High Stakes

"Some gambles give you a fortune, others break your purse into pieces. Sometimes, all you can do is cross your fingers and hope that Lady Luck is on your side." - Unknown.

Ciaran Xanderson is my OC. (As well as Kyran Wolf.)

Ilyse Arvernus belongs to DarkShadow777. (As well as Adol and Devany.)

 

This story is a crossover with DarkShadow's ongoing Livantia series, which you can read here.

(Tags: casino blackjack strip-blackjack mff cunnilingus facesitting missionary threesome triangle strap-on spitroast hair-pull arm-pull double-blowjob 69 anal oral-creampie)

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The sun shone brightly over the realms, the king of the stars bringing light and warmth to all. In a faraway land, gravel crunched under shoes and sandals under the moderate heat as two figures walked along a path, talking amicably about their adventures together.

The first, a male human, stood at 6 feet 2 with whiteish pink skin, azure blue eyes and short dark brown hair. A simple grey tunic bore initials "C.X." in dark purple and dark grey pants completed the picture. The other, a female elf, was merely 5 foot 6, but was much plumper than her companion. Freckles dotted pale white skin, braided orange hair twisted down from her head to her hips, emerald-like eyes were looking into the first figure's, a yellow triangular gem sat inside her forehead. The elf wore a dress, dark green and decorated with a simple brown belt that matched her fingerless gloves.

Ciaran Xanderson and Ilyse Arvernus walked along the path, slower than they normally would. They had to wait for the other members of their group to catch up. The group had been held up by a small army of bandits, so Ciaran had grabbed Ilyse's hand and broken through a gap in their ranks, incinerating those who followed. Both the wizard and the princess knew they'd all make it through. Ciaran could vouch for Kyran's skill and power, and Ilyse had only good things to say about Adol, Giovanna and the other's fighting abilities.

Ilyse suddenly nudged Ciaran and pointed out a large building behind him. Despite it being as tall as two two-floor houses, he hadn't noticed it beforehand. So absorbed had he been in his talks with Ilyse. With her emerald eyes, her expertly-sculpted face, her beautiful voice, her full lips, her masterpiece of a body, her luscious boobs, her plump ass...

The princess interrupted his thoughts about her. "Do you know what it is, Ciaran?"

"Oh! Um, let me think." The building had a sign over the front door saying 'The Stakes' and a small list was nailed to the wall next to it saying 'Now with added bar!' and a list of drinks. "Seems to be a gamblehouse." Ciaran concluded.

"Gamblehouse?" The princess asked.

"Yeah, a place where you can bet money to play games. You win the games, you get more money back or some kind of other prize. It can be pretty addicting if you don't restrain yourself." Ciaran told her. "It's been a while since I've done any gambling. Want to go in?"

"Um...sure. Trying new things and that kind of thing." Ilyse smiled.

The two headed inside and were greeted with the smell of alcohol and perfume. Ciaran was thankful that the smell of tobacco wasn't present; he despised cigars and cigarettes. The floor was decorated in dark red carpet with black lines criss-crossing over it. The walls were decorated in a similar fashion, and large lanterns hung from the black ceiling, illuminating the entire building. Waitresses and waiters in white jackets/dresses with smart black trousers/skirts and shoes/heels roamed, carrying many kinds of drinks.

"Hello, there! Welcome to The Stakes! How can I help you both?" A snow elf waitress had come up to them and warmly greeted them. Her name tag read Hollie.

"Well, we're both new here, so we're not really sure." Ciaran informed Hollie. He was downright awful at Poker and Roulette was never his kind of game-too much dependence on luck. That left either Craps or... Yes, that would work nicely. He turned to the princess and asked "Want to play some Blackjack?"

"Blackjack?" Ilyse asked, curious.

Ciaran explained "You basically have to get as close to 21 as you can without going over it. Aces are either 1 or 11. Jacks, Queens and Kings are 10. You can hit to get another card, stay to end your turn or double down to double your bet and hit one card. There's also splitting, but I don't understand that part."

