Work Text:
When she first posed the question Caleb didn't answer right away so Jester waited patiently. She let him take his time. Caleb, she knew, liked thinking things over.
"Why not ask Fjord?"
Jester shrugged, her face heating up. "I don't know, things are a little weird with Fjord. Things are always a little weird with Fjord. And I think he's nervous about sex, you know."
"Hm. That is true."
"You're not nervous about sex, are you Caleb?"
"No, I'm not." Caleb scratched the back of his neck. "I'm fine with it. But I guess I just don't really understand why this is something you want. I mean, with me." He seemed earnest enough and wasn't looking at her with the concerned pity that Jester sometimes noticed. That was good. Pity was really not what she was after right now.
"Well," she said slowly, "I like you and you like me, right? We're friends, right?"
"Right."
"And I know I want to have sex someday, with someone I’m in love with right, but I think, something I've realised, is maybe I don't know as much about it as I thought I did? Like, maybe there are some things I'm missing. So what better way to figure it out than with you, my friend!" She beamed at him. "I trust you, Caleb, and anyways isn't it supposed to be fun?"
Caleb's pale face had been steadily growing redder but he hadn't attempted to escape the conversation yet so Jester took that as a win. “Ja, it’s supposed to be fun.”
“And we always have fun together, right?”
“Right.”
“So we should have sex!”
Caleb rubbed his forehead with an expression of long suffering. “That’s quite a leap you’re making there, Jester.”
Jester adopted her best serious expression. “Okay, I was a little bit joking. I know it’s a big thing to ask. I’m not totally stupid, you know.”
Caleb softened. “I know.”
“But I am asking. Really honestly truly.” She reached out and grabbed his hand. “It’s not something I want to be scared about. And you make me feel safe.”
“I make you feel safe?” The scepticism in Caleb’s voice was so palpable it had a job and two kids and a mortgage.
Was that was this was about? Trust Caleb to be more worried about his own perceived failings than what Jester was actually asking. She just barely stopped herself from rolling her eyes. That wouldn’t have played well. “Obviously, would I be coming to you with this problem if not? C’mon, Caleb, you just said you knew I wasn’t completely stupid. Do you not think I’ve thought about this?”
Caleb’s expression went immediately serious. “You’re right. No, I- I don’t think this is something anyone would ask lightly. I am…sorry if I treated it that way.”
She patted his arm consolingly. “It’s okay. I know you get caught up in your head. But I’m still waiting for an answer. Yes or no. You don’t have to explain it at all, just yes or no.”
It was a positive sign of how far Caleb had come with the Nein that he was still sitting here at all and hadn’t yet fled for the hills. He looked at her, and Jester could see the familiar calculation in his eyes. Normally that look was directed at a problem the Nein had encountered, and it was slightly unsettling to have the brunt of it now on her. But Jester waited patiently. If there was one thing she knew about Caleb, it was that he needed time to consider all the angles.
She did, however, turn and pose herself slightly to show off the more flattering of the angles currently involved. Caleb noticed and snorted, but his eyes followed the curve of her hips.
If it had been anything else Jester would have been wheedling by now. “Caaaleb,” she would be saying, “Caleb pleeeeease.” But she stayed quiet and let him decide.
“I don’t want,” Caleb began, and stopped. He took a deep breath. “I don’t want this to make things…strange. Will this make things strange?”
“Things are already strange,” Jester pointed out. “I mean, in general. Things cannot get much stranger. We live strange. We eat strange for breakfast. Sometimes literally depending on what Caduceus is cooking."
“I mean between us specifically,” Caleb clarified. “I like this group, Jester. I like it very much. I like you.”
“Aw,” Jester beamed, regarding him fondly, “I like you too.”
“Which means I don’t want to risk ruining things because I- I don’t want to risk ruining things.”
“It won’t ruin anything!” Jester promised him, and she was certain of that. How could having sex with Caleb ruin anything? Worst case scenario, it was bad sex and things were a little awkward for a few days until Jester could start teasing Caleb about it and everything went back to normal. “I won’t make anything awkward. I have already seen you naked, Caleb. And covered in mud and poop. And mind-controlled. And-”
“That is true,” Caleb interrupted hastily just as Jester was building up a good head of steam.
