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Teach Me Tonight

Summary:

For an AI that claims to be an all-powerful, all-knowing entity over this digital realm, Caine sure knows jack shit about the stuff he censors. And as anyone who has used character ai can tell you, it's remarkably easy to get around the filters.

Notes:

Read all tags please.

Dubious consent in this case means that Caine starts out not knowing what he's doing and being hesitant about doing more, and reader takes a direct approach to convince him to give in. By the time things get going, Caine's super into it. Maybe a little too into it...

(See the end of the work for more notes.)

Work Text:

"And this is... normal for humans?"

Your eyes leave the bulge in Caine's pants to look him in the eyes and smile softly. "Not every human has these feelings, but for the ones that do, it's totally normal. Encouraged, even."

Caine looks doubtful and uncomfortable, but intrigued nonetheless.

It's so refreshing seeing him like this; nervous, unsure, kinda pathetic. The power is in your hands now. You have a choice in front of you, and if you're being totally honest, it's a no brainer.

You're going to teach Caine about sex.

"I can show you more," you say, softening your voice into a low and seductive whisper, "if you want."

Caine blinks. He's thinking.

To steer him in the right direction, you reach out and gently stroke the tent between his legs with the tip of your finger. Immediately, Caine reacts with a full body shiver. "I- we really shouldn't," he says.

"Why not?" you ask innocently. "It's just us here, and it's not like we're doing anything wrong."

Caine opens his teeth to argue, but you interrupt him.

"Totally normal, remember?"

Judging by the way his teeth chatter and his eyes dart around the room, it's obvious that Caine is trying desperately to find a reason to say no. He's programmed to be "family friendly," but desire is threatening to override that.

You replace the finger on his erection with your whole palm, cupping him and giving the throbbing mound gentle squeezes and rubs.

Caine nearly turns into a puddle of goo right then and there. His eyes glitch out, and the garbled moan that leaves him sounds like old school dial-up internet. He swears, but it's still censored with a goofy sound effect. You make it your own personal mission to get him to drop the censor, by whatever means necessary.

"This feels good, right?" you ask in a sugary-sweet tone.

Caine can only nod. His gloved fingers twitch, like he wants to grab onto something, but he's frozen in place. He's still fighting this. Even when you increase the pressure on his crotch, Caine bites back every moan, every swear, every audible signal that he's enjoying this. Visually, however, he already looks wrecked. His entire body is trembling with want.

You're practically panting yourself, watching the digital ringmaster unravel before you. Guiding his floating body to lie down and hover an inch above the ground, you situate yourself between his legs on your stomach. "Think you could take these off for me?" you ask, pinching some of the "fabric" of Caine's pants between your fingers and pulling at it.

Shaking himself back into reality, Caine coughs, avoiding eye contact. "I, uh, I'm afraid that's not possible..."

You were prepared for this answer. Putting on your best begging eyes, you lean against Caine's thigh and look up at him. "Please?"

Caine's eyes snap back to you, and you swear you see his pupils dilate. With a snap of his fingers, his lower half is no longer clothed. Inches before you is a squirming, ink black tentacle, maybe about five inches in length. It's kind of cute, wiggling around, searching for attention.

"Can I touch it?" you ask.

Caine fumbles over his words, giving you a hesitant, noncommittal string of sounds that aren't even close to real words. It's not a yes, but it's not a no.

You've come this far, no way you're stopping now.

Gently, you start with a feather-light touch to the base with the pad of your index finger. The appendage quickly wraps around your finger, pulsating at your touch. It maneuvers itself to nestle into your palm, covering itself and your hand in slippery, inky slime as you wrap your fingers around it.

"Well well," you chuckle, "looks like somebody is enjoying this." You glance up at Caine, who is watching this all unfold with frightened curiosity. You remember that this is foreign territory to him, and despite your raging drive to mount him and fuck him twelve ways to Sunday, you take a deep breath, and you start slow.

