Chelsea vs. Clark: Who's the Boss?

The following is a very short story I wrote for a very dear friend. I hope you enjoy it as much as she did.

Chelsea couldn't believe what was happening as she squirmed helplessly on Clark's lap, and was starting to really regret engaging in this physical competition with him. In a few moments her ass would be bared and she would be spanked into submission. She was normally used to winning but her lucky streak was clearly over and soon she'd have to accept the new identity of "Blue Monkey" and call Clark "Boss". She also realized that deep down a part of her enjoyed the idea. She could feel her panties starting to get wet from her own arousal at her predicament.

This evening had been weeks in the making. Chelsea and Clark met online and discovered a mutual love of embarrassing contests in the style of Truth or Dare, and that both of them were switches who could enjoy having to answer humiliating and personal questions as much as forcing the other to answer them. They had learned so much about each other, and she had given up the embarrassing and cruel nickname of "Blue Monkey" that kids in school had given her when she was a child. The more they chatted the more clear it was that they couldn't remain switches forever, though. Someone had to be the dominant one... the "boss". And they couldn't decide who until Chelsea proposed a meetup and a physical contest: they would wrestle and the first one to get their bare ass exposed and spanked into submission would agree to become a slave to the other.

Chelsea figured they would be evenly matched but as the match started she realized she had bitten off more than she could chew and as they struggled, groping each other in the hotel room, she soon found herself overpowered. Clark had decided to make a big production of her defeat, hauling her to a standing position as he sat in the chair by the bed, then making her lie over his lap like a petulant child about to be punished, which is where she presently found herself.

Toying with her, Clark pulled her panties up into her ass crack, giving her a hard wedgie that exposed her cheeks and pulled tightly into her womanhood. Chelsea gasped and blushed at the sudden intrusion, and caught her face in the reflection of the bedroom mirror. Staring back at her was a mixed look of shame, arousal, and acceptance.

"Oooh... look at these beauties," Clark gloated as he grabbed and jiggled her ass cheeks, causing ripples across the pale flesh. "So ripe for spanking!"

He placed his flat palm against her cheek and rubbed it slightly, then stopped. "Oh, but wait! Contest rules are that your ass has to be bare!" He locked a finger around the fabric in her ass crack and pulled tighter. "It practically is... but rules are rules. Let's turn this Blue Monkey's ass red, shall we?"

Chelsea was transfixed by her reflection in the mirror. "That's it. That's what the face of a Blue Monkey looks like," she thought as her last ember of willpower died out. She lowered her eyes in acceptance but her gaze then fell upon her cleavage in the reflection, fully exposed from her t-shirt, ripped from the initial struggle after the contest started.

Clark gripped the waist of the blue panties and started pulling them down over her rump.

"Wait!" Chelsea cried. "My tits!"

"What?"

"Look in the mirror! My tits!"

"What about them?" he asked as he paused her disrobing and leaned towards the mirror to get a better look at her cleavage.

"Don't you want to see them?"

"Oh, I will! Once you surrender from your spanking you'll do a lovely Blue Monkey dance and striptease for me and jiggle them for my amusement."

"Well of course... but since you're about to win and get all my secrets, can I tell you one of my kinky fantasies?"

"By all means."

"I love making my tits jiggle and watching them jiggle. I've touched myself while jiggling my own tits in the mirror. If you're going to spank me into submission, I want to be topless and watch my tits jiggle with each slap. I think that would be a fitting end for me and make it just that much hotter."

"This is some kind of trick."

"No! Look... I'll sit on the bed and you can stand and undress me. Then I'll be a good girl and take my spanking."

"Well you being a good girl is nice, but I want you to be a good Blue Monkey."

Chelsea blushed. She knew what he was making her do, but she rationalized that the contest rules only made it count if she said it during a spanking. Despite her self-assurances, she still gulped hard before speaking. "Yes. I'll be a good Blue Monkey".

Clark smiled wickedly and helped her to her feet, then spun her around and sat her on the bed as he stood up. "Keep your hands behind your back," he ordered. She complied.

First was the torn T-Shirt. He pulled it up over her head and down her arms, leaving it bunched up at her forearms. Her white bra was holding back her massive 42DD breasts. He reached over her shoulders to fiddle with the clasp.

"I can't believe you gave up your tits before the spanking," he openly mused as he struggled with the awkward angle. "You must really want to be my slave. This is one of my easiest conquests ever!"

Chelsea blushed again and hung her head in shame as the clasp finally came undone and he pulled the straps off her shoulders.

"Welcome to the loser club, Blue Monkey," he gloated as he pulled the cups away from her breasts that fell free and sagged under their own weight. He lifted the bra up over her head, and like the T-Shirt before it, let it fall down by her wrists behind her back. He sat back in the chair, admiring her massive mammaries. "Now then, be a good Blue Monkey, lay across my lap, and let's make this official."

Chelsea slowly arose. Her pajama bottoms were at her ankles and her powder blue panties were pulled halfway down her thighs, but Clark's gaze was fixated on her tits. She started swaying her torso back and forth.

"What are you doing?" Clark said, not taking his eyes off her giant breasts.

"Do you like them?" Chelsea asked in her sing-song brogue, leaning forward and rolling her shoulders to make her breasts sway and jiggle.

"Uh... yeah..." Clark replied, his voice trailing off. He watched her breasts sway and gradually began to sway himself in sync with them, falling into rhythm with her.

Chelsea moved forward, her hands still behind her back. As Clark stared at her nipples and licked his lips she slid her right hand out of the shirt and bra.

"You want to taste? I really love having my titties sucked. Please suck them."