“And I trust you as well! And, you already make everything awkward, so you can’t really make this worse if it goes badly.”
A small internal battle seemed to be raging in Caleb’s brain, and Jester waited it out. Patiently. Posing.
“You want to learn about sex,” Caleb probed, eyes flicking back and forth.
“M-hm! You’ve have sex with people before, right Caleb?”
Caleb shrugged. “Not with too many people. Some of it good, some of it bad. For various reasons. It does not make me an expert.”
“You still know more than me. And you know, you’re pretty cute.”
Caleb made a little assortment of spluttering sounds, but he looked vaguely pleased. Jester mentally fist-pumped and high-fived herself. She was the best at compliments.
“Alright,” Caleb said finally, eyeing her, “yes. I will have sex with you.”
“Really?!”
“Really.”
“Yay, Caleb!” Jester flung her arms around him for a quick hug before springing back and beginning to fumble with the buttons on her dress. “I’m so happy!”
Caleb squawked. “Wait- r-right now?”
“If you like!”
“I said yes but I'd like some advance warning before it happens!” Caleb protested, face flaming red. Jester stopped and frowned, a suspicion dawning on her.
“Caleb,” she said, “you do want this, right? Like, you’re not just saying yes to make me happy?” The thought was upsetting. “I wouldn’t be very happy at all if we have sex and then later I find out you didn’t want to do it with me. I won’t be mad if you don’t want! Really! I promise!”
“No! No,” Caleb said hastily, and then stopped and took a breath. “Wait. I mean, yes. I said yes, I meant yes. I do- do. Want this.” His face was still a brilliant red sunset. “I would, ahm, very much like to have sex with you. Perhaps I want it too much. But I still would like a day or two, just to get my head around it, ja? I’m not as spontaneous as you are, Jester. In anything. And this particularly, I’d like a bit of time.” He hesitated, and then continued quickly, as though he was trying to cram the words into the space between them as quickly and unobtrusively as possible, “In my life I have sometimes not had as much time as I would like, in matters of intimacy. I would appreciate it now.”
“Oh!” Jester exclaimed, relieved and touched. “Oh, Caleb. Of course. Will you just let me know?”
“I will,” Caleb promised. “Soon. Thank you.”
“No,” Jester said, and planted a sloppy affectionate kiss on his cheek, “thank you. You’re a good friend.” She topped it off with an exaggerated wink.
“Oh, ah, em.” Caleb stuttered and blushed somehow even further. “Right.”
The next few days were both normal and different. She winked at Caleb a lot more, and was delighted to find that he had become much more susceptible to blushing in response to said winks than he ever had been before. But otherwise nothing changed outwardly. Inside, however, Jester was excited. She was looking at Caleb in a new light as well, examining him in new ways. When he leaned across the table to offer Nott more bacon at breakfast she noticed the fine bones of his wrist and the bend of his elbow. When he fidgeted with the stylish new Xhorhasian coat he had acquired, she noticed the way it draped flatteringly over his shoulders, which were bony but broad.
Caleb was handsome when you got right down to it. Part of it was that he had picked up his personal hygiene far, far more than it had been when the Nein had first come together, but he cut a striking figure as he’d always done, fairly tall when he didn’t stoop, and with bright inquisitive eyes. She knew him too, and knew him well.
She was anticipating knowing him better.
As it happened she didn’t have long to wait. Two days later Caleb came to her quietly and asked if she was planning on going into the city with the others. He himself, Caleb said, was staying home. Everyone else was not. He had blushed when he’d said it. Jester had beamed.
She had noticed too when he had scuttled back to the library, and he’d flashed her a parting glance, his eyes quite dark.
Jester shivered delightedly, and thought that she wasn’t the only one of the two of them who’d been taking notice of the other.
About an hour later they had the Xhorhaus to themselves. Nott had been given an extensive shopping list by Caleb, who’d claimed to be too busy with a certain boring-looking book he’d found to go out, and after making her excuses -needing to teach Sprinkle Xhorhasian, wanting to touch up the paint in Yasha’s room, having scheduled a nice long chat with the Traveller- Jester shooed the others out the door and closed it with a bang. Then she scurried into the library.
