The Challenge

Peter and Dex were already seated in the living room with their slaves kneeling at their feet when Theo and Ashley came in. Theo had taken the long way to get there, grabbing the bottle of bourbon off the table where the men had left it. He pushed the bottle into her hand and whispered.

“Offer to freshen their drinks.” He ordered. “Host first.”

“Hello sir,” Ashley said, approaching Peter and presenting the bottle like a club hostess she’d seen in a movie once. “Mind if I top off your glass?”

“Be my guest,” Peter said with a smile, holding up his tumbler. “See, Danielle, Ashley is a very obedient little girl. You should try it sometime.” He gently pushed her shoulder, a small tease instead of a firm rebuke. Ashley didn’t like being called ‘little girl’ but given the school girl’s outfit she’d been wearing all day, it was obvious why he thought of her that way. Indeed, Ashley had barely noted that she was nude in front of all of them, as were Danielle and Madison. It was just becoming her normal state of dress.

Well, if Danielle and ‘Daddy’ were growing quite comfortable with the situation, Dex and Madison absolutely were not. Madison was kneeling, with her shoulders rolled forward as if trying to cover as much of herself as she could without breaking any rules. And Dexter sat on the end of the couch nearest the door, and looked as though he might make a break for it at any moment.

“Master Dex, would you like more to drink?”

Dex looked up at her like she’d spoken an alien language. Ashley presented the bottle again, and his eyes tracked from the label to her breasts, to her face, back to the label, to her breasts… finally the neurons all fired in the correct sequence.

“Yes! Drink! Please.” He said, thrusting out his tumbler so fast that it sloshed a little of the remaining **** onto Madison.

“Hey!” She said, wiping her self. She looked like she was about to curse him out or something, but realized her company and backed off. “Master Dex, would you like me to clean up before we start?” She put on her ‘submissive’ face, which to Ashley just kind of looked like a pout.

“Oh! Uh, no. There’s no need.” Dex said. He took an overly large drink of the whiskey and coughed as it burned his throat. Theo chuckled a little but managed to hide it behind his hand.

“What are the rules then?” Peter asked. Notably he directed the question at Theo, as Dexter was being no help to anyone.

Theo cupped his chin as he allowed Ashley to fill his drink. He’s barely touched it. She noticed. Ashley saw that both Dex and Peter seemed a little flushed, but Theo was his normal self. He’s been letting them out drink him… smart. Ashley beamed at her luck in finding such a crafty master.

“No need to overcomplicate this.” Theo said. “Slaves keep their hands behind their back, fingers interlaced. Game’s won when the first girl swallows every drop. If she dribbles down her chin on your carpet, that’s a forfeit. Sound good?”

Daddy gave a thumbs up, as he was taking a drink. Dexter just nodded, though both he and Madison still looked like they’d rather be anywhere else. Loosen up, guys! Ashley thought. She gave Madison a wink, but it didn’t seem to help.

“Alright then, let’s begin.” Theo wasted no more time, he unzipped his jeans and pulled out his massive hog. It was already half-hard from watching their little show upstairs, but given the stakes of this game, that wasn’t enough for Ashley.

I need to get him off. We need to win. Ashley wasn’t sure how much of that was Theo’s threat or how much was her natural competitiveness, but it didn’t really matter when her master’s dick needed to be sucked. She slid his head past her lips and down slightly onto the shaft, then bobbed softly on the head itself for a few moments. That’s something Stonebridge mentioned in passing. Ashley thought as Theo shifted in his seat, enjoying the sensations. These lessons are working!

She tried a few more tricks that had been filtering around the class, and Theo’s dick grew to its full, impressive size as a reward. Ashley wasted no time in capitalizing on her owner's response to her ministrations and pushed herself all the way down on her master's length to start up her body's natural reaction. Her efforts were met with hearty convulsing that begged her psyche to eject the harsh intruder and pushed her salivating to its limits to help in the process. Under normal circumstances she would have liked to save the move until later. Deepthroating him was her trump card, her sure way of eliciting his praises for her should she feel the deep rooted need for it when all else failed. Now she had to forgo those turn of events, she would need the lubrication to properly work on her master in a manner that would grant her the winning title. She had only ever seen Danielle work on her Daddy dildo and by the judge of that display, the little minx was assuredly going to give her a run for the money. With the luring threat hanging over her, winning against the other slaves had to take precedence over her own satisfaction.

