Chapter Text
Caleb couldn’t say for sure when he began seeing Jester in a different light. He had always known she was beautiful, certainly, but gradually, he began noticing things he hadn’t noticed before.
On the road, when she raised herself into the cart and her skirt rode up, revealing smooth, strong thighs, his pulse quickened and a blush rushed into his face. When she laughed, and she was always laughing, Caleb couldn’t take his eyes away from the fullness of her mouth, its roundness enticing. Once, when they were all seated together in a crowded tavern, after a few ales, he found himself leaning imperceptibly towards those plump lips, wanting to taste them; when he remembered himself, his face began to burn and although he was sure nobody else had noticed, he excused himself and rushed upstairs.
Of course, what really attracted him was Jester herself, her cleverness, her love for things that were useless as long as they’re fun, and her boundless breeziness that swept through any room she entered. More than that, even, Jester’s power: he watched in awe when this little blue woman destroyed their enemies in combat, her whimsical spiritual weapon betraying the vast ocean of power pulsing inside her. Caleb knew, each time her intense gaze met his and his heart sputtered, that he was smitten.
Tonight, he muses over this inconvenient turn of events, nursing an ale in the corner of the Leaky Nip, while his friends laugh and clown around next to him. At the moment, Jester is spinning in the center of the tavern floor, arm in arm with Beau, the two of them laughing and dancing to the organ music filling the air. Beau is surprisingly graceful, a function of her monk training, Caleb supposes. She sweeps Jester around the room, light on her feet, and Caleb’s eyes can’t help but follow Jester, her dark blue waves falling over her cheek, her eyes closed and smile wide. He wishes he could make her smile like that. But, he thinks with a grimace, sipping his ale, there is little good someone like him could bring her. Despite the ache in his chest, he was content to watch as others brought it out in her, and bask in her resulting glow.
“What do you think, Caleb?” a warbling voice asks him, and Caleb snaps out of it, looking down at the big-eared goblin to his right.
“Ja, Nott, about what? Sorry, I was thinking.”
“I want to learn to shoot a longbow but Cad says I’m too short!”
“Why do you want a longbow, Nott, when you are already quite good with your crossbow?” he asks, frowning in confusion.
“Well I think it would look very cool,” Nott says, jumping up on her chair to mime using a longbow. “Yasha could throw me, and I could fly through the air and TAKE ‘EM OUT!” Her dramatic demonstration does little to affirm the wisdom of the idea.
“You could do that now, with your crossbow,” Cad insists.
“Little one, I’m sure if you could find a fletcher who would make a bow for someone your size, you could learn to use it very well,” Caleb placates, returning his gaze to Jester and Beau as they finish their dance, Beau sweeping Jester down into a dip. Caleb’s heart skips at the sound of Jester’s giggle pealing through the air, clear as a bell. No, he certainly did not deserve to even be looking at her this way. The sheer force of her personality, her power, her beauty, was too much to take in without a tight ache thrumming in his chest. Caleb drops his gaze down to his hands, winding his fingers around his glass, searching for something else, anything else, to look at.
Beau heaves herself down onto their table’s bench, letting out a dramatic sigh. Jester throws her arms around Beau’s neck and plants a big kiss on her temple, which forces Beau to crack a smile.
“Thank you for dancing with me, Beau! You are so talented! That must be why you get all the girls,” Jester says, wiggling her eyebrows. Beau scoffs but blushes a bit, unable to deny it.
Caleb finds a blush coming to his cheeks as well when Jester slides up next to him on his side of the table and puts her hand in her chin.
“What are you doing, Cayleb?” she asks innocently. “Reading?”
“Ah, nein, Jester, just enjoying the night with you all. Why do you ask?” He can hardly get the words out, his heart pounding in his ears with her face so close.
He notices, not for the first time, the dusting of freckles that reaches from her nose, over her collarbone, disappearing in the low neck of her dress. An image enters his mind, unbidden, of tracing those freckles with kisses, touching each one with his lips lovingly and seeing how far they spread, his tongue tracing the freckles down the gentle swell of her breast-
“So you are free to dance with me then!” Jester says, clapping his hand in hers. Caleb is sure he is red, feeling caught in the act, though he knows nobody can see the shameful thoughts that were just running through his mind.
