The Outlaw and the Amazon Ch. 03

Willcock knew he had to act. He had to face Purple and do something about that cane of hers, and he needed to not be smothered to unconsciousness.

The first thing to do was make Red let go. Since his mouth was already in Red's tits, he started licking and kissing and sucking. His hands went to pry Red's hands away from his head, but the angle was poor, so he moved one hand to her pussy. That got a reaction. Red gasped as he inserted a finger into her, her grip loosening.

The moment Purple heard Red's gasp, she lunged while shouting "I won't let you sully her!" and tore Willcock away from her, trying to stuff him into her own bosom. He decided to use his proximity to Purple to attack her without needing to fear her cane and started groping her tits, which was enough to make her moan.

That prompted Red to come rushing in and start pulling him away, saying "Don't sully her honor, take on someone who can fight back."

Willcock shoved Red away, sighed, and asked: "You two know you are just protective of each other, right? If I were to guess, your objections are less about 'the honor of nobles' and more about the honor and safety of a person you care about."

He pointed at Purple. "You don't face duels from people stronger than you very often, but judging by how your cane is made and your build, you are a fencer, and thus are vulnerable when grappled. You can oufuck people from a dominant position but are not used to submissive positions, and putting you in one will result in a quick defeat for you. Your friend? Rival? Over there does have a point."

"You say I will be defenseless against people stronger than me?" Purple sneered at Willcock. "Then why don't you show me exactly how that would look?"

"May I?" Willcock asked Red, and after getting a hesitant nod in return, turned towards Purple. "Let's begin."

Willcock rushed at Purple, baiting out a stab of her cane and then grabbing it and yanking it out of her grasp. After he dropped the cane on the ground, he pressed into a much less confident Purple and moved one hand to her pussy and the other to her boobs.

He whispered: "Am I allowed to tear your clothing?"

The shocked Purple responded with "Yes. I had it made for today."

In place of replying, Willcock tore open her pantyhose and started fingering her pussy, while ripping her tight shirt and groping her breasts directly, without cloth in the way.

Purple gasped and mewled and moaned, but she was not defenseless. Her left (regular) hand went to his nipple while her right (prosthetic) hand started jerking him off.

Deciding that Purple needed more stimulation, he licked her neck and inserted a second finger. Purple started moaning even louder in response, and her left hand went limp. Her prosthetic hand on his cock lacked technique and warmth, but its rhythm remained steady despite its owner's loss of focus. The hand was probably some kind of automaton.

Willcock glanced back at Red, who was pacing around nervously. Judging from her behavior, she wanted Purple to learn this lesson but didn't want her ravaged by some stranger, and couldn't decide whether Willcock's actions were already inexcusable or not yet.

He turned back to Purple and dodged an attempt at a kiss. "No, no, save that for your loved one." he admonished her, adding a third finger to her pussy and pinching one of her nipples. Within five seconds, Purple was cuming, howling like a banshee. Worth noting that the prosthetic hand had not stopped its movements for even a second until Willcock wrenched it away.

Willcock turned to Red. "Relax. All I will do to her. I think you need a humbling too. You reacted a lot to me teasing your cunt. Makes me think that all those old men are strictly on light-touches-only contracts, right?" He advanced on her, a cruel grin on his face. "You haven't had anyone just take you yet, have you?" With those words, he pounced.

Red tried to brace herself, but he tackled her to the ground. Once on top of her, he pulled her dress up and thrust his cock into her cunt, while his hands went to roughly grope her ass.

The effect was instant. Red's gasp, as he entered her and her moans as he groped her betrayed her sensitivity. She tried to retaliate, but her squeezes were mistimed and her hands could do nothing except wrap around him and hold tight.

It didn't take long at all to wring an orgasm out of her, but he didn't stop, pounding the sexy but weak woman into submission, delighting in her cries, until she came again.

Willcock withdrew from her and stood up.

"You need to learn to appreciate each other more," Willcock suggested once they recovered from their orgasms. "You can even put a bet on it, like 'The one to make the other cum must be obeyed by the loser for a day'."

The two gulped, sized each other up, then turned around and lunged at him.

