The Outlaw and the Amazon Ch. 03

How could anyone expect her to last any longer when both of them pleasured her and were pleasured by her at the same time?

Willcock knew better than to deny the inevitable. He was going to finish in Jeanette.

Jeanette, the beautiful, sexy, strong, and cute knight who was squeezing him dry with her ass.

Her moans were adorable, but it was her physique that aroused him the most. It was like fucking Judith, but this time he was the older and the stronger one.

With that said, if they hadn't met Amanda and the match moved to anal even without her, Willcock would have lost, especially considering it would have been two ribbons against five.

Speaking of, Amanda.

The woman had intrigued him at first, a brat that needed to be taught a lesson. When they clashed over the matter of Jeanette, he felt her dominance, and in his mind, she shifted from a brat in need of a lesson to a worthy opponent.

When she made Jeanette cry was when his lust turned to wrath, and while their reconciliation was sweet, the desire to give it to her rougher than she could handle and leave her broken had not gone away entirely.

He could see her face down on the floor, ass in the air as he pounded her into the floorboards, and he could imagine her riding him, wringing him dry, a smug smile on her face and her hair flowing wildly just as vividly.

Was it a surprise then, that when faced both of them at the same time, he succumbed?

The three came together, screams echoing in the small room.

Jeanette went limp and almost fell sideways, only remaining upright because of the support of Willcock's penis, Amanda fell down, along on the bed, and Willcock sagged as he filled Jeanette's ass.

The first to speak was Amanda. "That was amazing," she said, gazing at Willcock, "but I don't think I'm quite done. I still have a ribbon left, after all."

"I think I have one more go in me as well," Willcock said, straightening himself. "What about you Jeanette?"

"Jeanette?" He asked again, concerned, when he didn't get an answer.

It was only then that he heard a faint snore coming from her.

"Did she fall asleep?" Amanda whispered a question to Willcock.

"Seems like it." Willcock replied, similarly whispering, and withdrew from Jeanette, causing her to fall sideways onto the bed.

Amanda and Willcock looked at Jeanette, at each other, then at Jeanette again, and burst into almost contained giggling fits.

When they finished laughing, Willcock remarked "Gods, that is just so adorable." He chortled again, then addressed Amanda. "Are you fine with the last battle taking place on the floor, rather than the bed?"

"Perfectly fine," Amanda said, then added. "Actually, would you be fine with having it downstairs?"

"What, in the common room? Why?" Willcock asked, surprised.

"Well, I want people to know who is better. Puts some meaning behind it you know? I love humiliating people, especially in front of an audience, and I can imagine I could love being humiliated in front of a large audience, if it's by the right person, you know?" She winked at him.

"Alright then." Willcock shrugged. "Though, now that you've mentioned bets, how about the winner gets a victory round? Also, do you want to bet any money on it?"

"I would love a victory round. As for money, why not? How much?" Amanda agreed, with a glint in her eyes.

"I actually thought about making a betting pool for our match. We can bet however much we want on ourselves, with the appropriate rewards." Willcock explained. "I'll arange it.

"Well then," she winked at him and offered him her arm. "Shall we?"

They returned downstairs, both naked, causing only their coin purses. The conversation in the room didn't stop when they entered, but there were a lot of curious eyes on them.

Willcock approached the barkeep, said something, and then returned with three parchments, a pen, and three empty mugs.

"Ladies and gentlemen!" he shouted, and the whole bar turned to him. "I and this lady here, who some of you may remember from earlier," he pulled Amanda in next to him, "will be having a sexfight to first orgasm. Therefore, we are opening bets." He slammed the three mugs on an empty table.

"The rules are simple. You will bet on an outcome, and if you win, you will get a share of the TOTAL betting pool equal to your share of the bets ON YOUR OUTCOME. Simply drop the money in a mug and sign yourself and the amount you dropped in. Options are: I, Willcock, win; she, Amanda, wins; or a draw; that is, we climax within five seconds of each other." He opened his money pouch. "I will place a bet of ten silver on myself, and another five silver on a draw." He nudged Amanda, who cockily said: "Fifteen silver on me."

"Rules for us are as follows: No serious injuries, no kicking while they're down, leaving the ring is forfeit, being pushed out is not. Otherwise, everything goes."

They put the money in the mugs and signed themselves. "Betting is now open." Willcock said, then walked back to the barman and handed him his purse for safekeeping, with Amanda doing the same.