"O-okay." Ilyse answered, smiling.

They followed Hollie, who quickly found a table with nobody else except the dark-skinned human dealer, who greeted them warmly. Ciaran took out some gold and she held up a hand. "This isn't that kind of blackjack." she told him, already drawing cards for him, Ilyse and herself. She set one of her own cards face-down, the other face-up. Ciaran had forgotten that little detail.

The dealer had a 4 showing, Ilyse had 2 and 10 and Ciaran had 4 and 6.

The wizard told the dealer. "I'll hit." 3. "Again." 5. 18 wasn't exactly safe but Ciaran daren't chance another hit. "I'll stay. Ilyse?"

"I'll hit." The elf replied. The dealer turned a card onto her stack. 10.

"Bust. Sorry, sexy. As for me:" The dealer turned her second card over to reveal a 10. She turned over a card from the deck. 9. "Damn." The dealer muttered, beginning to pull off her single glove.

"What are you doing?" Ciaran asked.

"Oh, didn't you know? This is Strip Blackjack. You lose a round, you lose a piece of clothing. Which means the elf has to strip off something too." The dealer nodded to Ilyse. She placed her glove onto the table as Ilyse's shocked voice spoke.

"What?! B-but I, I really don't-" Ilyse stammered. Her cheeks flushed red "I d-don't want to..."

"Then either leave the table or I'll have to call security." The dealer told her flatly.

"C'mon Ilyse, it's not like I haven't seen it before. Even if it was by accident." Ciaran was trying very hard not to smile at this new development.

The elf clearly wasn't convinced. "Bu-but what about e-everyone else?"

"I'm sure the sight of my bare body when I lose a round or two will quickly made their gazes shift." Ciaran joked, giving himself an excuse to grin.

Ilyse answered a little softly "You need to stop degrading yourself like that, Ciaran. I know you're just joking but it sometimes doesn't feel like you are."

"Okay, how about I stop putting myself down while we're here, and you just strip without any more arguments?" Ciaran offered. Ilyse's look told Ciaran she wasn't exactly happy with this deal, but she nodded and took off a single glove.

"No; both gloves. The game will last for ages otherwise." The dealer informed her, shuffling the deck of cards. Ilyse sighed and took off her second glove, looking like she wanted to back out of this game.

The dealer dealt out another round of cards. Ciaran got a Jack and a King. Ilyse got 9 and 2, the dealer had a Queen showing.

"I'll stay." Ciaran told them both.

"I'll hit." Ilyse said, slightly shakily now she knew what she'd gotten into. Ten.

The dealer automatically turned over her card. Ace.

"What does that mean? We both got 21." Ilyse asked.

"It means you both drew, but I still lost." Ciaran informed her, already pulling his tunic over his head, glad to have an excuse to. There were no open windows in the building, and the combined heat of all the people had the wizard sweating.

"Hmm... Not bad." The dealer commented, looking him up and down. "You see so many guys with toned abs and muscles all over the realms, it's kind of a relief to see a man with a bit of fat on his bones. And with some chest hair, too! So many people underestimate how beautiful natural looks are..." She dealt out another round absentmindedly.

Ciaran found himself with a 2 and a 3. Ilyse had a 10 and a 7. The dealer had a 6 showing. "Hit." 5. "Again." 4. "Again." 2. "Again." Ace. "Again." 3.

The dealer spoke before Ciaran could. "Oh! You Charlie'd." At the wizard's raised eyebrow, she answered his question. "You drew 5 cards without busting. You win this round unless me or Ilyse can pull 6 or more cards without busting, or one of us hits 21." She turned over her other card to reveal a King. She hit another card. 8. She sighed and turned to Ilyse.

"Hit." Ilyse answered. 5.

"Ha! Come on, sexy: off with it." The dealer smirked, having already unzipped and stripped off her knee-high boots.

