NOVEL WEB Miss Fortune
Ahri gawked at Caitlyn with dazzling, golden eyes of hers. Her nine puffy tails swished back and forth. A grin crept across her pink, glossy lips.
“Impressive, dear…” She caressed Caitlyn with her eyes. “Very impressive.”
“I live to please,” Caitlyn managed to say. Even speaking got her muscles screaming.
The front of Ahri’s skirt shifted. Her massive cock began to lift but, Ahri took a deep breath and it retreated. “You have no idea how much restraint… my god, I mean, look at you, dear…”
Caitlyn planted one foot on the carpet. Her calf and thigh screamed at her but, she stood in spite of them. “Restraint? Why bother mistress, this is your house, right? Your house, your rules.”
Ahri laughed. “Oh, don’t try and tempt me, dear. You’re far too good at it.”
Caitlyn giggled and bowed her head. “As you say, Mistress Ahri.”
“Yes…” Ahri bit her lip. “As I say…” She shook her head and cleared her throat. “Anyway, rest up dear and rest well. This may well be your last rest of the evening. Round ten is right around the corner.”
“I’ll not waste a moment of it, mistress.”
“Smart girl.” Ahri glanced at Bel’Veth sprawled out on the carpet. She clapped her hands. “Clean up crew! Help Empress Bel’Veth back to her room!”
A side door on the other side of the room opened. A grizzled man smoking a cigar appeared, followed by a cloaked man wearing a brimmed hat. A few hours ago, Caitlyn might have covered her chest without a second thought. As her lack of reaction clicked with her, the men lifted Bel’Veth by the arms… tentacles. By the upper limbs. Not once, did they look her way.
“We’ve got names you know. We ain’t slaves.” The grizzled man gave Ahri the side eye.
“Yes, and you’ll do well to leave your names outside. Now chop-chop. That’s royalty you’re carrying there.”
“That’s one word for it…” The grizzled man muttered.
The cloaked man smirked at Ahri. “I’ve got no qualms about bein’ your slave, darlin’.”
Ahri shot him a withering look. The men hurried through the main double doors with Bel’Veth strung up between them.
“Who are they?” Caitlyn asked.
“Hired help who know how to keep a secret. Funnily enough, they hail from your next region. Bilgewater.”
“How many?”
“Three. You’re moving up, dear. Let’s see if you can go any further.”
“I can go all the way.”
“Ah, still so confident.”
“Come on, you still think I’ll only make it to round ten? After Bel’Veth?”
Ahri chuckled. “I guess we’ll see. Won’t we, dear?”
Caitlyn puffed her chest. Her ribs and diaphragm screamed at her. “We will.”
“Enjoy your five minutes, dear.” Ahri turned tail and left Caitlyn to her own devices.
Caitlyn rushed to the kitchen and poured herself a glass of water. Every inch of her screamed for the tallest glass she could find but, Caitlyn ignored them. With how big these cocks were getting, the last thing she needed was one pressing against a full bladder. Despite everything, she still had some limits. On top of the water, Caitlyn made herself a simple ham sandwich. Food is fuel. Without fuel, she’d burn out far before the finish line. With new-found energy, Cailtyn paced a few laps of the room. The soft carpet cushioned every step and the movement stretched aches and pains from her muscles. Once the tenderness in her legs had dulled, she moved on to her upper body and did some stretches. Her back and diaphragm were priority number one. She needed to be able to stay upright on a cock if need be and be able to crunch while on her back. Next, her wrists and forearms. And finally her jaw. There was no exercise for her ass or pussy so, Caitlyn wrapped some ice in a hand towel and held it to her groin as she lounged on the pile of cushions.
The double doors opened far too soon. Her pussy and ass complained to no end as she removed the ice. Though, their tune changed once Caitlyn caught sight of the figure strolling across the carpet. A woman with long, flowing red hair strutted to meet her. A tiny, frilly blouse fought tooth and nail to contain a pair of breasts larger than their owner’s head. All that kept it up was a thin, taught string that slung around her bare shoulders. Below the tiny blouse was open, bare skin from the top of the ribcage right to inches above the groin. A groove divided her toned stomach muscles in half right to the top of her belly button. Skin tight leggings bound two a set of slender thighs and the smallest skirt Caitlyn had ever laid eyes upon accented a pair of already wide hips. The gorgeous woman stood over Cailtyn with a shocked look. She lifted the brim of her pirate hat as if needing a better look.
