Over the Lap of Luxury Pt. 06

Notes: This is a spanking, discipline, and erotic humiliation series. There's both F/m and F/f content. The sexual content is consensual but the punishment scenes this chapter are very reluctant and more intense than usual. Please check tags. All characters 18 and over.

The only good thing to come from this new assignment was Portia changing their smart-bands' LED lettering to blue. The bands around their wrists were how servants were collared, politely and a little more discreetly, and blue signified that they were fully trained. It was something both took a little pride in, but Asher guessed that their punishments would increase along with their ranks. Neither had the excuse of not knowing better now.

The pressure was on after a few days of no progress with their latest goal: White-hat hacking the mansion's video surveillance system. Molly had already been kept shamefully naked when at home, wearing nothing but socks, shoes, and her smart-band. She failed to adjust, constantly blushing when witnessed by the myriad other workers in the mansion. Last night, she'd complained bitterly to Asher about the constant shame, hiding under his sheets and in his arms.

If watching his girlfriend suffer wasn't enough, Asher was beginning day five of chastity. The humiliating device around his genitals was a constant reminder of his submissive otherness, even more than his uniform and smart-band. He could feel it when he closed his eyes, or after hours, or even at four in the morning when woken suddenly by his body's natural reaction to certain exciting dreams.

One morning, an impatient Portia stood before them, arms crossed. "What is the problem? Why aren't you able to do it?"

Asher wanted to scream that being a programmer wasn't the same as being a hacker, but he refrained, desiring the ability to sit down again.

Molly spoke up on both of their behalves. "They don't teach you how to break into security systems in college."

"Then find another way," she said. "Be creative. Be intuitive. You're both very smart. Figure it out."

"Yes, ma'am," said Asher.

The two servants had an idea the following day. But to enact it, one of them had to check Nick's office, which was absolutely verboten. Asher volunteered for the job, because it was largely his own idea. It was complicated, but involved trying to get into Nick's laptop to have greater access to the local network.

Unfortunately, Nick ran a technology company, and was decent enough with it himself. His laptop was protected by a numerical code that Asher already knew from experience would lock itself up in ten failed attempts. With a look behind himself, he checked that the coast was clear. Then he tried to find clues, like birthdays and anniversaries.

In his search, he happened upon a collection of envelopes from Mrs. Bennett, who had been blackmailing Nick for years now. Asher eyed the photo in one of them, capturing Nick in the heat of a moment with a bot that mops hardwood floors. For some reason the man who was in an open marriage, permitted to date whomever he chose, seemed to prefer the bot's soft, wet, rhythmic stroking.

"Asher..."

His name was spoken, softly and coldly, a lot like he imagined serial killers talked. Asher looked up from his seat, normally Nick's leather desk chair, and slowly put the photo right back down. He didn't expect Nick back home from his trip so soon. "I- I'm- I was trying- Mrs. Darrow told me to get-"

Nick had a firm grip and was twice Asher's weight, built like a football player. He nearly dragged the thin servant boy into the library, where Portia was enjoying some literature. How nice it is to have a hobby in common with his mistress, Asher thought idly, before being thrown before her feet. He landed on his hands and knees and had the good sense to stay like that.

"He was in my office - rifling through papers, in the letters, looking at photos! Please punish him soundly, darling, before I do it myself."

"Asher! What were you thinking?"

"I thought maybe I could get in through the administrator privileges on his laptop, but I needed a code, and-"

"Quiet." Portia spoke down to him from her perch on the sofa while Asher looked pleadingly up into her eyes from the floor, sitting submissively on his knees. "You knew there wouldn't be a code in those photos."

"Yes, ma'am, I- I'm so sorry, I just- I was... there's no excuse. But I'm sorry!"

"You were curious. All intelligent people are naturally curious. But your obedience, respect, and servitude always come first. And by now you should know that! I'm going to have to punish you severely for this."

She got up, pushed the white button on the wall, and called to Molly over the intercom. "Bring Asher's small wooden paddle to the library, please."

The punishment Veronica once took with that very paddle flashed through his mind. It looked brutal. She was writhing and sobbing and screaming from the start. For embarrassing Portia's husband and breaking one of the biggest rules, Asher expected his bottom would be spanked even worse than that.