"Bu-but this isn't fair if I have to play naked and you don't just because-" Before Ilyse could finish, the dealer had already unbuttoned and slipped her own dress and skirt off, revealing generous breasts and a moderate figure.

"Just because you didn't bring in as many clothes? I've heard that sentence a hundred times. Probably all of your other arguments too." A titled head and raised eyebrow made Ilyse squirm; she knew she couldn't win this debate.

Ilyse hesitated, but hoisted her dress over her head, revealing her naked body. Her luscious tits, inverted nipples and voluptuous ass drew the eyes of quite a few men in the building. The wizard reached a comforting arm around her shoulders, and the men turned their gazes away, looking disappointed when Ilyse didn't throw his arm off. He also stripped off his shoes and socks, more to put Ilyse's mind at rest than anything else.

"Okay, unless me or Ilyse win or draw this round, Ciaran wins the game." She dealt out the cards and Ciaran found himself with a Jack and an Ace. "Blackjack! Lady Luck has taken a real shine to you!" The dealer sounded as pleased as she was surprised.

Ilyse looked a little worried as she looked at her Ten and 7. "What does that mean?"

"It means we can't win this round-we can draw at best." Ilyse squirmed uncomfortably as the dealer dealt her own cards. 3 and 4. She drew a Jack, then a 7. "It's down to you to win, Ilyse."

Ilyse shakily said "Hit." The dealer's hand holding the card seemed to turn in slow motion, until the card was face up. The Queen of Hearts' eyes looked at Ciaran, as if congratulating him for winning.

The dealer sounded ecstatic. "You win, Ciaran! Congratulations! I presume you'd like to claim the reward?"

"Reward? It's our first time here." Ciaran reminded her.

"Oh, right." She looked a bit deflated. "There is another clause to Strip Blackjack: the winner gets to do whatever they want to the loser, or losers. That means that my body-and Ilyse's-are yours." The dealer informed him.

"Wha-what?" The elf sounded as shocked as Ciaran felt, but without the excitement.

"Ilyse-" the wizard began, but he was interrupted.

"No, Ciaran. I couldn't possibly-" she mumbled a few words before she became coherent again "-with a stranger."

"I can sit it out if you want, Sir." The dealer informed Ciaran. "But I'll regret not being able to feel your skills firsthand."

"You won't be missing much." Ciaran answered.

Ilyse punched him lightly on the arm and adopted a surprisingly stern tone. "Ciaran, you told me you'd cut that out. You're an exceptional lover. N-not that I-I would know!" she tried to grin innocently at the dealer, but it was so obviously fake that Ciaran laughed.

"By the way, what's your name? I never saw your nametag." The wizard asked the dealer.

"Oh, right. Must have forgotton to pin it on again." The dealer sighed. "I'm Jacqueline. Jacq for short."

"Ciaran, I just-" Ilyse clearly couldn't find the right words.

An idea came to Ciaran. He didn't like it, but he also didn't want to make Ilyse do anything she didn't want to, and her needs were above his. "Ilyse, how about I do it with Jacq, and you just watch?" He suggested.

She seemed to perk up a bit at this idea. "O-okay."

"Then right this way, both of you." Jacq smiled. The wizard and princess gathered their clothes and followed her.

The room she led them into wasn't large by any means; it was about the size of a medium-sized  bedroom. It had a few paintings depicting scenery, but otherwise no decorations. There was a single bed in the centre and a couple of ornate chairs by the sides. The elf sat in one of the chairs, crossing her legs and arms.

The wizard stripped off his trousers and boxers. He was half-erect already, and Jacq embracing him, pressing her lips against his, only served to quicken the process. He reached around and groped her rear tightly, spreading the cheeks apart. He gave the left one an audible slap and she let out a small "Ooh!" of pleasure before she kissed him a second time. His hand reached up to her breasts and pinched her left nipple, pulling gently. Her breasts felt full and plump. He wondered how they tasted-

"Wait!" The elf stopped them, blushing furiously as they looked at her. "I've... I've changed my mind. I... I want this too." she told them, looking in the wizard's eyes. Ciaran hoped his mouth didn't betray his excitement.