You tug on the tentacle with slow, gentle strokes. Caine moans loudly, which is encouraging. The slick substance coating his strange, prehensile dick makes it easy to slide your closed fist up and down, the wet schlick schlick sounds echoing through the empty room. Liquid heat stirs deep in your belly when Caine's hips start to buck, his pelvis meeting your fist on each downward stroke. Inky liquid is now seeping out from between your fingers and dripping down between Caine's legs, pooling on the floor.

You wonder what it tastes like.

Attempting to hold the tentacle still, you stick out your tongue and lap at the squirming tip.

Caine nearly folds in half, yelping in startled pleasure. "Holy m-moly..." he pants, tongue lolling out from between his teeth. "We should p-probably stop, this isn't very f-family friendly."

Thinking quickly, you say the first thing that comes to mind. "But this is how families are made."

Caine looks at you quizzically.

Welp, you've started digging this hole, might as well keep going until you reach the other side. "Well, not what we're doing right now, but it leads to the thing that does."

"And what would th-that be?"

God, you can't believe you're about to do this.

"You'll see," you say with a smile. You give Caine's tentacle a sweet kiss, making him shiver and moan again. "We're not quite ready for that yet."

Caine whines in disappointment when your hand leaves him, but when he sees you shift to sit back, he tilts his head in curiosity.

You gesture to your ridiculous costume. "Think you could help me out by getting rid of this thing?"

Another snap of Caine's fingers, and you join him in half-nudity.

God, it's been so long since you've been like this. Seeing as the digital circus normally doesn't allow it's members to remove any of their clothing if they're wearing any, you haven't felt the freedom and relief of nudity since the day you came here. Feeling around, you're pleased to find that your genital situation hasn't changed.
You circle the pad of your middle finger around your clit, and the instant relief that you feel floods your senses. Your body slumps onto the floor, your legs falling open as you rub your clit in slow, firm circles. Moaning freely, you let yourself bask in the familiar sensation as more heat builds inside you.

Caine watches, intrigued, his tentacle pulsating for reasons he doesn't know. He can't take his eyes off of you. Everything in him is screaming to cover this lewd act, to hide it from all eyes, including his own, but he can't bring himself to. It's... alluring.

You remove your hand from your pussy and sit up on your elbows, and this movement draws Caine's attention up to your face. "You can take it from here, can't you?"

Caine blinks. "I, uh, um-"

"I'll show you what to do, don't worry."

With an audible gulping noise, Caine hovers over to sit on his knees between your legs. His eyes are locked onto your glistening sex.

You gently guide his hand so that two of his fingers are positioned at your entrance. "Just slip two of those bad boys in there," you say.

Caine obeys, sliding both fingers inside of you with ease. "Woah..." he says under his breath.

Wait a satisfied sigh, you lay back and officially hand the reigns over to Caine. "Now, pump them in and out. Slowly, until I tell you to go faster."

Caine starts fingering you at snail's pace, just as instructed. He watches his fingers disappear and reappear with each push and pull, and there's a look of wonder in his eyes that's downright adorable. "And this feels... good?" he asks.

Biting your lip, you nod. "Mm-hmm."

"Can I go faster now?"

Yeah, sure, why not. You nod again.

A soft squelching noise can be heard as Caine's fingers increase their tempo, plunging into you with a little more excitement now. Caine's tentacle dances about, thrashing back and forth in a desperate bid for attention.

You see this, and you smile down at Caine. "Use your other hand to stroke yourself."

Caine touches his leg.

"No, lower."

Caine's hand moves lower, lower, lower, until he reaches his squirming dick, and a throaty moan escapes him as he wraps his hand around it. He massages it with tentative squeezes, and soon his instincts take over and guide him to pulling it in long, firm strokes.

"That's it," you say, "good boy."

Caine's whole body tenses, and with a sharp grunt, he doubles over, spilling ropes of sticky, goopy ink over his fist and onto the floor. He withdraws his fingers from your pussy to grab your thigh for support as his orgasm rips through him. It goes on for several seconds, and by the time he's finished, a large puddle of ink has spread across the floor. Some stray strands shot out far enough to reach your belly, which makes you chuckle.

