Fandom: Critical Role - Campaign 2 - The Mighty Nein
Summary: Jester wakes Caleb up in a way that she knows she would love. The wizard does not object.
A/N: TICKLE FIC featuring my beloved lee!Caleb, ler!Jester, and in the next part ler!mollymauk too, sleepy tickles, aftercare, cuddles, breakfast in bed, tickling, teasing, bondage, polynein / widojest / widomauk referenced, soft fluff, wake up tickles, kinda dubcon but they have pre-established consent and safewords ok, premise based on this lovely text post
Inspired by these AugTickleTober 2025 days…
Day 5: Sneak
Day 16: Claws
Day 19: Mischief
Words: 2.1k … [read on ao3] [part 2 tbd]
…
The door just barely creaks as she slips into the room. Lucky for her. Jester tiptoes her way across the unexpectedly modest bedroom in their extradimensional mansion and begins fumbling behind the headboard for something. With success plastered across her face in the darkness, she pulls forth her prize. One set of padded cuffs emerges from below. Jester absolutely beams into the blackness filling Caleb’s room.
She gets right to work, careful to check repeatedly that she hasn't disturbed the wizard’s slumber just yet. It barely takes any time at all to get his arms into position, as he’s spread out, face-down in his pillows, snoring gently.
She just manages to suppress an excited squeak as she finishes; she watches the sleeping wizard cautiously, but he’d be huffing about if he’d awoken. She tugs experimentally at each arm restraint. The straps hold tight, looped under the bedframe and hooked securely to the cuffs around Caleb’s wrists, drawing his arms out toward the corners of the headboard.
Jester’s buzzing with excitement. Everything is in place.
“Caaaaaaaay-leb.” She nuzzles in close, whisper-cooing into his ear. “It’s time to wake up, Caleb.”
She starts at the backs of his hands and drags her fingers softly down from his wrists to his shoulders, then begins carding her fingers through his hair and over the back of his neck.
“Mm..” Caleb stirs, his voice gravely, and lifts his head slightly from the pillow, and Jester brings her hands back to herself with a self-satisfied look of pride.
“Yes, yes, yes! Perfect…” She whisper-screams to herself.
“..Jester?” Caleb slurs sleepily but stops before he can say more, trying to wrap his still-loading mind around why he can’t turn around and face her. He blinks his eyes, trying to will the exhaustion away. It’s still dark in his room. “What are you doing—” Something in his trained, wizard mind grasps for the familiar — something he can recognize, even if he can’t see. Then he registers them, feels the soft, familiar comfort of the well-made, leather cuffs his troublesome tieflings had made for him.
When one wanted to play with tieflings, he had learned, well—it wasn’t a terrible idea to have some restraints at the ready. Usually, though, this set of bed cuffs didn’t come into play until at least a little while after some kissing, a massage, a little warm-up tickling, foreplay, teasing, some—something!
“I wanted to wake you up, Caleb.” Jester explains in that soft, sing-songy voice, nuzzling into the back of his neck and making him scrunch his shoulders up weakly. She ghosts her fingers along his back. “In a nice way.”
“Ja, und I am now awake..” Caleb responds tiredly as well as a little hesitant. He tries, albeit unsuccessfully, to will himself not to twitch under soft, teasing fingers, barely there, quite certain even in his semi-conscious state that he can tell where she may be heading with this. Who is he kidding? It’s Jester. That’s exactly where she’s heading.
“So...?” He tries the restraints, tugs once, twice, deliberately but weak.
“Well, I mean, you still seem a little tired.” Jester continues excitedly. “Here, here, I’ll help!” She walks her fingers back up his back, scratching her nails gently on either side of his spine.
Caleb shivers, unable to stop himself from squirming under the tiny, electric jolts of ticklish sensation. “Oh—nehehein, plehehehease—” He drops his head and giggles into the pillow, soft and sheepish. “I cahahan’t..”
“You can’t what? You don’t have to do anything!” Jester insists, pinching at the edges of his shoulder blades. “Just relax and try to wake up nice and easy, okay?”
“I’m awahahake..” Caleb snickers lamely, shaking his head where it lays smushed into his pillow. “It’s too early for thihihis.”
“I’m being thorough!” Jester rebuttals. Then, true to her word, she sets her wicked fingers on a slow crawl from his shoulder blades straight out to the side and right under his arms.
