Archive of Our Own

"Caleb?"

Caleb's fingers halt on his phone screen, abandoning the text message he'd been in the middle of typing to Kelsey, a girl he'd been seeing for a while from the DAA. It'd gotten somewhat serious, or that's what everyone else had been saying, purely due to how long he'd been seeing her—compared to his past girlfriends, that didn't last long.

She'd even met you.

And you'd even liked her, which was a far cry from the usual sentiment you held towards his girlfriends. It didn't help that it didn't take them long to label you as Caleb's-psycho-little-sister-that's-weirdly-attached-to-him. And of course, from there the relationship never lasted long before he ended it.

The two of you getting along should make things easier for him. But, in reality, it didn't. Nothing about dating other people, when the woman he'd wanted all along slept down the hall from him, would ever be easy.

But if he couldn't have you, he should at least try to move on. If not for himself, for you. It wasn't fair to you, the way he thought about you. And that shame was something he'd been grappling with his entire life.

However, Kelsey had started to become hostile about you—even though he'd hardly seen you all year. If he had to guess, he'd say it was because Kelsey hadn't known you when she met you. His exes were predisposed to side-eyeing you because they'd heard things through the highschool gossip grapevine—that his little sister was grossly obsessed with him, and that he encouraged it. Not that he'd call it that.

So Kelsey was a lot kinder to you when you'd met. But lately, there'd been these irritating side comments thrown around disguised as playful jokes.

"She's adorable. Is it normal for little sisters to be that clingy?"

"Maybe we should go on a vacation this summer! Away from your little sister."

"Wish she'd get a man already, so I could have you all to myself."

It probably wouldn't be long until he ended things.

"Door's open," he calls from his chair, where he'd been studying the entire day. He really didn't need the head start on next year's classes, but Gideon and Blythe had come up with the idea of a summer study group, and forced him to join, moreso tutor, them.

"Hey," he smiles tenderly as you peek in, but his jaw clenches when he sees you, clearly having just gotten back from a date. Probably with that guy you'd mentioned you'd been seeing from your university. Jack, or something.

"Can I come in?"

"'Course."

You waltz in, looking so effortlessly beautiful, hair and makeup done, wearing a cute dress he'd never seen before, one that came to just your mid-thigh, straps a bit loose on your shoulders. It was perfect for summer, and it looked perfect on you.

You flop onto his bed like you own the damn thing, arms starfishing outward. Caleb clears his throat as he catches himself staring at your thighs, your dress riding up at the sudden movement.

"Can't believe we're both home for the summer," you sigh, taking his pillow and hugging it to your chest, "Last year you had flight camp."

"Yup, Nainai begged me to come home to make sure you wouldn't burn the house down this summer."

You glare at him, chucking the pillow at his face. Of course, he easily catches it.

"That was one time and that was because you weren't home so I had to fend for myself," you grumble adorably, "And seeing as you never taught me to cook, really it's your fault."

Caleb chuckles warmly, shaking his head. You turn onto your side so you can face him.

"How's Kelsey?" you ask, keeping your voice as nonchalant as possible. Really, you liked Kelsey—you did. But still, thinking about Caleb with any girl made you feel sick to your stomach. Probably because he was your big brother. And even if you weren't blood-related, it was still icky to think about. Naturally.

Caleb plays with his phone, absentmindedly spinning it in his fingers. The screen lights up—a text from Kelsey herself, but he ignores it.

"She's good. Same old," he says simply. She'll never be you—is what immediately came to his mind.

"You've been dating her for a while," you remark casually, "Longer than most of your other girlfriends. Must be going well?"

Caleb shrugs, "Longer doesn't always mean better." He mentally kicks himself for letting that slip, quickly diverting your attention before you question his cryptic words.

"How's uh—what's his name, the guy from your English lecture. Jack?"

Your eyes light up, unbelievably happy that Caleb had remembered anything about the guy you'd been talking about, "Jake? Jake is good. I actually just came back from the movies with him."

"That's great," he forces out, "Happy for you. Just…be careful, pipsqueak. For me, yeah? Don't wanna see you gettin' hurt."

Honestly, you were surprised how accepting Caleb was of your new…friend. It was unprecedented. It should make you happy—you'd always complained about how suffocatingly overprotective he was, but it just made you feel dejected. Like, after leaving for the DAA and meeting Kelsey, he didn't care about what you did anymore.

In reality, Caleb knew he had to be strategic with his overbearing behavior. Since he was no longer home to physically keep tabs on you, he relied on your social media and you to learn about your life. He couldn't come on too strong, couldn't force you to do anything, or rather, not do anything, you didn't want to do. You'd always had quite the rebellious streak, and now that you were grown and dating, he couldn't risk pushing you away or keeping anything from him.

But he'd still step in where he needed to, with or without your knowledge.

"I can take care of myself," you insist, "But yes, I will. I promise."

Caleb nods, propping his feet up on the edge of the bed, just a few inches away from where you lay. He watches the expression on your face—quickly able to read your fluster, knowing there's something you still want to say.

"So, how was your…date?"

Truthfully, he'd rather yank his hair out than hear the details of how another man got to spoil you, to wrap his arm around your shoulder and pull you close. To kiss you. But there was no way in hell he was letting you keep anything away from him, especially when it made you visibly nervous.

"U-Um, it was good," you stammer, "I actually wanted to ask you something. Something embarrassing."

Caleb's eyebrow quirks in intrigue. He was still itching at the seams, wanting to lock you away from the world, from Jake, but your words had him undoubtedly curious.

"I—uh. You…Do y-you…"

Caleb tries to remain patient, but your behavior was making him increasingly antsy. What the hell had you so damn flustered?

"Gonna keep me guessin'?" he chuckles, "What's up, pipsqueak?"

The next words out of your mouth had him choking unceremoniously on his own saliva.

"You and Kelsey…" you rush out before you lost the courage, "You've had sex, right?"

His face burns, matching your own blushing cheeks. Why the hell were you asking that? He seethes at the thought—the only reason you'd ask is if you…

"Yeah. Why? Are you and Jake—"

The image of you in the backseat of Jake's car, fingers curled in his hair, his body between your thighs. It was enough to send him into a blind, possessive rage.

"N-No! Maybe. No. We haven't," you fumble, covering your face with his pillow. Caleb eases fractionally, but his mind is caught on the word 'maybe.'

"Oh," Caleb says simply. But then his face hardens and he leans closer, his desk chair scratching the wood flooring as he rolls up to the edge of the bed, "Is he pressuring you to?"

"No! He's not—Jake's not like that." Caleb almost rolls his eyes at how you defend him so vehemently.

"A-And you've had sex before, right? Before her?"

Caleb's jaw clenches, "Yeah. Why the interrogation? You gonna tell me what this is about?"

You let out an exaggerated sigh, sitting up, hugging the pillow to your chest once more, like it could give you courage.

"I like Jake. But he's a lot more…experienced than I am. I don't want to be…bad."

At his silence you force yourself to continue, "S-So I was hoping you could…tell me what to expect. Like…I don't know—tips?"

You punctuate your own insane request by flopping back down onto the bed and covering your face with his pillow, squeal-screaming into it.

Caleb opens and closes his mouth, trying to find the words. Truthfully, his mind was blank after he realized you were likely a virgin.

He roughly drags his hand across his hair, gritting out your name and swearing, "Christ." That's all he can manage. Caleb's speechlessness makes you incredibly anxious. It was unlike him—he always knew what to say, what to do.

"F-Forget it, this is weird—"

"Look, if he's worth anything, anything at all," Caleb interjects, growling roughly, "He won't give a shit about experience. If he's the man you think he is, he'll be happy just to…just to be with you."

You whine, unsatisfied with his answer, "Ugh, I know all that. And he said he doesn't care. But I still…want to be good. I want to make sure I can…" You smother your face deeper into his pillow, voice muffled, "Make him happy."

"For fuck's sake," Caleb curses, raw and pained.

"I would've asked someone else!" you ramble, "But I didn't feel…comfortable. I even contemplated asking Kelsey, but the thought of her going into detail about my Gege…" You shudder.

Caleb freezes. Since when were the two of you that close? And why the hell did it make him so damn upset?

"You don't need a manual," he bites out, more aggressive than necessary—having an uncharacteristically hard time controlling his emotions. You pout, looking up at the textured ceiling—you'd expected him not to want to speak to you about this, but it was still disappointing.

"Look, if you're gonna do it…make sure it's what you want, okay? Not because you feel like you owe him. And please, please use a condom."

You perk up at his words, realizing he might be more willing to talk about this than you'd thought. Nodding eagerly, you sit cross-legged, looking at him so damn innocent and earnest.

"Tell me what guys like. Men are all the same, right?"

Caleb runs his hands down his face, "Fuck. You want me to give you a damn checklist?"

At your genuine, eager nod, Caleb concedes, knowing you'll pester him about this for days. And there was no way he'd survive that.

"Jesus—fine. Guys like…"

'I like,' he echoes in his head, "Knowing they're making you feel good. Sounds. They like knowing that you're into it too—so touch him back, be vocal. Eye contact. And if there's something you don't like, you make damn sure to say that. If you have any hesitation, you ask him to stop."

The checklist had quickly devolved from a list of things "guys" liked to a big brother lecture about consent. Which was not nearly as helpful.