"Y-yes..." Clark said dreamily, his mouth starting to hang open.

Chelsea took her right hand up to her right breast, and held it up like a nursing mother guiding her nipple to an infant's mouth. "That's right. Have a taste."

Clark leaned right into her breast and immediately began slurping away, his eyes closed. With one quick movement, Chelsea let go of her massive breast and brought her hand behind Clark's head, pushing it into her mound of flesh and holding it and him in place.

She let him suckle at her for almost a minute before she dropped her shirt and bra on the floor, and using her left hand, placed it under Clark's right armpit and gently guided him up off the chair. She took a few slow steps backwards until the back of her thighs hit the bed, and lowered herself into a sitting position. Sliding her left arm down to his lower back, she pulled him towards the bed, and he instinctively laid down on his side with his torso on her lap, knees wrapped around her hip, nursing her breast.

"That's it. That's a good boy," Chelsea hummed as she stroked his head with her right hand and rubbed his back with her left.

"I... can't... stop... sucking at your tits," Clark gasped as he briefly came up for air. "They're so amazing."

"I know," Chelsea replied as she reached down and pulled down his shorts and underwear with one quick tug. "... And that's why I will always win."

There was no gloating or teasing. Chelsea went straight to work slapping Clark's bare ass cheeks over and over. His left arm was pinned between her body and her right arm, his legs were held in place by her left elbow, and his free left arm could do little more but try to guess where she was going to strike, his vision obscured by the fact that his face was buried in her breasts. He did manage to block a few of her blows but his ass was getting progressively redder and redder. She watched the colour change in the reflection in the mirror with delightful satisfaction.

Chelsea then paused the spanking. "Why don't you take your punishment like a good boy, and I'll let you use that free hand to feel up my other tit. Wouldn't you like that?"

Clark hesitated for a moment before nodding in her breasts and drawing his hand away from his ass to start groping her massive left tit. She resumed spanking him without resistance, and enjoyed how with each strike he briefly squeezed her tit.

After a few more minutes of spankings Clark pulled back from her breast. "Please... stop. I give up."

"You're ready to surrender to me?"

He nodded meekly.

"Well I'll tell you when I'm ready to hear it!"

She resumed slapping his ass cheeks harder, counting out 20 swats for each cheek before stopping and lovingly rubbing his beet red and throbbing bottom.

"Now I'm ready."

Clark slowly looked up at Chelsea. His eyes were wet with tears and she couldn't tell if it was from the pain or the emotional release of giving in, but it was the moment she had been waiting for since they met.

"I give up. You win. I lose. You're the Boss, Chelsea."

Chelsea smiled wickedly. "Good boy," she said as rolled him onto his back across her lap. She looked him in the face.

"Well I guess you need a new name. You wanted to call me 'Blue Monkey', but you are never allowed to utter those words again. No one is. That's my secret that nobody will ever know."

Clark nodded submissively. "Yes, Boss."

"While I think of a name, let's see what my main prize is, shall we?" Chelsea said as she pulled his shorts and underwear fully down exposing his cock and balls to her for the first time. If he had been hard during the suckling, his cock had deflated during the spanking, and was a tiny little wrinkled mound barely visible in his unkempt bush.

"Ah, a grower eh? Well c'mon then. Get it up! Show me what you got!"

Clark looked meekly at her nipple and then back up to her. Chelsea rolled her eyes and nodded and he went back to sucking her tit. While she enjoyed the sensation she was only interested in giving him this pleasure so she could see how big he got.

It took a minute or so but eventually his cock started pulsing and becoming turgid, standing upright. She watched it, fascinated, until it grew no further.

"What the fuck? That's it? That's like 10cm!"

"It's almost 11.5cm," Clark said, as if the extra 1.5cm made up for the below average cock size.

"Wow," Chelsea exclaimed. "You're so tall and when I finally get a look between your legs there's nothing there but Clark's little dick. Wait... Clark's Little Dick. "Click"! That will be your new name! And I'll be able to call you that in public and only we'll know what it means."

"Yes Boss. Thank you, Boss."

Chelsea picked her phone up off the night stand and took several close-up photos. "These are 'before' pics. That tangled mess of pubes has got to go, and then we'll take new photos."

She then had him get off her lap and remove the rest of his clothes, taking full body nude photos and running her hands over his chest, playfully pinching his nipples to watch them stiffen.

"Now then, the first order of business," Chelsea announced as she got up on the bed and got herself comfortable lying on her stomach.

"Yes Boss?"

"You wanted to expose my arse so bad; do it!"

Wide-eyed, Clark reached down and finally pulled the wedgied panties out of Chelsea's ass and down her thighs, exposing her round bottom.

"Keep going, take them off."

He complied and soon had her power blue panties in his hands.

"That's your uniform from now on. Put it on."

He complied, and the panties didn't fit him very well, and looked especially ridiculous given the small tent he was pitching. She took some more photos and then directed him back towards her bare bottom.

"You dared to try and spank me, so to make amends you can get to work kissing every inch of my ass, and don't stop until I tell you."

"Yes Boss," Clark said as he fell onto the bed and started kissing her ass cheeks over and over, alternating between cheeks.

Chelsea smiled as she browsed her phone. Soon all of Clark's secrets would be hers, and she would use them to humiliate him for her amusement. He would spend the rest of his life serving her and her lovers, as his little dick wasn't worth her time.

She looked at the nude photos she had taken of him. The pubes would be gone soon. But what about his ass? He had a cute ass but it was completely bare. It needed something.

A tattoo.

Maybe "Property of Chelsea".

Nah, too obvious. He'd never see it anyway.

Then she had the perfect idea.

A small blue monkey.