Cursing, Willcock barely remained standing from the impact. Red slipped behind him, one hand going under his shirt and twisting one of his nipples, while the other went for a handjob. Purple jumped at him, mounting his cock, her pussy contracting with perfect timing to make him groan.

He counterattacked by reaching with one hand behind him and fingering Red while using his other hand to grab Purple by the throat, immediately reducing her aggressiveness.

When Red's handjob grew clumsy as the pleasure clouded her mind, Willcock withdrew the hand he used to pleasure her and the hand on Purple's throat, and used them to unwrap her from him. Once she lost her support, he grabbed her thighs and lifted her off of him, turned her around, and impaled her from behind, one of his hands wrapping around her wrists and the other going back to Red's crotch.

Red had recovered and resumed her assault, the pleasure steadily building in Willcock, but she was thrown off balance again when he pinched her clit. Purple, now getting plowed from behind with her arms restrained, lost much of her confidence and aggression. Willcock, deciding to leave Red be and finish off Purple, withdrew his hand from Red's clit and started spanking Purple's ass.

The situation being what it is, Purple found it difficult to resist Willcock's brutal attack, especially considering her previous orgasm, and quickly came, going limp. Willcock unceremoniously dropped her on the ground and turned around, grabbing Red, who had been jerking him off the whole time, and impaling her on his cock. After a minute of brutal thrusting, Red came too, leaving Willcock standing victorious.

Or so he thought. It wasn't even half a minute when Purple tackles him to the ground and mounted him in reverse cowgirl. Red saw this and got up too, sitting on Willcock's face, trying to smother him, and twisting his nipples.

Willcock has resigned himself to not leaving without losing at least one ribbon, but he was going to finish them off no matter what it took.

Red had foolishly positioned her pussy right over his mouth, making it easy for him to eat her out. To speed things along, he started groping her breast with one hand.

Purple was riding him, so he began thrusting up. He also used his other hand to give her firm ass a spanking.

Red found Willcock's mouth perfect, his tongue hitting sensitive spots she hadn't even known she had, and as Red had found earlier, she loved it when he roughly groped her. She couldn't possibly endure.

Purple bounced on Willcock's cock, panting. She was confident in her ability to dominate men when on top of them, yet here she was, losing control while riding reverse cowgirl. She had never known she wanted to be taken like this, but now that she was faced with it, she didn't have a chance of victory.

Willcock was going to cum. It was unavoidable. He has two beauties bouncing atop him, and he had just fucked a luscious woman to orgasm twice. He couldn't keep it up.

The three came together, panting and moaning. Willcock was the first to move, shaking Red off and lifting Purple off of his cock.

As they came to their senses, they found that he has taken all their ribbons (except for the white ones) and left behind one green ribbon. "The name's Willcock, by the way. And if you want more, I'll be at the Petal after the game ends." He said as he walked away.

Willcock decided he needed a drink after all this excitement, and ducked into a nearby bar. Halfway through a beer, however, he spotted a fellow man-at-arms trainee sitting alone at a table, a plate of meat and a mug of beer on the table, three red ribbons on her wrist.

Seeing her, he decided that he can rest while talking to someone he knows, and then he can take her ribbons while they were both in one spot.

"Hey, Judith! Can I grab a seat?" Willcock waved at her.

She looked up, noticed him, smiled, and nodded. "Of course, Willy. Sit down!"

Judith was large, a bit taller than Willcock, her frame filled out with tight muscle. She had a mane of red hair, and her skin was bare, except for strips of cloth around her chest and crotch. Her left eye was always closed, a scar running over it.

Willcock winced. He had explained to Judith some time ago that he prefers Willcock, but she just never seemed to get it. Or was just making fun of him, one of the two.

"Can't help but notice those ribbons you got, Judith. How's it going?" Willcock asked.

Judith sighed. "A lot of nobles who think they're tough, only to find they can't outlast a proper warrior." She perked up. "Oh, but there was that one priestess with big tits. She wasn't strong, but god, her fingers were magic. Got her once, but she got me twice, and then we parted ways. She might get two more from me, but I would get her last ribbon, and I still haven't found anyone who could give me a proper workout, so I wanted to keep going." She raised her mug and downed it.

"Oh, her. Yeah, I met her too. Got three but lost one." Willcock offhandedly mentioned.