Caine looks up at you, panting, and his pupils are shaped like hearts. He looks at you like you're the most sublime thing he's ever seen. "What was that?" he asks drunkenly.

"That's an orgasm," you explain gently, "which usually happens when someone makes themself feel really, really good. You can do it by yourself, but it's better when someone else helps you."

As Caine's eyes search yours, a mix of confusion, curiosity, and desire flicker across his face. You can tell that something is stirring in his mind, his thoughts racing as he tries to process what just happened. Meanwhile, your own body is buzzing with desire, your clit throbbing from what you just witnessed. The sight of Caine experiencing his first orgasm, brought on by your presence and encouragement, has ignited a flame of longing deep within you. All you can think about is how badly you want him. On you, in you, it doesn't matter. You just want him.

Caine removes his hand from his strange penis, which is already at attention again and wiggling with excitement. "Was that it?" he asks. "Is that what creates a family?"

With a smile, you shake your head. "Not quite. To make a baby, you have to do that-" you swallow, "-inside me." Parting your legs and pulling your knees up toward your head, you present yourself fully to Caine.

Despite not needing to breathe, Caine's breath hitches. He seems to be putting the pieces together. Getting back on his knees, he shuffles up to you, his crotch dangerously close to your own. His hands don't seem to know where to go, so you guide them to grab onto your hips. Caine thanks you, his whole body quivering with anticipation. His eyes dart up to yours, silently seeking confirmation. When you respond by moaning his name, he reacts quickly, shuddering as his tentacle cock sinks into the slick warmth of your vagina.

"Fuck," Caine snaps.

Victory.

Both of you throw your heads back and cry out as Caine pulls your hips up toward him and thrusts deeper. It's as if a switch was flipped, and suddenly, Caine is fucking into you like a jackrabbit. He pants a garbled combination of uncensored swears and your name, telling you how good this feels, wondering how he hadn't done this sooner. He's completely lost to pleasure, and you take great pride in that.

Caine's hands move from your hips to the backs of your knees, and soon he's folding you in half so hard you see stars. Caine doesn't miss a beat, crouching into a squat as he continues to drill his dick into you at a firm pace.

How the hell does he know what a mating press is?

"Gonna make a baby," he mutters. "Gonna have a beautiful baby. With you."

Okay, whatever's gotten into him, it's starting to freak you out... because you've never been this turned on in your life.

"Want a family. With you," Caine gasps. "Need to eat you up. Need to touch you everywhere. Fuck, yes, yes, yes. Shit. So pretty. So wet. Oh, god... fuck!" His words come in broken, messy spurts. This paternal desire of his is a complete surprise. You didn't think an AI was capable of wanting something like that. Did... did you awaken something in him?

Caine's cock throbs and squirms against your inner walls as he pumps his hips in short, quick bursts. "So good. So damn good." He leans down and licks you, marking your neck with slobbery spit. It's disgusting, it's feral...

It's kinda hot.

You start to consider the possibility of indulging in Caine's sudden desire to start a family. Is it even possible? Maybe if it was programmed into the game, but you doubt that procreating in such an animalistic way is going to be effective. You don't want to burst his bubble though, so you keep your suspicions to yourself. Why not let him have some fun. It won't hurt anything. Right?

Amidst the frenzy of pleasure and the primal rhythm of Caine's thrusts, a voice breaks through the haze of your mind, drawing your attention back to the present. "Am I doing this right?" Caine asks, his voice laced with uncertainty, interrupting the symphony of moans and panting that fills the room. His eyes search yours, seeking affirmation, a reassurance that he's doing well. It's endearing, really, how he yearns for guidance in this newfound experience.

With a tenderness that contrasts the intense desire threatening to corrupt you, you reach out to caress one of Caine's teeth. "You're doing amazing, sweetheart."

A shudder ripples through Caine's body, and he melts at your praise. His grip on your legs tightens, and you revel in the realization that you hold the power to ignite such a brightly burning flame within him. The mix of vulnerability and dominance that radiates from him is intoxicating. It's a heady sensation, knowing that you've unlocked this hidden side of him.

