The Wandering Sapphire

BY : justheretoread
Category: -Misc TV Shows > Threesomes/Moresomes
Dragon prints: 493
Disclaimer: I do not own Critical Role and I do not make any money off of this work.

Notes: I am unsure if there are any other Critters on here but figured I'll share here. For any Critter on here, this is an AU. Campaign 1 is 100% canon but Campaign 2 is not. I basically just wanted a PWP scenario where Jester interacts with characters from both campaigns (most of the Mighty Nein are probably traveling with Jester, such as Beau and Yasha being her body guards, Fjord being captain of the ship she travels on etc.). Also, as I feel the need to address this, I do not think Marion will disapprove of this life for Jester. Neither one of them were ashamed of what Marion did.


Chapter 1: The Del Rolos

“Happy anniversary, darling.” Lady Vex’ahlia de Rolo smiled at her husband.

“Happy anniversary, my dear Vex’ahlia. Gods, has it been 25 years already?” The couple was finally alone in Vex’s mansion after the obligated parties with family, friends, and diplomats. “I am so glad we can just come here to get away from all that. Just the two of us. None bustle of the castle.”

Vex smirked at that. “Well, actually I’ve arranged for some company tonight.”

“Oh? And who will that be? I didn’t notice Zahra and Kash at the party, although if you were keeping them a secret…” There was a look of excitement beneath the surface of Percy’s usual dry expression. Vex recognized it.

“Actually, I’ve sent a request to the Lavish Chateau. I know how much you’ve enjoyed our trip there.” The dark haired half-elf giggled at Percy’s blush. “Not that I had any complaints.”

Percy fiddled with his glasses. “Yes, well it was your idea. But I was under the impression The Ruby of the Sea didn’t leave Nicodranas?”

“She doesn’t. But her protégé does.”

“Courtesans have protégés? How does one get that job?”

“Looking for a new career, darling?” Vex grabbed Percy’s hand. “Well The Wandering Sapphire should be waiting in the bedroom.” The white haired Lord of Whitestone followed the Baroness of the First House of Whitestone and Mistress of the Grey Hunt into the bedroom. He felt at home here despite living in the castle. This is where they came to escape their titles.

Jester waited on the bed as her clients entered. She smiled. It was show time. “Welcome, Lady Vex’ahlia de Rolo. And Lord Percival Fredrickstein von Mussel Klossowski de Rolo The Third. My pleasure to meet you.”  The blue skinned tiefling walked up to the husband and wife. “I hope you like my outfit, My Lady. Ma--- The Ruby of the sea didn’t say anything about preferences you guys had for clothes so I took the liberty of picking something on theme for your other requests.”

Percy could imagine what Vex had in mind. The blue girl in front of him was dressed in all black. She wore a tight bodice that showed plenty of cleavage with extra belts and buckles. It flowed into a black dress. The ends appeared tattered, as if she ripped it herself. A pair of black leather high heeled boots, black lipstick, and a chain from her earring to the horns completed the look. The only things that distracted from the medieval dominatrix look was a pink backpack flung over her back and the unicorn tattoos on her bare shoulders.

“O, darling. You look wonderful. Although you seem to be packing light.” Vex looked around the room searching for some items she requested.

“Ah yes. Don’t worry, Lady Vex’ahlia. I have everything we need. This haversack is deceptively roomy.” She patted the pink backpack. “But first, we need to go over safe words and limits. I personally suggest something silly that would kill the mood but not too much. Like Hupperdook. I’ve had a client who used an ex lover before but that didn’t turn out too well. I ended up spending the rest of the session stroking her hair while she cried.”  Jester saw the awkwardness on the faces. “Not that I’ll ever reveal their identity or judge them. Trust me, that isn’t the worse thing I’ve seen. But where were we? O yea, safe words. I believe you’re the one who would be using it Lord de Rolo, although you might want one too Lady Vex’ahlia.”

Vex tried not to laugh at how bubbling the courtesan was. But she noticed how at ease Percy was among the humor. And she was too. “Please, call me Vex. And that’s Percy. And what may we call you? The Wandering Sapphire seems a bit formal.”

