The Crown Jewel

Princess Stephanie didn't know why anyone would think assigning Sir Sayen as her chaperone would be a good idea.

Whatever vows he'd taken, he made no secret of what he thought of her body. Combine that with his leanly powerful frame and notorious gambling streak and crooked leer and incessant irreverence, and Stephanie was certain that a drunkard would have been a more trustworthy chaperone than this... 'knight'.

Point in fact, she had been seduced to yet another game of blackjack, and--yet again--she was losing. Badly.

They were sitting on the floor of her royal carriage, the offending cards between them. Her pile of 'winnings' was an empty space beside her thigh while he had the heirloom jewel that she was supposed to be bringing to her potential future husband in his... along with her drawers.

Simple skirts hiked up to her hips (as per the terms of a lost bet), she sat cross-legged across from him so he had full view of everything down there (the terms of another lost bet), with the top of her shirt folded under her breasts so it bunched over the top of her corset and left her bosom spilling free (the terms of yet another lost bet), Stephanie knew she was about to lose this hand as well. Her ample chest was too cold with her nipples exposed like this, and her quim was quivering and swollen and dripping under the intensity of his gaze; it was impossible to focus.

His tunic wasn't doing much to hide the bulge in his trousers.

She had almost hoped that his scandalous requests would leave him too distracted to play properly, but she had no such luck. As soon as she put down this hand, she would find herself made a woman by that bulge, ruined for marriage, her maidenhood broken and her family--her entire country--disgraced.

Her virtue was the last thing that she had to left bet for her jewel.

(On some level, she knew that this was exactly what he'd wanted as soon as he suggested the game. She'd still fallen for it, and now she was going to pay for it.)

She couldn't bring herself to look at him as she laid down her cards with a snap; she knew he would be leering.

"...Well now," he said strangely. "Y'know, I didn't think I'd actually win."

"Must you rub it in," Stephanie snapped, and his wide mouth stretched into that crooked leer.

"Oh, I must."

The obvious relish with which he said the words made her gut squeeze in a way that she was sure was revulsion. Quite certain. "A-and I suppose you're just going to dive right in?" she demanded, voice wobbling, high and tremulous.

"What's stopping me?" he asked, innocent but for the predatory hunger on his face.

Absolutely nothing, and her tingling, empty sex knew that about as well as his twitching chub.

"Now then!" said her chaperone, looking at her with a fever brightness in his eyes and a fever flush on his cheeks. He licked his lips. "Where do we start."

He made her lay her cheek and chest on the seat, her knees on the floor and her rear up in the air, her legs spread to display her most private place. He dug his thumb into the cleft of her buttocks and spread them, uttering an appreciative noise as her wet inner folds were exposed to the elements.

"W-wait!" Stephanie squeaked. Her chaperone was just seconds from deflowering her, and she still had no hope of gaining back her jewel.

"Hmm?"

"Um--" She gulped, feeling like she was swallowing a birdcage, gilded and fluttering and large. "P-please me."

"'Please you'?" The deep, rich smugness was jarred by surprise.

Stephanie gripped the hem of her skirts and felt her quim drip a bit more. "I-I bet that you can't please me--f-five times!"

The word 'bet' set a different, much more familiar interest in his tone. "Oh?"

"If you can't--if you can't, then--I get back everything I've lost. You lose."

"And if I win?"

She squeezed her eyes shut tight, then came out with, "Then... anything! I'll do a-anything you ask."

Out of the corner of her eye, she could see that jagged, manic grin that said she'd caught him. "Make it ten and you've got yourself a bet."

She whimpered and clenched--ten?! She'd never survive that!--but nodded still.

Sword callouses traced from the round of her backside to the sopping entrance to her body--and plunged into her core without warning.

Stephanie squealed.

Visceral and invasive and only just gentle enough, they rooted around inside her, seeming to explore her and measure her, only to spread abruptly and stretch. She cried out again as it left jagged lightning lancing through her limbs and tears dancing through her eyes, and then squeaked as her nub was unceremoniously pinched.