Withdrawing him from where she had learned that her master belonged Ashley let the buildup follow the suctioning pull of his cock in her throat. Free of him Ashley spat out the heavy viscous mass that hadn't already attached itself upon him and eagerly slurped it all up as she took him in her mouth again, working hard to slathered his length in her saliva to give him a lovely, wet, sloppy blowjob that she knew would both feel good and look amazing for the other masters. Deciding to risk her position in the race to pause and take a well deserved breath, gasping from the toll that working her owner's monster took on her she used the opportunity to checked in on her sisters and scout on her competition.

Danielle was, as expected, enthusiastic about sucking Daddy’s cock. Eagerly working the tip of it as if she wanted to get to the creamy centre of a lollipop, a description Ashley saw eerily fitting to the girly girl mannerism that Danielle exuded. Her long flowing pigtails swishing with every delightful bob of the teen's head, begging to be grasped and pulled to impale it's owner on whom she was serving. In her short pause, Ashley managed to steal a glace Peter's face as well, and while she could still see some of the lingering doubts he had about the situation, she could see that deep down he was still a man. And regardless of the situation, a hot young blonde attacking your cock like it has the antidote to whatever vexes her is going to make a man feel quite pleased with himself. A reality where his deep satisfied breaths betrayed the protective facade that he fought to uphold for his own well being. Danielle was slightly annoyed at his physical response, but she dared not say so. But Ashley could tell by how hard she was working on it and how it wouldn’t reach full erection. The whiskey…

Whether it was the whiskey or something else entirely, Dex and Madison were not doing so well themselves. Madison had her eyes closed and was downing herself on his dick like it was homework or chores. Very perfunctory, and very much looking to get it over with. I would never let anyone see me act like that with Theo. Ashley made her smile that much larger. But its not like Dex is up for this either. He still looked almost distressed, and Ashley wasn’t sure it was just shyness any more. What is their deal? She wondered. A small tap from Theo reminded her she had a competition to win, and she threw herself back into it with gusto, swirling her tongue around his cock-head to scrape up the beady droplets of pre-cum oozing from her better's tip. The savory taste of it and his musky manhood got Ashley going again and soon had her set into a deep wet slobbering rhythm. Working herself steadily up and down, hands firmly interlocked behind her back as previously instructed, Ashley attempted to lock eyes with her owner, desperately seeking his attention which was otherwise occupied with the other masters. Look at me!

“Theo, you’re a damn lucky dog.” Peter said, toasting him with his glass. His words were slightly slurred. “When I was your age, I had to get pussy the old fashioned way. I’d have killed for a prime piece of ass like you’ve got there.”

Ashley blushed furiously at being discussed like this, but Theo possessively patting her head calmed that shame. Slightly.

“We were good friends for years.” Theo said. “She wanted me that whole time, but she couldn’t bring herself to make a move then. In truth we're glad she didn't, it would have been the wrong one. I'm happy that she was willing to become my **** once she legally could, now we finally have the relationship we both wanted."

Wait, that’s not exactly how it went… Or was it? In that spark of a moment Ashley felt unsure of the truth. He always had a better memory. And then there was Theo's commanding mandom firmly lodged between her lips working as both a physical and mental muzzle, signaling to her that she ought not argue against her master's telling of the events that led them here when her mouth had more important things to do. Not that she could deny any of it right now anyways, not with all the other masters present. It would make all of their sacrifices up to this point to be for naught. Theo’s got this under control. Just do your part and focus on his dick.