"That enough?" he snaps, rougher than necessary—nearly at the end of his rope. Where that rope led, he wasn't sure. To…pinning you onto his bed? To kicking you out of his room?

"I mean I guess," you grumble, unsatisfied, "Touch him back, make sounds, communicate…What else?" You hesitate before asking, "What do you like?"

At that, Caleb snaps. If this conversation went on any longer, there'd be no stopping his darkest desires from surfacing, taking over, and causing him to do something he wouldn't be able to take back.

"I'm not a damn tutorial. If you're that desperate for one, go watch porn. But for the love of God, please stop asking me to imagine my baby fuckin' sister like that."

You bite the inside of your cheek, a bit thrown off by his explosion—but not completely surprised. You weren't an idiot, you knew this was an incredibly uncomfortable conversation to have with anyone, let alone your big brother. But you're relentless.

"What should I watch?"

Caleb curses lowly, standing from the bed.

"Alright, pipsqueak. Conversation's over. Get out before I lose my goddamn mind."

He stands by the door and holds it open for you, watching you whine and climb off his bed.

"And for the record, we're not all the same."

Yeah. Some are worse than others. Like him—wanting his, for all intents and purposes, adopted sister. Watching you march out of his room, after nearly smothering yourself with his pillow, his scent—hiding the thickest erection he'd had his entire life.

But as he watches you, your cheeks puffed out in protest, arms over your chest—drawing his attention uncontrollably to your breasts, he can't help but reconsider.

The small bit of advice he did give you, had taken everything from him. It made him feel like he was…allowing it—giving you away like some father at his daughter's wedding, tying a bouncy ribbon on your perfect damn body and hand delivering it. Saying, "Here! Here's the most important woman in my life. Have fun!"

At least you were asking him for sex advice. He'd rather him, no matter how painful, than some exaggerated porno—some overacted exploitative garbage where the women were the least of the men's concerns. At least this way, he could control it. Some of it.

"Wait."

His voice is pained and hesitant, causing you to stop completely in your tracks.

"One question. One."

The way your eyes light up is criminal, bouncing back onto his bed, sitting up like an eager student. One question. You had to use it wisely. Sure, you could get your answers elsewhere, but you trusted Caleb's judgment more than anything.

Caleb sits a safe distance away from you on the bed, "What, now cat's got your tongue? Where was all this silence earlier? When you were trying to kill me?"

You roll your eyes, "Don't be dramatic. You said only one question so I have to pick wisely."

He chuckles darkly at how seriously you're taking this—finding it both endearing and unbearable, knowing how badly you want to please a man that wasn't him.

"How do you like getting your dick sucked?"

Caleb chokes, his Adam's apple bobbing painfully, "Jesus fuck. Ever heard of tact, pipsqueak? Not that."

The casual pet name is a poor attempt at trying to conceal how fucked you've rendered him.

"You said one question! What, did you think I was gonna ask 'what is a penis?'" You use your fingers to make air quotes. "Come on Caleb, be real."

"Fine," he snaps, "Only because I know you're not going to leave me the hell alone unless you get what you want. Brat."

He takes a deep breath. He knew how he liked it. He liked it best when they weren't too loud, so he could pretend it was you instead.

Your entire body is burning with embarrassment, but you were more than excited to hear his answer and apply that to the next time you saw Jake. But you'd be lying if you said you weren't a tiny bit curious about how Caleb liked it. After accidentally hearing him through the shared wall, you were definitely…intrigued about what was getting him to make all that noise.

Caleb takes a deep breath, "I don't know about Jason—Jake, whatever. But…slow, like you're savoring it, like you can't get enough. Use your tongue, not just your lips. And your hands. Don't be afraid to make noises—choke, gag, cry. God, just—"

His chest heaves as he works himself up, thankful for the pillow on his lap. He takes a deep breath, "And look at him. That'll drive him fucking insane." Drive me insane, his mind echoes.

You reel at the sheer amount information he's sharing with you. There was no way you'd be able to memorize all of this.

"Wait, so with my tongue…"

Caleb's heart stops when you simulate the motion by using your index and middle finger, tongue ghosting but not quite touching your digits.

Lord have mercy on his eternally damned soul.

"Jesus Christ," he forces himself to look away, "This wasn't the deal. I answered your question, now get ou—stop that."

"Just help me out and then I'll leave you alone!" you whine, refusing to put your fingers away, "This is just as embarrassing for me, okay? So let's just get it over with."

"I sincerely fucking doubt that," Caleb mutters under his breath. Against his better judgment, he tears his eyes away from the pillow on his lap and back to you where you practically have your fingers in your mouth, your pink tongue lolling out like a never ending taunt. Perfect.

And suddenly he's light-headed—unable to think clearly, to do the right thing. He croaks shakily, "Yeah, like that. But don't just let your tongue hang. Use it. And don't forget to suck."

The idea that he was helping you improve for another man—some idiot you'd met at university—pains him. But the visual of this was too great to pass up. In fact, he knew he'd be seeing this image again—when he was alone, when he was with Kelsey. It didn't matter.

"Like thith? I c-can'th," you lisp with your fingers practically in your mouth, but you can't seem to get your tongue to cooperate.

"Can you just show me?"

Caleb's eyes narrow and he scoffs shakily, "Show you how? I'm not whipping my dick out just so you can practice for your boyfriend. Go get a damn banana."

There's an awkward silence as soon as those words leave his mouth. He pinches himself internally and braces himself for your inevitable disgust—no fucking way he'd just said that.

"Would you?"

"Would I what?"

He knows what you said. He heard it loud and clear—how could he not? But he needed to hear it again, to see your perfect lips moving as you formed the words.

"Would you…teach me?"

You avert your eyes as you ask, unable to withstand his intense stare. You squeak with surprise when Caleb grabs your chin roughly, forcing you to look at him.

"You're gonna ask that and not even be able to look me in the eye?"

"W-Well it's embarrassing to ask!" you protest, "But it's jus' for practice. It's not even a big deal, it's not sex."

Caleb's fingers tighten painfully on your chin, "Not a big deal? Y—"

He cuts himself off—halting the lecture. He'd been completely ready to lay into you, to demand to know who instilled into you that sex, even just oral sex, was not a big deal. To remind you that your body was a treasure that no one deserved.

But when would he ever get this opportunity again?

Yeah, he was going to hell.

"Nah, it's not," he casually agrees with you. The sound of it so nonchalantly rolling off his tongue was absurd.

"Yeah!" you ramble, "B-Besides, who else would I ask? You're my Ge. You're the only one I trust."

Damn right he was.

"A-And it's just for practice, so you don't even have to worry about Kelsey."

Yeah, he wasn't. It was hard to think about Kelsey right about now. He should feel awful, but he didn't care.

"And we're not even related, so—"

"Okay, you've made your point Meimei," he says roughly. There's a brief silence, Caleb tilting your chin upward. You force yourself to stand your ground and face him—waiting for him to speak.

"If you're hellbent on this…" he trails off, fighting to keep his eyes forward and not down toward your lips, "Fine. Get on your knees."

Your eyes widen and your lip part with surprise, unable to move. Even though you had pushed relentlessly, you hadn't expected him to give in, knowing this was insane. No one would understand it, understand you.

Except Caleb.

"Wait I—"

"If we're doin' this we're doin' it my way. Or not at all," he whispers, releasing your chin and pushing you back. This was your out. It'd kill him if you took it, but he had to. As your Gege, his job was to protect you, and that would always come above everything. Including life-long desires that were presented before him on a silver platter.

"Ugh, fine," you grumble petulantly. Caleb watches as you scramble onto your knees, just as he'd instructed.

The sound of his belt unbuckling is obscenely loud, the zipper following soon after. You instinctively look away, just like you would every time you accidentally saw him shirtless around the house.

"Eyes on me, princess," comes his rough demand, "You said you wanted to learn. So make sure you learn." Your jaw clenches at the pet-name, unsure how you feel about the way it makes your stomach flutter.

"R-Right," you whisper, forcing your face back up.

Your eyes go wide, your lips parting with a hushed gasp, as you see how big he is—so big that his tip smears slick against his naval. He's neatly trimmed, his hair speckling along the angular line of muscles leading to his groin.

"What? Never seen one?" Caleb snaps, almost insecure—on edge, given the…situation.

"No! Just—" you trail off, picking your jaw back up. Just never one that big.

"Just never seen your big brother's, right?" Caleb finishes bitterly, unable to control his pessimistic mood. He'd dreamt of this a million different times, a million different ways. And not one of them included you having a boyfriend you were trying to practice for. He should be the only one you wanted to satisfy. Not the one you went to to get fucking lessons from, just to give the real thing to another man after.

"Why are you already hard?"

Caleb's face flushes nearly as red as his leaking tip at your torturously innocent expression.

Because just looking at you gives me an erection that doesn't go away until I pathetically jerk myself off in the shower to the thought of you.

"Was talkin' to Kels before you came in," he lies smoothly. As if Kelsey could ever get him this hard.

His words make you grimace with displeasure, a familiar feeling spreading throughout your chest. The idea that he was thinking of another woman, even if it was his girlfriend, made you seethe with jealousy.

But you didn't have much room to be upset. Considering Jake, and all.

"Okay, enough," he grunts as you open your mouth to talk back, "Did you want to practice or not?"

"Yes, yes!" you say, a bit too excited, afraid he'll rescind his offer at any moment, since he wasn't making any effort to hide his displeasure.