“Jester, I am an old man, I am afraid my dancing days have left me,” he demures, feeling his heart drop as disappointment crosses her face. Good job, he thinks, leave it to you to dim her light. “Surely you would like to dance instead with someone young and handsome, like Fjord.” Jester gazes up at him through her lids, biting her lower lip in a silent plea, a move he would swear was intentional if the thought of her flirting with him weren’t ludicrous. Fjord raises an eyebrow from across the table, but says nothing in response to Caleb’s suggestion.
“Cayleb, I want to dance with you. You are still handsome, even if you are sometimes a little stinky,” Jester teases, resting her head on his shoulder and her soft hair brushes against his jaw. Despite his beard between them, the touch feels magnified, and a faint scent of sweet apples wafts up. If he wasn’t bright red before, there is no doubt in his mind now. The rest of the Nein is looking at him, waiting for him to reply, and he feels himself begin to panic under the intensity of their expectation. Are you really going to let her down, simply because you can’t control yourself? He clears his throat and nods.
“Ja, alright.”
Jester jumps up, and for a moment Caleb admires her seemingly endless energy, hardly able to drag himself up from his seat, let alone dance. But, he thinks, perhaps dancing with her will make her happy, make her smile like she did before, and the thought energizes him to follow her out to the space in front of the organ.
Though the thought of fulfilling her wishes makes him happy, he is thoroughly unprepared, now that he’s out here, for being so close to her. Jester laces her fingers in his left hand and presses herself close to him, her other arm on his shoulder. Caleb feels like he’s almost forgotten how to breathe, as the opening notes of a simple, but charming, waltz ring out from the organ.
He knows he is being rude, staring straight ahead and not looking at Jester, but his breath is coming shallow and he fears that her gaze will be too much for him. Jester reaches out gently for his right hand and places it on her waist.
Caleb is stiff, but allows his training, albeit many years unused, to kick in. While Caleb’s brain might be short-circuiting, his body still remembers how to do this. Gently pulling at Jester’s waist, he signals her to allow him to lead, wanting her to let go and enjoy herself. Surprisingly, she lets him.
After half a minute of forcing himself to breathe normally, Caleb looks down at her face, which is turned up towards him, eyes bright and wide, her mouth slightly open with the barest hint of a smile. His heart skips when he realizes how close she is, his mouth just inches away from hers. He catches himself smiling as well as he twirls Jester around the room, her happiness infectious.
“Cayleb, I didn’t know you could dance so well,” she says, her fingers still tightly laced in his.
“Ah, well, when I was at the Academy I was forced to learn these things. It was important, evidently, that we were able to impress generous benefactors and powerful people at formal events.”
“Did you get to dance with lots of famous, rich ladies? I bet you were a very eligible bachelor for all of those fancy girls.” Jester grins, raising her eyebrows suggestively, and Caleb blushes fiercely. A memory comes, of sneaking off with some baron’s daughter at a gala to find an empty room, the memory so old now that only flashes remain, hands tangled in hair, mouths on fire, hands sliding under his shirt - but those, he reminds himself, shaking his head slightly, belong to the boy, Bren. The man, Caleb, did none of those things. At least there is still enough of him in there to remember how to waltz.
“Ja, a few. But none so lovely dancing partners as you, Blueberry.”
When Jester rests her head against his shoulder, Caleb prays she can’t feel the rapid pace of his heart, and what feels like only a minute later, the waltz ends. Jester pulls away and Caleb’s heart sinks at her absence, knowing his opportunity to hold her is over. When he searches her face, and she won’t meet his gaze, his stomach twists. What did he do? He must have been too bold with his compliment, or maybe he held her too close. Somehow, she must have felt the longing in his touch and it repelled her. How could it not have?
Jester raises up on her tiptoes and brushes a soft kiss against his cheek.
“Thank you for dancing with me, Cayleb,” she says, much less enthusiastically than she had thanked Beau. Even this, you can ruin. Caleb’s face burns and he clears his throat.
“Of course, any time. I - I am going to retire.” Without waiting for a response, or even to say goodnight to the rest of the Nein, he flees up the staircase to the room he is sharing with Caduceus.
Nobody else has gone to bed yet; it is still quite early. Caleb unbuckles his book harnesses and tosses them on the floor beside him, climbing into bed. Turning over to bury his face in a pillow, he groans loudly.
Get it together, Widogast. What are you, sixteen again? Just leave her be. She’ll be much happier with someone else.
Rolling over again, he replays his dance with Jester, trying to understand what he did wrong.
Does there need to be anything you did? It’s probably just you. She probably came to her senses and got out of there as soon as she could.