Caleb was indeed hunched over a book, but he looked up when she entered and Jester could sense a nervous buzzing energy about him that was certainly not normal for a Caleb who was actually reading.
“So.” She grinned at him. “They will be a few hours.”
“Ja. Right.”
“We have the place to ourselves.” She waggled her eyebrows and finally coaxed a chuckle from Caleb. “Are you ready to have some really hot fun seeeeexx?”
“When you put it that way, how can I refuse.” Caleb got to his feet. “Um, my place or yours?”
They went to Caleb’s room. It was closer, for one thing, and the lack of roommate was a bonus. Jester was almost positive Beau with her secret monk skills would be able to sense any hanky-panky taking place within a range of twenty-four hours in her immediate vicinity, and while she didn’t particularly mind anyone knowing what they were about to get up to, she knew Caleb was a much more private person.
Caleb turned to close and carefully lock the door, and Jester began eagerly skipping out of her clothes, untying ties and unbuttoning buttons. She wriggled out of her dress, pulling it over her head and when she re-emerged Caleb was staring at her, back against the door. Jester gyrated her hips at him in what she imagined was a devastatingly sexy manner. “Time to take off your clothes!”
“Skipping the foreplay I see,” said Caleb.
“Oh, we can do foreplay! Do you want to do foreplay? But I want to be naked for it, that’s all. Come on, I know you’ve got this nice new Xhorhasian look but it can’t stay on forever.”
Jester admired him as Caleb stripped down to his underthings. He had put on some healthy weight since they’d met, and while he was still gawky and lanky there were fewer ribs showing and his skin had lost the sickly pallor it had once possessed. He did flush very satisfactorily, as he did when Jester unlooped her bra and slingshotted it across the room.
She laughed at him. “Caleb. You can look at my boobs. That’s basically why you’re here, right?” She shimmied enticingly. “Look! At! The boobs!”
Caleb, who had averted his eyes in what seemed to be some sort of automatic preservation instinct, allowed himself to look at the boobs. Jester smiled, triumphant. “They are pretty good, right?”
“I can’t dispute that.”
“Oh, thank you.” Jester clasped her hands behind her back, momentarily unsure what the best way forward was. Somehow she suspected that it was going to be up to her to dictate the sequence of events. If she did nothing, Caleb would let them both just stand there awkwardly in their underwear until the others returned and caught them just staring at each other wordlessly. It was sweet really, how he was letting her make every step. But also a lot of pressure. Then Jester brightened. “Can we like, make out for a bit first?”
“It’s your party,” Caleb replied. “I’m just happy to be invited.”
Jester tutted, suspicions confirmed. “It’s our party.” She stood on her tippy toes to peck him on the lips. “Now go get on the bed. So we can reeaally get it started.”
Caleb obediently lay on the bed and Jester followed immediately to climb into his lap, straddling him comfortably. Caleb bit his lip but didn’t say anything.
He was half-hard already: she could feel him pushing up against her and shivered. She had imagined this happening before, always with nebulous, generically handsome imaginary partners. She hadn’t ever imagined it being Caleb here beneath her, looking a bit ruffled but still himself. His eyebrows were furrowed and his mouth downturned in a way that Jester had originally thought was permanent bad temper but had come to realise was just his thinking face. She rather liked that it was Caleb.
“Alright.” She shifted and heard Caleb sigh almost inaudibly at the friction. “What would you like me to do?”
“Anything you like,” Caleb said openly. Jester frowned.
“No, I mean, what will make you feel good? I want this to be fun for both of us, you know? I want to be gooood for youu.”
Caleb’s mouth quirked up at the corner. “Jester. Believe me when I tell you, I’m pretty sure I will enjoy myself no matter what you do.”
“Oookay but Caleb, I really have never done this before. And it’s always you who’s saying porn is not like real life. I don’t want to mess it up!”
“But you are an expert in being yourself,” Caleb said simply. “And that’s what I will enjoy the most.”
Jester actually blushed. “That was really romantic, did you know? When did you get so romantic?”