"Okay. Remember I said to use your hands. You can start with that."

For how reluctant he was acting, his instructions come out incredibly smoothly. You crawl towards him, a sight that makes his cock lurch.

"H-How should I? Do I just…grab it?"

Caleb's jaw ticks. He grips himself at the base, giving a slow, languid jerk. He bites back a vicious shudder.

"…Like that."

You reach your hand out, but hesitate, hovering so close that he can feel your warmth radiating off your fingers. Time feels suspended as Caleb watches you, waiting for the moment he feels your hands on him for the first time. Probably the only time.

He fights the urge to grab your hands, enveloping them in his bigger ones, and closing them over his cock himself. As much as he wanted this, he wouldn't force you. He needed you to cross that line on your own.

"Look, we don't have to—"

Caleb chokes, eating his words, when your hands close over him, too roughly, too tightly, too inexperienced.

And that only made him harder.

"C-Christ—ease up," he chokes out, "Don't fucking yank it off."

You pout, easing your grip, "You're being so mean to me."

God, that pout combined with your heavenly hands make for a dangerous combination.

"Not gonna baby you," he rasps, "You said you wanna be good, right? You can take it. You're a big girl."

You grumble, briefly wondering if he was nicer to Kelsey when they did this. The reminder of his girlfriend should make you feel terrible, but all it does it make you more determined.

Caleb was your Gege. Yours. If he was gentle and sweet with anyone it should be you.

Besides, this was just practice. No different than watching porn. You had nothing to feel guilty for; you weren't doing anything wrong.

"Fine. What's next?"

Caleb grunts, "Move up and down. Jus' like that."

He fights to keep his moans at bay, watching your beautiful face scrunch in concentration. Truthfully, he definitely could feel your inexperience in your hands—and yet, it's the best he's ever had.

"Is this okay?" you squeak, mesmerized by the stickiness spilling from his tip.

"Yeah," his abdomen heaves, "You can move up. The tip is more sensitive, so—"

He groans, fisting the sheets as your thumb finds just that, stroking the soft skin and tracing the edges of his engorged head. He was a lot more sensitive than usual, and it was no doubt because of who had him in their hands. He might as well be a damn virgin himself.

"Sorry, too much?" your voice is apologetic and you move to release him. But Caleb is faster, holding your hands in place and not allowing you to retreat.

"No," he growls, "You're doin' good."

The praise makes you grin with satisfaction, "Oh…good! What else?"

He chuckles darkly, "Speed. Slow first. Then faster. Yeah, juuus' like that."

Caleb throws his head back as you start jerking him off with both hands, picking up on a few things on your own—like how you twisted your wrists as you moved up and down.

"W-What else did I teach you earlier?" he fights to remain unaffected. Just practice, after all.

"Umm, you said I shouldn't forget to suck," you say, looking up at his darkened eyes, "But I don't think…I can fit this in my mouth."

Caleb's muscles lock up, not expecting you to go as far as to actually want to suck him off. His cock lurches in your fingers at the thought. He had to tread carefully.

"Don't worry about it pips. You did good for your first time. We can stop here," he strokes your chin, words dripping in the condescension he knows gets you worked up enough to challenge him.

The glare you shoot at him is icy and fiery all at once, not even realizing he'd purposely gotten under your skin hoping you'd want to prove him wrong, "I still want to try."

That's right. His little trooper.

"Sure, why not, since I'm already…" he feigns coolness, gesturing to his bare cock. You easily fall for his calmness, annoyed by the way he seems so collected. No way you were that bad at this. And you'd prove it.

"Teeth back," you repeat inaudibly to yourself, "Lips, tongue…"

Your hands are still wrapped around him when your slowly bend down towards his erect length. Caleb's scent is so distinct—a manly musk that's mixed with the cologne he tends to wear. It makes your mouth water, saliva coating your tongue.

"Jus' start with the—"

He sucks in a sharp breath when he feels your tongue against the underside of his tip, where the skin is softest and he is the most sensitive. You're warmer than he'd imagined, your soft muscle tentatively lapping up the shiny trail of arousal, unable to stop from moaning at the surprising taste.

You find yourself enjoying the unique mix of sweet and saltiness. Encouraged by his reaction, you lick his cock from the base, your saliva coating his hair, to his angry tip. His thick thighs tremble beneath your hands that brace over them to support your weight—his hands twitching with the need to touch you.

"Does it normally taste like this?"

Suddenly self conscious, Caleb demands, "Like what?"

After another torturous kitten lick, you hum thoughtfully, "Sweet."

He groans, realizing you enjoy it, "Sometimes. If he takes care of himself, maybe."

You nod trustingly, staring at the slit of his cock, "'Kay, I'm gonna…" Tentatively, you close your lips over him, letting the girth of his tip stretch your mouth. Caleb curses, fingers grappling for purchase.

"Fuck, fuck," he groans. With your warmth encompassing his sensitive head, he's unable to maintain the nonchalant charade. You moan with surprise when his hips buck upward, shoving another inch into your mouth. His hiss reminds you to pull your teeth back.

"Y-Yeah, jus' like that, pips," he huffs, "Slow, just like I said." Savor it.

You nod with his cock in your mouth, eyes trained on his defined abdomen in concentration. Slowly, you take more of him—another inch. Then another.

Caleb's knuckles are white as you reach just about half way, your tongue still working at the underside of his shaft, massaging that prominent vein. His slick coats your mouth, causing you to salivate naturally and his lap to become a lewd wet mess.

"That's enough," he forces out, "You don't have to take more." This time he's serious, not trying to reverse-psych you. If you went any further he might bust, and there was no coming back from that.

You glare at him through your eyelashes, assuming he thinks you can't take more. You were no quitter.

Plus, you wanted him to make those same sounds you'd heard countless times through your shared wall.

You fight through your gag reflex as you try to take him to the hilt. Your throat groans in protest, stretching unnaturally at the foreign object. And Caleb can see that. See his cock bulging out of your neck as you take every inch, your throat impossibly tight and warm.

"Wait—God," your name rolls off his tongue in ways that were anything but appropriate for what you'd both convinced yourselves was happening. The sound of your amateur sucking was obscene—wet, lewd, filthy.

Moaning in response, you focus instead on the things he'd taught you. Giving your throat a break, your hands grip his base, wet with a mix of your saliva and his pre. Your tongue focuses on his twitching tip as you move up and down. The sounds he makes are the perfect encouragement, fueling you with confidence.

"Oh—shit…" he pants, trembling fingers finally finding your hair, gathering it up to hold out of your face, away from the mess around your mouth.

And then his fingers are tilting your chin up just slightly. He jerks when the change in angle causes your teeth to graze him—but the pain is welcomed, reminding him that this was very real.

"Eyes, remember?" he growls, "Look me in the eyes when you take me."

Staring into his galaxy eyes, you blush and and obey. It made the moment anything but nonchalant and "just for practice." This way, neither of you could pretend this was okay. Certainly not to Kelsey or Jake. But that's the last thing on Caleb's mind as you look at him through your teary eyelashes, eyes hooded as you choke on him.

"Such a quick study," he grunts, attempting to salvage the charade. His thumb shakily strokes your jaw, "You're gonna be so damn good—"

He's cut off by the sound of his ringtone blaring, Kelsey's smiling face lighting up the screen, groaning when your throat tightens in surprise. Caleb's stomach twists—not with guilt, but at the reminder of how fleeting this facade was. Your own chest clenches with displeasure at the interruption—especially from his girlfriend.

"Dammit. Jus' ignore it," he pants, not even realizing how desperate he comes off, "Fuck, just—"

"It's fine, just pick it up."

Caleb hisses when you pull off of him, expression unreadable—thrown off by your flippant attitude. But then he just smirks.

"Keep goin,' yeah?" he whispers gruffly, picking up his phone with one shaky hand, "Good practice on keeping quiet." Your eyes widen when he picks up the phone while simultaneously gripping your hair at the back of your head, pushing you back down until his cock smacks your face.

"Hey, babe. What's up?"

"Babe?" you mouth, rolling your eyes at him—making your displeasure known. He shoots you a crooked grin, holding his phone between his shoulder and ear. He grips the base of his cock, squeezing your cheeks with the other until you're forced to open your mouth for him.

You take him back into your mouth, tongue lolling out and using your hands—one at his base, the other carefully stroking the soft skin of his warm, heavy, sensitive sack. The faint sound of a female voice on the other line makes you all the more desperate to prove yourself. Caleb bites the inside of his cheek so hard he nearly tastes iron.

"Good fucking girl," he hisses quiet enough where you should be the only one that can hear him. Your heart flutters and you sink him back into your throat, inch by inch.

"S-Said sounds fuckin' good," he grits into the phone, "Dinner. Tomorrow. Yeah."

Caleb's grip nearly crushes the phone when you make that little throaty gurgle as you take him deeper. He can vaguely hear Kelsey on the line asking if he's okay, but he can only respond in clipped phrases.

"That's good, Kels," he grits out as she starts going on about something insignificant, his fingers gripping your hair and guiding you up before pushing your head back down. You struggle to breathe with his fat cock spearing in and out of your lips, but you're determined to prove you can.

"U-Uh huh," he mutters, looking down at you—smearing the spit dripping down your chin with his thick thumb. It's devious, the way he silently praises the way you take him, all while listening to his girlfriend go on about something he has no interest in. Especially not when you remember to look at him, your eyes finding his again.