While Portia waited for Molly to return with the horrible little paddle, she ordered Asher to stand up straight and put his hands on his head. She began undressing him.

The stripping proved to be a punishment in itself. She lowered his pants and underwear, giving her very dominant husband Nick a good view of his penis, shriveled up in its chastity cage. He acknowledged Asher's predicament with a wicked grin, anger still churning in him. "Keeping him like that for the next five years would be fair," he said.

"Maybe I will," said Portia.

"Please don't, I'm so sorry," said Asher.

"Don't apologize to me. Apologize to my husband," said Portia, giving Asher's newly bared bottom a solid spank with her hand.

"Ah! I-I'm very sorry for going into your office and um... looking where I shouldn't have looked. Sir. Please... please please-"

"Please what?" asked Nick.

"Please have mercy on me," said Asher, every word a terrified, trembling whisper.

"No," said Nick, he paced a little through the private library, as though trying to walk off his rage. It seemed like his attempt was unsuccessful. "You deserve to get the spanking of your life. I want you reduced to tears. Once you're bawling like a little boy I'll know for sure how sorry you are."

He'd never cried more than one or two tears after his worst punishments, and so he looked to Portia for help. She only shook her head at him. "He's right. That's what you deserve, Asher. I know you're overwhelmed with your new assignment, but you need to figure it out. There are worse punishments out there than what you'll receive today."

Asher lowered his head from pure anxiety, and stood there shivering and waiting, his pants still shamefully around his ankles and his hands folded over his head. Nick kept looking over at him, seeming to enjoy the servant boy's total humiliation as some payback for his own unwelcome embarrassment earlier. As the seconds ticked by, Asher heard Nick's words repeated again and again in his mind. Spanking of your life...

Molly finally came into the library, still naked aside from shoes and socks. She handed the little wooden implement to Portia. A wide-eyed glance Asher's way showed how empathetic she was to his plight. She knew he'd been caught, but didn't even know the full extent of it.

"Mmm." Nick took sight of the newly denuded servant girl for the first time, and seemed to finally cool off, strangely, when he was probably very hot under the collar. It seemed Nick shared Portia's taste for an ample bosom and bottom. "Well, well, well, my darling, I love what you've done with Molly."

Portia gave him a pleased smile, but quickly returned to her focus on Asher, whose heart-rate was reaching new levels. She pat her lap and only gave him one pointed look, and he knew to obediently lay down for the spanking of his life.

His bare bottom was already high up over her thigh and she made it worse by sliding him forward. Now his head was just about on the floor between his forearms, and his feet ended up off the floor behind him. His bottom was particularly prominent now, his vulnerable sit-spot in a prime position to receive a blistering from the paddle.

"Nick, please hold his ankles down. Molly, please get his wrists."

Molly knelt before him and clasped her soft hands around each of his wrists, and Nick more gruffly secured his ankles. Portia further immobilized him with an arm around his waist, and rubbed his exposed bottom with the paddle. He felt so helpless and embarrassed, as it seemed like three people were all punishing him at once.

"Asher, never go snooping around Nick's office again. Not even for this. Do you understand me?"

"Yes, ma'am! I'll never do it again!"

"You had better not, boy!" shouted Nick.

"No, sir! I'm sorry, sir!"

"Molly, hold him down as tight as you can. He won't be able to stay still with the paddling he's about to take."

"Good," said Nick, and Asher moaned in agony.

Portia tapped the paddle against his left cheek, aiming, and then cracked it down hard. He yelped without even meaning to do it. Every single hard smack against his flesh caused a helpless reaction like that. He constantly pulled impotently at his restrained arms and legs, and after only a dozen smacks he began to shriek from the pain. His backside was on fire now, and somehow getting worse. Over and over he howled out his cries.

"AAhh!" he screamed. "I'll never do it again! AAAAHH!"

"And you'll respect my husband and his office?"

"YEESSSS!" he cried, before devolving into only shrieking again and again as Portia disciplined his backside.

Portia sometimes slowed her pace, sinking severely hard swats of the paddle into his sensitive sit-spot. She preferred most to spank him rapid-fire, peppering his entire backside in searing pain. He writhed continuously over her lap, squirming and fighting as much as he could while secured in place. No attempt at a kick made it past Nick's firm hold.