“I guess I’m just in the mood for it all of a sudden.”
Jester giggled. “You’re funny. Alright, I’m going to kiss you now.” And she did. With enthusiasm.
Caleb was actually not a bad kisser, not that Jester had much empirical evidence to compare him against. He let her set the tone of it, and agreeably opened the kiss when Jester tried licking into his mouth. He kept his hands by his sides, though, and while Jester would have liked to be touched and groped a little, she had free range with her own touches and buried her hands deep in Caleb’s long hair as the kiss got messier. Her tail flicked along the length of Caleb’s leg, stroking at his calf and nudging his ankle. It was a sensation, bare chests pressed up against each other and combined body heat shimmering between them.
She rubbed herself against Caleb, hearing and feeling his short gulp of air as his erection brushed against her lower stomach. She could feel a growing damp path in the fabric of his underclothes. “Can we- ?”
"Remember just- carefully," Caleb said, his voice quite tightly controlled. "Go slowly. I don’t want to hurt you, if you try to go too quickly or all at once, okay? Don’t worry about me, take care of yourself first."
"Okay, okay." Jester wriggled on his lap. "Slowly, I know, Caleb. I do know some things."
"I know you do." Caleb's lips were red with kissing but fingers were still clenched against the lumpy mattress like a man clinging to a cliff edge.
Jester reached up to stroke the side of his neck soothingly. "I think it's you who needs to relax maybe," she said, concerned. "Are you sure you're okay with this?"
"I'm fine with it," Caleb reassured. "I'm just finding it, ah, hard at the moment."
Jester snickered. "Yeah, you're finding it hard."
"Jester," Caleb chided, and then whimpered as Jester rolled her hips experimentally. "Now you're doing that on purpose."
"I sure am! I need to learn about sex somehow, but looks like I am already pretty good at it." She leaned down and gave him a sloppy kiss on the cheek.
"Can I...?" Caleb uncurled one hand from the twisted sheets and tucked two fingers into the waistband of Jester's underwear.
Jester nodded, not trusting her voice not to squeak. She was having fun kissing and it certainly felt nice to make Caleb all flustered and bothered. But the growing heat between her legs pulsed and she could feel a spreading dampness of her own at Caleb's touch.
Caleb’s fingers were bony and bent and when they pressed lightly against her clit it was all Jester could do not to shout aloud. As it was she sucked in a sharp breath which was released in a moan. “Caleb.”
“You’re wet,” Caleb murmured, rubbing a small circle with two fingers, slipping them down to nudge at her folds before pulling back. “You like me doing this?”
“Very much,” said Jester shakily. “Keep going.”
“I’ll do a lot more than just this. If you like.” One finger entered her, not enough to feel a stretch but it was still Caleb’s finger, sliding into her wet heat for a moment before another joined it.
“Oooh,” Jester said, clapping a hand over her mouth.
Caleb reached up to tug it away, still gently sliding his fingers in and out shallowly with his other hand. “Don’t be quiet. I want to hear you.”
“Oh,” said Jester, a little breathless. “Okay. Caleb. I think you might actually be very sexy, did you know that?”
“Wow, I am so flattered,” said Caleb drily, but he flushed. “Can you- take these off?”
Jester rolled off Caleb onto her back to shimmy out of her panties. She got to her knees and dramatically swung the bit of cream-coloured cloth about her head twice before letting it fly off her finger into a corner of the room. Caleb rolled his eyes, smiling bemusedly and Jester giggled. “Was that sexy of me?”
“It was messy of you. Come here.”
She clambered eagerly back onto Caleb’s lap, feeling the rasp of his underwear against her bare skin with a shiver. Caleb kissed her sweetly, his fingers tracing shapes down her shoulder blades to her back, around her waist to her stomach and through the dark curls of hair between her legs.
“I will have a better angle if you lie down with me,” Caleb said, not a direction or even a request, just a statement. Jester was quick to take it to heart, slipping off Caleb’s thighs to land beside him on the mattress. Thank all the gods for Xhorhasian luxury: there wasn’t a bed in the house that couldn’t sleep at least three people comfortably.
