Cuckqueaned By Her Sister, Ch. 01

This story has a harshness rating of 1.65 (out of 3) and is categorized as Romanticized, which means that it contains positive-ish depictions of things which in reality would be evil or unsafe.

All characters depicted are above the age of 18.

I do not consent to the use of this story, or any of my other work, in the training of AI language models.

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Anna sucked diligently on her boyfriend's cock.

There was a weight resting on the top of her head. Her mobile phone. Not Jesse's, of course. His would have worked fine, but...

It was more humiliating if he looked at pictures of other girls on Tinder on Anna's own phone.

"Ooh," he said, perking up, and his cock twitched in her mouth. A flash of shame went through her, just in anticipation. "This one's *hot*. Look at that. Black hair, green eyes... Ooh, and her tits are a *lot* bigger than yours."

Her cheeks flushed scarlet, and the jealousy and humiliation were coursing from her pounding heart out through her veins, putting little spikes in her flesh as they went. He *knew* that she was sensitive about her breasts. She'd always been, well, *flat*. She'd been mocked about it for years. She'd told him that, time and time again. That it *hurt* to be reminded of that.

So of course he took every opportunity he could to remind her that other girls had better tits than she did.

She couldn't blame him. God, no. She was such a slut. He always pushed her boundaries, and she always ended up thanking him for it in the end.

It was hard to argue with her own body. When her cunt was as wet as it was, pulsing with every painful spike of shame...

She didn't let the seal of her lips around his cock break. Not for a second. She was going to be his good girl. She was going to endure getting mocked and shamed and humiliated, and she was going to make sure Jesse felt as good as possible while he did it to her.

The weight on her head vibrated, and she heard the ping of a text notification.

"Hmm," Jesse said, picking up the phone. "Ohh. This one's *really* hot."

What? Who was...

"Violet," he said, slowly. Deliberately.

Oh. *Oh.*

He took a fistful of her hair, his movements methodical and unhurried, and asked:

"Your sister?"

Her mouth still full of cock, Anna nodded.

(Her little sister. Her shy little innocent Violet, who'd just started college, who...

Who, let's face it, had always been twice as pretty as Anna.)

She hadn't been expecting Violet to text her *now*!

"Hmm," Jesse said again, still peering at the phone screen. "Yeah. *Fuck*, she's hot. Look at those eyes! She's like a younger and prettier version of you."

Anna shuddered deeply.

This -- this was a new, desperate, bottomless pit of humiliation. Yes, of *course* Violet was better than her. Younger, just as Jesse had said. Prettier, like she'd always been. Shy and sweet and diligent, probably smarter, too, and...

Well, being younger didn't mean her breasts weren't larger.

"Ahh..." Jesse was saying, bucking his hips into Anna's mouth. His cock was pulsing, getting close to orgasm while he stared at her sister's face, and the *humiliation* --

"Should I call her?" he said.

Anna's heart almost stopped.

"She's saying she wants you to call. I could ring her up. Tell her her sister's busy sucking my cock like a little slut. I wonder if she knows how good at head you are?"

Her eyes were wide with horror. She shook her head. That was -- that was --

Jesse laughed. "I'm kidding, I'm kidding."

Anna let out the breath she'd been holding, through her nose, disturbing Jesse's wiry pubic hair. She -- she hadn't been sure. Jesse *might* do something like that.

His hand came to rest on her head, holding her tightly in place. "I bet her voice is cute, though," he mused. "I'd love to hear it. I mean, look at her expression. She's not even trying to look adorable, is she? It's not forced at all. She's just looking up at the camera with those big, trusting blue eyes..."

Anna squeezed her eyes shut and sucked harder.

"Did you take this picture, slave?"

Obediently, Anna nodded. Tears were threatening to leak from beneath her eyelids. This -- it was too much. Surely. Treating Anna like a slut who was only good for pleasing Jesse's cock was one thing, but *Violet...*

(It didn't stop her pussy from clenching desperately around empty air with every objectifying thing Jesse said, though.)

"You should have shown off more of her body, slut. All I can see is her face."

If Anna's mouth hadn't been stuffed with Jesse's hard cock, she would have been babbling apologies. Because of course! Why didn't she think, when she took that cute photo of her baby sister to use as her contacts image, that her sadistic boyfriend might someday want to get a better look at Violet's chest while he was enjoying Anna's mouth and otherwise basically ignoring her?