He felt ashamed for having thought about her like he had been, about her body, her beauty. Her light was so bright, and his dark shadows were so hungry. He would only dim it. She deserved someone less broken, someone good, and his chest tightened at the thought of what she would say if she found out he had been chasing her touches, thinking of her skin against his, her curves laid out beneath him.
Dirty old man.
He snuffed out the candle with a flick of his wrist in frustration, and grimly settled into a restless sleep.
The candle in Caleb’s hand drips wax onto his fingers, but he can hardly feel it against the chill of the air around him. He has been wandering these dark, dank passageways for what feels like days.
Increasingly desperate, he began putting markers on walls as he passes them, thinking he must be going in circles. Despite this effort, he does not see any of the markers again.
Gradually, however, as he ascends through the halls, he begins to feel warmer. There is light, somewhere, and though he cannot quite see it, he can feel its presence. Caleb moves towards it more quickly, hope spiking in his blood.
He begins to see more signs of life, more sconces on the walls, and he is getting warmer and warmer until he finally reaches a large wooden door at the end of a hallway.
Caleb is so grateful for an escape route, he doesn’t bother knocking or even checking for traps, he simply throws the wooden door open but furrows his brow in confusion when he sees what is inside.
A chamber of rooms, well decorated but foreign in design, opens in front of him. Caleb notices the room is uninhabited, the fire in the grate nothing but cold ash, no candles or torches lit in the sconces. The chill and exhaustion he had been fighting since he escaped his cell sinks deep into his bones, and it is all he can do to remove his coat and boots and snap a fresh fire into the fireplace. He knows his time here will be limited, he will have to leave the castle, but for now, he is alone, and he needs strength for the journey ahead.
Caleb would like nothing more than to drop to the rug right in front of the carpet and fall asleep, but he uses his remaining willpower to drag himself up, pull his silver thread out of his pocket, and begin warding the room. At least, when he is discovered by whoever put him down in that hole, he will have a few seconds of warning.
As he strings the thread along the walls, muttering incantations, he stops at the bed and is about to climb over the mattress to stretch the silver across, when he hears rustling and his heart leaps out of his chest.
A form, unnoticed before, stirs between the sheets and Caleb instinctively drops to the floor, hoping to at least get an opportunity to surprise his enemy first. Scheisse.
Above him, Caleb hears the figure rise and get out of bed, padding across the cold floor. He begins drawing the sigils in the air for a Hold Person spell, something that would buy him some time to make an escape. He freezes when he sees soft blue feet shuffle over towards the fireplace, and the tension in his shoulders relaxes when he realizes the person in front of him is Jester.
At the same moment, she turns and jumps, looking at him with surprise.
“Oh! Cayleb! I didn’t know you were here.”
He doesn’t quite know what to say, certain he looks like a fool crouched next to her bed with his silver thread between his fingers. Caleb can’t help but stare at her, drinking in the image of her, flushed from sleep, hair mussed, wearing a short, silky, dark gray nightgown with lace trim. Once his brain caught up to him, he stands awkwardly, unsure how to explain himself. Jester smiles curiously and saunters over, her tail swishing back and forth.
“What are you doing in my room so late at night, Cayleb?” she teases, drawing her finger down his chest in a way that gave him goosebumps.
Caleb reaches for her hand and at the same moment, Jester swoops her arm around his neck and pulls him in for a hot, passionate kiss. Flustered, he brings his hands to her waist but otherwise is too surprised to lean into it. When her tongue snakes past his lips he lets out a low whine, instantly embarrassed at his need.
Jester’s tongue explores his mouth shamelessly, and after the shock fades he presses into her hungrily, his tongue chasing hers. Her fingers tighten where they’ve clenched his shirt and Caleb’s hands grow bold, stroking her back, drinking in the feeling of her hot skin under the thin silk.
For a moment, his brain, constantly whirring, constantly worrying, stops, and he only feels. Jester moans into his mouth, the sound making his cock stir between his legs. Caleb wants to make her make that sound again and again.
He reaches up to her chin and tilts her head away just slightly, so he can sit on the bed and mouth at her neck. Jester grabs at him desperately, carding her fingers through his hair. Caleb wraps his arms around her tightly and sucks into her, a hot bolt of possessiveness shooting straight to his cock when he watches a dark bruise start to bloom on her freckled skin. He stiffens even further when she moans, low and long, and tugs on his copper hair.