Judith paused and sizes him up again. "You?" She said, disbelief clear in her voice.

"Alright, I only made her cum twice, but she pulled a cheap shot and gave one ribbon as compensation." Willcock admitted.

Judith continues looking at him strangely. "Hey, it's been a while since we last sparred, alright? And we never had a sexfight, either, just wrestling, so you shouldn't just assume." Willcock defended himself.

"Seems you ain't little Willy no more." Judith said, thoughtful.

"It's Willcock, thank you very much, and you are three years older than me. Not much space to be calling me little." Willcock snapped at her.

"Well, little Willy, you're gonna get a chance to prove to me you aren't so little anymore." She seemed to cheer up. "Give your senior the workout she deserves."

"Oh, I will, don't worry about that. Any rules, are we going for all three ribbons, any bets?" Willcock said, standing from the table and finishing his beer.

"Let's see how things will go. I wouldn't mind losing them all here, but I don't know if this old lady is enough to satisfy your curiosity, or if you want to go to any pretty young things after we're done?" Judith asked him, eyes twinkling and a small grin on her face.

"All in. I will pound you into dust, won't even break a sweat." Willcock shot back.

"Good," Judith growled and pounced on him.

Willcock found himself under her. "Wait, here? In the common room, where everyone is?"

"What, are you afraid everyone will see how little you are where it counts?" Judith teased.

Willcock took a deep breath and sat up, having Judith sitting in his lap. "Alright then."

Judith raised herself a little and both of them removed the layer protecting their genitals. Judith took a look at Willcock's cock and remarked: "It isn't small, but I've had bigger." While she was talking, she was not stable, and Willcock used her moment of imbalance to topple her to the floor.

"Hey!" Judith protested, only for Willcock to silence her with a kiss. While she was flailing, he took the opportunity to insert his cock into her and start pounding away.

Judith broke the kiss and sat up, pulling him out of her. "You little shit." Her eyes radiated lust, embarrassment, and wrath. "You - mhhhmm!" her words were interrupted by another kiss, flushing her cheeks. When Willcock broke it, he told her "You wanted a workout, no?" with a grin.

Now that they were both standing, Willcock had a better angle to fuck her, and so he fucked her. He knew, however, that he would need an edge, as she was stronger than him.

Judith's feelings were complicated. 'Little Willy', who she has been adoring, mentoring, and generally being his friend, older coworker, and childhood crush since he was nineteen, the last nine years (except the last one, he grew out of it after three years), was having a sexfight with her.

What's more, while he couldn't quite match her, he was stronger than anyone else she had fought that day, and she wasn't lying about craving a workout. On top of that, he was a great kisser.

One part of her refused to recognize that a three-year difference meant much less between 28 and 31 than between 19 and 22 and insisted on going slow and coddling him, defeating him without any actual fighting.

Another part of her demanded that she ride him into the ground and work out all the sexual frustration her weak opponents had inflicted upon her.

Yet another tried to make her guide him through the act, ever the mentor, and another demanded that he be treated with the respect he now deserves, and so was also in favor of riding him into the floor, and more demanded she conquers the specimen before her.

While Judiths' mind was in turmoil, Willcock decided to be experimental this time around and use light touches, under the assumption that a tough woman like Judith would have grown resistant to most rough handling.

Therefore, when his growing tempo drove her to decide to be rough and start squeezing him dry, one of his hands trailed along her spine, while the other tickled her belly button.

This sudden assault left Judith reeling, his skilled thrusts hitting all the sensitive spots, and his teasing being more effective than he could have anticipated. At that moment, she made an unconscious decision. She would treat him with the respect he deserves, and so would give this fight her all.

While she was thinking about all that, he used her lack of focus to put her on the ground again and get a better angle. From this position, where her options were limited, he would guess the odds being 50/50. Not good enough for him, so he decided to tip them in his favor.

He noted the way she blushed when he kissed her, could guess how she saw him, and other considerations led to him choosing kisses as his tool of choice to throw her off balance. So he leaned forward and locked lips with her, pushing his tongue into her mouth.

Judith was marveling at how Little Willy could match her, how his cock could make her feel so good, her tempo speeding up to match and overtake his, knowing full well that he will do the same to her afterward, when he kissed her, forcing his tongue into her mouth, with her not skilled enough to stop him.