“O yes. My name’s Jester. So, Percy, have a safe word yet?”

Percy walked over to the bed and sat down. “Victor.” Vex gave him an expression he hasn’t quite seen before. It was close to whenever Grog has done something dumb. “What, she said something silly and will kill the mood. Trust me, it qualifies. You got a better one?”

“Well, I was thinking ‘Life needs things to live’ if I need one.” Percy just sighed at that reminder. “So what’s next, do we take off our clothes now?”

Jester sensed the history between the two. They had more shared experiences in a human life time than most elves and dwarves could ever hope for. She smiled “Not yet. We still need to go over what you both want, what you are comfortable with, and what you don’t like. And of course if there is anything I need to avoid. Especially you, Percy, as your wife was the one who contacted The Lavish Chateau.” She took out a handwritten list. “Let’s see, some bondage for Lord de Rolo, some sensual loving for Lady Vex while her husband can ‘do nothing but squirm until his cock is so painfully hard and desperate for release he is begging to sign away Whitestone just to cum’ (my, you do have a mind for this Vex) and some pegging to wrap things up.” At Percy’s blank look she explained. “It’s where a girl fucks a guy with a toy.  Mm, now that does seem like fun. Now, is there anything you want to add or avoid? Could be anything from how you want me to talk to you to any sex act not on here or whatever. Or any pet names I should know about.”

Percy thought about that for a moment. Overall there was nothing really new on the list. Although there was something not mentioned directly. “I call Vex by her title at times in bed. Especially when she’s tying me up. And um, compliment me when the opportunity arises.” He watched Jester write down “praise kink” with a check next to it. Percy never knew it had a name, but it seemed to fit. Vex certainly didn’t need encouragement to bring that in. “And avoid belittling and degrading talk. Zahra tried that once and it ruined the mood.” He thought more about some awkward times. “And while I like bondage, please avoid pain. Not all of it, any physical activity is going to bring some layer of pain but no rough spanking, drawing blood, whips or anything like that.” Jester wrote something else down and drew a line through it.

Percy was surprised that Jester didn’t ask for an explanation. He expected to have to explain the torture he suffered at the hands of the Ripley and the Briarwoods. “Also, Vex likes the tiefling antimony.” Both women looked at him like a college professor talking about sex. “I mean, she likes it when a tail rubs against her body and caresses her or when you nibble her neck with fangs.” The tiefling scribbled that down.

“Mm, yes I do darling. Thanks for remembering.” Vex kissed him on the cheek. “So, are we ready, Jester?”

The tiefling fumbled through her backpack in search of what she needed. “One second, just taking out the fun stuff. Mm, I think silk will do.” She pulled out some rope alongside a leather harness, a small bottle and a few dildos. “So, do either of you have a size preference?”

Percy spoke first. “You can choose, dear. You know what I like and can handle more than I do most days.”

“The pink sparkly one” Vex answered immediately.

“Ah, my favorite. Trust me, you’ll love Spinkles.” The blue woman smiled at Percy before putting the other toys away. “So shall we begin?”

Percy nodded. “At your leisure.” He began unbuttoning his jacket.

“Stop, darling. Let us do that.” Percival stopped immediately at his wife’s order. The two women approached.

“Such an obedient boy. O, this is going to be so fun.” Jester unbuttoned his jacket next. She gave him a quick kiss on his cheek. “Arms up.” She removed his jacket and shirt. “Normally I’ll just rip these off, but you look so tasty in them. It’ll be a shame to ruin such a regal look.” As she folded the clothes Vex took off Percy’s pants.

“On the bed, darling.” Jester passed Vex’ahlia some rope. “Thanks, Jester. I’ll take his legs while you get his arms.”

Jester giggled and went to work. She tied one of Percy’s hands to the bed post. “Is that good, Percy? It isn’t too tight is it?” Percy nodded. “I need you to speak to me, please. Cutting off the circulation could lead to losing an arm.”