"Well, that changes things. Jacq, I want you to get Ilyse ready." Ciaran told the dealer.

"It would be my pleasure, Sir. And hers." the dealer added, giggling. Jacq knelt before Ilyse and began to lick the elf's already wettening opening. Ciaran had forgotten that Ilyse was completely against lewdness until it was being shoved in her face, from which point she could happily swim in it.

Jacq's tongue darted up and down along Ilyse's pussy, the elf moaning loudly in answer. Every few seconds, Jacq thrust her tongue into Ilyse's opening, and the princess let out a small squeal, her legs contracted slightly. Then once her legs had gone back to their spread position, Jacq would do it again, and they'd nearly close again. It was quite melodic to watch. Ciaran saw a familiar glint in Ilyse's emerald eyes and knew she was ready to move on.

"Ilyse, could you sit on Jacq's face so she might eat you out better?" Ciaran asked. The elf eagerly nodded and the dealer pulled back.

Jacq lay down on the bed and Ilyse's plump body descended onto her mouth, already prompting a squeal from the elf. Ciaran joined them on the bed and rubbed his cock against Jacq's wet opening, eliciting a small and muffled moan from her. Ilyse bent forwards and Ciaran mimicked her action until the two's lips met. Her tongue instantly darted into the wizard's mouth and played with his own.

As they two's tongues began to swirl, Ciaran pushed his hips forwards and penetrated Jacq. The dealer's legs wrapped around Ciaran's waist as he started to fuck her. She was both tight and wet, and her moans muffled by Ilyse's plump rear only served to speed up Ciaran's thrusting, which in turn made her lick Ilyse's pussy faster.

The wizard's thrusts sped up, his tongue still dancing with the elf's, his right hand squeezing her breast firmly, his left rubbing the dealer's bead. Ilyse cupped her hands around Ciaran's face and pulled his lips into hers, both of them breathing through their noses. Ilyse's moans intensified at Jacq's treatment of her nethers as Ciaran began to fuck the dealer faster. Ciaran recognized the tone of her moans and knew she was close, lifted up his left hand and roughly pinched both of her nipples and pulling them hard.

"AH! CU-CUMMING! HHHAAAAAAAAAAAAHH!" Ilyse broke the kiss and announced her rapturous orgasm with a scream of delight.

"That sounded good." Ciaran commented. "Think you can keep yourself on all fours?" Ilyse nodded at his question, getting off of the dealer's soaking wet face as Ciaran pulled out of her.

Jacq cleared her throat, getting the wizard's attention as she sat up. "Sir, I have a strap-on if you wish for me to use it on her."

"Strap-on?" Both Ciaran and Ilyse were confused.

"It's like a penis, but it's made out of sanded and polished mammoth tusk. Unbreakable, and scuplted just to feel like the real thing." Jacq explained.

Both Ciaran's and Ilyse's eyes lit up as she finished. "Take her mouth with it while I get her pussy." Ciaran told her.

"Yes... f-fuck me... from both sides..." The panting elf asked of them.

"As you wish." Jacq smiled, headed to the wall and moved a painting showing a tree losing leaves in autumn. There was small alcove behind it, that she retrieved a small chest from. She placed the chest on one of the chairs and opened it before taking out the strap-on. Ciaran could see she wasn't joking-it looked just like the real thing, except it was white as milk. The dealer got in front of the elf as Ciaran took position behind her, placing his cock at the entrance.

"We'll penetrate her together. On my one." Ciaran told the dealer.

Jacq answered. "Then please start the count, Sir-I'm eager to feel her gag on this thing."

Ciaran chuckled and answered. "Three."

"Two." The dealer smirked.

"One!" Ciaran shouted.

