'd done, but it made Rose's clitty drool in her cage.

Rose spun and lifted the hem of her dress over her arse and bent forwards to show off her curvy, girly butt. Seeing her stockings and garter straps, Sienna felt herself get wet. Rose was certainly a very sexy femboy, and Sienna had no clue she could want to tease a femboy this badly. She didn't want this to end.

When Rose lifted off her dress and tossed it to the side, standing now in a matching bra and panty set, as well as her garter belt and stockings and heels, she continued to dance and just seemed so much more into it. The tiny lump underneath her panties showed clearly the shape of her chastity cage but each second that passed helped Rose lose herself in the fun of this.

She wiggled her arse, she shook her hips and she tossed her hair around showing off every inch of her fine body, stripping off her bra next to reveal her pink and feminine nipples, then finally pulling down her lacy thong to show off her tiny clit locked away for the pleasure of this man and her sister smirking a devilish grin.

With her fully exposed, wearing only stockings, a garter belt and her high heels, Harry joined the scene. Sienna made sure not to get his face in the shot. He sat down in his armchair, and Rose got on her knees in front of him. She looked deep into his eyes while she ran her hands down his thighs, and then kissed the bulge underneath. She fiddled with his belt, and then unzipped him to expose his big dick. He was bigger than average, but even a small dick would look colossal next to her clit in its cage.

This was the part that Rose knew well and she needed no encouragement. She sucked her partner's balls and stroked his dick slowly. She took her time, salivating all over his hairy, wrinkly balls and sucked hard on each testicle, applying gentle pressure to each and then pulling both into her mouth. Harry let his head fall back and just enjoy the whole experience. Rose was a master at this. When she started playing with his dick, licking at the head, continuing to stroke up and down, before running her tongue up and down each side of his shaft, Sienna couldn't keep her free hand off of herself. She trembled, utterly failing to keep the camera still as she unbuttoned her jeans and began to massage her clitoris. This show was making her so hot, she couldn't wait to see Rose get her arse filled.

Soon enough, Rose was taking his whole length of Harry's cock with each thrust down her slutty throat. It wouldn't be Rose's first blowjob captured on camera, but Sienna loved it more than those she'd seen.

The teen girl kept rubbing herself, and felt the edge of an orgasm creeping into her mind. Her heart beat faster and the orgasm encroached quicker when Harry forced Rose to stop, lifted her up and placed her on her feet, bent her over, and began to lick at her arsehole. Rose moaned loudly to such amazing treatment.

He was quickly able to work his tongue into her well-trained hole. All too rapidly, his warm tongue was replaced with a large dollop of saliva when he spit on her arse, and pushed a finger in. Then two fingers. Three. Four. Then his fist. Sienna climaxed to the sight of Rose taking an entire fist into her arse and only being able to spasm and quiver and whimper pitifully. A long strand of pre-cum drooled down, hanging and bouncing around as she quivered uncontrollably. Sienna wanted nothing more than to go and collect that on her hand and smear it on Rose's face and force the femboy to taste her own arousal. But she kept filming for the sake of Rose's audience who would doubtlessly love watching her get fucked as much as Sienna did.

With Rose's arse utterly exhausted, Harry picked her up, forced her legs up either side of her head, wrapped his arms around them and locked his fingers behind Rose's head, and then speared her onto his mighty dick. Rose was locked in a full nelson, getting thrust down onto this big dick, again and again. Her screams were loud and primal, and staring into her sister's lustful eyes while she got pounded by a real man made her shake with incredible energy. Her mind spun wildly, she knew this feeling from the night she returned. Rose was about cum, about to blow her sissy load with a cock inside her for the first time, sealing her fate.

Her screams hitched, and her clitty began to shudder, but Sienna shook her head, and Rose felt a pain shoot through her core.

"Don't cum." Sienna silently mouthed to her. The cock inside her felt incredible, and the humiliation was about to make her dribble. But dressed like this, feeling so submissive to be getting fucked by a real man, Rose did as asked, and fought off the edge she was teetering on.

Harry put her down eventually, and fucked her in cowgirl position on the chair. He bent her over the table and really fucked her hard from behind, before finally forcing her to the floor in a mating press and finishing himself deep inside her.

Sienna finally put her phone away and headed over to Rose. She watched the femboy as she walked, but then hopped up into Harry's arms. The man held her as they kissed passionately, while Rose struggled to stand. Harry put Sienna down, and they remained still. Harry watched Sienna's soft lips.

"That was awesome. You really gave it to that sissy. You owned that bussy. And you, Rose, were perfect too. A good little fucktoy for Harry's superior dick. Here, you can use my phone to upload the video. Your fans will love it, I know I did."