"How big are your sister's tits, Anna?" Jesse asked, his voice low.

Oh. Yes, of course. There was the question. He already knew the answer, but he was going to make her confirm it. She squeezed her eyelids more tightly shut.

He reached down, strong rough fingers digging into her left A-cup breast, and chuckled. "They bigger than yours?"

Anna nodded, her cheeks painfully hot with shame.

Jesse chuckled again. "I suppose they'd have to be, wouldn't they? Not like they could be *smaller* than your little flea bites."

A spike of pain, deep in her heart. It *hurt* when he talked about her body like that.

"But, oh, man," he said, a sort of poisonous faux-sympathy seeping into his voice. "Wasn't that... Well, you know. Humiliating? Growing up, watching your little sister flowering into womanhood when you -- " He laughed. "Still had a chest like a little girl's..."

She just sucked obediently, tears leaking from beneath her eyelids. What could she say, even if her lips were free? He was right, of course. She'd been so, *so* jealous of Violet's body. She remembered the dread she'd felt, when (after years of her mother, and Violet herself, reassuring her that she was just a late bloomer, that it ran in the family) Violet's breasts had started to grow in. Started to get attention from the boys, right in front of her. She remembered telling herself, desperately, that it was just a trick of the clothes Vi was wearing, or the way she was standing. That her sister wasn't *really* just genetically superior to her.

Hadn't been long before she couldn't lie to herself anymore, though. And Anna... Well, she'd rubbed herself to sleep at night more than once, crying softly, thinking about her sister's perfect chest.

(Yeah, maybe she was kind of fucked up.)

Jesse leaned closer to her, strong hand tugging roughly on her hair. "She ever make fun of you about them?" he asked softly. "Was she a cute little brat, showing off her hotter body to get one over on you?"

Anna trembled, and shook her head. Violet -- Violet wasn't like that. She was much too sweet to ever make fun of anyone. And -- and anyway, she didn't even *realize* she was hot. Let alone how Anna felt about it...

"Ah," Jesse said. "I guess it must have been everyone *else* who mocked your tiny little tits, then."

Yes. Yes, it had been.

"But I bet they compared you to her..."

They had. Of course they had. Kim and Allison had known perfectly well what Anna's sister looked like, and they'd wasted no chances (in between making out with the boys Anna'd had crushes on) to point out how much better Violet was. How she couldn't blame her family line, how even her little sister was a *real* woman...

As if it was *her* fault that her breasts were pathetic little pinpricks, and always would be.

"Can't blame them, you know," Jesse said, sighing in pleasure as Anna's diligent tongue rubbed the edge of his glans. (After all, just because he was mocking her and humiliating her and dredging up all her adolescent traumas to make her feel worthless and insecure, that didn't mean he didn't deserve to have his cock worshiped like a king's. No, as he never failed to remind her, it was her duty to *reward* him, for being so good at crushing her pride.) "You look so *similar*."

He was still gazing at the phone, its soft light reflecting off his features. Still staring at the face of Anna's sister. "Really, the only difference is how much more attractive she is."

Her eyes snapped shut again and she whimpered around Jesse's cock and sucked harder. He moaned.

"*God*, I wish it was Violet's cute little lips on my cock. But -- but you'll do -- as a -- substitute -- "

Then he grunted, held her head down against his groin, and finished in her mouth.

She'd had a lot of practice swallowing his loads, of course. She couldn't count the number of times he'd made her suck him off, and she'd learned very quickly, the first few times, what he'd do to her if she wasn't quick enough to swallow and some of his seed escaped her mouth. She shuddered at the memory, and finished sucking down his come.

(The come he'd put in her mouth while looking at a picture of Anna's sister. While fantasizing, openly, about how much he'd rather be fucking Violet...)

Jesse pulled his cock from her lips with a pop and a satisfied groan, and tossed her phone casually onto the bed behind her.

(It was his bed, in his apartment, which was small but well-furnished. Anna didn't live here, at least not technically, though with the amount of time she spent here, getting fucked in Jesse's bed, or doing his chores, or sitting at his feet and leaning against his calves while they watched videos, she might as well have.)