They both thrust, and Ilyse's body shook with pleasure as both cocks pushed deeply into her body. Ciaran's hand slapped against her right cheek and she let out a moan onto Jacq's strap-on. Jacq, smiling widely, reached down and grabbed her braided pigtails in one hand each and began using them to pull herself into the elf's mouth harder. The elf's moans became louder at this, even with the strap-on bulging in her throat.

Ciaran, following a similar thought, bent forwards and took hold of Ilyse's arms. The elf let him take them without any resistance,now being supported only by Jacq's hands pulling her hair. Ciaran pushed himself deeper in Ilyse's warm, wet pussy, contracting with the pleasure of being spitroasted like this. The wizard felt the inner pressure quickly building, and could only announce his orgasm with a soft sigh as he felt himself shoot one, two, three shots of cum into the elf's tight wetness.

"Would you like me to get you hard again, Sir?" Jacq licked her lips as her sentence finished.

Ilyse piped up, cum still leaking from her pussy. "Can I do it instead, Ciaran? I'd like to taste your sweet cum..."

"You can share, you know." Ciaran told them, a soft chuckle interrupting his panting as he lay on the bed.

The two women instantly descended onto his cock. Jacq's mouth planted kisses along the side while Ilyse's tongue slid over every drop of white she could find, greedily drinking it down. The women switched sides and repeated their actions, the wizard already half-mast. Jacq's mouth wrapped around his meat and she began sucking with a kind of fury. It felt like every remaining drop of cum in his shaft was being milked out by her lips.

Ilyse suddenly let out a small yelp of pleasure. Ciaran saw that Jacq's hand had reached up and groped the princess's ass as she sucked Ciaran's meat. She took it out and joked "I used to be a pirate. I'm still a sucker for good booty." Ciaran's chuckle turned into a moan as Ilyse began to suck on the tip of his cock while Jacq squeezed her ass, her other hand pulling Ilyse's nipple.

By now, Ciaran was rock hard, but he didn't want Ilyse to stop for a second. Nor did the elf seem to want to stop, as the dealer had began toying with her voluptuous cheeks. Jacq sucked on a finger while spreading Ilyse's ass, before running the finger around Ilyse's rear opening. She prodded and poked a little, making the elf squirm as she began to deepthroat Ciaran's shaft. Judging from the moan that shot through the wizard afterwards, Jacq had pushed her finger inside Ilyse and had started fucking the elf's hole with it.

The dealer began to roughly fingerfuck the elf as Ilyse tried to suck on Ciaran's shaft, but the pleasure broke her concentration, and she seemed unable to do anything but moan. The wizard didn't mind a bit, though. Eventually, Ciaran pulled Ilyse's mouth off of his cock and she panted like a dog. Her tongue was even hanging out.

"What next, Sir?" Jacq asked, licking a little more pre from the wizard's erect pole.

"I'd like both of you to eat each other out while I pump Ilyse's plump rear." Ciaran told them.

"Yes... I want your cock in my butt, Ciaran..." Ilyse responded.

Ilyse crawled onto the bed and lay on her back, her pussy facing Ciaran and Jacq. Jacq joined her and straddled the elf's face, already letting out a small moan at the feeling of Ilyse's tongue against it. Ciaran placed himself before the elf and rubbed his wet cock against her tight sphincter before pressing the tip against it. Jacq began licking her pussy, and the elf's ass opened up, giving Ciaran the chance he needed to push inside, prompting a cry of pleasure from her.

Without preamble, the wizard began to push deeply into Ilyse's tight hole. The elf's cries were muffled by Jacq's pussy, and Jacq's cries muffled by Ilyse's. Her ass was tight as a glove, warm as a sauna and wet as an lake. It even seemed to squeeze down on the wizard's cock every time he pushed inside. It felt nothing short of divine (which, Ciaran reflected, shouldn't be a surprise).