Caleb chokes, heart stuttering at that glassy doe-eyed expression, his fingers threatening to shatter the glass screen of his phone.

"Nothing," he snaps a little too harshly into the phone, "Nothing's wrong—Shit."

Caleb can feel his orgasm fast approaching, unable to continue keeping it at bay when you look at him like that. And cumming down your throat, marking you in such a primal way way…he'd never recover.

"Fuck—I gotta go Kelsey," he doesn't wait for her response before he hangs up the phone, tossing it aside with a loud clatter against the nightstand, next to yours. With his other hand, he roughly grips the base of his cock, physically stopping himself from finishing.

You squeak with surprise when he yanks you off, "Caleb—?"

"That's enough practice," he snaps, much more aggressive than he means to as he moves to pull his underwear back on, "You know what you're doing."

"B-But you didn't…cum," you say. He curses at how painfully innocently you say the lewdest things, l, like you had absolutely no idea what they did to him.

"You don't have to do that, princess." The endearment comes out naturally, "In fact, you never have to do that." His words are bitter and clearly directed at something else, shaking with the weight of the willpower he'd needed to not continue—to not have his way with you.

"But I…" The words 'want to' die on your tongue. You wanted to be prepared, after all—was the line you were still running with.

The silence between you two is charged, the air permeating with the distinct smell of sex. Caleb knows he has to be the one to push you away, to draw the line, because he couldn't trust you to. But knowing versus wanting were two very different things.he couldn't trust you to.

"You what?" His question is soft but comes out more like a demand, still on edge from the sudden loss of your warmth.

"I-I'm scared," you admit, "I don't know what to expect. When he…"

You gulp nervously, suddenly shy again. Caleb's teeth grind at the implications of your words, doing his damned best not to imagine it.

"If you're scared, you aren't ready. And you shouldn't be forcing yourself to be."

"I'm ready!" you say defensively, "But will you…show me? How it'll work?"

Caleb's eyes narrow, "How what will work?"

You flush, "Y-You know. You know what I'm talking about!"

"No, I really don't," he whispers huskily, finding himself leaning closer, his cock still out, boxers abandoned and pooled at his knees. He knew what he wanted it to mean, but he didn't know if that's what you meant, "Spell it out for me."

"I hate you. Okay, fine," you grumble and concede, "Sex. Like, what will he do and how should I…act?"

Caleb stares at you blankly. There was no way you weren't doing this on purpose, right? He felt like you were pulling a cruel prank on him, testing to see how far he'll go just for fun.

Well, two could definitely play at that game—a game he was all too familiar with. Pushing each other until the other inevitably conceded, screaming uncle and begging for mercy.

You gasp as he guides you backward, your back hitting the soft mattress and your stomach knotting in…excitement.

"If he's good…he'll take care of you."

Caleb's thumb brushes slowly across your lip, smearing the residual saliva away. It makes your breath catch, which doesn't go unnoticed by him.

"He'll take his time and make sure you're ready before he does anything."

"Ready?" you squeak, squirming underneath him, even though he hasn't put any of his weight on you.

"Yeah," Caleb whispers, eyes drawn to your puffy lips. He'd made you like that. "Here."

His fingers gently tug at the hem of your dress, right between your thighs. He doesn't touch you, but it's enough to make you gasp when you realize what he means. The sound goes straight to his dick, harder than he's ever been his entire life.

C'mon, pips. Say uncle.

"And then?" you ask, so earnest it genuinely confuses him.

"Then…" he mumbles, barely a whisper, "And only then…you'll let him inside you."

"I-Inside…" you stutter, unable to think clearly from his proximity, "Inside me."

"Yeah," he murmurs, "Here." He gently presses on your lower stomach, over your dress—unable to stop from imagining what it would be like to do exactly what he's explaining.

"It's gonna hurt, right?" you look at him with wide trusting eyes.

"Yeah, most likely," he whispers, heart thundering every second he looks down at you.

Your next request comes out shaky and hesitant, but you force the words out.

"Can you show me?"

Caleb nearly falls on top of you as his joints buckle, violet eyes darker than you've ever seen them—even more than when he was pissed.

"What the fuck are you—"

"I-I don't mean put it in!" you say defensively, "I j-just mean like show me where. And how the motion would be. So I'm prepared.

Caleb stares at you with an unreadable expression, making you squirm. You should've known not to ask that.

"H-Hah! Got you. J-Just kidding okay? Now, get off m—"

Caleb captures your chin before you can roll out from under him, "So now you're kidding, pipsqueak? I was going to say yes."

Your eyes widen with surprise, "Really?"

"Yeah," he pauses briefly before repeating your earlier words, "It's Gege's job to make you happy, right? To make sure you're prepared."

The two of you just stare blankly at one another, expecting the other to cry 'uncle.' But it never comes.

You take a deep shaky breath, "R-Right. Show me then."

His eyes shine with inexplicable emotions for what feels like a full minute, before he sits up on his knees between your parted legs. His fingers dance on your bare thighs, slowly pulling up the hem of your dress.

"Okay," he says, steeling his voice from wavering, "He'll go…here."

He gently pulls up your dress until it pools at your hips, revealing your bare thighs to his predatory gaze. His eyes follow the expanse of your soft thighs up…until he gets to your panties. The black polyester sits low on your waist, pretty and lacy. Finally remembering to breathe, he forces his eyes back to yours.

"This okay, princess?"

You blink at him, dazed and nearly delirious, but ultimately nodding, "Y-Yeah. Just do it."

Caleb grimaces at your detached words. But ultimately he doesn't stop, his fingers reaching for the seams of your underwear. He doesn't pull them down, his thumb brushing soft circles just a few inches above where your clit would be.

"When he's down here, you should be ready, wet," he rasps, dizzy at your intoxicating scent.

"Wet," you breathe out, blinking slowly at him, "Like right now?"

Caleb's eyes snap down to your clothed cunt. Because of the dark material, he hadn't initially noticed.

Fuck.

It wasn't just a tiny blemish. You were soaked. No wonder he could fucking smell you, his mouth watering like a damn beast. He felt his cock lurch, fearing for a second he might cum just at the sight of you.

"Is that enough?" your voice cuts through his trance.

"Not sure," Caleb finds himself saying, "I'd have to…check closer."

It's a lie he should feel ashamed for, but he feels nothing but anticipation, hope, that you'll be naive enough to agree. It was obvious you were dripping. He certainly didn't need to check.

"Check? Like…with your eyes?"

Caleb chuckles dryly, "How else, pips?" He thinks about lying and saying he needs to check with his tongue. But he knew better than to push his luck.

You gnaw on your lip but nod, "O-Okay."

His blood pounds so violently he can feel his heartbeat in his cock, his thumb trailing downward and pressing his digit gently into you—wedging your panties between your lips.

"Caleb—!" you squeal, not expecting that, "W-Wait…"

"Just checking," he reassures you, his voice low and soothing—the exact tone he knows calms you down.

"Fuck…" he grunts as your slick coats his thumb. He'd gotten you this wet, just from feeding his cock down your greedy throat.

"What?!" you panic, looking down at him between your spread thighs, "I-Is something wrong?"

"No, nothing's wrong," he quickly corrects, "Yeah, you're wet enough princess."

He doesn't remove his thumb, instead slowly moving it up and down. Just a few millimeters, not enough to draw your attention to it but enough where your breath quickens audibly.

"Oh good," you breathe a sigh of relief that's is so painfully trusting, "What next?"

Caleb gets onto his knees before hovering over you, bracing his palms on either side of your face to support his weight above you.

"He'll climb on top, like this," he whispers huskily, his cock swaying inches above your thighs—still hard, "Or you can be on top too, but for your first time he should take care of you."

"Okay. On top," you repeat as if memorizing instructions, "And then?"

"Then…he'll line himself up here."

Caleb's hands reach between your legs and firmly taps his length on your cunt. It makes a wet smack.

"Line himself…as in—" you gulp, looking down at his swollen erection against your cunt.

He doesn't think, knowing if he does he'll stop himself, grabbing his thick base and pressing his length against your slit, his tip nestled against your tight entrance.

"Yeah, like this," he feigns nonchalance, as if this was the most normal thing in the world. His thick tip wedges the fabric of your panties deeper into you.

"Caleb—i-it feels…" you trail off, strangled and overwhelmed. The way you say his name has his knees buckling, which causes him to inadvertently grind against you, his cock thrusting up and rubbing firmly against your clit.

Your hips arch as you cry out, the friction bringing tears of pleasure to your eyes and torrid groan from his lips, all reason out the window.

One "wrong" move and he could bury himself inside of you. And you'd probably let him.

"He'll move like that," Caleb grits out, pretending the slip was entirely intentional.

"Mmnngh…" your moan makes Caleb's jaw clench painfully, "Just l-like that…?"

He knows you aren't confused, more-so overwhelmed. But he can't help but grasp the opportunity.

"Yeah, just like this."

He shifts his hips, thrusting his cock along your folds—still flimsily covered by your soiled panties. The action mimics the movement of sex, effectively fucking your lips. For Caleb, that alone feels like heaven.

"It feels good," you choke out and writhe, to which Caleb bites back a tortured groan. He was making you feel good.

Caleb watches as you sit up on shaky elbows, eyes glued to your pelvises pressed together. Emboldened by your awestruck expression, he hooks your pathetically ruined underwear with his index finger and pulls them completely to the side, allowing his thickness to sit right between your lips, his bare skin against yours.