Jesse, with his handful of Anna's hair, turned her around and shoved her toward where the phone was lying there, screen glowing in the dark bedroom, Violet's pretty face staring up at the ceiling.

"Give her a call," he said.

Anna started. "Wha -- Now?" While she was... naked, among other things. Jesse kept her naked pretty much all the time when she was in his apartment. Girls were supposed to be beautiful decorations, he always said, and what better way to make her entertaining to look at than to make sure her body was always on display? Just about the only time he'd let her wear clothes in his presence was when he wanted her to wear something so lewd and revealing that it was even more humiliating than just not wearing anything would be...

Jesse slapped her hard on the rear. The crack echoed in the small space, and Anna flinched and lowered her head, heart racing. "You don't want to keep her waiting, do you?"

"But I..."

She was so cute and sweet and *innocent*, Violet. It just wouldn't be -- *right* -- to talk on the phone with her while Anna was naked in the arms of her boyfriend who loved degrading her in ways Violet had probably never dreamed of --

Jesse took a handful of the flesh of Anna's bottom, which, while rather meager, was not nonexistent. He squeezed, hard enough that it hurt.

"Do as I tell you," he said in a low voice, straight into her ear.

Anna shuddered bodily. She glanced at the phone -- could practically *see* the submissive thrill just lying there for her on the bed, to fill her heart when she obeyed --

She plucked her phone from the comforter, swiped to Violet's contact page, and pressed the call button.

Just one ring and a half, and the connection clicked and Violet answered.

"Hi. Anna?"

"Yeah, it's me. Hi."

(She was struggling to keep her voice level. Jesse had squeezed her ass harder as she called, and then released it, and the way it was making her *feel* to obey him, against her own feelings about what was right -- just like when he pushed her limits just a little farther than she was okay with, only deeper, sharper, *better* -- )

"Uh, I'm -- well. Anna, would you uh, could we meet tomorrow? At the park, I think. Just..."

Despite herself, Anna smiled.

It was very, very curious to observe the parts of her: the part that was listening to her sister's shy, adorable voice, loving her, wanting to protect that particular purity that she'd always displayed -- and the part that was feeling Jesse's hands slide up her bare sides, exploring the expanse of her skin, using her and controlling her and turning her on, the part that would probably come on the spot if Jesse told her to explain to innocent little Violet how her boyfriend had been humiliating her --

She caught her breath, let the saner part win out, and thought about her schedule. Tomorrow was Saturday. She'd be free. She could...

"Okay. Yeah, I'll be available at ten. You're thinking of -- "

Jesse pushed her down, facefirst, a hand at the small of her back. Then he nudged her legs apart, one followed by the other, and climbed on top of her. She felt the head of his cock pressing hard against her vulva and pressed her lips tightly together.

She could do this. She could talk normally.

"-- of Sentinel Park?"

"Yeah," Violet said. "Yeah. Exactly. I'm -- uh, I'm sorry. I know you didn't really want me to contact you this evening, I just... I really needed to hear your voice?"

Jesse thrust hard with his hips and drove his cock deep into her.

Anna struggled hard not to gasp. He was *big*, and the feeling of him rubbing against her deepest parts --

"Yeah," she managed, breathless. "Mhm. I don't mind."

"I -- " Violet hesitated. "Sorry. Are you busy? Is this a bad time? I can -- I can call back later?"

Jesse's lips found Anna's ear. "Say no," he murmured, so close that she could feel the words vibrating her eardrum. "You can talk to your sister while I fuck you."

She shuddered violently. "N-no," she said, struggling mightily to sound unperturbed. "This is fine. I can talk."

(The deep rush of pleasure that came from doing exactly as Jesse had told her was made so much better by the perfect counterpoint of his hot shaft hilting itself inside her just as she spoke.)

"Ah. Okay," Violet said.

(She was probably still worrying. But she trusted Anna with her life, Violet did. If her big sister said it was fine, then she'd believe it was fine.)

"I've just... You know. It's been pretty lonely. I haven't gotten to see you in like a month!"

Jesse was taking her harder now, and Anna's mind went blank for a moment. She had to suck in every breath to make certain she didn't gasp or moan.

Oh, this felt so *good*. So wrong, and so good. Getting used like a sex doll while her sister listened, oblivious, so innocent and so undeserving of this disrespect -- while Jesse was probably thinking about how -- about how --

-- about how much tighter Violet's virgin cunt would feel than hers --

She squeezed her eyes shut and came, hard.