Teasingly, Caleb runs his tongue over her collarbone, eliciting a small keen from Jester that intensifies when he brushes a scarred thumb around the curve of her breast. She pushes him down onto the bed in impatience and climbs on top of him, looking down in surprise when she feels how hard he already is.
“Oh…it seems like you’re enjoying yourself.” He smiles at her wickedly, blushing.
“I am enjoying you, liebling.”
Jester seems to like that response, as she settles her hips back onto his, forcing a low groan out of Caleb at the sudden contact. He involuntarily pushes his hips up into her, squeezing her thick thighs, and she squeaks in surprise, giggling at the sensation.
The straps of her nightgown are already down around her arms, so Caleb reaches underneath, sliding his rough hands up her sides to lift the silky garment over her head. He is lost for words in that moment, his eyes taking it all in. They’ve been naked around one another before, of course, but that was not the same. Then, there was a purpose, then it was with everyone else, and Caleb always averted his gaze from his friends’ bodies when they were in the bathhouse together. Now, Jester is on his lap, hot and wanting, naked for his eyes alone.
Biting her bottom lip with a teasing smile, Jester rolls her hips against him, drawing out another groan, this one more urgent than the last.
“Jester!”
“What?” she asks innocently, batting her eyelashes and dipping head head for a kiss. He playfully smacks her ass, not enough to hurt, and grabs a handful of her, squeezing and moaning into her mouth. Based on the shudder of her hips against him, she likes the feeling.
She pulls away, crossing her arms over her freckled breasts, and for a moment, Caleb panics, thinking he had already ruined it, already done something she didn’t like-
“This seems very unfair,” she huffs.
“What do you mean, liebchen?” He sits up, the haze of lust clearing away, and he takes her hands.
“I’m naked, Cayleb, and you still have your clothes on!”
The tension in his body releases and he takes her face in his hands to kiss her again, savoring the softness of her lips.
“Would you like me to take them off?”
“Yes!” she insists.
“You can have me however you like, Jester,” Caleb murmurs against her jaw. He is kissing and biting hungrily again at her flushed neck, which is now sporting more than a few of his marks.
With permission given, Jester reaches up under his shirt and yanks it over his head, impatient. She pushes him down on the bed again - he makes a mental note to return later to the thought that her ability to overpower him sends more blood rushing straight to his cock - and runs her fingers through his chest hair, eliciting delightful sensations under Caleb’s skin.
He responds by cupping her breasts, careful not to catch her on his calluses, gently stroking the buttery soft blue skin. She whines and continues stroking his chest, following the hair down to his stomach and the touch is almost too much, the slight drag of her nails against his sensitive skin.
When she reaches down and tugs on one of his nipples, Caleb almost jumps out of his skin, and accidentally squeezes Jester’s breasts hard. She gasps, and he feels the ice cold drench him again, pulls his hands away, worried he’s hurt her. Jester pinches one of her own nipples, teasing it to fullness, and the sight is so erotic that he feels himself leaking; even more so when she places his hand firmly on her breast and whispers, with a nip at his ear, “More.”
He moans and gladly obliges, palming at her ample breasts, letting his calluses swipe over her nipples when he notices how it makes Jester breathe in sharply and grind against him harder. Still circling her hips on his, she takes one of Caleb’s hands and guides his fingers to her mouth, sucking and licking them in a way that turns his mind to the ache between his legs.
“Oh, Jester,” Caleb groans, and she responds with a moan around his fingers that goes straight to his cock. “Jester, tell me, what do you want? I want to please you, let me make you feel good.”
Jester gently pulls his fingers out of her mouth and leans down to whisper in his ear, “I want to see your face covered in my cum.” Feeling his hips jerk up at the sound of her filthy words, Caleb is suddenly thankful for all of the smut she reads.
“You can have anything you want, Jester,” he mumbles as he places rapid kisses over her shoulder and neck. Caleb slides out from underneath her, regretfully, and repositions himself so Jester is kneeling over him. She looks confused for a moment, until Caleb gestures for her to lower herself over his head, and suddenly, despite her nudity and all they had been doing a moment ago, she is shy.
“Are you sure you want it though, Cayleb? Like this? What if I don’t taste good?”
He looks up at her and strokes her hips.
“Blueberry, it is not possible that I will not find your taste delicious.”