The touch felt like it popped something in her, crashing waves of pleasure made sharp and unkind by their abruptness, and she shuddered into her arms with a noise that sounded like sobbing but didn't feel like sobbing, and Sir Sayen hmphed triumphantly.

"One," he said cheerfully, and panic jolted through her body and left her burning brighter than ever.

She gasped and shuddered and whimpered as she tried and failed to get her body under control, barely heeding the shuffling behind her--and then found something very hot, very blunt, and very big aiming to replace his fingers.

She barely had the time to shudder again in another surge of burning, gushing alarm before the knight took advantage of that gush as lubricant for his member, and deflowered her without so much as a by-your-leave.

Time splintered for her, her maidenhood broken and her body suddenly occupied by a prick that felt much too big for it, pounding, throbbing heat stretching her quim out so much it must have been preparing her for birth as it rearranged her belly for her, and then snapped back to reality with her muffled shriek.

His hand was wet as it covered her mouth, his prick pulling free only to ram home again, and he groaned while Stephanie's world shattered on its axis. "Damn. Always knew your cunt'd feel this good, Princess Pretty."

She would be entirely unshocked that he had thought about sticking his prick in her at some other time, when the throb of it didn't have her courting the edge of another crushing release.

A few more thrusts that made her vision go white and she was plunging over the edge again to the sound of her own sobbing and Sir Sayen's still cheerful, "Two."

"Three," came a bit slower, requiring him to fondle her bud as he plundered her body for longer than just a few simple, mind-blowing thrusts, but it trundled along quite tidily, ripping her asunder all the same.

She was slack and trembling as he pulled his member out of her entirely, then easily manhandled her onto her back, spreading her legs wide and ready before he impaled her on his lap. His mouth found her breast, sucking at the tight peak and making all her limbs stutter in the overwhelmed ecstasy it sent through her quim, and held it between his lips as he resumed his conquest, a buttock in each of his hands as he made her bounce for it.

Her body was all too willing to hand over her fourth wave of surrender, indicated by the four fingers he held in the air as his mouth remained occupied and her sex desperately attempted to milk him for the seed it was denied.

it only got that seed once it had gone lax, allowing his thrusts to stutter and pulse and leave hot spurts of his essence on fertile ground--spoiling her womb and completing the last step of her deflowering.

Stephanie swallowed down her tears--of horror, no doubt, no doubt--and gasped, "S-see? I w-win."

Instead of taking his defeat, her chaperone merely leered at her from between her bare, ample breasts, panting and sweat-soaked. "Now, wh--... who said this was the end?"

She frowned, rattled confusion soaking the wrung-out sponge between her ears, and he lifted her off his prick, depositing both buttocks on the edge of the seat as her quim released the long ropes of his seed onto his lap and panting against her thigh for a long moment, which answered none of her unarticulated questions.

Then he pushed his mouth into her overused muff, the searing lave of something that had to be his tongue cleaning up the substances leaking from it, stinging and far too much, and Stephanie wheezed, lungs and vocal chords giving out as he wrung number five out of her as well.

"Six," followed it with the help of his fingers, and, "Seven," with the help of his other hand stroking the tight bud of her anus.

His prick was erect again after that, and firm enough to mount her again--but it seemed that her body had nothing left to give him. No matter how he ruined her with it, number eight never came.

He soiled her womb once more, after a pain-stung but deliriously pleasurable eternity of thrusting, and then left her empty.

It was several long minutes before Stephanie could summon her will and senses enough to speak.

"You... should have ag--... agreed... to five..."

Sir Sayen's bark of laughter was loud and abrupt and seemed to startle him as much as it startled her.

"Touché." He grinned his crooked leer at the roof of the carriage. "But a bet's a bet. The jewel and drawers are yours, your ladyship."

She waved her fingers, dazed, then dropped her head onto her arms and let herself float.