“Well, aren’t you just adorable?” Her voice, smooth and low, dripped off her tongue with every word.
Caitlyn found words to be a foreign concept. She went to stand.
“Oh no, sit, sit. You must be so sore.” The woman knelt and eased Cailtyn down by the shoulders. The top half of her enormous breasts filled Cailtyn’s vision.
“It- It’s nothing really.”
“Nothing? Bel’Veth was nothing to you?”
Caitlyn shrugged and managed a grin. “Could have been worse.”
The woman laughed. “That’s the fucking spirit. Oh, you’ll do well here. Very well.”
“I plan on it.”
The woman looked her up and down. She bit her plump lip.
“Can I know your name?” Caitlyn asked. “Or whatever you’d like me to call you.”
“Sarah. Or Miss Fortune. Either’s fine.”
“How about just, Miss?”
Miss Fortune laughed. “Fuck no, that makes me sound like your fucking teacher.”
Caitlyn blushed and giggled. “True.”
“No, the only title I’ll let you call me is Captain.”
Caitlyn quivered. “I like the sound of that.”
“Do you now? Well then, Captain it is. Only… that makes you sound like you’re a part of my crew.”
“O- Oh well then I can just-”
Miss Fortune put a finger to Caitlyn’s lips. “You need to look the part.” She placed her hat on Cailtyn’s head. “There, much better. Now, give us an “argh”.”
Caitlyn laughed. “Uh… arghhh?”
“Come now, you’d get laughed off the ship with an arghhh like that. Get it nice and low, good and gravelly.”
Caitlyn cleared her throat. “ Arghhhhhhh .”
Miss Fortune leaned closer and traced a line up Caitlyn’s belly. “Your first mate material for sure.” Under gravity’s influence, her breasts bulged against the meagre restraints of the frilly blouse.
“Do you take care of your first mates?”
“Oh, yes. Very special care.”
“Would you like to know my name?”
“Please, everyone out there knows your name by now, Caitlyn. Now, so the fox doesn’t fucking hound us. Can I get a yes out of you?”
“Yes, I consent, Captain.”
“Ooo, you’re right.” Miss Fortune pressed her plump, sweet lips against Caitlyn’s. “That does sound good.” She gave Caitlyn’s nipple a swift pinch.
Caitlyn gasped and Miss Fortune got to her feet.
“Are you comfy?” She asked.
“Yes, Captain. Very.”
“Good. Enjoy yourself.”
Miss Fortune hooked the thin straps of her blouse with her thumbs. She pushed her chest out and leaned forward until her breasts were bulging. Caitlyn found herself gawking. Breasts that big weren’t real. They were for porn stars and models. Not real people. Yet, here they were, right in front of her eyes.
“I said, enjoy yourself, Caitlyn.” Miss Fortune glanced at her pussy.
“Oh, yes. Sorry, Captain.” Caitlyn covered her pussy with three fingers and began rubbing in circles.
Miss Fortune bit her lip. “You’re more than forgiven.” Eyes locked on Caitlyn’s pussy, Miss Fortune stood up and took a step back.
She lifted the straps of her blouse and shrugged free. The blouse fell to her waist. Her breasts spilled free with a gentle bounce. A thought ran through Caitlyn’s mind. Are they natural? A dumb thought, really. Why would a pirate want fake boobs? Of course, they’re real. They’re probably more of a nuisance than anything. Caitlyn wanted to bury her face between those nuisances more than anything in the world. She rubbed her pussy a little faster
Miss Fortune gave her fat, pink nipple a pinch. “Do these excite you?”
“Yes, Captain.” Caitlyn’s breathing deepened. Pleasure quivered her tender insides.
“Just wait until you see downstairs.”
Miss Fortune brushed her hair out of her face and turned around. A tiny gap separated the top of her thighs. Apart from that, they touched completely. Her ass stretched her leggings to their limits. Buckles secured them down the sides of her legs. She stuck her round ass out, bent over and flicked open each and every buckle. The leggings parted into two and fell to her ankles, unleashing a modest cock and a tight, shaven ballsack.