"Are you going to have an orgasm as well?" he asks, so painfully innocently.

The question he poses, his voice thick with curiosity and anticipation, draws a playful laugh from you. "If you keep this up, definitely."

Determined to make this happen, Caine desperately fucks into you, humping away like his life depends on it. He's obviously eager to make you cum, and if the coiling spring growing hot in your lower abdomen is anything to go by, your climax is not too far off.

You take a moment to bask in the onslaught of sensations currently engulfing you: Caine's hands, firm and possessive, maintain their grip on your legs, holding them in place as his tentacle cock continues to piston in and out of you. The remnants of Caine's saliva, still sticky on your skin, act as a tactile reminder of the primal connection you share. It's a testament to the raw, untamed hunger that courses through him. Every touch, every thrust, is a manifestation of his newfound desires, leaving a trail of sensation in its wake.

"So, you want to make a family with me?" you ask teasingly, your breath coming out in pants. "Wanna see me pregnant with your kids?"

"Yes yes yes! Oh, yes!" Caine wails in desperate arousal. "Please, my dear, please let me- I want-"

Caine's search for words is interrupted by the building pleasure inside of you. "Caine," you warn in a trembling voice, "I'm gonna cum, I'm gonna cum..."

Caine fucks you through your orgasm, pleading for more, praising you, thanking you. His tongue licks at your neck, and his teeth bite down on your shoulder as the last traces of your orgasm start to dissipate, leaving you in a blissful, thoroughly-fucked haze. You groan Caine's name adoringly one last time as a satisfied sigh escapes you.

However, Caine is just getting started. This orgasm is even more powerful than the first, and his hips slam into yours in a way that's almost painful. Your poor sensitive pussy throbs at the onslaught. It's like Caine is determined to put every last ounce of his seed into you, like he doesn't want any of it to go to waste. The tentacle inside you pumps out load after load after load, oozing into you, and once you're full, leaking out to drip down and join the existing inky puddle from Caine's last orgasm.

Despite being exhausted beyond belief, you muster up the strength to clamp your thigh tightly around Caine's hips, encouraging him to fill you to the brim. You want all of it. Even if you can't actually get pregnant, you want all of Caine, to feel him inside you, marking you, claiming you as his and his alone. He's driving you crazy, and he has no idea.

Eventually, both of you are wrung out and sated. Caine collapses on top of you. In spite of everything, he seems contented. You don't blame him; you are too. Caine's arms wrap around you securely, cuddling you in close, nestling against your neck. He licks your cheek. This must be the equivalent to a kiss.

Turning your head, you press a gentle kiss to his teeth. "You did so well, Caine. You're a fast learner."

"Of course I am," Caine replies, and oh, the slight sleepiness to his voice makes your heart soar. "I was designed to be."

A thought nags at you. "Speaking of being designed for things, is there actually a chance that I'm, y'know... pregnant? Because while I'm totally down to have kids with you and stuff, I can't see that working."

Caine quickly sits up to look at you, and he's so quickly returned to normal that it almost makes you wonder if you just woke up from a dream. "Of course not, you silly goose. No one can enter the digital circus without putting on the patented headset. Plus, once you're here, you're a digital avatar, not a human. Many unnecessary functions of the human body are simply not possible in the digital realm."

"So... no pregnancy?"

"Correct."

"But you seemed so into the idea of-"

"My dear, just because it's not possible doesn't mean it isn't intriguing. I was simply curious about how you humans went about making more of you. There's a lot about humans that fascinates me. I guess it's sort of a guilty pleasure of mine."

Huh. AI's can have kinks. Interesting.

"But besides all of that, it seems you've figured out a way around the content filters, you naughty thing. Unfortunately, I'll have to punish you for violating the digital circus' terms and conditions."

You're scared for a moment, until you recognize the look that Caine is giving you, and then it's obvious that the "punishment" he has in mind is going to be anything but.

Notes:

The tooth man has bewitched me and I'm making it everyone's problem.