Caleb stroked a finger along the soft inside of her thigh and Jester shivered delightfully. “I’m going to touch you again, okay?”
“Yes, please,” said Jester, eyes wide, and Caleb reached between her legs with intent.
He pushed a finger slowly through the plump folds of her labia, stroking at the sensitive flesh there and teasing her entrance without actually penetrating. “It’s nice to be able to take time,” he admitted quietly, rolling his thumb over her clit. Jester wanted to arch against him, find more friction and pressure, but she held back. There was a high flush on Caleb’s cheeks and she could see how hard he was. She wondered if he got off on this, the slowness, the talking.
“I like being able to learn what you like.” He said it candidly, matter-of-factly, but once more Jester noted his cock jump. “What makes you cry out. What makes you blush- you have a very cute blush, Jester.” Two fingers slipped inside her then, easy with how slick she was. He began to move them, in and out a few times, coaxing her open. A third finger slipped in, long and thin. Jester imagined how they looked inside her, Caleb’s delicate fingers stroking her.
It felt good, it felt incredible- and knowing that it was Caleb who was doing this to her made it all the better. It was tempting to just let him finger her open like this, slow and relaxed until she came. That sounds like a great idea. But at the same time, it wasn’t her end goal, not this time.
“You’re still wearing stuff. That’s not very fair.”
“Hm. You do know how much I like fairness.” Jester her best not to whine when Caleb slipped his fingers out to tug off his underthings.
He had a nice cock, straight and flushed a pretty pink. It was hard, very much so, and leaking from the tip. Jester reached between her legs to wet her hand on her own slick before giving Caleb a gentle tug, and enjoyed the way he groaned.
“I want your dick in me,” Jester said. Her clit was beating quickly in time with her heart. “Caleb. I want to ride you. Is that okay? Can you just lie back and I’ll find out what I like?”
Caleb sucked in a breath, his eyes wide. “Wow. Okay. You sure know how to talk to a guy.”
“Are you being sarcastic?”
“Not at all.”
The head of Caleb's cock slipped easily inside when she moved over and Jester squeaked as it did. It hadn't looked particularly larger than the other cocks she had ever seen, but the feeling of it pressing up into her was far more than she had expected, far more real.
"Are you alright?" Caleb gulped beneath her, legs trembling. He was so clearly restraining himself and it was quite sweet. But Jester wanted this, had asked for this.
She nodded. "Just- surprised, I think." She sounded breathless to her own ears. "Can you- put it in further?"
"Not a problem," Caleb croaked, pupils blown. "Ah- fuck."
"Are you alright? Am I doing okay?"
"More than okay. You’re- this- it’s very good.”
Awkward as it was the compliment sent a hot flush running up Jester's neck and cheeks. “You can touch me if you like, Caleb," she told him. "I don't mind. I'd actually like it."
Caleb didn’t need to be told twice. He lifted his hands to cradle her breasts, rubbing a callused thumb gently over one nipple, circling around the edge of the dark blue areola. Jester sighed happily. It felt so nice to be touched. To be touched by Caleb, who was strange and awkward but kind and thoughtful. His skin was warm, and she thought about the fire humming underneath his fingernails. Caleb could harm so easily, but in his careful hands she felt perfectly safe.
“Is this alright?” Caleb murmured again, squeezing gently before running his hands down her stomach to settle on her generous thighs.
“Yes,” Jester said, voice high, and bounced experimentally in his hands, sinking a little lower onto his thick erection. Caleb made a strangled noise and his hips jerked up almost instinctively, Jester’s eyes going wide as he thrust deeper. “Ah!”
“Shit, sorry! Sorry!” Caleb apologised hastily, squeezing tighter at her hips in worry. There was a bruise at the small of her back from the Nein’s last tussle, and Caleb’s fingers pressed just against the border of it, producing a pleasing ache that only exacerbated the rush of sensation.
“Don’t apologise,” Jester scolded, “Caleb. It feels- I like it.” There had been a moment of discomfort but it had already passed. She arched her back, sinking down a little further. “I want to try moving, okay?” She bounced again, and eased her way down, forcing the tension out of her thighs until she was finally sitting completely in Caleb’s lap with his cock buried to the hilt inside her. The stretch of it felt incredible: full and heavy and addictive. She liked the way they looked together as well. Caleb’s narrow, freckled hips beneath her much wider ones. The pale skin against the deep blue.