A modest cock? In a house of giants, yes. But compare her to any of Cailtyn’s toys, and they’d be outclassed any day. At this rate, when I’m done here, a normal cock may never satisfy me again. Even so, she couldn’t take her eyes off it.
Miss Fortune’s tiny skirt brushed the top of her cock’s shaft. She undid a single button and tossed it aside. Turning around, she glided her hands over her body. Over her heaving breasts and fat, pink nipples. Over her toned stomach and slender waist. Over her rolling curves and juicy thighs. Her red hair streamed past her waist in luscious, wavy locks.
“Are you ready, First Mate Caitlyn?”
Caitlyn swallowed a moan. “I am, Captain.”
“Really? I’m not sure. Can you handle me?”
“I-” The moan fought to be free. “I can, Captain!”
“I don’t know…”
Caitlyn moaned. Her hand whipped into a frenzy. “Please, Captain! Please fuck me!”
Miss Fortune laughed. “Slow down there, sweetheart.” She crawled on top of Caitlyn. “Fuck you?” Her hand pressed again the pillow beside Caitlyn’s head. “No, not yet.” Her thumb traced Caitlyn’s bottom lip. “Any Captain worth her salt takes care of her crew. Especially her first mate.”
She flashed Cailtyn a grin before disappearing between her legs. Cailtyn’s hand got knocked aside and replaced by a pair of plump lips. A lingering moan escaped Caitlyn as she melted back into the velvet cushions. Of their own accord, her hands found Miss Fortune’s hair and stroked her red, wavy locks. To grasp them may as well have been to grasp silk. It passed through her fingers like the fabric of an expensive dress.
Pleasure coursed up Cailtyn’s spine. Moans passed between her lips unimpeded. Her back arched. The back of her head pressed against the pillows. Her hat fell over her eyes. Without the sight of the ceiling to occupy her eyes, her mind honed in on the euphoric movements of Miss Fortune’s mouth. Lips and tongue moved as one across every inch of her pussy. Top to bottom. In straight lines, in circles, in zigzags. Not just the clit but the whole pussy. Caitlyn’s chest rose and fell as soft lips and a wet tongue squeezed every ounce of possible pleasure from her. She coiled her fingers, taking fistfuls of the silky hair.
The pleasure began to climb. “Captian!” She let out a long, shuddering moan. “Captian…” Higher and higher the pleasure climbed.
It reached the summit. And then fell.
Caitlyn’s back hit the cushions, her hands pulled on the silky hair, her feet kicked the air and somewhere far away off in the distance, her voice cried a laughing moan. Orgasmic waves washed through her, from groin to chest, to the ends of her finger and then the ends of her toes. With a shaking hand, she lifted her pirate’s hat. Miss Fortune should have been grinning at her, or eye fucking her, or approaching for a hungry kiss. Instead, she kept on eating her out, as if the orgasm hadn’t even happened. In the midst of her orgasmic haze, Cailtyn was about to tell her to stop when a smile pressed against her pussy and a slender finger slipped inside her asshole. Then two. Then three.
“Fuck! Captain~!” Caitlyn melted into the cushions.
Over the top of her breasts, Caitlyn saw Miss Fortune grin.
“They really haven’t been taking it easy on you. I slipped in - easy as that!” Her fingers twisted, pulled and plunged.
“Th- They helped me - helped you; I’m all ready for your use, Captain. For your f- oh fuck… your fingers and y- your cock o- or anything you desire! Oh my god!”
The world melted. Pleasure hit like a punch to the gut. She found herself sitting up with handfuls of the cushions, moaning her head off as she squirted all over Miss Fortune’s massive tits.
Miss Fortune laughed. “Lucky! I caught you at the fucking best stage of ruination. Sweetheart, you’ve cum so many times that you’re in a constant state of over-sensitivity.”
Tremors rattled Caitlyn’s body. “Wh- What does that mean?”
Miss Fortune licked Caitlyn from clit to collarbone. Her lips hovered above hers. “It means you’re about to cum more than you’ve come today combined.”