"He should start slow," he murmurs, demonstrating by pulling his hips back and slowly thrusting up.

"Start slow…" you bite out, huffing for air, "Meaning he'll eventually go quicker than this?"

Caleb's abdomen tightens with displeasure as you remind him of the reality of the situation—imagining you spread open like this for Jake. But he pushes it aside.

"Yeah."

"…W-Will you show me?"

Oh, come on. You had to be doing this on purpose.

But who was he to deny you? He'd never been quite so strong-willed when it came to you.

"Sure," he grunts, fingers moving your hair out of your eyes. His Adam's apple bobs painfully when he looks back down, allowing his hips to do what you'd just asked. The sound of his heavyset balls colliding with your wet skin fills the room, making the both of you thank heaven that your grandmother was out doing her afternoon taichi in the park.

"O-Oh, God," you whimper, clawing at everything in sight. The comforter. The pillows. His skin.

Caleb's tip catches along your entrance, dangerously close to slipping right inside of you—so slick with both your combined fluids that even your virginal resistance was no match.

"O-Okay, pips?" he forces out, thumb catching your tears.

"Nnngh…y-yes," you gasp as he nearly pushes into you again, "It feels…good."

Your praise makes him growl, thrusting his cock up against you again—tip smearing messily against your naval.

"Good," he grunts, "It should. It should only ever feel good."

"B-But when he puts it in…i-it'll hurt right?"

Caleb falters, squeezing his eyes shut as he uncontrollably imagines what kind of face you'd make if he finally breached your perfect entrance.

"Maybe," he grits out, "Yeah, probably."

Your eyes are wide as you nod, the tears in them making Caleb lose his remaining grip on reason. He never wanted you to experience any pain. Unless it was from him.

It was his job as your Gege to prepare you for anything and everything, for the outside world he so desperately craved to protect you from.

That's all this was.

For a second, he almost believes himself.

"It doesn't have to," he whispers, a low purr, "It won't hurt. If you've done it before."

Your eyes widen in genuine curiosity, making his gut twist with a flood of guilt.

"What do you mean? How?"

"If you've already had one inside of you," he grips the base of his cock, gently tapping it on your sopping cunt to demonstrate, "It won't hurt—since it won't be your first time."

The meaning of his words finally dawns on you, your blood pounding in your ears as it sinks in.

"W-Wait—you and me?!"

"No, course not pips," he keeps a straight voice, expertly maneuvering your disbelief in a way only he knew how, "We wouldn't actually."

He lines himself up with your entrance. Just demonstrating.

"I'd just put it in," he whispers, stroking your cheek reassuringly, "Just to stretch you out. That's all. That way when you and…"

He trails off at the thought, trying to recompose himself—still pressed against you sweltering warmth, "That way it won't hurt for your next time."

"And…that's okay?" you ask with wide and trusting eyes, "It wouldn't actually be sex?"

"Nah, 'course not," he reassures, unbelievably cool and confident, "Just to break your hymen."

You make a face, "That sounds like it'll hurt!"

"It will," he reasons, "But you want your first time with Jack to be good, right?"

You're so conflicted you don't even correct Caleb's mistake. To be honest, it was hard to think about Jake when Caleb looked at you like that, your naked lower halves still grinding together.

"Of course I do…" you trail off, stifling a moan, "But…"

"I'd just be doing my job as your Ge," he rasps, stroking your jaw reassuringly, using the gesture to remind you that he only ever has your best interests in mind. But that didn't mean those interests couldn't also benefit him.

Your trusting but conflicted expression is his undoing. It's the push he needs to do what he knows will tip the scales of your hesitation.

"But if you're too scared of the pain…" he rasps with just the right amount of condescension, moving to get off you, "We don't have to do anything you can't handle, pips."

He chooses his words so damn carefully, using them just right. He knows you the best. And just like before, it fires you up just how he'd wanted it to.

But you weren't blind. You knew Caleb had a silver tongue. And while he was the one who grabbed your shoulders and turned you in the direction he wanted you to go towards, you were the running when he released you.

"I am not! L-Let's do it then."

Caleb is still for a split second, your words seemingly going in one ear and out the other.

"You sure, princess?" he asks coolly, repositioning himself back atop you.

"Yeah," you snap, embarrassed, "Like you said, it's not actually sex. And it'll be quick, so…"

"Right." That was what he said, after all.

"Not sex," he reaffirms as he braces his forearms on either side of your head, his bangs tickling your forehead.

"Just practice," you whisper breathlessly, gasping as his shaft presses fully against you and he begins to move his hips, just like he had earlier, creating that same addicting friction.

"Just practice," he parrots, using that self-assured older brother voice that works on you without fail, "You want to be good, right pips?"

He knew he was full on coercing you now, using the insecurities you'd shared with him in his favor. He could deal with the shame later. Right now…

Right now he needed to be inside of you.

You nod with a determination that makes him smile, unbelievably smug and proud.

"I want to be good," you repeat, steeling your voice. It was true, you wanted that more than anything.

But who you wanted to be good for? The lines were starting to blur. Maybe both. Or maybe…

You look up at his glittering dawn-break eyes, "Caleb, please. Teach me."

His eyes widen at that. You were begging him—begging him to put his cock inside of you.

"Yeah?" he grunts, slipping his fingers under your head and gripping gently, "You want me to teach you?"

You can't help but bite your lip at that. The undeniable allure to his velvety voice, the way his heated stare refuses to let go of yours, the way he speaks to you. It forces you to confront one thing—yeah, you wanted to learn.

But you only wanted to learn from Caleb.

Not trusting your voice, you nod. He swears, fingers tightening at the back of your head. He has to hold himself back, his body instinctively lurching at your wide-eyed nod of consent, trying to bury himself within your warmth.

"Okay," he voice is much steadier than he feels inside, stroking your damp cheek and breathing out your name, "Just puttin' it in. Nothing else."

You stay completely still as Caleb repositions himself. He stays hovering above you supporting himself with one palm while the other comes between your bodies to firmly grip his base and line himself up with you.

At your gasp, he considers stopping one more time to ask if you're sure. But that dark manipulative shadow inside of him wins, not allowing him to risk you changing your mind and ending the night before he's gets the chance to be inside you.

Instead, he takes your hand, intertwining your fingers with his and holding it above your head.

"Gege's got you," he soothes, ghosting his lips against your forehead which he so often did. Except it didn't feel so harmless now.

"Y-Yeah," you stutter as you feel his thick tip spread your lips around him, "I know. Still…scared."

Caleb's heart twists at that but he can't go back now, "I know, pips. Don't worry. Jus' gonna put it inside. That's all."

At your determined nod, he looks down where he's one inch away from taking everything he's ever wanted.

"Deep breath for me, princess."

His gut stirs with twisted pride when you diligently obey, looking so damn beautiful as your chest rises and falls with your shaky exhale.

"That's my girl," he murmurs warmly, practically purring. You squirm at his words, lips parting to say something, only to be cut off by your own strangled cry when he pushes into you. You're unfathomably wet, but even the copious slick isn't enough to ease him completely inside—your entrance tight and unforgiving.

"Jesus," he grits out as your nails dig into his hand and your sweltering heat envelopes only the tip his head.

"Caleb—!" you pant, the back of your head sinking into his pillow when you throw it back in pain, "Ngh…it h-hurts!"

He gently shushes you, rubbing soothing circles into your knuckles, "Shh, I know. I-It's supposed to." His own voice wavers, fighting to maintain control as your cunt forces him deeper like a damn magnet.

"I don't know i-if I can—" you moan. Your free hand claws at his shoulders. You don't push him off, but it's enough to make him pause, as much as it pains him to do so.

"You're doing so good, baby," he praises, completely sincere, "It's s-supposed to hurt. You're so fuckin' tight, so I have to stretch you out a bit."

You groan, not at the sting, but at 'baby.' You'd heard him call Kelsey that earlier, and it'd made you cringe. But when he called you that?

"Mmnngh…A-Am?" you whisper, unable to get complete sentences out. His pretty little praises distract you from the pain, allowing him to sink another centimeter into you.

Caleb bites the inside of his lip, his chest clenching at your adorably broken words, "Yeah you are, pips. Doing so damn good f'me."

He feels you flutter around the small bit of him that's inside you, a smirk etching onto his face. Of course you'd tighten when he praised you.

"Can you take more?" he presses his thumb against your bottom lip, "Or you tappin' out?"

You glare. Even if you had been planning to ask him to stop, you sure as hell wouldn't now.

"Fuck—!" Caleb stutters, hunching over you, when you wrap your trembling legs around his waist and pull him closer. You clearly hadn't thought your actions through, because it makes his entire bulbous tip pop into you and a sharp ripple of pain to shoot through your whole body.

His entire field of vision goes white. Your squeal of pain barely registers to him, his ears ringing when he feels your gummy walls envelope the most sensitive part of his body, unlike anything he'd ever felt before.

One of his hands slam into the headboard, gripping on for dear life to keep from cumming prematurely. It feels like an eternity passes before he can function again, your pained mewls finally reaching him.

"Wait, t-too big. I can't," you whimper, "Unngh..It won't fit."

"You can," he grunts, gripping your chin with his free hand, "You are. Look."

