Over the Lap of Luxury Pt. 06

He saw a crowd of staring, amused shoppers when he stood back up. Heat warmed his face even worse than his bottom, and his eyes focused hard on the floor. "I'm sorry, ma'am. It won't happen again," he said for the sake of the cameras and Portia's future praise.

Once they were safely back in the Bentley, she gave him what he sought. She wrapped her arms around him and squeezed him tight. "Good boy. Good. I know that was humiliating, but I don't think anyone will bother with the footage of us speaking to Miles and Sean now. You did well. I think a good bonus in your paycheque this week should cover your emotional damages."

That was tongue-in-cheek, but Asher suspected she would actually give him a little tip. "Thank you, ma'am."

"And I think you've earned yourself an even more exciting bonus tonight," she said, tapping the necklace chain where his chastity cage's key now dangled.

Asher was later told that the conspiratorial meeting with Miles went well overall. Though, there'd been some push and pull at first. Miles had told Portia he'd already anonymously alerted authorities to Sean's abuse, and nothing was done. She insisted it would be different coming from herself and Nick, with far more indisputable evidence.

Wanting to help his secret lover, Miles agreed. There was hope for Sean in her plan, and he didn't have a better one himself. He shared all the necessary video security system codes to help them with their goal. Unfortunately, he refused to just send over the video files himself, afraid of being caught and implicated. This only meant the plan would largely stay the same the night of the party. Asher would have to get the files himself once he was separated from the group.

After Miles had gone, Portia kept her promise to Asher. She went downstairs to visit him after dinner, and held the chastity cage key up for him to see.

"You've earned a reward," she said. "You now have a way to gather the video evidence, and we have a new ally. But Molly helped you with her astute observations, and I think she deserves a reward as well. Maybe a reward you can give her yourself."

Asher found this to be even better news, in his opinion. Just looking at the key in her hand made him begin to stiffen with need. It had been getting worse instead of better the past couple of days, as he'd been caged for nearly two weeks. An eternity for a twenty-three-year-old. The ring at the base of his cage prevented his erection, yet again, an increasingly frustrating sensation.

Portia called Molly in and told the still-naked servant girl to lay on her back. She obeyed, laying flat and looking up at Asher and Portia. "You haven't been kept in chastity officially, Molly, but it's been a long time for you too. Hasn't it?"

"Yes, ma'am," she said.

Portia caressed her with light fingertips over her breasts, listening to her pant. Then she slid her hand between her legs, rubbing softly. Molly arched back and groaned.

"Do you want to come, Molly?"

"Please, ma'am."

"Pleasure her, Asher," said Portia. "Be a good boy and make her come hard."

Asher looked helplessly down at his groin, where just under his pants, his penis was still bound up in its cage.

"Not with that, silly boy," she said, giving him a firm spank over his pants. "Is that how a good servant boy pleasures a woman?"

"No, ma'am," he sighed miserably. He enjoyed all manner of pleasuring women like Molly and Mrs. Darrow, but he felt truly bereft of the ability to enjoy them the way men typically did. As a submissive guy, he didn't realize he'd miss the carnal pleasure of a hot, wet vagina wrapped around him as much as he did.

Portia paid no heed to the pout on his face and began to strip him, methodically and slowly, taking off each piece of his uniform with care. By the end, he was naked aside from the cage, still attached snugly around his genitals. She ignored his pleading look and kissed him on the cheek.

"There. You're ready, beautiful boy. Get down on your hands and knees on that bed and serve her."

Asher knelt obediently and began to run his fingers over her, using her soft moaning as a guide. He loved being able to do this for her, pleasuring her as she squirmed delightfully under him. He kissed her lips and neck as his fingers found their way down her stomach. He used to firm fingertips to rub tight circles against her clitoris. Molly was soon panting hard, her breasts heaving as she gasped.

He moved to worship her beautiful breasts with his lips. Molly had the kind that would entice just about anyone. Large and soft, spotted with tiny pink nipples. Once he'd enjoyed his fill, he kissed down her stomach. She arched into him as he explored every fold between her legs with his tongue. His name was whispered between her moans. "Oh my God, Asher, ahh," she squirmed. "Please... Asher, please, please..."