The wizard began to roughly drill into the elf's ass. As she licked Ilyse, the dealer took his hand and placed it on the back of her head. Getting the picture, Ciaran pushed Jacq's face into Ilyse's pussy as his hips slapped loudly against the princess's buttocks. The elf shrieked in pleasure in answer, and Ciaran and Jacq both smiled. They both had one goal now: to make Ilyse cum a second time.

Ciaran began to spank Ilyse's rump cheeks as he roughly pounded her tight aperture. Her cries of "Yes! More!" added fuel to the lustful fire both the wizard and dealer felt burning inside. Jacq began to finger the elf's pussy while sucking hard on her bead with the same fast, no-nonsense rhythm that Ciaran had adopted.

Ilyse's moans became higher pitched, getting louder and louder until she let out a scream of pure bliss "AH! I'M CU-CUMMING AGAIN! MMMMMMMUAAAAAAAAH!"

The elf's second orgasm caused her ass to contract rapidly, causing the sensation as Ciaran pushed into her to increase tenfold. He already felt the inner pressure building yet again, and told the two women "I'm close!"

"Please give it to me! You already came in Ilyse's pussy!" Jacq sounded close to begging.

Ciaran couldn't deny that it was only fair Jacq got a load too. He pulled out of Ilyse's ass-prompting a squeal from the elf-and pushed his cock in Jacq's gaping mouth. Her tongue instantly began circling it rapidly with the same fury she'd used before, and the wizard wasn't able to hold back long. He felt his cock spurt two more loads into Jacq's mouth, and she pressed a thumb at the bottom of his cock, milking the last drops out that she could.

Ciaran pulled his softening cock out of Jacq's mouth, and sat down in a chair. He was completely spent, but the word "satisfied" wouldn't give his mood anything close to justice.

Jacq got off of the quivering elf and walked to the wizard shakily, speaking "I see that Ilyse was right about you. You are an exceptional lover." her gaze turned to the elf "Is she alright? Not hurt? Maybe I was a bit rough..."

"No, she's just tuckered out. Both orgasms were pretty powerful ones." Ciaran answered, already knowing that was the case.

"Elves." Jacq sighed. "For such a lewd woman, she certainly covers her inner self up."

"Long story." Ciaran answered. "Suffice to say she has yet to come out of her shell."

"I know the feeling." She sighed sympathetically. "Well, I formally ask that you come again soon, sir. Maybe your blackjack luck will continue?"

"Maybe it will, but me and Ilyse have a job to do. We both appreciate the distraction though." Ciaran smiled. "I'm sorry you never got to cum, though."

"Don't worry about that. It takes a very special kind of sex to make me cum, and we don't have the equipment to do it here." Jacq answered, a bit of red filling her light brown cheeks.

After a jug of cold water to wake Ilyse up, the three got dressed, Ciaran bade Jacq farewell (Ilyse unable to do anything but blush), Jacq got them a small bottle of whiskey to share, and they left the gamblehouse.

Once they were outside, they kept heading along the path until they came across the rest of their group, who'd stopped at a small inn for a breather. Ciaran gave a wave and Kyran pointed them out. Ciaran and Ilyse both jogged the last few meters to their friends and companions.

"Where have you two been?" Prince Adol asked, sounding suspicious.

"Playing Blackjack in that The Stakes place. I won." Ciaran shrugged nonchalantly.

"Ooh, did you get a prize?" Devany asked excitedly.

Ciaran looked at Ilyse, who blushed. "Yep. In a way, we both did."

Kyran raised an eyebrow with crossed arms. "No details for us?"

"Hmm... Nope." Ciaran answered. "Just because I know how much it'll annoy Devany."

Devany pouted "Oh, you utter tease!"

Even Adol laughed. "Well, shall we continue? We've had our break, and we still have a ways to go."

Ilyse, clearly eager to put some distance between herself and what had just happened, nodded enthusiastically. Ciaran let out a small chuckle and followed after her along with the rest of the group members. They still had a mission to carry out, and they would carry it out. Still, Ciaran kept the souvenir bottle of whiskey close as they walked.