The pre-cum leaking from Theodore onto her tongue made her mewl in delight around him. Even if she had been allowed to, Ashley didn’t want to stop sucking that glorious dick that gave her such sweet encouragement. The blissful submissive sensation it provided filled some deep unnatural yearning that had awoken in her since her enslavement and now burned brighter than usual in the company of her sisters that shared in a ****'s delightful purpose, but at the same time, succumbing to that need was making it even harder to follow the narrative that Theodore presented to the other masters. Ashley tried to connect what Theo told Peter to her own memories of what happened which blurred together with what they had been making up since that night. Sure, there was the thing with Bruce that **** this solution on us, but that was my fault. I messed up, and Theo was there with a way to fix it. As always. Was it really the only way out to make me his **** though, or… Maybe I did want to be his **** the whole time and didn’t want to keep looking for another way. I did beg him to take ownership of me, didn’t I? Ashley felt confused about the whole thing for a moment, he’d shocked her and walked her around naked, pierced her most intimate body parts and humiliated her in front of her parents, and taken her money and virginity. But I’d been wet damn near every time. Including right fucking now. Thinking of all the things Theodore had to do to her as her owner was all the persuasion she needed to settle her questioning. It had to have been the only way, even if it wasn’t how they had envisioned their lives, he was too dedicated to his role for it not to be. I need to match him. It has to show that I asked him to be my master. She greedily slurped down more of his cock. God he’s got good dick!

"Isn't that right Slut." Theo asked out of nowhere, staring straight into her eyes like she had wished he did just moments ago.

What was the question? Ashley nodded while holding the tip between her lips, moving the impressive piece of flesh between her master's legs like a crank. Her display of agreement had Peter and Theodore clinking their glasses together in a nonchalant yet undenyingly cheerful manner, a show of understanding between peers that acknowledged the fine reality of things.

As she sat there, surrounded by the slurping, squelching and moaning sound of two women actively serving their owner's which bounced against the walls to form a cacophony of lewd raw lust had Ashley wanting to slip one hand down into the folds of her pussy lips to succumb to the energy that permeated the living room. Gripping her fingers tightly against each other she clenched down, whitening the length of her fingers to keep her fantasies from seeping into action. She needed to keep her hands where they were to give Theo the blowjob that conformed to his rules, the blowjob her master ordered her to perform, the one he deserved for his troubles. You don't have permission. She sternly told herself, imagining Theo's voice in her head to make her self imposed order stick. In mild astonishment Ashley found it working, allowing her to loosen her hold and let the blood flow back into her fingers, pleasantly tickling her slender hands.

“Dani here has got the relationship she wanted too.” Peter said, taking hold of one of her pigtails and laughed. “Sure wish I was your age to keep up with her. I have some nights where I gotta tie her to the bed so I can get some sleep.”

“I’m only a mile or so away, Pete.” Theo said, with an abundance of familiarity. “If you need to send her over for a night, I’m game.”

Danielle squeed again, muffled by Daddy’s cock.

“I’ll take that into consideration.” Peter said, his lips loosened by the booze “Dex, how bout you, man? You look like you’re worried Maddy’s gonna bite your tackle off.”

“Oh, I’ve just been working her hard lately.” Dex said, nervously. “She’ll have to tie me to the bed so she can get sleep.” Peter laughed but Theo’s eyes narrowed, and his voice was razor-serious.

“I wouldn’t accept half-performance from Ashley.” Theo took a hold of the ring in her collar. “I’m her master, and I get her best. Every. Single. Time.”

“Maybe she’s hungry.” Dex said, causing Madison to groan slightly into his dick, but given the criticism leveled at her, she did pick up the pace.

“I’ve got some extra **** food here.” Theo said, pulling a smaller thermos from the backpack he’d left on the couch. “On the house.” He said as he tossed it to Dex. Does he know how it tastes? He can’t! …Right?

Dex unscrewed the cap and offered it to Madison, but she shook her head without taking her mouth off his dick. Theo and Peter shared a quick glance.

“Yeah I wouldn’t let Dani turn down food like that. Rude.” Peter said. He opened a table next to his chair and pulled out a paddle, which he also tossed to Dex. It had raised reversed imprints that would leave the words “Daddy’s Girl” stamped on whomever got paddled with it. “Buddy of mine got that for me as a gag gift, but I think you can use it.”

Dex looked trapped, but he screwed up his courage and pushed Madison off his dick. He held up the paddle in one hand and the thermos in the other.

“Choose.” He ordered. Madison looked at him with pleading eyes, but his flitted to Theo and Peter - and to the two women currently blowing them for all they were worth. “Choose.” Madison nodded at the thermos.

“Hands behind the back.” Theo reminded.