He tilts your chin down, forcing you to watch where he's inside of you. Caleb twitches as your eyes widen and your lips, swollen from his cock, part in awe.

"See? You're doing so good," he coos, trying to encourage you, "You want to feel good, right? Then you have to put up with just a little more pain. You can do that, can't you?"

You bite your lip, looking back up at him. Right. It'd feel good later. With…your boyfriend. The thought that it might not feel good now, with him—with Caleb, made you feel bitter.

"Hey," he tilts your chin back up to meet his eyes, "You with me?"

His hypnotizing eyes bore straight into you, darkened by his thick eyebrows. It's all too much—the intensity of his gaze, his thumb rubbing circles into your chin, his tip, the one he'd just been teaching you how to suck moments ago, nestled inside of you.

"Yes," you whisper, lip trembling, "O-Okay. Keep—nngh…keep going. Just…just rip off the bandaid. Don't go slow. I-I'll chicken out."

Caleb groans, wishing you could hear yourself—hear what you were offering him. He pinches his wrist, reminding himself he was just putting it in. Nothing else.

"Good girl," Caleb exhales a labored breath, forcing himself to stay grounded, "See how brave you are?"

You want to bite back, but his words are more genuine than they are patronizing, "J-Just do it."

"What, first taste of cock and you're already demanding things?"

"Caleb!" your voice is squeaky with embarrassment, "I swear, if you d—"

But of course, he takes that moment to push another thick inch into you, stealing your words away. The pain makes you squeal, a dull pulsating ache that resounds from where his cock stuffs you full—even when it's barely a quarter of the way in.

"So fuckin' tight," he rasps, holding your thighs flush against his sides, "Can't believe you've never let anyone else in here, hm?"

"Huuurts, Ge," you whimper, nails raking down his back. He's still wearing his tank top, so you're clawing at the fabric, almost trying to tear it off.

"F-Fuck—I know, pips. I know, I'm sorry," he groans, fisting the sheets. He tries everything he can to ease the pain—pausing, slowing down, soothing touches. But your agonizing mewls continue, and he can't stand the sound of you in pain.

His body acts before his brain can catch up, face dipping down. His lips easily find yours, slotting himself against you and swallowing your cries—both the ones of pain and the ones of surprise.

Your eyes fly wide when you feel his mouth on yours, instantaneously distracted from everything except his lips. They're soft—unbearably tender compared to the pain that radiates from your thighs. It's different from the kisses you'd shared with other people in the past, with your boyfriend even. You'd found those fun, but clumsy and awkward.

But with Caleb…it felt natural—as easy as breathing. Your body reacts on instinct, fingers finding his soft hair—not quite pulling but not allowing him to withdraw either.

You were kissing your big brother.

Or he was kissing you. And you were letting him. No—you couldn't kid yourself, you were kissing him back.

Was this still really just practice?

"Mnngh—C-Caleb?" you gasp against his lips when he gives you a centimeter to breathe.

"J-Jus' to help with the pain," he's already preemptively defending himself, "Don't want to see you hurting."

You're hesitant but you nod. Caleb groans and leans back in, surging at the opportunity and letting his tongue explore into you. You're softer, sweeter than he could've ever dreamt up.

With his tongue down your throat, he can't help but sink himself the rest of the way into you. And you hardly notice the sting of it, too focused on how he maps out your mouth, exploring and discovering all the things that make your cunt tighten around him.

"Took it all," his breath is warm against your mouth, "See? Knew you could do it. Perfect girl."

"Oh god," you gasp for air, "Th-Think I can feel you in my tummy."

Caleb's eyes snap down, pulling away from your tear-soaked face to catch an eye-full of the mess between your bodies. Your arousal had smeared against his pelvis, making the delicate veins there even more pronounced. A slight reddish tint colors the slick, a sight that fills him with a sick, twisted satisfaction—possession.

He did that. He took your first time. You let him—gave it to him.

His palm flattens against your naval and applies light pressure, making you whine and arch into his hand.

"Yeah?" he grunts, biting back a hiss when you squeeze him, "You took me all the way here, baby. Even for your first time."

The sting slowly starts to fade, only the sound of both your ragged breathing audible as you're both silent—taking it in.

"Still hurts?" Caleb mumbles, his own muscles trembling in protest for the lack of movement, his body demanding he thrust.

"Nnngh—No. Not as much. It's not so bad anymore," you moan when he shifts to reposition his weight. He's so big the ache doesn't fade, but it's dull now.

Caleb's head falls back with his own pleasured grunts, the slightest movement making ecstasy shoot up his spine. But he couldn't move. You'd agreed just on this—just putting it in.

You force your head up so you can see where your bodies are connected, skin crawling at the light smear of blood.

"D-Did it work?"

Your innocent question sparks a sinister desperation in him.

Lie.

"Almost," he rasps leaning down to scrape his teeth against your ear. The change in position shoves him deeper, your cervix protesting the thick intrusion, "Need to do it again to make sure you're stretched right."

"Nngah…Again?" you groan at the pressure, "But…"

But as he looks at you with those eyes, those stormy purple stern big brother eyes, you instantly fold.

Nodding slowly, "O-Okay Caleb."

"Good girl," he presses a kiss to your pulse, just below your ear, "Gege's got you. You know that."

Your words are swallowed by your whine as Caleb pulls out of you. The feeling is completely foreign, but the emptiness is worse than the pain.

He chuckles at your adorable whine, able to tell you're already starting to enjoy the feeling—enjoy his cock, "Ready, princess?"

At your determined nod, Caleb pushes back in, unable to hold his own sounds back, "Oh, fuck."

"Caa—leb," your cry comes broken and desperate. The feeling of being stuffed so impossibly full is starting to feel confusingly addictive. It hurts, with him being impossibly thick, but it also makes your core tighten with an odd sensation, one similar to the sensation you felt when you'd touched yourself in the past. Only ten times more intense.

"Another," he grunts, "N-Need to do it one more time."

You cry out, a mix of pain and ecstasy, when he pulls out only to push back in just as quickly—no chance to protest even if you'd wanted to.

"Sh-Shit," he growls, "Again. Moan for me again, jus' like that."

He's almost entirely lost himself—unable to continue acting like this is anything but what he's wanted for the past decade, moaning and trembling like a damn teenager getting his first blowjob.

"Nnngh—wait…" you gasp with wide eyes when he grinds into you, the feeling intensifying and shooting through your nerves as his coarse hair rubs against your hardened clit.

"Jesus fucking Christ…" he groans your name into your shoulder, hips stuttering. He's not quite thrusting in or out, but grinding against you to get the faintest friction from your perfect walls.

"Caleb it feels funny," you writhe, burying your own face into the crook of his neck when he presses your thighs against your stomach.

He can barely hold it together, realizing he has you in the meanest fucking mating press. His hips move on their own accord, snapping into your cunt with a wet 'thwack' of skin against skin. He was well past just "putting it in."

"Funny good or funny bad?" he demands.

"Mmnngh…g-good? Still hurts. But it's starting to feel better. That's a good sign right?"

His jaw clenches tightly. The idea that he, his cock, was making you feel good is enough to send him into a frenzy. With a smooth roll of his hips, he thrusts again into you—nearly five times as many as he originally promised.

"Haah—yeah," he murmurs, voice velvety and reassuring, "Thas' exactly how it should be."

You nod wordlessly, wrapping your arms around him and hugging tightly and seeking a safety only he can provide you. He feels terrible, watching you snuggle into him like a scared fawn—trusting, naive. All while he was debating how he could justify continuing, because he sure as hell wasn't stopping now.

"But I have to keep goin' okay?" he whispers sweetly into your ear, "It's better this way. If your body is used to it." Another thrust, slower and tender— coaxing you to say yes.

You're confused, skeptical, of his words, but at this point the thought of him pulling out—of leaving you empty, is unfathomable. You didn't want him to stop.

It'd only prepare you better, right? For your boyfriend.

"Okay, i-if you think it will help," you whisper, teary-eyed, "Unngh…you can keep going."

Caleb's eyes darken to a blackhole of intensity, and before you know it his lips are on yours again. It takes you a second to catch up, letting him in and letting his tongue tangle with yours.

He must've kissed you again to distract you—it made sense, why else would he? Because as soon as he did, his hips started moving again, a slow sensual pace that's still firm enough to sting your newly fucked entrance.

Caleb's throat bobs thickly as he lifts his head. He hooks both his hands under your thighs, pulling you roughly to his body, thrusting back into you. You scream at that—but it barely hurt anymore, it's just an overwhelming sensation of sharp pleasure.

"Sorry, princess," he whispers genuinely, but not stopping, "G-Gotta get deeper. Make sure you're really ready."

"S'okay," you groan, "Doesn't hurt so much any—mmnngh—more."

"Yeah?" he grunts, another thrust, "Good girl. When it feels good, then you can ask for more."

"M-More?"

"Faster. Harder," he growls darkly, "Deeper. Should all feel good when I—he's inside you."

"C-Can we try that then?"

Caleb's hips stutter, "'Course we can, princess. Tell me what you want to try."

It's hard to think when Caleb doesn't stop moving inside you—his cock so long it feels like you're choking on it. At your dazed expression, Caleb grips your jaw, brushing his lips against yours again, making it even harder to think.

"C'mon, use your words babygirl. Can you do that for me?"

Normally, those same words might make you glare at him, but with him buried inside of you, stretching you so sweetly, you obey—happily.