The tavern erupted with noise: people arguing over who they were betting on ("But she's so small, he's gonna snap her like a twig!" "She went five zero on some poor schmuck earlier today. No way a cocky muscle head like him takes her."), and the relatively high initial bets made other bettors bet higher, so their payout, when/if they won, wasn't pathetic. In the end, there was a total of 500 silver and loose change, with 200 on Willcock, 250 on Amanda, and 50 on a draw. The crowd had split into two groups: those who favor Willcock and those who favor Amanda.

"Looks like they think I'm better, old man." Amanda said as she blew the crowds a kiss, receiving cheers in response.

"Just means more earnings for me." Willcock counters, likewise receiving cheers from his part of the audience.

A circle was made out of chairs and tables, and Amanda and Willcock stepped in. The rowdy patrons contest them down. "3! 2! 1! Begin!"

They lunged at each other, neither having the patience for strategy. Amanda took the lead, slipping behind Willcock and hugging him from behind, one hand in his mouth and the other jerking him off. Her crowd cheered ("Get him!", "Grab his balls!", "Make him beg!"), but then he elbowed her and used her shock to pull her off him and hug her from behind, both of his hands grabbing hers: one being guided to her breast and the other to her pussy, making her finger and grope herself.

The crowds once again cheered ("Cum! Cum!", "Stop pussyfooting around and fuck her!") and groaned ("C'mon, stop enjoying it and get out!" "And this is what I bet on?"), depending on who they bet on, and all of them were staring at them, at her, pleasuring herself. It was humiliating (everyone saw her have this done to her). It was insulting (it implied that she wasn't good enough to use his own hands one). It was intoxicating, and she had to escape now.

Willcock, enjoying himself, leaned in to blow in her ear, only for her to violently shake her head, hitting him and forcing him to let go.

"Didn't you say upstairs that you were going to punish me for what I did to Jeanette?" Amanda taunted as they circled each other.

"You looked so pitiful when she made you cum, I thought you didn't deserve punishment anymore." Willcock shot back.

They lunged again, scrambling for positions. This time, they ended up in a 69, with Amanda on top. She immediately started deepthroating his cock and tickling his balls while he ate her out and spanked her. The crowds were cheering on the person they bet on and heckling their opponent.

Amanda felt him quivering, but noted that she was close herself, and decides not to risk it. She got up, to boos ("Stop running away and finish him!", "It's meant to be a sexfight, not a running away fight.", "You had him on the ropes!") from the crowd, and quickly dodged away as he tried to sweep her off her feet.

"What, running away?" He taunted.

"Just wanted to give you a fair chance." Was her retort.

In their third clash, she jerked him off and he fingered her, while their other hands went at each other's nipples. The crowd cheered ("Now this is a good show.", "Make him cum!", "Destroy her!")

They both trembled and moaned, but this time they committed. Amanda started twisting his nipples rather than pinching. Willcock inserted more fingers. Amanda changed her approach from jerking him off to massaging his glans. Willcock moved his hand from her nipple to her throat and started choking her.

Willcock came first, but as his cum landed on the floor, his fingers went askew and hit a spot Amanda had not been bracing herself for, making her cum with him.

As the echoes of their screams lingered in the room, the crowds erupted, most praising the performance, some demanding a refund, etc.

"Since it's a tie, would a missionary bonus round be sufficient?" Asked Willcock as he collected his fifty silvers.

"Sure." Said Amanda, slightly annoyed. She hadn't lost, but her opponent was collecting winnings and she wasn't, so it certainly felt like a loss.

Willcock noticed her annoyance and gave her her 15 silver back.

This got him a punch on the shoulder and the money returned as they went back upstairs.

In their room, they found Jeanette still lying on the bed. Seeing the ribbons on her, they remembered the game.

"I suppose I came first, so the ribbons are yours." Sighed Willcock. Then he stopped. "Wait. How many times did we make Jeanette climax?"

"Four, I think?" Amanda answered. "Why?"

"She had five ribbons, and we just took each others ribbons, so she's the only one with ribbons left. We never took her ribbons, so this was one continuous fight. In other words, she should get yours and mine, and we should get two of hers each." Willcock explained.

"Hmmm~." Jeanette yawned and stretched. Then she noticed the duo. "So, who won?"