Percy chuckled. “Well, won’t be the first time. But no, that’s perfect, Miss Sapphire.” He moved his arm slightly.

“Miss Sapphire? Mm, I quite like that. I’m a bit too young to go by ‘madam’ I think.” Jester climbed onto the bed and straddled Percy’s bare chest. “Other hand, please.” She tied the other arm while still on top of Lord de Rolo. Then Jester lowered herself down to kiss him. As soon as he began to kiss back she stopped and started kissing his neck.

“O gods” Percy moaned. He was completely tied to the bed now. Jester sucked on his neck while she pumped his cock with her hand. He didn’t even realize she grabbed it. He moaned and tried to thrust into her palm.

Vex noticed. “No moving, Percy. Or else I’ll just have to take this cutie to another room and leave you here. Isn’t she sexy? I think she’s sexier than The Ruby of the Sea, don’t you Percival?”

“Yes, Lady Vex’ahlia. More beautiful by far.” Percy’s breathing was labored. Jester still massaged the cock.

Jester backed off from his neck. It was already red. “And will you be saying that without your cock in my hand? Besides, The Ruby isn’t here. There’s no need to compare.” She crawled off the bed and left his cock. “Such a good boy, and such a pretty cock. I’m going have fun with you later. But for now…” She bounced over to where Vex was. “So, do you want a mark to match your husband’s?”

“Fuck yes.” The half-elf grinned and pulled the courtesan into a kiss. The kiss was longer and deeper than the last. Jester allowed Vex to enjoy it for a bit. Jester nibbled at Vex’s lip. The older woman whimpered into the blue lips. Her dress came off without the kiss breaking.

Jester moved to Vex’s neck while still undressing the Lady of Whitestone. Vex moaned as the little fangs dug into her. It wasn’t enough pressure to break the skin, but Vex knew it’ll leave a mark. “O darling, don’t you think I’m a bit old for hickies?”

“Please, you’re not that old Vex. Trust me, I’ve had much older.” She giggled at the memories. Then seeing Vex about to respond “and not just elves and dwarves. Besides, even if you are an old married couple, you’re a sexy old married couple. Trust me, Lady Vex’ahlia, you’re a certified milf. And I’m sure that with that age comes experience none of the blushing virgins I see have.” She emphasized the point with a hard suck against Vex’s neck. “I hate teaching. And I’m sure you know how to cover love bites with make ups and scarves. It is a bit chilly up here.”

“O darling, you’re good.” Vex meant that. Both the flattery and the foreplay were excellent. She shuddered as the blue horned woman went lower.

Jester sucked Vex’s nipple into her mouth. Vex breathed harder. The blue tiefling smirked then quickly brushed her fangs across the nub. “Do you like this, Vex? Want me to play with your titties? They’re so fun.” Jester’s mouth moved between each breast. “I could do this for hours.”

“Fuck, don’t you dare.” Vex grasped Jester’s horns. “I’m not as patient as my husband.” She looked over at him. “So, darling, enjoying the show?”

“Pelor, yes. You’re so beautiful. Both of you.”

“Your husband is such a flatterer. So, time to step things up?” At Vex’s nod Jester dove between her legs. “So, you want it fast, right?” Another eager nod had Jester’s tongue inside the half-elf. “I knew you’ll be sweet.” Jester’s words went unheard. Vex’s legs locked around her head and muffled any sound.

“O yea, faster please. Yes, please, more. Just shove that blue little tongue into me and fuck my brains out.” The tiefling happily obeyed. “O, darling, she’s fucking amazing.”

“I can see that.” Percy’s cock was painfully hard.

Vex tightened her grip on Jester’s horns and shoved her face deeper. She screamed out an orgasm. Jester continued sucking and licking until Vex spoke again. “Sweetie, you’re so good. But I think you need a reward.”

The traveling concubine kissed her way back up Vex’s body. “And how do you want me, Lady Vex’ahlia”? Her face glistened.

“Up. And finish undressing.” The Sapphire did so. Not quite a strip show, but enough to draw the attention of both Whitestone rulers. As she did so, Vex grabbed a blanket and a pillow. She set up a makeshift bed and lied down. “Now, I want the Wanderign Sapphire to sit on my face tils he gushes all over me.”

