Chloe learns a hard lesson

“I just think I could beat most men in a fight.”

Joe put his glass down and wondered if he’d heard her correctly. “Wait, say that again? You think you could beat a man in a fight?” 

“Yeah. I think I could take a guy. I once wrestled my best friend and I beat her easily. I’m really strong.”

“But have you ever wrestled a man? 

“No. But what’s the difference?” 

She wasn’t joking. Joe took another sip of his drink and smirked. 

It was their fourth date. Chloe was 21. She had dark, shiny hair, and was an only child from a wealthy family. 

They’d had sex on their previous date. Her young, supple body was mouthwatering. When Joe had gone down on her, she’d come easily. 

He stared at her across the table. She smirked and sipped on her wine. “What? Do you disagree?” 

Joe laughed, not sure what to say. Then he had an idea. 

“Well, what if we put your theory to the test?”

“Go on?”

“What if you and I fight?”

“Like a wrestling match?”

“Exactly.”

“I’m interested.”

 “And whoever wins, takes the other as their prize.”

Chloe’s pupils dilated. “That sounds fun. But if I win, I want to use my toys on you.”

“What toys?” 

“Oh, you’ll see.”

“Deal”, said Joe. 

“Is everything up for grabs?” Chloe asked, raising her eyebrow. 

“Do you mean my ass?”, said Joe. 

Chloe nodded. 

“Sure. But that goes for both of us.”

Chloe looked at him menacingly over her glass and said, “We have ourselves a deal.” 

—

They arranged to meet at Joe’s. He’d laid mats out on the floor. In the middle of the mats was a pair of handcuffs. They agreed that whoever managed to handcuff the other was the winner. 

Joe was sure Chloe was joking, but she’d been trash-talking him all week, telling him what she was going to do with his body. Apparently, she’d had a fantasy of topping a man for years. 

Chloe buzzed the door and Joe let her in. She walked past him, brimming with confidence. “Hey Joe. I hope you’re ready.” 

Joe smiled and looked her up and down. She had her silky brown hair up in a ponytail and was wearing yoga pants and a sports bra. She was athletic, but probably weighed 30kg (66lb) less than Joe. Chloe had a backpack over her shoulder which she placed at the side of the room. 

He had to respect her self-belief, but he was going to have to teach her a lesson. Years of getting exactly what she wanted were about to come to an end. 

Chloe looked out over the small arena Joe had prepared in his flat. All of the furniture was pushed aside, and there were large, soft, inter-locking mats in the middle of the floor. 

“So, this is where the magic is going to happen?” She spotted the handcuffs Joe had placed in the middle of the mats and her eyes lit up. “Shall we?” 

They both started to warm up. The match would last as long as was necessary. The winner was the one who handcuffed the other. And once the wrestling was over, the winner could do as they pleased to the loser. Joe was about to ask what was in the backpack, but he decided to find out later. 

Chloe re-tied her ponytail and made a “come here” gesture at Joe. It was time. 

She moved towards Joe and wrapped her arms around his head, trying to pull him down. He stood straight, never breaking eye-contact. When that didn’t work, she grabbed Joe’s leg and tried to lift it, but Joe stuck it to the mat. She kept trying to move him, but Joe just watched her, never in any danger of losing his balance. 

After a few more efforts to take Joe to the ground, he heard Chloe sigh heavily. Now it was time to attack. 

Joe put his hand on the back of Chloe’s neck and forced her down to the mat. She tried to resist but buckled under his weight. She grabbed his wrist with both hands and tried to pry herself free, but Joe held her in place. After while he let her go. She bounced back up, trying not to look flustered. 

She came at him again, but this time Joe grabbed both her legs and placed her down onto the mat. He climbed onto her chest and pinned her wrists to the floor. She tried to struggle, but there was no way she could get free. Joe was so much stronger than her. 

He stared into her eyes from his dominant position. She looked like a deer, caught by a wolf. 

Joe kissed Chloe’s neck and she let out a gasp. She was obviously turned on. Her cheeks flushed pink and she bridged her hips, trying to get Joe off her. It was futile. Joe licked her cheek, then kissed her, pushing his tounge into her mouth. She stopped struggling for a second, letting Joe have her. 