Plump lips locked hers. Massive breasts engulfed hers. A throbbing cock rammed inside her pussy. It filled her almost at once and while it wasn’t as long as some of the others or as long, it was perfect. Caitlyn moved her hips with the push and pull of Miss Fortune’s cock, melting with each stroke. All the pain that ice failed to defeat melted away in mere moments, leaving nothing but pleasure; euphoric, heavenly pleasure. Her captain knew her pussy like it was a second home. She found all her most sensitive spots; all the spots that made her gasp and squeal. She kept her rhythm perfect so as to never leave a moment for pleasure to lull. Her hands meandered around her body, sliding over her curves, pinching and pulling, grabbing and spanking. Her tongue pushed her back into her mouth, pressing it into submission.
Miss Fortune bit Caitlyn’s lip. A smirk formed. Her thumb wandered onto her clit. “Two,” she whispered.
Miss Fortune’s thumb rubbed circles into her clit, applying heavy pressure. A gentle wave of pleasure became a tsunami and crashed against Caitlyn with the weight of the world. Every part of her body contracted at once. Her moan caught in her throat. A pitiful, little squirt gushed over Miss Fortune’s cock.
Before Caitlyn even had time to process to orgasm, the world flipped and she found herself biting a pillow. Miss Fortune’s groin clapped her ass as she lay into her with an assault of heavy thrusts. As she fucked Caitlyn into the floor, she reached between her legs.
“Three,” Miss Fortune whispered.
Caitlyn managed only a choked squeal before the third orgasm hit her. She collapsed onto her side, sliding off of Miss Fortune’s cock. Her pussy contracted into long, heavenly pulses. Giggling, Miss Fortune lay behind her. She cupped Caitlyn’s breast, nibbled on her neck and guided herself back inside Caitlyn’s contracting pussy. Slow, wet clapping filled the air as her groin met Caitlyn’s ass over and over. Pleasure shivered up her spine with each, slow, gentle thrust. No sooner did the third orgasm fade than the fourth began to creep into the light.
“You’re gonna make me cum again…” Caitlyn moaned.
“That’s the idea.” Miss Fortune pinched her nipple. “Four,” she whispered against her neck.
The fourth orgasm began to bubble to the surface. Miss Fortune clasped her hand over Caitlyn’s mouth. Her pace exploded from a stroll to a sprint. Insane pleasure erupted all at once. Caitlyn moaned into her captain’s palm, clutching her wrist and pushing her ass back with each thrust.
“Take it all,” Miss Fortune moaned. “My sexy, tight, little first mate.” She slapped Caitlyn’s ass.
A crack - like a whip - snapped the air. Beautiful heat stung her ass cheek. Miss Fortune’s breathing quickened and became heavier. Her heart thundered against Cailtyn’s back. She twisted Caitlyn onto her stomach and pinned her to the pillows by her shoulders. Caitlyn’s ass lifted all on its own, earning her a panted laugh from her captain.
“Good fucking girl.” Miss Fortune nibbled her ear as she positioned herself above Caitlyn.
Slowly, she dropped her hips and slid into Caitlyn from above. As her cock filled Caitlyn, her balls rested just above her clit. The cock slid back. Then slammed back into place. Slow thrusts hammered Cailtyn’s pussy. Her captain’s balls slapped her vulva. A battering ram of pleasure assaulted Cailtyn’s body, crashing through her from groin to nape. Her pleasure ramped and ramped, threatening to peak after only a few thrusts. A trembling troubled her captain’s body.
“F- Five~”
Pleasure screamed. As did Caitlyn. She fell flat against the pillows. As did Miss Fortune. Her giant tits squished against her back. Her throbbing cock missed her pussy. It pressed against it, twitching and throbbing. Hot, heavy breaths filled Caitlyn’s ear. Caitlyn lay beneath her captain’s warm, sweaty body with a grin plastered across her face, riding the dying moments of her orgasm to completion. It sputtered to a stop but, even so, little tremors of contractions tickled her afterwards.
“You can cum if you want, Captain,” she whispered. “I don’t mind.”
“N- No way. I’m going for a record.”
“What’s the record?”
Miss Fortune kissed her neck. “Eight.”
Butterflies fluttered about in Cailtyn’s stomach. “Eight?”
“Does that excite my first mate?” Miss Fortune rolled off of her and spooned her side.
Caitlyn rolled over to face her. She blushed. Despite everything she’d done today - everything that had been done to her - she blushed. “Uh huh~”
Miss Fortune grinned and kissed her. They fell deep into each other’s arms and deeper into each other’s lips. Caitlyn explored her body; the tender muscle of her hips and the squishy pillows that were her breasts. Slender arms and slender thighs. Soft skin and softer hair. And somewhere, somehow along the journey, her hands found their way to her soft, slender cock. She stroked her shaft, thumbed the tip and cupped her balls.