(Oh, this was *so* unfair to Violet. She was supposed to be listening to her sister's feelings, comforting her, being a good sibling. But -- but getting humiliated like this, made to ignore one of the people she loved most in the world, being used as a masturbation aid so Jesse could objectify her sweet, adorable Violet -- )

"I've just -- been really lonely," Violet was saying. "You know -- ever since Erica moved away. Well, ever since college started, really. I mean..."

Jesse was grunting softly as he fucked her, no doubt feeling an incredible sadistic thrill with every deep thrust. Anna just hoped it was quiet enough that Violet wouldn't hear.

"Don't -- don't worry," Anna said into the phone, keeping her voice level despite her most intimate parts getting invaded every other second. "I'll be there tomorrow. And we can spend as much time together as you need."

Over the line, Violet took a deep breath. "Okay," she said. "Thank you. I'll see you then. Bye?"

"Bye!" Anna managed, and hung up.

Jesse let out a long, deep grunt, buried himself balls-deep inside her, and came.

"*Fuck*, that's good," he said.

It started deep in her heart and fled out into the rest of her like a pressure wave: a flash of violent twisting jealousy. He *never* came that fast. Not for her. Let alone when he'd just finished minutes before.

And it was because he hadn't been thinking about her, of course. He'd been thinking about her younger, prettier, tighter sister.

Jesse took hold of Anna's shoulders and flipped her around, onto her back. He was still inside her, getting soft, and she could feel the warm seed he'd left there too.

(He never used condoms, of course. Why would he allow anything that would diminish his pleasure? He made her take the pill. The side effects were her problem.)

He was holding her down, now, and her whole body was flush with arousal. He licked his lips, those piercing grey eyes of his staring down at her naked body.

He wasn't licking his lips in desire, of course, because he was looking at her bare breasts, and no one in the history of the world had ever been attracted to Anna's breasts, because they were too small to be worth anything. He was probably anticipating getting to humiliate her more.

He plucked the phone from where it was held in Anna's half-limp fingers, and lay it on her chest, right between her breasts. (If she'd actually had a real woman's body, that probably wouldn't have been possible, because the valley between her breasts would have been too narrow to easily fit a smartphone, but Anna's chest was little more than a flat plain, and the phone rested there effortlessly.)

He tapped at the phone's screen. "Hmm. Photos... Yes, here are those ones I made you take... Ah, here we are. The 'Violet' folder."

Anna shuddered.

He was going to look at all of them, wasn't he? They were -- they were *normal* pictures; it wasn't like Anna had her sister's nudes on her phone, she wasn't quite *that* grotesquely perverted -- but --

"Ooh. There's a *lot* in here. Oh, man, you weren't kidding. Her tits *are* larger than yours." He chuckled. "No **wonder you're so insecure."

Anna swallowed, rubbing her thighs together as best she could with Jesse holding her down, still inside her.

*"*Anna, do you have any idea how unbelievably hot your sister is? I mean, she's *petite*, but -- well, I mean, she's still got more of a woman's body than *you*, obviously, and... Mmmm. God, I'd like to squeeze that ass."

He was using the pictures Anna had taken of Violet to turn himself on. Looking at them, on Anna's own phone, resting right on top of her body. In every way, she was being used to objectify her sister. She... she liked being used. She loved it. But this was -- just -- so *much* --

(How would Violet feel about it? That was the question. But Anna really found it hard to guess. She was so *shy*. She'd -- no, *surely* she wouldn't enjoy this the way Anna did.)

"How old is she?" Jesse asked, conversationally.

Anna swallowed again, feeling suddenly very vulnerable. "She... she just had her nineteenth birthday, sir."

So -- so she *was* of age, obviously. If it had been otherwise... Well, Anna would have safeworded out much earlier. And possibly slapped Jesse. But -- she was still so innocent. And yes, of course it was hot to think of her boyfriend taking that innocence and twisting it for his own pleasure, but --

"Is she submissive?"

Anna bit her lip, hard, and thought about Violet's shyness.

The way she blushed, every time anything even implying sex came up in conversation. How diligent she'd always been with chores, when they were growing up; how she'd never once complained about being told to do something. How much genuine joy it seemed to bring her whenever she could make other people happy.