“Well, only fair to return the favor.” Jester moved over and lowered herself. She faced Percy as she did so. “So, how hard should I ride your wife’s face?”

Percy took a second to realize he was supposed to answer. “Start slow. Let her tease you, she’s a master at it. Even if she doesn’t have the patience for it herself”.

Before Vex could retort Jester lowered herself down. “Mm, yes she seems quite skilled.” Vex slowly licked at Jester’s folds. Vex moaned into Jester as she felt something rub across her breasts. It took her a moment to figure out it was Jester’s tail. The blue skinned woman continued to rub the half-elf’s body with her tail.

The more Jester moaned, the faster and lower her tail moved. “Lady Vex’ahlia, I’m going need you to listen, ok? I want you to tap my butt with 3 fingers. Can you do that?” Vex did. “Good. Now if anything I do is too much for you or doesn’t feel good or make you uncomfortable, just tap me like that again.” She paused for the message to get in. “Now, Vex, you are going to continue eating me out like I’m you favorite cupcake. Maybe blueberry, or black moss flavor. But when I start fucking you with my tail, I want you to go faster and faster as I fuck you. Is that ok with you, darling?” Jester lifted herself up just long enough to see the half-elven woman nod.

Vex was so focused on tonguing out the younger woman on top of her that she almost missed the tail teasing her own lips. The sudden cold though caused her to gasp. But she adjusted and soon she was in sync, moving her tongue just as fast as the tail.

“So, Lord Del Rolo, have your wife ever been tail fucked?”

“Never, Miss Sapphire. But I’m sure she’ll enjoy it.”  Percy loved the view. “I’ll have to tell Zahra and Lilith about this trick.”

“Just be careful, and use lube for the first time. Although your wife is so wet and sloppy I don’t really need it. Plus I know what I’m doing.” Jester’s tail dipped a few inches in. “ So tell me, should I give this little tease a taste of her own medicine, or should I give her all I got?”

Percy didn’t hesitate. “Give her all you can.” Vex knew he would, he never denied her anything she wanted. Jester’s tail began going in and out of her. Slower than she wanted, but more. The feeling was weird, but pleasant.

Vex kept up her end of the bargain. Her tongue went deeper and deeper as the tail did. Soon it was pistoning in and out of Jester. The tiefling moaned louder and louder. She was unable to speak out her next direction, but it didn’t seem needed. She pumped her tail a bit quicker into Vex’s cunt at the same time Vex moved her hands to start fingering the tiefling. “Naughty girl, but keep going.” The two women came at the same time.

Jester fell off of Vex’s face and quickly slid down to cuddle and caress. Once she regained herself, she pulled herself close. Vex’ahlia kissed her deeply, the taste of Jester still on her lips. The tiefling smirked into the kiss. She bought her tail up between them. Vex licked her own juices off of it. “Mm, I do love the way I taste.”

“You should, you’re extra tasty. Like chocolate. Although, a bit more like honey. So, do you think your husband has suffered enough.”

“Mm, I don’t know. What do you say, darling? Are you willing to hand over all of White Stone to me just to cum?”

“It was yours from the day we met, love. You know that.” Vex couldn’t help but roll her eyes at that.

“Aww, he’s so sweet” Jester muttered as she put on the leather harness. “So, do you want to lube me up, Lady Vex’ahlia?”

Vex lowered to her knees without answering. She grabbed the lube and slathered some on her fingers. “Rub it into your hands first, warm it up. I can’t really do that.”

“So I noticed. It was, unexpected. Most tieflings are, well” Vex blushed as she trailed off. She didn’t want it to sound like an insult.

“Warmer? Yes. Well, I take after my father in some areas mama always said. I hope it isn’t an issue. It isn’t that noticeable for most of my body, but my tail…” For a moment, Jester was uneasy. She was still relatively new at this.