Sienna and Harry spoke in hushed tones as Rose logged into her DigiHoles account and uploaded the video. She stealthily turned her eyes upwards to spy Harry sliding his hand down Sienna's jeans and panties to feel just how wet she was.

"No looking unless you're given permission, sissy toy." Sienna demanded. Rose quickly glanced down again. It took all her power to look away. She had never been this horny.

After a bit more playing, Sienna took back her phone and let Rose look up. She kissed the femboy on the cheek.

"Good boy. You really know how to work a dick, Myles."

Rose's eyes widened and her heart stopped. Beads of cold sweat dripped down her forehead.

"Oh, come on, don't treat me like an idiot. Obviously, I knew. And you know that I knew."

"Did you know before I arrived today?"

"I was ninety-nine percent sure when I looked through 'Rose Gold's' profile on DigiHoles. But that one percent of me that doubted it bothered me."

Harry just about had his clothes back on. Sienna strolled up to him.

"I need to get back to work. I'll give this sissy a ride home." She then kissed Harry on the cheek, and whispered something into his ear.

Something-something-see-you-something-something-at-nine. Rose couldn't make out any more than that. She put her clothes back on and headed out the house with her sister. Sienna led the two around into the alley where she had hid her car. They got in, and Sienna took a moment to stare at her sissy brother.

"You make a cute girl."

"T-Thank you."

"You're welcome. We're going to have a proper talk about all this later. But right now, all you need to know is that from now on I own you and you need to do everything I say, or you'll get a punishment. You'll call me Miss Sienna or Mistress. Understand?"

"Yes, Miss Sienna."

"You can go home and dress as a boy if you want. But I get out of work at quarter past four. I'll text when I'm on my way home. When I do, I want you to strip nude, get your chastity keys and prostrate yourself by the door waiting for my return. Don't cum. I'll know if you have. But don't worry, I plan on letting you cum tonight." Sienna started the engine, and Rose was happy to remain quiet for their journey. But Sienna's eyes lit up. "One last thing, could you send me the names of the shops where you got your clothes? They're really cute."

"Umm, sure."

"Good boy."

Myles got a shower and cleaned Harry's cum from his arse. He was always a good sissy, and would never take the cage off before he completed a roulette he began. Now under orders from his sister to keep the cage on, he had long since dismantled any resistance he could muster to disobey that particular order. So he struggled through a shower and made sure to hose himself down with cold water to try and distract himself from his lust, but it didn't work. He was left cold and horny, rather than just horny.

When Sienna text that she was on her way back, Myles stripped down to his chastity cage, and went downstairs to await his sister's arrival. He placed the keys in front of him, and tucked his knees, placed his elbows on the floor, and pulled his stomach and chest down as low as he could. He kept his forehead to the floor, and awaited the sound of her car and her soft footsteps.

"Good boy. You really wouldn't want to upset me on your first day as my slave. I wouldn't have hesitated to refuse you an orgasm if you disappointed me. And I still won't. So you better do everything that I say."

"Yes, Miss Sienna." Myles told her. She pressed her foot down against the back of his head, and remained there for a moment.

"This feels right. This feels like your rightful place, doesn't it? Naked on your knees in front of your little sister? How humiliating does this feel? Would you like me to close the door?"

"Yes. I'm so embarrassed right now."

With that, Sienna lifted her foot from Myles and closed the door.

"You can get up now."

Myles did as she offered, but felt more humiliated now that she could clearly see his cage. He didn't stand that much taller than the average girl, but without any accessories to accentuate his already girly features, he could still pass as a man, and that made him feel even more humiliated than wearing his cage as 'Rose', where he passed as a girl just trying to seal away any remnants of masculinity.

"First things first. I want you to make me a cup of tea while I put my feet up."

Sienna took her seat on the settee while he slave ran around the kitchen to fetch her a cup. He soon brought one over and placed it down on the coffee table. She signalled for him to step before her, and then down. He got on his knees and she rested her now bare feet on his cage. It sent powerful jolts through his body and a bit of pre-cum leaked out onto her toes.

Sienna dangled the keys in front of his eyes.

"Now, I want you to know that at any point at all, you can have these back. All you need to do is demand them. You want me to be your girlfriend, I'm yours. But just know, if you take them back you can never be my slave again. I don't think you will ever ask for them, because you want to be my pet. You want to be dominated and humiliated, and you want to dress up as Rose and get fucked by real men. I knew it when I offered to give you a handjob and you chose to cum to the sound of my voice teasing you what a real man got to do to me. I know that with proper encouragement, you'll be able to do that in chastity. I'm warning you, Myles, if you choose to be my slave, you'll never get to touch your hard clitty ever again. Does this sound like something you want?"