His fingers slipped inside her soaking wet entrance as he focused his tongue over that tiny but most sensitive and pleasurable spot.

Behind him, to his surprise, Portia physically rearranged his lithe body as he worked his tongue against Molly. She grabbed him under his hips and pulled him higher up on his knees, so he bent forward at a deep slant. Then she spread his legs and reached between them, teasingly stroking him over his cage before finding its lock with the tiny key.

In only seconds, she freed him, and he grew to his full size nearly instantly. It was glorious just to express himself at all this way again. He'd feel like a real man with this rock hard erection and Molly crying out his name, but he knew he was almost certainly about to have his ass pounded by his mistress.

His mouth was still busy with Molly's sweet sex, lapping up with his tongue, stroking her right over her most sensitive area rhythmically. She cried out and reacted by squeezing his head a little between her thighs. For a moment he was stuck, unable to breathe, but minded it very little. "Mmmph," he said only when it became something of an emergency. Molly released him if only so he could finish his work.

He was free, but aching for release now. Portia, behind him, didn't stroke him at all. He whimpered over the absence of her warm hand, and then whimpered louder when he did finally feel her fingers on him, ignoring his penis and only rubbing oil into his hole.

Still, the servant boy had grown to enjoy this most submissive form of pleasure. He panted just as much as Molly, feeling his mistress slipping a finger deep into him. His soft cries of pleasure vibrated through Molly's hard little rosebud and turned her breathy gasps into throaty moans. Portia opened him with one finger, and then two, each thrust equal parts shameful and delightful.

He didn't dare get up from his position to see, but he heard his mistress attaching the strap-on to her hips, tightening the harness. He'd never had this before, and desired it so deeply that he arched his back a little further, presenting his opening to her. With his body alone, he begged her to take him, fill him, fuck him, by holding himself in such a submissive pose.

Portia took him all at once, slowly but steadily sinking the well-lubricated dildo strapped between her legs deep into him. He gasped, and cried out such a loud moan that Molly squirmed and pushed into the vibrations coming from his mouth. Asher was now sandwiched between them, his back entrance filled deeply, his fingers rubbing inside Molly and his mouth sucking on her clit.

Portia's hands grabbed his hips, held him tight, and took him with only long, slow thrusts until he was ready for more. Then she thrust harder and faster into him. Each powerful push made him groan against Molly. It had been so long a wait for this, to serve his sweet-tasting girlfriend, to feel his mistress pounding him from behind. He cried out as a certain shift from Portia made it so every thrust into him stimulated his prostate. Knowing that Molly could see Portia from her position, dominating him like that from behind, only made him harder.

Molly writhed under him, pushing her sex hard against his lips, and he happily ate her up, swirling his stiffened tongue in hard circles. He fucked her hard and deep with his fingers, balancing on his forearms, now shaking with the intensity of it all. Molly shook under him too, her muscles tensing, her thighs going back to squeezing his face against her. He dared to push further, slipping one soaking wet finger into her back opening. Molly arched and cried out, just what he hoped. He felt the first of her growing spasms while he practically suffocated there between her legs.

"Good boy, Asher," Portia praised him as she rocked hard against him, forcing his virgin hole to swallow every last bit of the strap-on. "Keep going. Make her come."

Asher felt his own erection twitching as if possessed under him. Molly cried out loud and long, both holes starting to hug his fingers, and Portia sunk the full length into him again, filling him to the hilt. He suddenly moaned hard, surprising even himself, feeling his body building up without a single touch to his pulsing erection.

Molly came right then, screaming and gasping, her pussy and ass both squeezing his fingers in unison, her clitoris spasming hard against his tongue and lips.

Asher had no time to react, or ask his polite permission, or anything. Portia pumped the strap-on fast and deep into him, pounding him as Molly screamed out her pleasure, and he helplessly felt his own body tumble over the point of no return. He shuddered and groaned, spurting one powerful and long white line after another, without even a single finger upon him. It was intense and strong and drawn out, as if his body had to use some extra effort to shoot without experiencing the kind of penile stimulation it normally did. He practically screamed, on his forearms and knees, trembling with the powerful waves tearing through him.