“Not at all. It’s different, but damn good. I can just imagine how it’ll feel with you and Zahra switching off on me.” She shuddered and continued the sloppy handjob on the dildo in front of her. Once it glistened, she gave the fake cock a peck on the head. “All ready, do you want me to open my husband up for you?”

“Yes please. I was going to plug him, but I thought it’ll be sweeter to see you do it. You two seem perfect for each other and it’s quite adorable to watch a couple in love.” Vex raised an eyebrow at that but took the lube over to Percy.

“Ready for your turn, darling? It’s time  to put on a sex show for The Sapphire. She’s a professional, so we better make it good, Percy.” Vex bent down and kissed him. Percy kissed back, but passively. Vex always took charge like this. Her tongue hungrily explored her husband’s. She nibbled on his lip a bit.

Then she stood up and walked to the other end of the bed. She crawled onto the bed til she was between his legs. Without a word she took his cock in one hand and licked from the base to the tip. “You’re so hard for us, baby. I love it.” She looked over at their guest. “Do you want me to make sure he doesn’t finish until you get a turn? I don’t want you to be left out.”

“No thank you, Lady Vex. Just do whatever you want. It is your anniversary, after all. Trust me, I’ll be able to work no matter what. Well, unless he passes out. But then, that’s why I love couples as clients. There’s always two of you. Just make sure he’s open.”

“Oooh” Percy moaned as Vex did just that. He looked down to see his wife had 2 fingers inside of him already and half his cock down her throat. “Oh, Lady Vex’ahila, please, I can’t take much more.”

She pulled her mouth off the cock. “Do you want this, Percy? Well then, beg for another finger. Beg for me to open you up for our guest and you’ll cum as much as you can tonight.”

“Please, Lady Vex’ahila. Shove a third finger in. Fuck, come on, prepare me for the beautiful woman who just fucked you in a way we never even thought of before.” She did so, and took her husband back into her mouth. “O yes dear, that feels so good. Pelor, you could do whatever you want to me. Hell, if you wanted to shove your whole fist up there I’ll let you. Go on darling. Open my butt up for that big strap on. Fuck, I’m so close.”

Vex pounded her fingers in deeper at the same time her nose met Percy’s groin. She smiled best around his cock. He came and she pulled back, using her other hand to keep pumping. “That’s it, make a mess for me, darling. You know you’ll clean it up.” She continued milking him. She chuckled as she removed a strand of cum from her eye. “He’s all ready for you, Miss Sapphire.”

As the two passed, Vex gave Jester a quick kiss. Just enough to give the Wandering Sapphire a taste of her husband’s seed.”Yummy.” The blue woman handled her pink strap-on as if it was real. “Now lift your legs a bit. And try to spread them as much as you can. That’s a good boy.” Jester double checked the ropes to make sure they were still tied and there was no sign of circulation being cut. Then she came closer and lifted his legs a bit more.

She smiled at the slight gape Vex has opened. It was clear this wasn’t Lord De Rolo’s first pegging. “Ready for Sprinkles?” She gave him a look when he just nodded.

“Yes, Miss Sapphire. I’m ready for Sprinkles.” Percy was unable to focus on how ridiculous his words were. He felt the dildo at his entrance. Jester thrust forward and in him. She slowly worked it in and out, going farther each time. Somehow, Percy’s natural curiosity came out. “How long is it, anyways?”

“7 and a half inches. A little on the big size, but nothing obscene. I got most of it in already.” She looked down at his hardening cock. “And you clearly like it.” She slammed her thighs against his.

She looked back at Vex. The Half-Elf was sitting on the chair rubbing her own pussy. Once Jester was sure Percy had no issues taking it, she asked “So, Vex, how do you want me to fuck your husband?” She knew who was in charge here.

“Fuck him fast and hard. He’s always complaining about me teasing him, so give it to him all at once. He’s earned it.”

Jester instantly picked up her pace. She grabbed hold of Percy’s legs again and lifted them up above her shoulders. Percy was a bit shocked at her strength. She also wrapped a hand around Percy’s cock. “Normally, I’ll be worried about this. But your wife here seems to know your limits well. And I bet she uses you like this a lot. You’re so pretty tied up like this, taking a fake cock without any struggle. I know I couldn’t resist doing this every night if I was her.”