Chloe squirmed beneath him, desperately trying to get out from under his weight. Joe stared down at her again and said, “do you still believe you can beat a man in a fight.” She looked up sheepishly. 

Joe considered letting her up, but remembered the messages she’d sent him, and decided against it. He was going to teach this brat a lesson. 

He took one of Chloe’s wrists and turned her onto her front. She tried to resist, but soon she was lying face-down with Joe sitting on her lower back. Chloe wriggled and kicked her legs, but she was trapped. Joe picked up the handcuffs. He dangled them in front of her face and said, “I think it’s time we put these on.” 

He pinned her arms behind her back and fastened the cuffs on her wrists. Once they were on, he stood up, looking down at his defeated opponent. He was rock hard. She’d never looked hotter than she did now. Her yoga pants hugged her round ass cheeks, and her breasts looked firm beneath her sports bra. “That was pretty easy Chloe”, he mocked.  

She was furious. How could Joe have beaten her so quickly? She lay handcuffed on her back, embarrassed to have put up so little fight. In desperation, she said “Joe I didn’t actually think I could win. Let me go and we can forget about this stupid bet.” 

Joe smirked. Well if you didn’t think you could win, why did you bring your backpack full of toys? Chloe’s heart sank. She lay helpless as he walked over to the bag and picked it up. “Let’s see what you had in store for me.”

Joe unzipped the bag. He threw his head back with laughter when he looked inside. “You kinky little bitch! I can’t believe you brought all this for me!”

He emptied the bag onto the mats. Chloe watched the contents fall to the floor. Joe threw the backpack aside and inspected her repertoire. 

Chloe had brought almost every toy she owned and had purchased a couple especially for this event. 

There was a red ball-gag, a leather whip, a cane, nipple clamps, a collar and leash, a butt-plug, a pen, and a stap-on dildo bigger than Joe’s dick. 

“Jesus Chloe. You really thought you were going to dominate me, didn’t you?” 

“I… I…” 

“Admit it.”

“Ok yes. But I wasn’t going to use all of them.”

Joe gave her an evil look and said, “well I am.”

—

Joe went to his room and got the spreader bar and vibrator out of his cupboard. He was going to enjoy this.  

He returned to the living room and looked at his prize. She was kneeling, her hands cuffed behind her back. Chloe’s eyes widened when she saw what he had in his hands. 

“Joe, come on. You can’t be serious?” 

“You’re going to learn a hard lesson, Chloe.” 

She rolled her eyes. 

“That’s exactly what I mean. Your attitude needs an adjustment.”

He stood over her, looking down at her cute, brown eyes. “From now on, you’re going to call me ‘sir’, and do exactly as I say. If you don’t, there will be consequences. Do you understand?” 

“Fuck you.” 

Joe laughed. “I hoped you’d say that.”

He grabbed her by the ponytail and pulled her up to her feet. She tried to struggle against him but he controlled her easily. He brought her face up to his and whispered in her ear, “in about an hour, you’re going to beg me to cum in your mouth.” 

She spat in his face.

This riled him, and he threw her to the floor. “That was silly Chloe.” 

Joe grabbed her yoga pants and underwear and ripped them off aggressively. She was naked from the waist down. Her pink pussy glistened with excitement. 

Joe got the spreader bar and attached it to her ankles. She tried to kick him off, but he quickly had her secured. He turned her onto her front so that she was face-down-ass-up and put his foot on her neck. 

He picked up the whip and said, “this is what happens to girls who don’t respect their superiors.” The first strike landed hard on her left ass cheek, and she jumped at the impact. He brought it down hard again on her other cheek, already noticing the skin turn pink. 

She struggled against his foot, the handcuffs and the spreader bar, but she was completely immobilised. After each whip lash, she yelped and squealed. The more strokes landed, the stronger her reaction. 

“How does that feel princess? Are you enjoying your punishment?” 

“Fuck you, Joe.” Came back. 

“Hmm. That doesn’t sound like a lady who’s learned her lesson.”

Joe took his foot from her neck and moved behind her. He placed his foot on the spreader bar, pinning her ankles to the ground. Then brought the whip round in an underhanded arc, landing the leather tassels directly onto her pussy. 