"F-Faster, please. Can you go faster?"

He can't help but grin at that, "Look at you, learning so damn quickly. You want me to go faster, princess?"

Now, you really do glare, "Yes! Don't tease. You said I should be prepared for—"

Caleb cuts you off with a mean thrust, fast just like you'd asked, but also much harder.

And he doesn't stop at just one. You'd asked for faster, and he would give you just that.

"Demanding girl," he grunts between thrusts, "Like that? Is this what you wanted?"

All you can do is moan, overcome with this new feeling of ecstasy. You'd felt physical pleasure before—getting a massage, when Caleb would play with your hair, and obviously when you touched yourself. But it was never like this. This was unprecedented to you.

"Feels so good," you moan, embarrassingly whiny, "M-More."

He twitches inside you at your desperate plea, "More what? What do you want from Gege?"

"D-Don't make me—mnngh! H-Harder—!" you squeal when Caleb squeezes your nipple roughly through your dress, delivering swiftly.

At this point, the charade was up. He didn't even bother trying to fake it anymore—this was the best thing he'd ever experienced and there was no hiding that.

"G-God," he groans your name roughly, "You're doin' so good. Feel how perfectly I fit in you?"

Your stomach flutters, walls subconsciously tightening, unbelievably turned on by the clear evidence that he was also enjoying himself.

"F-Feels good for you too?" you slur, unable to speak clearly. His hand slides beneath your thighs, your dress bunched around your waist, grabbing a fist full of your ass.

"Hell yeah," he squeezes your soft skin, "You feel incredible—fuck."

He swears as your cunt wrings against him. Of course you had a praise kink. Spoiled little brat.

"You like that, hm? Like it when Gege tells you how perfect you are?" he grunts, feeling pressure building in his gut—impossibly tight and unstable, since he'd been edging himself since you walked into his damn room.

"Oh god—yes!" you cry, as embarrassing as it is, "W-Wan' to be perfect for you."

Caleb's rhythm falters, nearly choking. For him.

"Christ—shoulda known that you were always such a good fuckin' girl," he groans, "Just needed'ta fuck the brat out of you."

Your eyes blow wide at his words. Fuck. Not 'teach.'

His brutal reminder of the reality of the situation makes your ears ring, "B-But we're not…th-this isn't…This is just practice."

Caleb chuckles, dark and bitter, "Sure it is, princess."

Your cry out and cling to him for dear life when he hauls you onto his lap, wrapping his thick arms around your entire body and guiding your legs around his waist. With you straddling him, you're forced to take his entire cock every time he lifts you with his muscular arms and grinds you back down onto his thighs.

His lips are at your ear, "Does that make you feel better? Telling yourself that? When you're sitting on Gege's cock—taking me aaaaaall the way here?"

He yanks your dress over your shoulders, finally exposing your body fully to him—your panties long gone, and you hadn't been wearing a bra to begin with. Caleb's lengthy fingers dig into your soft stomach, putting pressure on where he's nestled inside of you.

"Oh—!" you gasp as your vision whites out, your walls clenching inward, "D-Don't…" But for all your feeble protests, your hips instinctively roll against him.

"Don't what?" he removes his hand and uses it to move your hair to one shoulder, placing wet kisses on your exposed neck, "You want me to stop?"

His hands still and the pleasure all but stops, leaving you dumbfounded on his cock. You think you'd been close, because when he stops your body hurts worse than it had when he first penetrated you. Every muscle in your body, every nerve ending, screams in protest at the sudden momentum loss.

You look at him with wide, expectant eyes—silently pleading with him. He simply raises an eyebrow at you.

"What? I think you've had more than enough practice," he murmurs, tucking your hair behind your ear, "That's what this is, right?"

"Yes, but…" you're genuinely at a loss for words, unsure how to deal with the conflicting emotions raging inside of you and the void of emptiness. You knew you were well beyond "practice"—you had been for some time. And yet, everything that'd happened up until this moment, you could do the mental gymnastics to justify.

What was a few more cartwheels?

"N-Need more practice," you pout, squirming on his lap, the brief movement alone gives you the friction you're desperately craving, "Not ready yet."

"Yeah? Baby needs more practice, hm?" he grips your hips and looks up at you, jaw sharp and locked.

"Mnngh—mhm," you gasp as you roll your hips again, thoroughly enjoying the petname. Caleb's fist shoots out, fingers gripping the headboard to keep from cumming. Watching you attempt to bounce on his lap was excruciatingly hot, threatening to have him finish inside of you right then and there.

"Haven't c-came yet," you whisper with a furious blush, forcing the words out, "What if I can't? N-Need to check if I can."

You bite your lip, hoping Caleb will take the bait.

Caleb's neck bobs and his head falls back at the combination of your words and perfect cunt smearing across his lap. His other hand slides up your back, stroking every inch of your spine on the way—gentle and tender. But then he roughly grips your hair, his hips simultaneously thrusting up into you, smiling arrogantly when you squeal.

"More practice? Or you just want more of Gege's cock?"

He only gives you the one thrust, leaving you rolling your hips and whining desperately for him, "Yes—!"

Caleb groans as you clench, another slow thrust into your perfect heat, "Yes what, princess? Which is it?"

You chew on your lip, unwilling to say it. That would mean admitting a truth you'd been running from far longer than just today, far longer than from when you walked into his room, flopped onto his bed, and asked him to "teach" you. When you don't answer, he stops again, pulling your chin down to face him.

"Caleb, please!" you wail, body reeling from the whiplash of his teases—the way he continuously gives and withholds your pleasure.

He wipes your tears with his thumb, bringing it to his lips where his tongue swipes against it, taunting you.

"I can't give you what you want unless you say it," he leans closer, your faces inches apart again.

"Y-You know," you whine, "S-So just give it to me."

"That's one way to get what you want," Caleb barks out a rough laugh, "My brat's back already, huh?" His arms wrap around you, locking you in place as his hips buck up—strong and punishing.

"W-Wait!" you wail, unprepared for such a brutal movement—though your body takes him perfectly.

"Wait? Wait for what?" he chuckles into your ear, nipping at your earlobe, "You wanted me to fuck you, right? That's why you're actin' like a brat?"

Holding you firmly, he lifts you again, only to slam you back onto his thighs. The pleasure is intense, especially against your newly stretched walls. And yet, your body takes it all and begs for more.

"Yes!" you cry out, eyes rolling back when the rough movement causes your hardened nipples to brush against Caleb's own clammy chest, "W-Wan' you so bad."

Caleb groans, not expecting you to actually say it out loud since you were always so incredibly stubborn, something he adored. But he liked it even more when that brattiness turned into submissive pouts, fluttering eyelashes, and whispered Gege's.

"Haah—You want what, pips?" he grunts, voice labored with the strength of his lap bouncing you up and down, "You still want Gege to teach you?" Another mind-breaking thrust straight into your belly.

"Or you want Gege to fuck you?"

He doesn't even bother pretending anymore. He's kissing you—your lips, your neck, your collar. Everywhere he can reach, now that he doesn't have to pretend this is anything other than what it actually is.

"Th-That!" you gasp, toes curling and digging into his lower back, "Mnngh…oh god, just like that." The edges of your vision start to blur as your stomach starts to coil—something you'd felt before but never like this. Never this terrifyingly explosive.

"Say it. And say it correctly," he hisses as he feels himself on the cusp of exploding inside of you. Your walls have clamped down impossibly on him, gripping onto him and refusing to let him pull out.

At your teary cheeks and fucked-out expression, Caleb softens, hit with a brief moment of clarity. He cups your face in both his palms, nose brushing against yours. Despite his brutal thrusts and demanding words, his violet eyes are gentle—coaxing you to say what he wants to hear.

Your name is infinitely tender when he speaks, "C'mon—fuck... J-Jus' say it for me. I need to hear it."

Caleb's desperate plea cuts through your pleasure-induced haze. It's utterly impossible for you not to viscerally react to how he looks at you.

How could someone simultaneously look like a wolf and a puppy?

"Caleb…" you moan, equal parts affectionate and needy, "I-I…"

Your heart hammers as you gather all your courage. With your nails digging into his thick shoulders, your lips find his and you whisper, "Want you. Want you to make me cum. Want you to kiss me. Want you."

The tentative swipe of your tongue across his bottom lip breaks him—completely thrown off by you initiating anything, let alone this intimate of a kiss. Not quick and dirty, not reluctant and platonic, not teaching and practice. Slow, genuine, and desperate. Just like your little confession, now replaying in his mind—over and over.

Caleb's fingers roughly weave into your hair, ensuring there's not even a millimeter of space between you. The other finds your ass, possessively gripping one cheek, all while his strong thighs bounce you up and down.

"Want me, huh?" he smirks, wiping the spit from your lips and licking it up, "Not Jake?"

Your eyes widen at that, cheeks flushing deeply, "D-Don't say that. Don't remind me."

"Why?"

He lifts you, pressing you flat into the bed again, wrapping your legs around his waist, "You should think about him."

Not letting you speak, Caleb fucks into you with renewed intensity—the mention of Jake, even if it was his own doing, sends him into a frenzy, "Think about what you're gonna tell him when you show up to his place stuffed full of my cum."

You don't know what turns you on more, his filthily absurd words or the idea that he's not pulling out.