"Well, according to the rules, you did." Willcock said, ignoring a spluttering Amanda.

"Wait, so you got each other?" Jeanette looked at them.

"Yep." Answered Willcock.

"Do what you want with the ribbons. The fact that I am the last one with a ribbon out of this group is good enough for me." Jeanette said with a smile.

Willcock sighed repeatedly, and handed his golden ribbon to Amanda, who gave him back hers, and they each gave Jeanette one regular ribbon while taking two regular ribbons from her.

"Now, we can stay here, or, there is a bar at the fringes of the Lustful Quarter where a bunch of people I met during the game will meet. We can wait there until the game ends. Do you want to go there together with me?" Willcock asked.

"Sure." Said Amanda.

"I'd like that." Said Jeanette.

"Then off we go." And so, after they packed up, they left for the Petal.

The journey was uneventful, despite the golden threaded ribbon on Jeanette.

When the trio arrived at the Petal, it was largely empty.

"While we wait, how about that reward round?" Willcock asked. "Or would you rather a rematch with less at stake?"

"A rematch. I'll beat you properly this time. Jeanette~, do you want to come to watch me make him my toy~?" Amanda asked.

"Otherwise private?" Willcock inquired.

"Yes." That was all Amanda said on the matter.

Willcock separates from the group to arrange a room and then returned.

"They have a bunch of different options here for modifiers to sexfights. Pain is pleasure, underwater, in complete darkness... And we only have to decide when we are there. Interested?" Willcock asked.

"Maybe later. Now, I'd rather have a true test of skills." Amanda replied.

In the room, Willcock and Amanda stripped off the clothes they wore for their journey through the streets and got on the room's bed.

"Before we start anything, safewords and gestures. When we invoke them, everything immediately stops. My safe word will be berry, and my gesture will be tapping out and rapid blinking. What about yours?" Willcock asked, unusually serious.

"I guess the same." Amanda answered, not taking it seriously at all.

Willcock sighed. "Jeanette, if you feel that one of us is in danger and we should stop, tell us, alright?"

"Um, sure." She agreed, and the rematch between Amanda and Willcock began.

Amanda tried her trick of climbing on her opponent's back and jerking them off while sticking fingers in their mouths, but Willcock grabbed her hands, yanked her off of him, and these her onto the bed.

Before she could recover, he kissed her and started forcefully fingering her.

As she gasped in pleasure, she tried to reach his cock, but he grabbed her hand and put it on her breast, just like he had during their fight in the bar.

When he broke their kiss, she gasped for breath, while he stared her in the eyes, his eyes full of lust and cruelty. "I never gave you that punishment I promised you, did I?"

At that moment, Amanda learned that Willcock can be actually terrifying.

She tried to say something witty to dispel the mood, but he kisses her again, forcing his tongue into her throat. He grabbed both her hands at the wrists with one of his hands and used his other hand to finger her relentlessly, adding finger after finger as she moaned and trembled, then came.

He made her cum this way one more time, letting up with his kisses for just long enough to let her get a breath, before kissing her again. After she climaxed for the second time, instead of letting her rest, he lined up his cock to he pussy and entered her, then kept pounding until she orgasmed, then releasing her hands and pulling her around and planting her face first into the bed, while positioning her ass high.

Here, he stopped kissing her and instead started taunting and insulting her, calling her a slut, a bitch, a whore, and many other things.

He then slid into her ass, beginning to pound slowly, then speeding up, until she thought that if he went any deeper or faster, something would tear. With his hands free, he also spanked her as hard as he could, leaving a bruise with every hit. Regardless, she still didn't tap out. He came with her, then made her lie down and licked and bit her neck while twisting her nipples.

She just was just lying there, not trying to resist anymore, having accepted her position, when he got up and started talking to her.

"I haven't hurt you too much, right? I bought a healing salve if you need it." Willcock asked, worried.

"It's already over?" She asked in disbelief.

"Yes. I didn't want to hurt you for real, and I tend to get too much into this kind of role. Speaking of, I take back every insult I said during this. All of it was just playing a role." He continued. "Would you feel better if we swapped roles now? You got to commit some therapeutic revenge?"

"No," she laughed. "I want to earn that. I will have a rematch at a later date, and then I'll repay what you did to me."

"If you're fine, we should do and see if someone arrived. Wouldn't want to leave them waiting, after all." Willcock left the room, the other two following him.