“Uuugggghhhh. Fuuuck.”, said Chloe, writhing against the pain. 

Joe smiled and landed another few strokes. Usually he’d be gentle with a sub’s pussy, but with Chloe he didn’t hold back. The lashes were heavy and constant. 

“You could ask me to stop, you know. You just need to use the proper etiquette”, Joe said, continuing to land his whip on Chloe’s labia. 

He saw her consider it, but instead muttered “you’re a bastard.” 

Joe brought the whip up high, down across his body, and landed it on Chloe’s ass cheek again. He did the same on the other side, then the other. He found a rhythm, and listened with satisfaction as the heavy leather connected with Chloe’s bare skin. 

Every so often, she let out a high-pitched squeal, which only turned Joe on more. 

Then he stopped abruptly. Chloe winced, bracing for the next impact that never came. She looked back at Joe, who had the whip over his shoulder. 

“Alright sweetheart, what next?” 

She glared, furious at her treatment. But said nothing. 

Joe went over to the toys with a spring in his step and decided what to use. He picked out the nipple clamps, the vibrator and the cane. He also brought a belt from his room. 

“Now Chloe, you’ve not been very well-behaved so far. So I’m going to show you what happens to bad girls.” She clocked the new instruments he had to torment her with and groaned. She was still face-down-ass-up, cuffed, with a spreader bar attached to her ankles. 

First, Joe tied the belt around Chloe’s waist – he planned to use it to hold her still. Then he pulled up Chloe’s sports bra to expose her breasts. They hung pleasingly. He took her left nipple between his fingers and attached the first clamp, then did the same with the right. She winced as small metal clips pinched her skin.

He stood back and marvelled at his work so far. Chloe’s ass and pussy were pink from whipping. She was helpless to stop Joe from doing as he pleased. 

He felt the weight of his wooden cane in his hands and smiled at Chloe, who’s eyes were glancing between Joe’s face and the toy. The vibrator lay between her feet.  

“Alright Chloe. It’s time for round two. Remember, you can always ask me to stop, but you have to use your manners.”

Joe took his cane and started tapping the bottom of Chloe’s feet. Her toes curled with the pain. He tapped harder and harder until she was flinching with every strike. Then he started caning the inside of her thighs and across her ass. Some of the harder stokes left deep red lines.  

She yelped again. The cane stung more than the whip. She was desperate for it to stop but couldn’t bring herself to ask. Chloe grimaced as Joe landed strike after strike. 

Joe put down the cane, knelt on the spreader bar, and picked up the vibrator. Chloe’s eyes widened again. The buzzing made her tremble. She started to say “Joe, please…” but trailed off. She heard him turn the setting from low to high and swivelled her head, looking for an escape route.  

Joe placed the head of the vibrator directly onto Chloe’s clit. She bucked and squirmed, trying to break the contact, but Joe held her hips in place with the belt and knelt on the spreader bar, rubbing the head of the vibrator in small circles around Chloe’s clitoris. 

Her eyes were closed and fer face twisted in a mix of pleasure and pain. She let out long “uggghs”, “Ahhhs” and “ohhhs”. Joe smiled as he remembered how quickly she’d cum when he went down on her. He knew she wouldn’t hold out for long. 

He spanked her bright red ass cheeks which drew powerful reactions. She was squirming, moaning and yelping. 

Joe spat on Chloe’s asshole and started to rub it with his thumb. He felt her squeeze and release, squeeze and release. Chloe arched her back then crunched her abs, but the whole time Joe held her in place and kept the vibrator on the sweet spot. 

Suddenly Chloe’s back hunched and she yelped, “fuck fuck fuck fuck fuck fuck”, releasing into a powerful orgasm. She rocked and wriggled, continuing to come as Joe held the vibrator to her clit. 

Soon the sensations were becoming too much. Joe made eye contact with her and said “you can stop this if you ask nicely.” He was still massaging her ass as he vibed her pussy. 

She scrunched her face and blurted, “please… please sir… take the vibrator off my clit.” 

Joe took it off immediately, and she slumped to the floor. 