Caleb’s pupils were blown wide and he was tracing meaningless little patterns with his fingers against her side. She spread her legs a little more and tightened around him, drawing a gasp. Ooh. That was interesting. She did it again, feeling the way his cock fit inside her clenched heat and how it twitched, filling even more as she moved. She raised herself and thrust down, enjoying the warm friction building between their skin as she picked up a rhythm.
“Does it feel good when I move like this?”
“Yes,” Caleb gasped, head thrown back, “yes, gods it feels good, don’t worry about that, oh fuck, fuck-”
Jester laughed a little breathlessly, the muscles in her thighs beginning to burn comfortably as she moved more quickly, changing the angle ever so slightly until it was perfect. Caleb was so deep inside her, swollen and fat. “I think that’s what I’m doing.”
“Yes, yes you are,” Caleb babbled. It was a heady feeling to have reduced their clever wizard to near incoherency.
She could feel the hot humming building behind her pelvis and reached down to drag Caleb’s hand over to her clit. He let her and automatically began little circular motions with his thumb. Gods but Caleb knew what he was doing. She wondered who had taught him. If she had a name she would have Sent them a very appreciative thank you.
“You can come in me,” Jester rocked forward to whisper in his ear. “You can fill me up if you like.”
“Fucking hells- Jester. You need to- ah- stop reading so much- porn-”
She giggled, a sound which broke off into a gasp and then a small shriek as Caleb began to move his hips in earnest rather than just letting her do all the work. He increased the pace, gripping tight to her thighs and bouncing her on his cock, driving home in just the right places while keeping up the almost harsh stimulation of her clit. The heat welled unbearably between her legs, throbbing and pulsing and then Jester was coming in a rush, more vigorously than she ever had while playing with herself, clenching tightly around Caleb. The swollen thickness of his cock seemed overwhelming inside her with the orgasm pounding through her body, and Caleb snapped his hips a few more wild times underneath her before tipping them both sideways and pulling out to spill across both their bellies with a near inaudible groan of something in Zemnian.
They both lay there panting. The air between and around them was thick with the smell of sweat and sex in a way that should have been slightly disgusting but Jester found she didn’t care much. Caleb’s skinny chest was rising and falling rapidly, white come streaked across his skin and in the dark reddish hair which ran up from his groin.
“Oh. Oh. Caleb. I think I like sex.” It hadn’t been a given, Jester realised. She had assumed that she would enjoy it, but there were people she knew who didn’t. But sex with Caleb, at least, had been good.
“A relief to hear,” Caleb returned, out of breath. “Ah. Fuck.” He closed his eyes and rolled over face-first into the pillow.
“Are you going to fall asleep?” Jester asked curiously, sitting up to look at him. “Caleb?”
“Yes,” Caleb said, muffled.
“No round two?”
“Nein. I’m an old man. I need sleep. Go find someone else if you’re still looking for experience.” He sounded like he was smiling.
“Maybe I will,” said Jester mock-haughtily, but she hadn’t really been looking for more. Not at the moment. They would have to clean up first, but a nap really did sound like a genius plan.
She leaned over and kissed him sweetly, right between his bony shoulder blades. “Thank you, Caleb.”
Caleb turned back over onto his side to gaze at her, laughing a little hoarsely. His eyes were soft and sleepy. “I think I might have to be the one thanking you. I haven’t, uh…well. It’s been a while. Since I last enjoyed myself like that.”
“Well, if you like, maybe we could do it again sometime maybe possibly?”
“That wasn’t very subtle at all,” Caleb informed her but he was smiling now. The little half-expression that he sometimes flashed, but Jester could see it clear on his face.
“I don’t think anything that just happened was very subtle,” Jester pointed out, and she reached out to run a light finger over his now-limp cock, up through the mess on his stomach and coming away sticky.
Caleb sucked in a breath. “Well. We’re not very subtle people,” he said, and sat up to return the kiss.