Caleb chokes and barks out a sadistic laugh—pre-cum oozing into you as your gummy walls contract in excitement, "Of course you like that. Your body can't hide anything from me."

"Shut up," you whine, nails digging into his veiny forearms as he brings you closer and closer to the edge.

"I promise you, pips," he grunts, "I'm the only one who can make you feel like this."

"I-I know," you gasp, agreeing instinctively, "I know Caleb."

"Hah…Jake can try all he wants. But you were—fuck—made for me. Always were."

You nod fervently, losing yourself to his rhythmic hips, "Caleb, please!"

"That's why you haven't let him fuck you, right? You were waiting for me? Waiting for Gege to take you?"

"Yes!" you scream when he licks his fingers and then uses the slick to rub at your clit, "Y-Yes, okay?! W-Wanted you this—nngh—whole time. I'm so close, please!"

"Hell yeah, you are," he groans, "God you're squeezing so tight. Gonna cum for me?"

You nod erratically, thighs painfully sore from being spread open for him like this. But he keeps them wide open for him, red from the powerful impact of his skin on yours.

"Mmnghmhm—w-wan' to cum for you," you moan, embarrassed by both your words and the sounds you make.

"Yeah? Tell me who's making you cum."

"Nnngah—y-you Gege!" you gasp.

"That's right," he grins, "Gege. And I'm the only one you're ever gonna let have you like this. Isn't that right, princess?"

Your head swims at his words, the implications clear even in your cock-induced delirium.

"W-What about Kelsey?"

Caleb's hips stutter at that, "That's over."

Your eyes widen, "S-Since when? You—mmngh—were just sayin' how you guys were doing good!"

"Yeah. And then my little baobei meimei came into my room and spread her legs for me."

You whine at the crude bluntness of his words. He chuckles and leans in, placing open-mouthed kisses on your neck, punctuating his statements with firm thrusts that are meant to prove his point.

That he'd been yours since he deemed himself your big brother.

"But if you want to know the truth…it was over the moment it began," he purrs, "Because the girl I've always wanted sleeps across the hall. Leaves globs of toothpaste in the sink. Steals half the fries off my plate."

Your heart skips two beats—one at his words, the other at the way the hot tip of his cock nudges a spot deep inside you that makes you scream.

"B-But you always order extra because you know I do that. So is it really stealing?"

Caleb laughs—warm, genuine, and not dripping with self-reproach for the first time since you'd entered his room.

"Spoiled brat. I s'pose not—it's all yours anyways."

You lean in and kiss him, words failing you. Caleb's hips stutter and he grunts in surprise but doesn't miss a beat, kissing you back hungrily. His eyes are glassy and his lips puffy when he pulls away.

"So? Say it, pipsqueak."

You yelp, his hips snapping so forcefully into you it sounds like he spanked you. Gone was that warm sunshine smile you loved, replaced once again by Caleb's mean teasing smirk. Which, undeniably, you also loved.

"Nngh—Caleb! Say what?! What now?" you wail as he uses his cock to pull the words he wants out of you. His tone already has you fearing that he will withhold your pleasure from you, a terrifying thought given how close you were. Having your orgasm stolen from you at this point might actually destroy you.

"Say…I'm the only one you're ever going to let in here," he licks his thumb and presses it forcefully down on your clit making you squeal and thrash, "In this perfect little cunt you let Gege have."

His thrusts grow punishing, demanding you tell him what he wants to hear, "Y-Yes—oh God, yes Caleb! I-It's—I'm yours!" Your answer is desperately genuine, spilling your most well-kept secret, in hopes that he will let you cum.

Caleb swells at that, both his dick growing impossibly at your sweet little confessions and his heart pounding painfully.

"Thas' my girl," he grunts soothingly—fighting to stay in control as his own impending climax threatens to overwhelm him, "You're so close, aren't you princess? Gonna cum all over Gege's cock, huh?"

You don't get to warn him when your orgasm hits, because you're completely unprepared yourself. You can't say anything but his name—over and over, raking his back scarred and bloody.

"Just like that, perfect fuckin' girl," he rasps, "S-So tight—shiiit."

He wants to talk you through your orgasm, but it becomes impossible when your pussy clamps down so tightly that his vision blacks out and his cock explodes inside of you.

"Milking me so f-fuucking good princess," he groans, spilling white ribbons into your greedy walls. He takes both your wrists into his, raising them above your head and pressing them into the mattress to keep you from squirming, using you as he pleases.

"Perfect little cunt. Belongs t'me." His lips start at your earlobe finding their way to your breasts, leaving marks along the way—ones he fully intends on being visible to anyone who looks at you.

His fingers are digging into your thighs, eagerly hiking your legs up against his side. He has your lower half completely lifted off the bed, practically holding you by your thighs like a doll, dragging you onto his cock repeatedly. It's a sight he was desperately searing into his memory—your wrists bound, tits bouncing and bruised, spine arched beautifully toward him, eyes white as they roll back.

"Caleb—! Nngh…so good, s-so good, so good!"

Your grandmother wasn't home, but you had elderly neighbors Caleb knew would be gossiping about the sounds coming from your house to everyone, including your Nainai. As much as he loved your cries, he devours them with a messy kiss to quiet you.

Who was he kidding—you were both long past the point of excuses. He wanted his tongue down your throat as he came in you, stuffing you from both ends.

When he pulls away, your eyes are squeezed shut—it helps you make sure you don't get absolutely swept away by the high tides of the pleasure he forces into your body, gently gripping your throat to get your attention.

"Look at me. Please. Need to—sh-shit—see you."

Your rolled back eyes struggle to stay open, but you're determined to be good for him, "So full, Gege. So warm."

Caleb groans at your adorable and filthy praises. It was pathetic how it squeezed another rope out of him, his cum starting to pool out of you even despite his cock plugging you full. His hips finally still, breathing uneven and heavy.

"God…look at you…" he sweeps your sweat-dampened hair behind your ears, "You were perfect."

Your cheeks flush, his praises settling heavily on your chest. Caleb chuckles when he feels you clench around his still-hard cock, but he doesn't tease you about it. His muscles tremble as he hovers above you, but he's not willing to pull out yet.

"You took all of it," he leans down to kiss your temple, "Your first time and you were incredible."

When you squeak with discomfort, Caleb's face snaps back up and he freezes.

"Shit, sorry pips," he reluctantly pulls out of you. He's barely softened, and the sight of pink tinging the milky essence running down your thighs makes him hard again.

Your whine is involuntary— you hadn't wanted him to pull out, the gaping emptiness leaving you hollow. Looking down, the sight between your legs makes your eyes widen. The faint streaks of blood make your heart thunder, reminding you of the reality of what you'd just done.

You had sex. For the first time. With Caleb.

You don't bother trying to, again, justify it as some meaningless practice lesson. He'd already forced the truth out of you anyways.

"Y-You came inside me," you squeak, teary-eyed but not accusatory—a confusing mix of satisfaction and panic unfurling in your core.

Caleb freezes at that, the fear in your voice making that natural overprotectiveness surface. Except this time, he's protecting you from himself. And considering how the sight of his spend pooling between your thighs made him scarily satisfied, he knew he was definitely something to be feared when it came to you.

He fumbles for an excuse, any way to protect you from the reality of the moment you'd just shared, "S'okay, princess. Had to mark you up. But it'll be okay. It's your first time so…it's safe."

He bites back a cringe, embarrassed by the ridiculousness of his own words, "Besides, I've got you, okay? Gege's always got you."

You almost want to laugh. You were a virgin not an idiot. But he makes you feel impossibly safe, so even the thought of the consequences don't scare you for long.

Caleb sits on his knees, still between your legs. His eyes are predatory, memorizing the sight before him. You—spread, swollen, stretched. He catalogues every mark he's left on you, smirking with satisfaction when he imagines your boyfriend finding each and every one.

And with impeccable timing, your phone, discarded haphazardly on Caleb's nightstand, rings. Twisting your neck to the side, you see Jake's contact photo. Seeing his actual face on your phone, versus imagining it, were two very different things. Caleb's jaw sharpens with displeasure, the ugly feeling of possessive jealousy blooming throughout his entire body.

"Shit," you whisper, instantly feeling guilty. You move to grab your phone, but Caleb captures your wrist.

"Don't."

Your eyes snap to his, wide with surprise, "Why not? You picked up when Kelsey called. And I was—"

You trail off, heating up at the memory of his cock down your throat while he spoke to his girlfriend. You continue, "Besides, I have to pick up. He was supposed to come over at 6. If I don't he'll just show up."

"What is this, tit for tat?" he raises a mischievous eyebrow at you, "Then you can answer it while I'm going down on you."

You roll your eyes, your phone still ringing, "You cannot be seri—Caleb!"

He roughly drags you to him, your body sliding across his bed as he hooks his arms around your thighs and places your calves on his shoulders.

His breath is warm against your cunt, the copious moisture there making you even more sensitive, "Answer it."

"N-No!"

"Answer it."

"You're such a child!"

"And? Answer it."

"No!"

Silence finally comes, your phone sending the call to voicemail and leaving just the sound of your uneven breathing as you watch Caleb stare at the apex of your thighs like he was looking at the world's most decadent dessert. And he hadn't eaten in weeks.

"Whatever, I'm not stoppin'," he gives you a toothy grin, kissing your inner thigh—using his tongue to slowly clean up the mess he'd left there, "Haven't had a chance to teach you how to take my tongue yet."