He put his face close to Chloe’s and made intense eye contact. “That wasn’t so hard, was it?” She stared. “We might just make a good little sub out of you.”

Joe removed the handcuffs, the belt, the nipple clamps and the spreader bar. Chloe rolled onto her back and closed her eyes, exhausted from the punishment. 

“You’re not done yet, little lady. But you have permission to take a five.” 

—  

Chloe lay flat on her back, her arms outstretched, breathing deeply. Joe had tired her out, and she was now in that sweet spot of exhaustion and surrender. He’d proven he could overpower her, inflict pain, and make her cum. 

He watched her, deciding what to do next. Her cheeks were pink and she was shiny with a layer of sweat. Joe admired her wide hips and perky breasts – she’d removed her sports bra, so was now completely naked. 

Joe stood over Chloe. She opened her eyes and looked up at him, saying nothing. 

“Alright Chloe, you’re going to do exactly as I say. If you don’t, you’re going right back in those cuffs and spreader bar. But this time I won’t be so merciful. Do you understand?” 

She nodded. 

“What was that?” 

“I understand… sir.” 

He could still hear resistance in her voice, but she was beginning to break. 

“Good. On your knees.” 

She sat up to a kneeling position and looked up at Joe. He was still in the shorts and t-shirt he’d worn for the fight. He took off his top, revealing a muscular chest and shoulders. Looking down at Chloe, he pulled out his large, hard dick, dangling it in front of her face. 

“Suck”, he ordered. 

She looked at his dick, then leant forward and took it in her mouth. Initially she just held it there, but then started to move her head back and forth, each stroke taking it a little deeper. 

Joe put his hands on his hips and let his head fall back. He closed his eyes and enjoyed the sensation of Chloe’s hot, wet mouth on his cock. Without looking down, he said “you know what you’re doing.”

Chloe sucked on Joe’s dick, quietly loving the feeling of it in her mouth. She used her hands, one massaging his balls, the other jerking gently. Her teeth didn’t touch his shaft.

Blowjobs were one of Chloe’s favourite sex acts. She looked up, giving Joe her best puppy dog eyes, and moaned slightly as she took his dick deeper into her throat. It was a relief not to be whipped and caned. 

Joe put his hand on the back of her neck and pushed his dick deep into her mouth, making her gag and pull away. He pulled her back and put it deep into her throat again, holding it there until she coughed. Her ass still burned. 

He let her go. The spit was running down her chin and her eyes watered slightly. A pleasant shiver ran up his spine. 

Joe pushed Chloe gently to the floor and she fell willingly onto her back. She drew her knees to her chest and waited for him to have his way with her. Joe spread her legs, lined his shaft up with her wet vagina, and slid his dick deep inside her. She moaned and closed her eyes as he filled her.

He started to thrust slowly into her pussy. She was tight, but she was so turned on and wet his dick slid easily in and out. They both moaned loudly. 

Joe kept on fucking her, exploring her mouth with his tongue. He kissed her neck and sucked on her nipples. 

He straightened up, holding both of Chloe’s ankles in one hand. She was flat on her back, her legs together and to one side, as Joe slid in and out of her pussy. 

Chloe loved how Joe’s dick felt inside her. He was long and thick, and she felt vulnerable looking up at his big hands holding her ankles. She let out gentle “ah’s” every time he pushed inside her. 

“Do you like being fucked, Chloe?” 

‘Yes”

“Yes what?” 

“Yes sir.” 

“Good girl.”

She blushed at her submission. 

Joe stopped and put her feet aside. He savoured the wetness all over Chloe’s pussy and inside her thighs. 

He went over to the pile of toys and picked up the collar and leash. Then said, “I’m going to train you to be my little pet.” 

Chloe said “yes sir” under her breath, making Joe smile. The fight had left her.

He fasted the collar around her neck and clipped the leash to the ring. He stood next to her and said, “all fours”. She got onto her hands and knees, looking up and Joe for guidance. He said “Good girl. When I give you that command I want you there, with your back arched and your head up. Do you understand?” She did as she was told, sticking her ass out and her chin up, looking forwards. 

“Walk.” 

He pulled on the leash gently, and she started walking on all fours. She stayed at his heel, looking up every so often at the man holding her leash. 