Portia pulled back, and Asher collapsed forward and rolled to his back. Both servants lay on the soft bed, spent and panting and hot. A couple decades older and wiser and more used to delaying her own gratification, Portia simply began to tend to them and clean them up. She was sweet to her helpless servants in this way, making it easy on them when their hearts beat like rabbits, recovering from mind-numbing orgasms. Asher could guess she'd visit Nick soon, and they'd both be laying in bed beside each other just as spent before long.

She tended to Asher's previously caged penis, revelling in its newfound freedom so openly that it was still daring to stand at half-mast. She cleaned him up and soaked the chastity device in the bathroom. By the time both servants were calm and comfortable again, she broke the news. "What did you both forget?"

Molly squeaked in shame straight away. "To ask."

Asher winced as he nodded. He could barely even speak at the time, his whole face crammed deliciously between Molly's legs. But it wasn't a servant's place to have protracted debates about the rules. He had to accept all his punishments, even if it wasn't always fair.

"We can handle this slip-up right here and now," said Portia.

She pulled up Molly's legs, making the poor thing squeak in embarrassment. She was still on her back, but now her creamy bottom was presented to Portia in this shameful position.

"Spread your legs," ordered Portia.

Molly did, her legs splayed wide and her feet held up in the air. Portia spanked her lower cheeks hard, each whack leaving a little pink splotch behind. Her naked, large breasts kept jiggling up and down, undulating against her with each and every spank. Asher couldn't help but stare, trying to record the scene before him into long term memory.

The punishment wasn't severe, nor did it come close to bringing Molly to tears. But it became intensely humiliating and much more painful when Portia redirected her hand, now aiming it right between her widely spread legs.

"Oh no, please, no, ma'am! Not there!"

"But here's where you were naughty, wouldn't you agree? Stay still."

Molly shrieked in surprise as Portia's hand smacked her directly over her bald pussy. The completely bare skin and the orgasm she'd just had all served to make her extra sensitive. Even though the swings weren't very forceful, Portia had her servant girl squirming and helplessly trying to shut her thighs. Asher was ordered to hold down her ankles and keep her spread open for punishment. He couldn't help himself, enjoying what he witnessed now. It wasn't brutal, but so shameful for Molly, to be spanked right on her most intimate place.

"Ooow, I'm soorrry Mrs. Darrow!" cried Molly, yelping as another spank right between her legs turned her a little more pink.

Portia was pretty methodical about it, giving her tight little vulva a good sound spanking without making her scream or cry. Molly's whole face was red from the humiliation though, and it looked like it really stung. She whined and squealed with each spank. A few swats in a row landed firmly over her clitoris, drawing the most desperate sounding cries.

By the time Portia let her go, she'd taken at least a couple dozen smarting, burning smacks between her legs. Now the gaze of Portia was directed straight at Asher.

He backed up against the far wall, holding frightened hands over his penis. "No, I'm sorry, please no, ma'am!"

She retrieved him and thankfully only bent him over her lap on the bed, in the usual position he took for a bedtime spanking. His backside was perched up over her leg, and his arms straight out in front of him over the mattress. A hand rubbed over his skin. "Men's bodies can't handle what ours can," she teased him. "A smacking there has to be done more carefully than I care to deal with tonight. Let's just spank your little naughty bottom until you're a repentant boy."

"I'm already very sorry, ma'am," tried Asher.

"We'll see," she said, and began a fairly sound spanking, her hand rising and falling with the same firm strength she'd used on Molly's upturned cheeks. They were all strong and well-aimed swats, enough to draw at least a grunt from him every time. Asher was wiggling and fighting to not protect himself with wayward hands before long.

She stopped to rub him when he began kicking up his ankles, reacting to his growing discomfort. Here he understood this spanking was more to amuse her than a true punishment. She wasn't actually annoyed with him. A little playful squeeze to the fleshy base of his cheek teased him and made him moan.

"Did you enjoy getting your bottom fucked, sweetheart?"

"Yes, ma'am," he admitted. He must have, to have lost all control of himself without a single touch. It made him flush from slight embarrassment, knowing he reacted that way to a woman taking him hard up the ass with a cock-shaped dildo attached between her hips.

"Good," she said.

Portia turned him back over, allowing him to sit up, and gave him a kiss on the forehead. Then she did the same to Molly, as both her servants were in her good graces.