He could fuck his sister like a girlfriend. She could be his and they could have the closest thing a brother and sister could have to a normal relationship. He wanted that, but he cared for her, and he could never make her go a life without good sex for his selfish desires, so he nodded.

"Yes, Miss Sienna, that's what I want."

"Good boy. You better start getting used to being my slave, so do the housework while I watch TV."

That evening, there was a knock on the door. Myles jumped up and wanted to hide. Sienna hadn't let him dress at all, he was still nude. But her eyes froze him.

"Answer the door, sissy toy."

"B-But Miss Sienna, I..."

"Now! I'll let you have that one for free since it's your first day, but you never talk back, okay? If I give you an order, you obey me or you get punished."

"Yes, Miss Sienna."

Myles walked over to the door and couldn't believe he was about to answer. He felt his future unfurl before him: Prison at the age of twenty for indecent exposure. He'd be charged with the maximum sentence. And he'd definitely be feminised in prison and turned into a sissy bitch. The other inmates would fuck him like they intended to get him pregnant.

When Myles opened the door, he felt relieved to find Harry stood there. But then panicked when he realised that Harry would put two and two together and see Rose for who she really was.

Harry stepped in, and Myles closed the door behind him. Sienna rushed up and hopped into his arms again. Myles simply stood pathetically awaiting Harry to put down his darling sister. He watched helplessly as Harry groped her sexy round butt.

"Come on, I can't take it anymore. Fuck me now." She cried out. She led Harry over to the settee and got on her knees. He began to fuck her doggy style, and Myles moved around to watch. Her eyes met his.

"Eyes down, sissy toy. No looking unless I tell you it's okay." Harry pulled Sienna up so her back pressed against his chest, and he pulled her shirt over her head. She unhooked her bra and tossed it at Myles. "That's as much as you're getting tonight. Enjoy. Just look at your little cage and keep telling yourself 'this is why I don't get to fuck my Mistress'. Listen to my moans and cum shamefully. If you can't cum, you won't get to cum tonight."

Myles got down on his knees and stared at his little clit twitching in its cage. Yet, Sienna's moans did sound so hot; she clearly loved the feeling of a real man tossing her around. In actuality, Harry was rather gentle with her, and she almost tricked herself into believing she was his tiny teen girlfriend.

From those first few seconds, Myles knew that this would work, that he was pathetic enough to cum from the sound of his little sister having sex with someone else while in chastity. And upon the thunderous cries of her first orgasm, he squirted all over himself.

"G-Good... Boy... Myles... Oh fuck... He's so... Big... Fuck, I love this... I never want it... To stop... Myles, beg... Harry to keep fucking me..."

"Mister Harry, please keep fucking Miss Sienna. Fill her with your sperm when you're done."

With how crazy asking Harry had made Myles' heart go, he realised now that cumming this way didn't make him any less horny. He still felt mad from lust.

"Don't worry. I'll make sure your sister has an unforgettable night."

"Thank you, sir."

"Good boy, Myles... Now... You've cum now... No more... Tonight. Okay?"

Myles nodded and whimpered at the same time. Holding back was more painful than when it was him getting fucked by Harry. Sienna didn't feel the need to keep quiet for her brother's sake. And her voice rocked through two more orgasms that night, before Harry filled her with cum, and let her dress up.

Soon enough, the three stood at the door to see Harry off. Sienna looked so cute, in the glow of her orgasms. She fidgeted with her nails at her waist. Her whole posture seemed small and submissive.

"I had fun tonight, Harry. I hope your wife doesn't find out about this."

"Me too." He replied. He kissed Sienna again. "She's a good woman, but I couldn't resist you and your sissy brother. But you better not tempt me again."

"Then this is goodbye. I hope I see you around town from time to time."

"Yeah, see you Sienna. You too, sissy."

"Yes, Mister Harry. I'll make sure to say hello if I see you."

"Not if I'm with my wife. I don't want to have to explain that one to her."

Sienna saw him out while Myles remained inside. His clitty started to hurt when she still hadn't returned after five minutes.

After ten, she came back inside. And glanced down at Myles on his knees. She fell back against the door and let out a massive sigh.

"I hope his wife sucks his cock every morning. He deserves it."

"Miss Sienna, can I ask where you met him?"

"Through a friend. For the past few days I've been getting ready to catch you in the trap. You're lucky I found you so quickly. Today was the first day I put my plan into action. I caught you first try. I expected to have to use a dozen apps and find a load of random femboys first. Now, how about you go get dressed in your boy clothes? You can treat me to dinner at the pub."