"Probably," Anna said quietly.

She would -- *God*, she would be such a good slave, wouldn't she? Thinking of how good it would make Jesse feel -- how much he'd love to have her at his beck and call, there to be used however he liked --

It was impossible, of course. And it made her feel kind of guilty just thinking about it. But --

Jesse leaned closer, eyes intense.

"Is she a virgin?"

Anna shuddered.

"Yes," she whispered.

Because she *definitely* was. Violet was so, so withdrawn, and she trusted Anna so much (and that trust was misplaced, because here Anna was helping her boyfriend objectify her), and... If Violet had so much as been kissed on the cheek, Anna would have heard about it within the day. She'd never dated a boy. Not once. She was much too scared and nervous and reticent.

(No matter how much she obviously yearned for affection...)

Jesse fell upon Anna and kissed her hard.

His tongue was probing her mouth, with an excitement she'd rarely felt before. Of course. It was *hot*. Everything about this was hot. His girlfriend's younger, prettier sister, and she was a submissive virgin? Jesse liked deflowering virgins. He'd certainly taken great pleasure in fucking Anna for the first time, back on the day they'd met...

Anna had never been quite as shy as her sister, but it was a close thing. She'd gone to the park one day, and seen a man there, out walking, and she'd screwed up all her courage and gone to talk to him. And he'd thought she was cute, clearly, or maybe just that she'd look good crying after he'd made all her deepest insecurities come true, and he'd taken her home with him, and... She'd gone along with it. Because she *needed* to find a boyfriend eventually, she needed someone to desire her, and he'd complimented her and validated her and she'd been practically swooning --

And then he'd stripped her. First her clothes, and then her dignity. He'd found all her weakest spots and stuck his needles in them, and set about systematically dismantling whatever fragile sense of pride years of painful teasing had left her with.

And she'd *loved* it. She still had no idea how many times that night she'd felt the unfamiliar sensation of coming all over a man's hard penis, while Jesse alternately mocked her and comforted her until there was nothing left but a pliable slave who'd do anything he asked for a scrap of affection.

... It had been the same park where she was talking with Violet tomorrow, the one where she'd met Jesse. Violet didn't know that. She was aware Anna had a boyfriend. Knew his name was Jesse, knew he lived in Albany. She didn't know much else about Anna's relationship.

And, well... Anna enjoyed what Jesse did to her. She really, truly did, even if from the outside she might look miserable and broken when he was finished with her. But the mere idea of subjecting Violet -- so much kinder, so much sweeter, so much purer -- to the same degrading pressures that had practically reshaped Anna's mind --

It was only fantasy, Anna reminded herself. If Violet never *learned* that her sister's boyfriend had been making himself feel good by talking about her like a sex object -- that Anna had participated -- then it wouldn't hurt her...

Jesse sucked hard on her lower lip one last time and pulled back. His cock was starting to get hard again inside her.

He was grinning. It was a handsome grin. He was a good-looking guy, after all, with his clean-shaven look and his strong cheekbones and his mop of brown hair. That was part of why Anna had talked to him, all those months ago. What a wholesome face he had. You'd never think to look at him the kinds of things he was into...

He stared her straight in the eyes, and said:

"Slave, I want your little sister naked in my bed by Sunday night."

Her eyes went wide and her lips parted and she *shuddered*.

He was going to replace her. He'd found someone just like her but *better*, and now he was going to make Anna facilitate her own obsolescence. He'd get a taste of how Violet's firm round tits felt in his hands and he'd never want Anna again. Violet's superior body was going to steal her boyfriend from her, just like she'd been afraid of deep in her heart for ten years or more.

*God*, it *hurt*. She was so jealous she could *cry*.

And her pussy was soaking Jesse's sheets.

... But she couldn't. She *couldn't*. **She couldn't possibly do this to Violet. It'd *break* her. She'd never be the same again...

Jesse's hand came down and found her left nipple, small and pebbly, mounted on its pitiful little pancake of a breast. He pinched, hard. Didn't let go.

"That wasn't a request, slut," he growled.

She squeezed her eyes shut.

*Good girls do as they're told good girls do as they're told good girls do as they're told --*

"Yes, sir," she whimpered, and came harder than she ever had before.