Miss Fortune pressed her forehead against hers. “Magic~ Magic fucking hands…”
“Not magic, captain. Just practice.”
Miss Fortune looked her in the eyes with a melting look. “If you make it to the end of all this, you’ll be a f- fucking goddess.”
Caitlyn giggled. “Am I not now?”
A moan spilled out of Miss Fortune as she melted against Caitlyn’s body. “You’re perfect. Fucking perfect. God, slip your bottom leg through mine - I need back inside you right fucking now.”
“Yes, Captain.” With a smile, Cailtyn slid her leg through Miss Fortune’s. How she knew what to do next, she hadn’t a clue but, she found herself hooking her other leg over Miss Fortune’s hip.
Miss Fortune seized her ass with both hands, buried her face into Caitlyn’s breasts and thrust inside her. It was an awkward entrance but, once she was inside, Caitlyn melted into bliss. Her sweet, high moans mixed with her captain, ragged, husky groans to create gorgeous music in the muggy air. Miss Fortune massaged her ass, breathing life back into the bruises left by Camille. One squeeze was all it took. Caitlyn came at once.
“Six!” Miss Fortune gasped.
Caitlyn’s heart hammered in her chest. Fire burned in her chest. She flipped Miss Fortune onto her back and rode her into the floor like she was trying to break it. Miss Fortune gawked at her like a fish. Her eyes rolled back, and her head followed suit. Caitlyn grasped both of her giant breasts. Under their own weight, they’d flattened against Miss Fortune’s chest. She spread them apart and plunged her face between them. They engulfed her face in soft, warm heaven. An hour ago, Caitlyn might have fucked her captain she filled her pussy with hot cum but now, her orgasm-riddled pussy devolved her into a spluttering, trembling mess in mere moments.
“Fuck!” Miss Fortune gasped. She slapped Cailtyn’s ass and that alone almost made her cum all over again.
“S- Seven,” Caitlyn managed.
“After all that, you still have fucking energy…” Miss Fortune lifted her face. She looked at Caitlyn like a piece of meat. “What I’d do to you if I had you all to myself~”
“D- Don’t cum and you do, Captain.”
Miss Fortune laughed. “You’re not making it easy.”
“Where’s the fun in that?” Caitlyn ground her hips.
Miss Fortune tensed. Her cock twitched so violently inside Caitlyn that she thought she might have cum there and then. “Fuck… You cheeky, little, fucking slut.”
One moment, Cailtyn was on top of Miss Fortune. The next, she had Caitlyn in the air by the ass. Cailtyn’s legs wrapped around her slim waist and her arms wrapped around her neck. Miss Fortune’s cock never left her pussy. Thoughts left the equation. Caitlyn locked her lips and grinded her hips. Kissing and fucking like animals, they stumbled their way over to the couch. Rather than taking to the cushions, Miss Fortune pressed her up against the back of the couch. It teetered and squeaked. Crazed thrusts pounded Cailtyn’s pussy. One hand left her ass and snuck up her body, finding her nipple and giving it a sharp pinch.
“Cum, you little whore,” Miss Fortune panted into her ear.
“Make me,” Caitlyn moaned.
She fought her orgasm with all her might - service be damned. If her captain beat her record, she might finally cum and then, it’d all be over. It couldn’t end. Not yet. It felt so good. So unbelievably, fucking good. It had to last forever. She had to feel good forever. But, Caitlyn was but a falling leaf and her captain was the howling wind. Her eighth orgasm hit her like a truck. No matter how hard she fought, Cailtyn’s body gave out on her. Her squirt returned with a vengeance. She went limp. And the world fuzzed. All that stopped her from hitting the floor as she came were her captain’s strong arms.
“Eight…” Miss Fortune’s crazed thrusting ramped down to a gentle, patient fuck. She lifted Cailtyn off of the back of the couch and gazed into her eyes as she held her.
“That’s it, sweetheart. Enjoy yourself. You’ve earned it.”
“P- Please don’t cum, Captain - don’t let it end.”
“But it has to, sweety.”