"Alright, I want you to listen. First, I want you to find a way to steal all the data from Sean's smart-band without making it obvious or touching Mrs. Bennett's phone. Second, find a way to set off Asher's health alert. That way he can realistically fake a medical emergency at the party."

They nodded to her, but Molly raised a question. "Ma'am, won't the video evidence show that Sean's smart-band safety alerts were ignored?"

"They will, but then the data will back up the video files. So easily faked these days. This is the kind of bulletproof evidence you need to take down someone as powerful as Mrs. Bennett. We can't have anything go wrong with this plan. I'm serious. Be careful and use your heads!"

"Yes, ma'am," they said.

The two got to work that very evening, using every trick they'd ever learned. Molly was given her uniform once again, and Asher was no longer caged. The threat of chastity still loomed over him, especially if he and Molly got up to no good when they were supposed to be working.

During the next few days, Asher came to realize he loved watching his girlfriend studiously bent over a laptop just as much as bent sensually over for other activities. She was so intuitive and smart, the way she worked out ways to toy with the little electronic gadgets on their wrists. Seeing her this way, in her element, in the zone, was a different kind of attractive. He found himself staring at her like a schoolboy with a crush.

Asher was no slouch himself, and when he wasn't dreamily watching Molly, he was hunched over his own laptop. But his best idea came to him in the shower after his morning workout. He hurried to his laptop in just a towel, and pecked at the keyboard. "I think I've got it. I know how to make sure it won't mark his band as synced. Then she won't catch us in the act."

Molly stood over him, looking over his work, and agreed. "That's it! That has to work. We'll try on mine."

The only issue was the fading on and off LED lights that signaled the syncing smart-band. People in the party might see it, so they'd have to do this quickly. Otherwise, the plan worked perfectly. Asher had done it.

"You're a real hacker," said Molly, teasing him.

"No," he said.

"Hacking is very naughty. Punishable with a year in prison. But maybe I can promise not to tell the authorities if you let me..."

"Oh?"

The two sighed in unison instead of continuing. This would get them into serious trouble. Chastity cages or not, all servants were expected to save their bodies for their mistress. And if Molly spanked him, even a little, they'd both get so worked up it would be torture to just stop cold and go no further.

So they walked away that day, and went back to work.

Two long days later, Molly had accomplished her own goal. Her ingenuity was more perseverance than epiphany, but it worked just as well.

"Guess what?" she told Asher. "I've not only figured out how to fake a medical alert, but I think I've just found a way to block all our data, including our arousal responses and climaxes, from Mrs. Darrow's phone."

Tampering with that aspect of the smart-bands wasn't exactly the task, but Molly seemed most focused on that in particular. Especially since it had been six days since their last release, and much longer since Molly could truly explore her dominant side.

"Mrs. Darrow will punish you so badly if this doesn't work. And probably cage me again."

"It will work!" insisted Molly. "I'm ninety-five percent sure I've got it. This was her plan, probably, to have us reward ourselves if we figured this out. If you were my servant, I'd incentivize you just like this."

"I'm not sure that you're the same kind of dominant as Mrs. Darrow," said Asher. Molly gave him a glowering look, so he added his polite title for her dominant side. "...Miss."

"Look," said Molly, tapping at the hacked app on her phone. Asher's band suddenly went to an alert, for no reason whatsoever. He was impressed. She'd truly figured out how to fake a health emergency and it was exactly like the real thing. With another tap to her phone, both bands went dark. The LED letters that spelled SERVANT were black. "See? They're both offline now."

"Wow," said Asher. "So... we... anything we do..."

"Get on your knees."

He was quick to obey, and Molly yanked off her panties, lifting up her skirt for him. He admired the view, all tight except for her slightly protruding rosebud. She was thinking about this moment for a while, it seemed, already so excited under her panties. Asher understood what he was asked to do, and began kissing her slightly parted slit immediately.

She groaned and pulled his head closer to her, both hands gripping his hair. A tent grew in his pants as he pleasured her with the soft point of his tongue. He was sitting on his knees, cheerfully being used like a sex toy, Molly crying out her pleasure above him. She thrust a little into him, fucking his face as he desperately tried to keep up.