There wasn't anyone they knew in the common room yet, so the trio took their seats. Willcock ordered a beer, Jeanette wine, and Amanda a wide assortment of pick-me-ups ("Because I'm not done yet.").

The first ones to arrive (besides the trio) were the two noble ladies that Willcock dubbed Red and Purple, alongside a knightly noble lady who was obviously related to Jeanette. She looked just like her in the face and wore her hair in a braid. She even wore similar armor, though much more revealing. The one big difference was that where Jeanette was lean muscle, the newcomer seemed composed entirely of bulging curves, her exposed breasts and thighs seemingly as soft as marshmallows.

When they walked in, the knightly lady spotted the trio and tan over to them, hugging Jeanette and fussing over her, while Jeanette was visibly embarrassed and pushing her away.

"I'm fine, sister!" Jeanette said after she unburied herself from her sister's bosom. "Willcock and Amanda would never hurt me or let me be hurt."

"Not unless she asks for it, anyway~." Amanda cheerfully and unhelpfully added, earning a glare from Jeanette and prompting another round of fussing from the lady.

When Willcock was done chuckling at the poor girl, he stood up and introduced himself, providing enough of a distraction for Jeanette to escape, putting a chair between herself and her sister while Willcock spoke.

"Greetings. I'm Willcock Cockwell. We have spent a wonderful time with Jeanette, during which she came to no harm."

"Oh, where are my manners? I'm Beatrice, of house Amberhead, and I'm Jeanette's older sister." The knight introduced herself. "I've come to take my dear sister home, as father believes house Clarille to be above such vulgar activities."

"And what about you? What are your opinions on the matter?" Willcock asked as Red and Purple were finally reaching them, having slowly waddled over.

"I believe," Beatrice said, "that it is excellent entertainment for younger ladies, and it gives you something to talk to if you ever go across the eastern channel. But enough about me. Come on now, Jeanette, father wants you home!"

Seeing the disappointment on Jeanette's face, Willcock once again intervened. "Lady Beatrice, is the lord of house Amberhead expecting Jeanette home by any specific time? If not, and if you have no other pressing matters to attend to, you might wish to spend some time in this fine establishment, maybe converse with your companions over a glass of good wine?"

Beatrice was clearly considering it. "Well..."

"Plus," Willcock forged on, "the game is still on, and to leave the Lustful Quarter now would be to forfeit. Also, there will be more participants coming here, and maybe some who have lost all their ribbons will be willing to help you relive the sexfights of your youth?"

"I suppose... a while should be fine." Beatrice decided, then turned to Jeanette, who was now two chairs away, and left to sit next to her, much to Jeanette's dismay.

As she left, Red and Purple approached Willcock and Amanda.

Red closed in first. "Hello there, handsome." She addressed Willcock. "I didn't have time to introduce myself when we last met. I'm Lucretia Gilkes, but feel free to call me Lucy." She leaned close, her vast chest gently swaying as she smiles seductively. "Now, when we parted, so u said something about wanting more of me. Was I so good you would desire me again?"

"Lady Lucretia," Willcock responded, annoyance clear in his voice, "I fear you misunderstood my words. I said you should come here if YOU wanted more. I am willing to humor you, but you don't get to claim you seduced me like that when I took seven ribbons from the two of you and you two together only took one from me."

Amanda, chuckling, said, "Well, if you're looking for someone to destroy you, you could have just asked me." She licked her lips. "I'd be more than willing to make you squirm for me."

"And who are you?" Lucretia glared down at Amanda (who, a reminder, was almost a head shorter than her) coldly.

Amanda grinned. "Amanda Shade, but everyone calls me Amanda."

"Well, if you're a daughter of the Shade family, you might be worth my time, if only barely." Lucretia scoffed.

"So, do you want to get a room? Make sure no one else can see your shameful defeat?" Amanda leaned forward, a predator's smile on her face. "Or will we fight elsewhere? Like in that ring over there?"

"Alright then. Don't complain when I smother you." Lucretia answered and walked up to the ring.

"Do we start naked?" Amanda smiled up at Lucretia. "Or are we going to be tearing each other's clothes off?"

"Don't be so barbaric. We will strip each other, of course." Lucretia scoffed. "Now come and submit. Just look at your chest! You obviously can't compete with me." She cupped her tits as she spoke.