Madison rolled her head back and let Dex pour the thermos into her mouth. She swallowed as fast as she could, but he poured too quickly, and the cum gruel leaked from her mouth, down her cheeks and dripped onto her bare breasts before she could catch up.

“Did she lose?” Danielle asked.

“Nah, that was just food.” Theo said, somehow making himself referee and contestant at the same time. But the other men didn’t question it. Madison, now smeared with Theo’s cum gruel, shook her head as it took its effects and then attacked Dex with a lot more energy.

With Madison growing bolder than she had before and Danielle finally getting Daddy rigid it had finally become a real race. Three cocks and three **** whores doing their best to get them off. The heads of the girls bobbing up and down in tandem, a morbid likeness of cylinders in an engine, perfectly synchronized. The sounds of pleasure from both master and **** edging the girls on in their pursuits, each giving it their all as their masters tensed beneath their feminine touch. Set to prove to their male counterparts what a woman's skill set could accomplish.

Ashley hearing Danielle pleasurable sexual squealing and Madison's frustrated grunting in stereo pushed her onwards, fearing that the other masters were close to finishing, Ashley deemed it time to show them the difference of a **** trained by Theo. Opening her throat up to accommodate him, much like when her talent was first crudely discovered on her first day of being owned, though now perfected, she rapidly **** herself up and down on Theodore on her own accord, fucking her own throat with his cock, a feat none of the other two girls were close to mimicing. The deep guttural noise of Theodore entering and widening her only to be pulled out moments later drowned out that of her sisters' efforts in pleasing the manhood in front of them. Soon Ashley had even Theodore fighting against his body’s urge to release his seed in her gullet. Her eyes bulging open from the strain it took on her body, staring into her master’s to seek his attention saw his hand clenching the armrests in her periphery. Though it was a race Ashley's display cemented that it was far from a fair one to begin with and that mischievous play her owner had set up had yielded the desired result, for both Dex and Peter were slowed by their drinking, while Theo reveled in the drunkenness of power from commanding the room. With her head-start culminating towards the inevitable Ashley could sense it in the way his cock strained against her insides that he was close, but fighting it for some reason.

“Not like that Ash.” His order came calmly, yet with the full **** of authority that she had come to expect from him.

When she shifted her efforts back to that of a more traditional technique of performing a blowjob it was only a mere moment before Ashley felt the twitching in his cock that signaled his coming release. She had just enough time to clamp her lips around his head as he fired shot after shot against the roof of her mouth. Amongst all the slurping and gagging, Ashley could only hear the deep grunts of her master’s climax. I'm done and they’re not even close to finished. Is it worth risking showing off? He would love it. Making up her mind she tilted her head back as far as she could and opened her mouth to show him his gift to her. Look, we won! Tell me I'm a good girl.

“You’re not done. Swallow.” Theodore growled.

Hungrily Ashley swallowed every drop of her master’s seed, then stuck out her tongue to show him an empty, victorious mouth. Her face brimming with pride despite him neglecting to praise her.

“Told you you were a lucky bastard.” Peter laughed. “Lucky at cards, lucky in love.”

Love? Ashley waited to see how he’d react to that, but his face remained stone.

“I know how to work the cards and I've had to teach this one how to work that whore mouth.” Theo said, slapping his erection on Ashley’s still outstretched tongue, ignoring the rest of what Peter said. Peter didn’t notice, because he was soon cumming in Danielle’s mouth, who managed to look happy and pouty at the same time as she swallowed Daddy’s load.

The pair of them were almost cleaned up before Dex finally finished in Madison’s mouth, and she did better at catching his cum than she had Theo’s. Once the game was over and she could use her hands, Dex ordered her to clean up the “food” on her chest and chin and lick it clean, which she did, but not without an annoyed face the whole time. She’s still not getting it. Ashley thought.

“Well that was an entertaining evening.” Peter said as Danielle licked his cock clean. “What do you say, same time next week?”

Theo agreed easily, but Dex gave a non-committal response, to Madison’s visible relief.

“See you guys around,” Theo called. He sent Ashley to collect her clothes and sex toy from Danielle’s room while Peter paid out his winnings.

When she returned holding them all in her arms, the door was open and Theo was already in the car, waiting.

She started to ask for the chance to put those clothes on, but she was smart enough to hustle to the passenger seat and climb in, still naked.