Percy blushed. “All she has to do is ask”. He groaned.

Jester continued pounding in and out as she paid attention to his cock. Once he was fully hard again, looked back at Vex. “Can you untie his legs for me, Vex? I want to see what he looks like folded in half taking my cock. I bet he’s even more beautiful.”

Vex was untying the first leg already. “I bet. If only we had someone to draw it.”

Jester smiled. “I can draw a picture and send it when I’m finished if you wish. Trust me, no one but us will see it. Well, and The Traveler.” Vex gave a perplexed stare. “My god, don’t worry, totally trustworthy.” With that Jester grabbed hold of Percy’s legs and shifted him.

Once he was in position, Jester thrusted in again. She was slower, but went more deliberate. Percy was folded up with his own cock inches from his face. He figured out what Jester wanted. He would have begged for it if he had the ability to speak. Instead he moaned and grunted as Jester fucked his ass and pumped his cock.

Vex was a step behind Percy but soon realized The Sapphire’s plan. She bent down and took his balls into her mouth as Jester continued to sodomize and jerk off her husband. The room was quiet except for grunting, moaning, and slurping until Percy came again. He came all over his own face. Vex’ahila quickly bent down, still covered in Percy’s cum. “Let’s clean each other up, darling”. Jester pulled out and watched the married couple.


Later, the three of them were dressed and back in the front room of the mansion. “So, how long will you be staying in Whitestone?” Percy asked.

Jester was back in her black outfit. “Not long, probably another day or two. I need to, well make a tithe as Beau calls it then we’re off to Emon.”

“Tithe? I got to admit, I never heard of your god The Traveler and I doubt there’s a temple. No offense, just the only temples here are for Pelor. Well and the Raven Queen.” Vex had a look of longing at that.

“That’s fine. The Traveler cares less about where you tithe and more how. I usually leave them at brothels.” At their inquisitive looks Jester explain. “The Traveler is a fan of mischief. Nothing overly harmful, just things like a mysterious symbol showing up that a priest at a temple may think is blasphemy or switching around all the signs at a library or a brothel trying to figure out where the mysterious client who overpaid came from. Especially if they’re pretending to be royalty.” She remembered where she was. “Not that I would ever soil your name or anything, Molly usually uses a country no one heard of.”

“Interesting. But why brothels?” Percy asked.

“O, well Beau, one of my bodyguards, pointed out how much money I actually make compared to most of my profession. I just decided that wasn’t quite fair and I had plenty to spare. But I don’t it to seem like I’m taking pity on them or anything, so I usually send Molly or Beau or Yasha (I sent Fjrod once but that seems like a bad idea) as a client who lives a big tip. Although once I left a giant doughnut filled with gold at a brothel in Zadash. That was fun.”

Percy and Vex looked at each other. Percy adjusted his glasses. “Well, you said you were going to Emon? Lovely city. We have a keep and some friends there.”

“Yea. Hey, maybe your next client will be one of them.” Vex went through a mental list of all the possibilities.

Jester looked at them awkwardly “Maybe, although I tend not to name them. A bit of a risk.”

“Yes, I imagine most would be embarrassed if this came out. Not the type of thing most who can afford your services want public.” Percy looked at his wife.

“Buncha prudes” Vex muttered under her breath.

Jester chuckled. “If only that was the worry.” At the blank stares she explained. “Just imagine what could have happened if people knew I was coming here. A complete stranger coming from abroad to meet with the heads of a nation? I’m an assassin’s wet dream.”

Vex laughed at that. “Well, that is a bit of a worry. I’ll have the guards frisk you next time before you enter. Although won’t be the first assassins we fought off.”

Jester left shorter later, a substantial payment in a special compartment of her haversack. Percy looked at his wife. “Well dear, that was most special.”

“That it was.” She smiled as a thought came into her head. “Hey, isn’t Keyleth celebrating her Aramenté soon?”

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