“N- No, it feels so good. It can’t end. It’s too good.”
“What about the next round? Your strength?”
“Fuck my strength. Fuck whatever comes next.”
Miss Fortune giggled and slowed her hips to a standstill. “I suppose, I haven’t beat my record yet, have I?”
“Y- You haven’t?” Caitlyn perked up.
“And I’m nowhere near the inhouse record of fifteen.”
“Barely even halfway.”
“Barely even halfway~” Miss Fortune kissed Caitlyn hard. Her hips picked back up.
Caitlyn squeezed her trembling legs around her captain’s waist and dug her nails into her shoulder blades. They turned around and headed for the double doors.
“Moan,” Miss Fortune whispered. The mahogany doors touched Cailtyn’s bare back. “Scream. Whatever. So long as they can hear how much you love what I’m doing to you.” Miss Fortune nipped her neck.
“Yes, C- Captain!”
Miss Fortune buried her cock inside Caitlyn’s pussy. Caitlyn buried her face into Miss Fortune’s luscious, red hair. She moaned and moaned and moaned with all her might. At first, she exaggerated. Soon, they were real. Her ninth orgasm saw to that, and the tenth, and the eleventh. They erupted in quick succession, assaulting her like an artillery barrage. The hard, mahogany wood banged against her as she threw it back to let out her orgasmic screams. Miss Fortune wasn’t much quieter. She was losing her pace, her power and her rhythm; she was losing herself. The twelfth orgasm took far longer to arrive. It lingered for an eternity, teetering on the edge of euphoria. But when it hit, it hit. Tears streamed down Cailtyn’s cheeks as she laugh-moaned. She felt drunk and high all at the same time. Nothing made sense. Nothing was real. Just her captain’s plump lips, giant tits and hard, twitching cock. She locked those plump lips between moans, pressed her tits against those giant ones, and ground her pussy against that hard, twitching cock. Her abs screamed at her. As did her thighs, arms and back. But they could go to hell - her captain was in trouble and she needed to help her. It’s what she’s for. All she’s for.
Miss Fortune barely moved her hips at all. She leaned against the door with all her weight and panted heavy, deep breaths. But still, their groins clapped together and the lock of the double doors rattled. Caitlyn used her whole body to fuck Miss Fortune, pumping her pussy up and down her captain’s hard, twitching cock. Even as she came for the thirteenth time, Caitlyn didn’t quit.
“I- I can’t…” Miss Fortune whispered.
“Yes, you can!”
“I’m… gonna cum.”
“Don’t you dare! They’ve all heard us out there. Are you gonna let them gloat because you failed to beat the record?”
Miss Fortune tensed. “N- No fucking way!” She slammed all her weight into Caitlyn and fucked her like an unhinged, crazed beast.
Caitlyn threw back her head and moaned; loud and high. So loud she was sure any neighbours were sure to hear. Her energy, her determination and rage and euphoria all dwindled away as the fourteenth orgasm hit her. She didn’t even moan, merely croaking as she melted into Miss Fortune’s embrace. No matter. Her captain - her strong, beautiful captain - carried her across the finish line. The fifteenth orgasm came mid-stroke, just as the fourteenth faded. Caitlyn expected a mad dash after that but, through the haze and confusion, she saw her captain smirk. She slowed down and eased up.
“Wh- What’s that look for? Y- You didn’t think I was tired d- did you? I-” she shuddered. “- I can do this all fucking… fucking day. I’m not even close.”
Caitlyn stroked her cheek and smiled a gentle smile. “Never, captain. Not even for a second.”
Miss Fortune gazed upon her with a heavenly look. She thumbed her clit and locked their lips. As they shared long, gentle kisses, Cailtyn came one last time. A soft orgasm - delicate as a feather’s touch. Miss Fortune shuddered as Cailtyn’s pussy squeezed her cock.
“Six- six- six-” Cailtyn’s pussy relaxed. “- teen,” Miss Fortune sighed.
Slowly, they slumped to the ground - Miss Fortune’s load spilling all the way. As wave after wave of cum filled Caitlyn’s pussy, she and her captain held each other on the floor, at the feet of the double doors. But then, as good became great, two sharp knocks wrapped against the doors.
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Next chapter, Caitlyn fucks Nilah, The Joy Unbound