Caleb’s body jumps beneath her, trying to prop himself up onto his elbows or bring his arms down to no avail. “Scheiße- Jester! Don’t!” His voice is higher pitched this time, definitely awake. She always finds such delight in hearing his pleading become more and more frantic. He rocks slightly from side to side as she continues her attack.
“There’s nowhere to go.” She teases as he tries squirming from one side to the other, her nails following all the while. “You’re just gonna have to get tickled until you wake allllllll the way up.”
Caleb makes a desperate noise before crashing his face back into the pillow in a sad attempt to silence the laughter bubbling up inside his chest.
“Oh no, are you falling back asleep? Do you think I should tickle you somewhere else?”
He turns his head sideways as she brings her scribbling nails slowly down towards his ribs. “Whihihihhy did you decide to-ACK! Why-yEEHEHE?! WAIT! Wait, bitte! Not there! Ahahahaaa—”
“You’re a good sport most of the time, when I want to tickle you.” She begins to explain, nails spidering sinisterly at the top of his ribs as his laughter increases in desperation. “But you always try to sneak away or put your arms down when I tickle you all gentle like this, Caleb!” Jester explains with all the confidence of a used-cart salesman, while her blue nails spider relentlessly against each rib. “I think it’s really nice and relaxing to get tickled and I know you do too and—well, sometimes you’re kinda grumpy in the morning so I had this idea and well isn’t this so much better of a way to wake up?”
Caleb doesn’t answer, at least not with words. He knows there’s no arguing with her. He’s trapped, and Jester’s fingers are forcibly taking up more than their fair share of his thoughts. He just laughs, whines, and kicks out weakly in a pathetic attempt to dislodge her.
“I know it’s not exactly the time of day we usually use these…” She tickles quickly back up his arms to tap on the wrist cuffs she has him tied to the bed with before continuing back down with a spider crawl along his arms. “…but I think it works great for wake-ups! Actually, yeah —you should totally take my idea and try it out some time on like me, or Molly, or ohmygosh Essek—”
“Jester!” Caleb anguishes into his pillow, reminding her of his presence. “Mercy!”
His arms flex and tug weakly at the restraints on his bed. He’s trying to orient himself enough to listen and to figure out what to do next. He doesn’t even have the strength to hold his hands in a fist yet; his body is tired and tingling and why is he still so god damn ticklish when all of his other senses seem to be taking forever to catch up.
Jester keeps talking behind him- above him- next to him- somewhere—while Caleb cackles into the pillow.
“Are you sure you’re awake now, ‘Sleepy Caleb’?” Jester teases, drawing her fingers in unison from the outside edges of his exposed armpits to the center - over and over again. Slow. Deliberate. “Do you feel those pesky, tickly, ‘ickly spiders crawling all over you?”
“Nnnnnn— a break! P-plea-mmmmm-aaaahhaha!” He pleads unintelligibly to the bed, words failing him in the face of so much gentle teasing. The spidering tickles move all along his back and down his ribs and sides. Caleb makes another strangled cry into the pillow and kicks his feet out behind him, wanting to rid himself of excess energy. “Please!” He whines.
Jester lets up just long enough to scoot down his back. She moves back to sit just below his arse. To Caleb’s delightful horror she brings her tickling, wiggling spider-fingers to crawl back along the dip of his lower back—a particularly sensitive spot that she and Mollymauk share.
Caleb, it seems, does as well. He squirms helplessly, kicking even harder as he cries out against the bed. Everything tickles and tingles and it’s all ricocheting around his nervous system like a couple of loose spells. “Jester! Jess- AHAHA JESTER PleeheheheHEHEHEASE! AHH- Ohmeingott no, nonono, that wasn’t a breheheheak! JEHEHEHEHESTER!”
“Yes, yes, yes, Caleb! You sound so much more awake now!” Jester sings out loudly over his laughter in response, tickling along his spine now. “What’s the matter, why are you yelling, you don’t like my spider friends?”
“Gehehehehehehet away! Ehehehe nonono get-them-awahahahay hehehe! Nein! Hahaha get them off— off, off plehehehehease!”
“I mean but they’re like, barely touching you..” Jester pouts, crawling her spidering fingers from his spine out toward the backs of his bottom ribs. “You really don’t like them?”
“Sohohoho bad! Plehehease—” Caleb jolts, crying out frantically into the pillow beneath him, which sounds like he’s even begging harder now.
Jester smiles, delighted.