All the spanks felt white hot, tingling and smarting worse than any implement he'd ever taken so far. The paddle, even while small enough to be used over the knee, still got a big portion of his exposed cheeks at once. And Portia just landed three of her hardest yet on the most sensitive curves of his bottom.

"AAAHHH! PLEASE STOP! PLEASE NO!!" he screamed, trying to twist away from the paddle. All his nerve endings begged him to break free, but he couldn't. It was like his body went on autopilot; the way it will yank a hand from a flame, it attempted to shield his bottom from more of the paddle. But it was utterly impossible in the grips of three people, and the frustration of his helplessness to face his pain overwhelmed him.

This truly was the spanking of his life, as promised. His body was getting tired of fighting, even through the severely stinging pain. His muscles were weakening with exhaustion after all his fruitless writhing.

He went limp, and just about as soon as that, he felt something heavy in his chest and heart, a sort of cold mist. It made him twist his face a little. His next few shouts of pain all sounded congested. His eyes pooled with tears. At the next hard whack to his sit spot, he instantly fell into a fit of helpless sobbing. His back shook and heaved. He sucked in deep breaths only to scream-sob them out right after, tears falling freely.

At the sound of her bawling servant boy, Portia slowed his paddling to a halt. Her two assistants let his ankles and wrists go free without being told. Asher no longer struggled anyway. He was limp over Portia's lap, weeping with total abandon, his bottom burning terribly. It had been so long since he cried like this for any reason - in fact, not since he was a little kid. It relieved him as much as it embarrassed him. It seemed to help in some strange way, breaking into pieces like this.

Portia tried to settle him, rubbing his back and caressing his hair and scalp. At this point her efforts did very little to slow his tears, but Asher still appreciated the gesture. "Well, Nick?" she asked.

"Alright," he said. "I think he's learned to stay out of my office. At any rate he won't be able to sit at my desk, or anywhere else, for at least a week."

That was probably true. Asher's burning bottom was throbbing, feeling swollen and achy. The lingering pain mingled with some leftover guilt, and kept his tears flowing freely.

"There, shh," said Portia. "Your spanking is all over."

Nick walked off and Molly was told to go back to her quarters. Portia was left alone with Asher, so she helped him dress. Though she wanted him to sit by her side, Asher couldn't bear it, and put it all his weight on his leg and thigh, leaning against her. She cuddled him against her breast, petting his hair and letting him spill the last of his tears.

"I know that was harsh, but you had to learn. Sneaking into the main offices are not the way to solve this problem. If you had done that to Mrs. Bennett's office, you'd suffer a lot worse than you did just now."

"Yes, ma'am," he said, understanding. "Why didn't my band alert like Sean's last weekend?"

"He was being spanked just about that severely over unhealed bruises and welts, and you weren't."

He thought about that, how much worse it could have been, and summed up his feelings with a sad, "Poor Sean."

"Yes, and this is why we'll help him - and her blackmailing victims of course. If you can get it together and focus."

She kissed the side of his head, a little sign of her forgiveness. Asher sighed against his mistress, relaxing into her embrace. A strong sense of peace washed through him as his eyes finally dried. Portia rocked him a little like she might rock a small child, and Asher didn't complain.

His calmed mind showed him slower, clearer pictures of his ideas, until one stood out above the rest. It had the advantage of having nothing at all to do with hacking.

He recalled that when there was an incident with the cleaning crew setting him up for a punishment, Portia's personal assistant Raj was able to access all the security footage without any outside help. "Ma'am? Does Mrs. Bennett have a Raj of her own? Who else would have access to her surveillance system?"

"Now you're onto something, aren't you? She does have her own Raj; a man named Miles, not much older than yourself."

"Is there any possible way that we could talk to Sean alone?" he asked. "He could tell us if Miles is trustworthy. Or if anyone else might have the codes."

"It's hard to get Sean alone," said Portia. "Mrs. Bennett doesn't allow him a phone or access to the internet."

"There's one way," said Raj. They both looked up, startled to see him in the doorway. How long had he been there? "But it'll have to wait until Saturday."