As he stole her breath away with his kiss, his plunging cock making her feel more and more submissive, what broke her was him breaking the kiss, panting, and declaring "This time, YOU are MINE. I've grown up, Judith. Now, submit."

And submit she did, as Little Willy - no, Willcock, pounded her to and through her orgasm.

But apparently, that wasn't enough for him. Her moans were still echoing through the room and around the watching onlookers when his hands started to gently massage her breasts, and he gave her a peck on the forehead, then pecked her on the nose, blew hot air into her ear, gave her a long, drawn-out kiss on the mouth, licked her necks, and gently bit down on her collarbone.

He didn't stop there, though. Next, his hands ran along her muscled arms while he sucked on the slope of her breast hard enough to leave a hickey and sucked on her nipple, then moved on to kissing and licking the sweat off of her abs, giving special care to her belly button.

Continuing downwards, one hand trailing along the and he just kisses while the other gently massaged her ass, the trail of kisses led along her thigh and the rest of the leg, the hands massaging the muscles of her leg, trailing his lips, ending with sucking on her toes and then working his way up the other leg.

At the end of this journey, with Judith rendered trembling and unable to resist him by his teasing, his hands firmly gripped her thighs, and his mouth dove into her pussy. Her cute little gasps gave way to moans again, and she soon succumbed to the pleasure.

Despite the devastating orgasm she just went through, she rose to a seating position and held her arms outstretched. "C'mon. You won't take my last ribbon so one-sidedly, will you? Give me a chance. Fight me like a man."

Willcock nodded, grabbed her hands, and helped her stand. Then they lined up his cock with her cunt and began one final battle.

Willcock knew Judith was stronger and had more stamina, which meant she would have defeated him in a fair fight. Luckily for him, Judith had just cum twice in a row, which should be enough of an edge for him to win. Judith knew that too, though she believed she still had enough stamina to outlast him.

They moaned and panted as he pounded her and she squeezed him. They fought for several minutes, but then stumbled and fell backward, leading to Judith sitting on him, cowgirl style.

She made use of this development, slamming into him so hard the floorboards were starting to give. Willcock couldn't last long under such a brutal onslaught and swiftly came. She stood up from him, took one ribbon, unclipped two of hers and left them on the table, then headed for the stairs. As she was almost there, Willcock caught up and pushed her face first against a wall.

He interrupted her sputtering by whispering in her ear "We play for all ribbons, remember?" Then he took her from behind, one hand groping her tits and the other spanking her ass. She shrieked in pleasure as she hadn't had the time to brace herself, and turned around to level a furious glare against him.

"What?" He asked innocently. "You rode me, so now I'm taking you from behind. Fair's fair, no?"

Her glare remained, and she squeezed and buckled, not intending to give him the victory for free, but alas, she was too tired. Her grunts turned to gasps, which turned to moans, and then whimpers until she came one last time.

He took her last ribbon and said "There will be a party at the Petal after this. Both I and the priestess who took two of your ribbons will be there, so you can get your rematches after you rest up."

She gave him an unintelligible grunt in response. And with that, Willcock left the tavern and walked onwards, to his next opponent.

It took Willcock almost an hour to find his next opponent, but eventually, he stumbled upon a knight trainee with five red ribbons tied around her forearm.

She had a set of plate armor which revealed a dress on the bottom and had two pairs of ornate wings on its back. She wielded a massive sword, the edge gleaming with Luststone. She had long, blonde, partially braided hair, a silver tiara, and golden eyes.

She seemed distraught, frantically looking around the street.

"Can I help you, miss?" Willcock inquired. The knight turned to face him, and her face lit up when she noticed his ribbons.

"Yes! Oh, good sir, I would like to challenge you for those ribbons of yours. I have not had anyone approach me yet, and was starting to worry I was in the wrong place." The knight requested with a warm, adorable smile on her lips.

"Oh, I think they were just scared of your sword." Willcock pointed out, chuckling. "Not everyone can tell Luststone by sight alone, and it is a bit attention-grabbing. By the way, we're you intending our sexual duel here on the street, or somewhere more private?"