“I’m definitely gonna have to study with you and Essek some time… you guys can make so many cool spells and, well, we need to make a real tickle-spiders spell. It would be soooooo much fun. I would use all my spell slots on it.” She latches on to the back of either side of his rib cage and spider-tickles where he usually keeps his books. “Think about it, think about it.”
“Nhahahahahahahahot a chahahahance!” Caleb retorts, defiant despite his giggling. “Too bahahahad!”
“Ah! Rude!” Jester tsk’s at him.
The ‘spiders’ leave the backs of his ribs only to reappear on his sides and begin working their way underneath to his stomach, tickling lightly but deliberately into Caleb’s soft belly as they wiggle between him and the mattress.
“NONO-OHFAHAHUCK-WAITNO!” Caleb shrieks in surprise, trying to roll as violently as he can from side to side, hindered by the cuffs holding his arms outstretched and by Jester’s strong, sturdy form straddling him in place. “GETOUTOFTHERE! Ahaha-plehease– no nohoHOHO!”
“I can do this aaaaaaaaaalllllll day.” She teases, reaching further with each hand until one finger reaches his belly button to tease as well. “And so can my spiders.”
Jester considers, still tickling ever-gently along his stomach. “Maybe I’ll give you a little break, if you tell my little spiders that you like them—AND if I’m like 1000% sure that you’re awake for real.”
“I’m awake! I’m awake! PleheheheHEHEHEASE! I am! EHEHE-ahh haha Jester!” Caleb wails, pleading. “I ahahahaham going to dihihihie!”
“You’re so cute.” Jester slips her hands out from under him. “And, relax, I know you are squishy and all, but I wouldn’t let you die from a little tickling, don’t worry.” She winks to herself, leaning in to kiss the back of his head. “And if you did? I would heal you. And it would be the cutest way to die ever.”
Red-faced and exhausted, Caleb wheezes into the pillow below him, turning his head a bit to the side and deepening his breaths when he can finally stop laughing so hard. He takes in air, drawing it in greedily. “Bitte, have some mercy on me… it is so early.” He tries, looking up at Jester with one tired, pleading eye. “You’ve made a very effective alarm. Let’s go make some breakfast and—”
“Ooh, I am hungry!”
“Ja?” He smiles in relief. “So maybe we could–”
Jester cuts him off. “Oh! I know!”
Caleb eyes her, hopeful.
She takes a deep breath and then begins the familiar quick casting for sending.
“Wait- was machst du?–nein! Jester, what are you doing?” Caleb blanches in terror. “Wait! Wait! Who are you calling? Please–”
She begins speaking, ignoring him. “Heyyyyyy, Molly! Could you grab some of those yummy pastries and breakfast sweets and stuff and meet me in Caleb’s room? Okay thanks hurry up-” the spell fizzles out but she continues, “-okay? You can reply to this message- wait, was that too many words? Darn it. Did you get that?”
Jester waits a moment, tapping her toes into the mattress behind her.
She prepares to try again before she hears a familiar voice reply. “Sounds.. intriguing. Be right there, darling.”
“Okay, breakfast problem solved!” Jester claps her hands together.
“Ahahahare you going to let me up…” Caleb asks, already giggling in anticipation of Mollymauk joining them, “so I can eat with you all..?”
Jester laughs joyfully. “Nope!”
“I –why?” He pouts and tries to turn his head to look at her fully. “Please?”
She brings her hands up to Caleb’s forearms, wiggling her fingers like spiders once again. “You didn’t apologize for saying you hated my spiders and they’re very, very offended. It’ll take Molly a while to get breakfast together. And then we can feed you in between giggle-breaks.” She grins, leaning in to pinch his sides in delight.
“WAIT! I’m sorr-EHEHEHEHE!” Caleb’s lanky muscles jump under the touch, and he lets out a high pitched noise into the pillow, choosing to hide his face again rather than argue fruitlessly. Goosebumps raise across the backs of his arms and neck.
“Anyway, we need to make sure you’re nice and hungry when Molly gets here.”
…to be continued
…
A/N pt.2: this was originally gonna go a different way and be a shorter thing and then it ended up becoming part of something bigger and then it was gonna be tickletober and broken up into parts and then now its mid 2026 oops but you’re welcome here you go.. also I have like 4K words done but I’m still working on the end and I was like you know what I’m publishing it in parts fuck it, also speaking of fuck it lol when is it my turn for someone sadistic and silly to do this to me.