It turned out that every Saturday, Mrs. Bennett sent Sean out with Miles to shop. Mainly the two young men were told to get things that bored her, like medication, groceries, and household supplies. Raj had seen them out a few times while running small errands like this for Portia.

So Portia, Raj, and both servants went out to the local upscale grocer even though they had nothing in particular to buy. This was not the hidden village, and Asher supposed Portia probably shouldn't have dressed quite so extravagantly. Nor should she have remarked so enthusiastically about all the different types of bread. The other three held back their laughter at how she'd clearly never done her own grocery shopping before.

It was also an experience for many middle-class shoppers. They were well off enough to be employed, but rarely saw servants trailing behind their billionaire in person. With great embarrassment, Asher saw them staring and whispering behind hands to one another. He had a sinking feeling they were all picturing Portia punishing him.

All he could do now was keep following the rules and not earn a smack or two over his pants right in this crowded store. He held his hands obediently at the small of his back and kept following at his mistress' heels, but not so close as to bump into her.

Molly tapped his hand, gesturing with her head. She pointed out Sean, in his street clothes today, talking to another man. He was handsome and tall and very differently dressed than Sean in his tailored suit. The pair seemed oddly happy to be handling the grocery list, picking out the finest oranges.

"Sean and Miles," said Portia, noting the sighting to herself. "Okay. I'll see if I can come up with a reason to talk to Sean alone."

"I don't think it will be a problem, ma'am," said Molly. "Look at them."

Sean and Miles lingered in a gaze for much longer than normal. Then Miles brushed his fingers over Sean's hand, and Sean leaned toward him so close that they might kiss right over the display. But they backed away at once, as if realizing with a sudden horror that they were in a crowded store.

"They're in love," said Molly.

Asher could see it playing out in his head. The day Mrs. Bennett hired Sean, he was able to look past her cruelty and signed the contract because he found her assistant so attractive. While he almost certainly enjoyed his occasional trysts with Miles, the abuse he took was not a fair price. And it couldn't have been easy for Miles to witness it.

"My observant, good girl," said Portia. "I think you're right."

She strode over there with such conviction that Sean and Miles backed farther away from one another, frightened their love would be condemned. It took Sean just a moment before he said, "Mrs. Darrow." He and Miles both gave her a slight bow at the neck in greeting, as one typically does for royalty.

Now a lot of people were looking at the group, certainly curious about what connection the pair had to Portia Darrow. A few shoppers had already pulled out their phones. So Portia made it simple and quick and kept her voice as low as possible. "Sean. How have you been lately?"

It was her way of asking if the plan worked, if Mrs. Bennett had been spanking him with the less serious paddle and had stayed unaware.

Sean nodded when he said, "I've been much better, ma'am, thank you so much."

"Wonderful. Good boy. Miles, please come see me once you're off work tonight."

He looked curious, but worried and unsure. So Portia made his decision a lot simpler.

"It's for Sean."

He agreed with a polite bob of his head.

They immediately parted ways, not wanting to give anyone a reason to upload their boring footage online. But it wasn't quite good enough for Portia, who became paranoid that their meeting would be spotted by Mrs. Bennett on social media.

"Asher, bend over. Grab your ankles. I'll give them a real show."

"Please-" he whispered.

A peacekeeping bot rolled past. They were tall and angry cylinders that could keep the peace at a rate of ten bullets per second. Everyone stepped back a moment, but Portia hadn't forgotten her plan.

"Asher! Bend over, young man," she said louder, and those phones came out again, far more than before.

He whimpered, not for show but in an earnest reaction to this shame. But he dutifully grabbed his own ankles, bent doubled over. Portia retrieved his paddle from her purse. She'd gotten them both the real implements some days back, but neither felt its punishing sting aside from a few test swats in the store. Both paddles were marked as being squarely in the centre of the pain scale, promising a good sound spanking if desired.

Portia aimed the little paddle at the seat of his pants, and gave him ten smarting spanks right there in aisle two. The anticipatory spaces between spanks were all drawn out, as Portia played it up for the dozens of cameras capturing the moment. Asher helplessly squeaked out a cry for each and every swat, reigniting the sting from the spanking of his life a couple days prior.