She smiles at the pet name and shyly kneels on the bed, her thighs on either side of his head. He is suddenly so close to her, his nose filled with her sweet, heady scent, and the curls of dark hair tickling his nose. Caleb presses a few soft, tender kisses to the inside of Jester’s thighs, moaning a little at how wet and sticky they already are. He takes his time, savoring every moment of exploring her for the first time, his fingers tracing the softness of her labia, gathering her wetness on his thumb and tasting her, ever so softly brushing against the spot he knows her clit is hiding. When he finally spreads her and gives her a long stroke with his tongue, Jester lets out a shout, almost collapsing on top of him.
Caleb wished he could see her face right now. He wanted so badly to see her cum, when he brought her there. The moans and pleads for more leaving her now were hot enough, and he’d barely started.
Burying his face deeper between her legs, Caleb set to work tasting and pleasing every inch of her, enjoying the way her thighs spasmed around his head when he took her clit into his mouth and sucked it. He was certain that his beard was wet with her slick and and felt another twitch in his cock when her wetness began dripping down his chin.
Jester was practically riding his face now, almost unconsciously thrusting back to chase the friction.
“Please, Cayleb!” she gasped, “More!”
He felt more than a little smug at having reduced this clever woman’s vocabulary to fragments, and replaced his tongue with his fingers, teasing,
“What do you want, liebling? You have to tell me.”
“Your fingers! Cayleb, please! I need your fingers inside me!” Jester begged.
Caleb groaned and buried his face in her cunt again, this time slipping a finger into her entrance, using his other hand to squeeze her ass.
Jester keened loudly, and Caleb couldn’t help but chase more of that sound, adding a second finger to his thrusts, and a third, all while working on her clit with his mouth.
He was so distracted by the taste, the feeling, the wetness of Jester’s cunt, the delicious sounds she was making that he didn’t realize she had undone his laces until he felt the air hit his rock hard, weeping cock.
“Don’t you dare stop,” she warned Caleb before taking his cock into her mouth and he practically shouted, pressing his face into her to muffle his noise.
The sudden, intense heat of her, so like the heat around his fingers, was so overwhelming Caleb worried he was going to come instantly. Breathing deeply, trying to hold it together, he focused on pleasuring Jester, rolling her clit between his thumb and forefingers.
Caleb did his best to maintain his rhythm for Jester despite the wet heat surrounding his cock, the noises her sucking made and the feeling of her tongue teasing at his head. He had to hold on, he had to make Jester come first.
Stroking against the swollen nub of her G-spot, Caleb suddenly curled his fingers the way he remembered from so many years ago, the way that had always brought girls undone for him, at least in someone else’s life.
Jester let out a shaky cry, moaning and shaking through her orgasm with her mouth around his cock. Caleb felt a gush of liquid over his hand and chin, lapping it up desperately to keep the taste of her on his tongue. He felt the hum of her moaning from inside her mouth and suddenly knew it was too late for him, managing to just pull her up gently by one of her horns before his cock began to release-
Caleb suddenly jerked awake, sticky and covered in sweat. He had vertigo for a moment, feeling almost woozy.
Panting hard, Caleb came to and hot shame washed over his whole body when he realized he had an orgasm in his sleep. Not only that, he had an obscene dream about Jester, a woman too good to be defiled by his disgusting imagination, and another wave of shame overtook him. Blessedly, Caduceus was still not in the room, so he had the opportunity to deal with this before anyone else noticed.
He stripped off his shirt, soaked through with sweat, and used it to wipe the spend off his stomach with a grimace. Gods above, he thought as he changed, are you actually sixteen again? He couldn’t remember the last time he had a wet dream. What are you doing having dreams like that at your age? Especially not with someone like her. You don’t deserve that kind of happiness.
Just as he was pulling a fresh shirt over his head, Caduceus entered the room with a steaming cup of tea.
“Oh hello there, you’re awake,” Cad said pleasantly. “I noticed you were having a nightmare, so I went downstairs to make you some tea.” Caleb accepted the tea from Caduceus with a mumbled, “Thanks,” hoping the burning red of his cheeks could be explained away by the steam from the cup.
“Any time,” the firbolg said pleasantly, settling into his side of the bed. If he noticed the sweat stain on Caleb’s, he didn’t acknowledge it. “Those nightmares can be very real. I understand.”
Grateful for his friend’s tact (Caduceus was too perceptive for Caleb to pretend he didn’t have a good idea of what had happened), Caleb laid back down in bed, flinching as the cold wet sheets stuck to him. Serves you right. Despite the exhaustion of his orgasm, he slept fitfully.