“Kneel.”

She sat back onto her heels.

“When I say kneel, I want you to put your hands on your thighs, facing up, and open your mouth. Do you understand?”

“Yes sir.” She opened her mouth and put her hands on her thighs. 

“On your back.” 

She lay flat on her back, hoping it was what he wanted. 

“Spread your legs.” 

She did. 

“Good girl.” 

“All fours.” 

She got onto her hands and knees, remembering to round her back and keep her chin up. 

“Stay.”

Joe put the leash down on her back, walked over to the pile of toys, and picked up the pen, ball-gag and butt-plug. 

—

Chloe stayed in position, accepting her fate. She knew there was nothing she could do. If she resisted, there would be painful consequences.

Joe knelt in front of her and placed the red ball-gag in her mouth. She held it there while he fastened it behind her head. She dribbled down her chin. 

He moved behind her and told her to arch her back. She did as she was told. He spread her cheeks, spat on her asshole and pushed his thumb slightly inside as he massaged her tight little ring. She moaned through the ball-gag as his thumb pushed entered her. She listened to him suck and spit on the butt-plug. 

Kneeling beside Chloe, Joe put a large hand on her throat, and held the wet plug in the other. She looked at him with a sideward glace, as he said “alright girl, the more you relax the easier this will be.”

She nodded slightly and looked straight ahead. He started to press the butt-plug against her asshole. She closed her eyes and tried to relax. She let out an “uh” as it popped inside. Her ass gripped it tightly. There was now a sparkly jewel where her asshole had been. 

Joe said “good girl”, then uncapped the lid of the pen. He sat behind her, and drew an arrow on one of her ass cheeks, pointing towards her pussy. He wrote “fuck me here”. Then did the same on the other cheek, but directed the arrow at her asshole, and wrote “plugged”.

Chloe had no idea what he had written, but she knew it was humiliating. She blushed as she stayed obediently on all fours, gagged and degraded.

Joe moved to her face. She cast her eyes downward as he wrote “SLUT” across her forehead. She knew what he’d written by the tracing of the pen. 

He took her leash and said, “walk”. She shuffled forwards, gripping the butt-plug every time she moved her legs. 

Joe looked down at his defeated opponent and felt a wave of satisfaction. He’d been hard on her, but he knew she planned to do the same to him, so didn’t feel guilty.

He walked her in a circle, pulling on her leash when she left his heel even slightly. 

“Kneel”. 

She looked up at him, her cheeks stretched slightly with the ball gag. He loosened it, letting it hang around her neck. He grabbed her ponytail and put his dick into her mouth. 

“Remember I said I was going to make you beg for my cum in your mouth?” 

She nodded. 

“Well let’s hear it.” 

She tried to speak with his dick in her mouth, managing “Peas ‘ur ‘um ‘n ay ‘ouf’”.

He made her gag, then pulled his dick out. 

She spat and said, “please cum in my mouth sir.”

He put his dick back in and started thrusting hard into her throat. Holding her head in place with her ponytail, he unleashed a tsunami of cum into her mouth. It was one of the most satisfying orgasms he’d ever had, his dick pulsing again and again as he deposited more cum inside her. Chloe’s eyebrows raised as her mouth filled with Joe’s hot semen. 

“Swallow.” 

She closed her mouth and swallowed his load. 

Joe let out a long, accomplished sigh as his dick went slightly flaccid. 

He bent down and kissed Chloe on the lips, pulling her in by the leash. 

“You’re a good girl, you know that?” She smiled happily, nodding. 

“Let’s get you unplugged.” 

She stuck her butt in the air. It burned as Joe gently slid out the plug. 

“Up.” 

She stood. Joe looked at her and grinned, “do you still think you can beat a guy in a fight?” 

She shook her head, “no sir.” 

“Good. Then you’ve learned a valuable lesson.” 

Joe scooped her up and put her over his shoulder. She giggled at being lifted. He carried her to his bedroom, and put her under his covers. 

Disclaimer : BDSM & related rough kinks require proper communication, sound risk analysis, correct tools, mutual understanding, patience and practice. Do not try any scenes listed out without due precaution.