There were few words to describe how much Laura hated her situation. She tugged futilely at the silk scarves tied around her wrists for the twentieth time, but she was still tied and helpless on her bed. She tried to relax, but she was face-down and being slowly screwed up her ass; relaxing was more difficult than usual.
Jim had though that after three or four months of having Laura in hopeless financial domination, he'd have grown tired of coercing humiliating sex out of her. He'd been wrong; though Laura wasn't really his type, his sheer hatred of her and the feeling of power as he took his pleasure from her thin, angular body was one of the greatest aphrodisiacs he'd ever experienced. Sweat ran down his body as he clutched her by her shoulders and slowly sank his thick cock into her quivering ass again and again. With anyone else, in any other circumstances, he'd have gone just a little faster and gotten off a lot sooner. With Laura? The long, slow, humiliating and painful sessions of anal in bondage were transcendent.
To be fair, she seemed to enjoy herself a scant few years ago when she constantly crushed his hopes and dreams as Jim was dating Diane, Laura's daughter. He'd been a struggling college student at the time, and Diane was clearly "too good for him." When the relationship had crumbled, Jim thought he'd seen the last of Laura.
He'd focused his energies on building success in the meantime and had managed to aim high and invest well. He'd accrued so much personal wealth and potential that when Laura fell on hard times and burned all her other bridges, Jim was the only person she could turn to. After the death of her husband left her with debts too great to manage, Jim had agreed to cover all of them, and a large amount of expenses she couldn't afford, in exchange for pleasuring him.
Even at a thousand dollars an orgasm (two thousand for anal), the debt was being repaid far, far too slowly for the older woman's tastes. She whimpered as Jim slowly plowed her aching back door, groaning in relief as the tightness and power rush finally brought him to a powerful orgasm. He trembled as his throbbing cock pumped gush after gush of hot cum into her bowels, then slowly withdrew before rolling onto his back. He pulled loose the slipknot on her wrist as he got his breath back; the more-or-less regular workouts were keeping him in good shape.
Laura slowly untied her other wrist and rolled onto her side. "Two?" she asked.
Jim nodded. "That's the deal. Two thousand when it's anal. That makes five thousand this week... not bad at all."
Laura grimaced... with fifteen thousand dollars of expenses a month, IF she could keep up this pace, she'd only be able to pay off a small amount of the back debt. The deal, as much as it let her keep all her nice things and services, was more akin to slavery.
"Do you want to shower with me, again?" she asked. She would rather have cuddled a rattlesnake, but she could occasionally manage to get him off with a handjob in the shower afterwards. Every spurt of cum was another chunk taken out of her debt.
"Sure, we can both use it," he agreed.
In the shower, under the hot running water, Laura soaped his back and ran her hands over his muscular body. She had almost no interest in sex, but she was learning what it took to please a man. As the soreness of the evening's activities leeched out of her muscles, she considered her next actions carefully.
"You said, if I could get Diane involved, doing things with her would earn twice as much?" she finally asked, as she started to soap his cock.
Jim raised an eyebrow. "I did," he agreed. "But she's out east with what's-his-name. Doesn't seem likely."
Laura curled her fingers around Jim's member and gently squeezed. "They broke up. She wants to move back home."
She could feel the throb that brought to his dick. She capitalized by starting to stroke him softly, lathering him and letting the soap lubricate her gentle manipulations. "Wouldn't you rather have her?"
Jim moaned and leaned back against the tile wall of the shower, letting Laura work at earning another grand. Physically, Diane was much more his type, softer and curvier than her mother. She was also a great lay. She'd been downright cruel in breaking off their relationship, though. He wasn't hating the idea of things going in the direction they were heading.
"That's... that's really good," he said. Laura felt him hardening in her hand and went down to her knees in the shower, getting in a better position to work out a load of cum.
He looked down at her. "Tell you what," he said, brain working even as his cock was filling with blood. "It's twice as much to have her instead... but if you're both there when she brings me off, I'll give you three times the going rate."
Laura's hand slowed as she considered the ramifications, but she picked the pace back up pretty quickly. "So... if Diane and I are both there, and she makes you cum, it's three thousand dollars?"
Jim nodded. "Or six," he said, "if you're there when I cum in her ass."
The offensively perverse thought made her clench her fist reflexively, bringing a little yell from Jim. "Or not," he said, moving to take her hand away.
"No, no, please," said Laura, realizing she was about to lose out on a chance to make her debt actually go away. She leaned in and suckled on the head of his cock as she stroked more gently, and Jim relaxed back against the shower wall.
Her sucking lips and lapping tongue soon brought another spurt of his goo into her waiting mouth. She swallowed it down; she'd have spit his cum out, but the last time she did that, he'd stayed away for a week. When she swallowed, he was sure to be back in a few days.
"You're getting very good at that" Jim said. Laura nodded, happy that she was pleasing him and assuring more payments in the future, rankling that she was becoming a proficient sex slave.
She stood up and finished rinsing them both off. "I'll talk to Diane," she said. "She's not going to be happy about this... I don't know if she'll agree."
Jim shrugged and turned off the water. "That's a 'you' problem," he said. "It's the difference between paying your debt off in years or paying it off in months. I'm sure you'll think of something... you seem able to convince Diane to do things."
The words stung exactly as they were meant to. Jim dressed and left, not sure when he'd be able to come back. Laura watched him leave, part of her hoping he'd be gone for a good lone time, part of her needing him to come back as soon as possible. Not for the first time, her stomach knotted from the conflict and tension.
Jim didn't really think much would come of the situation; Diane and he had not left on good terms, and it seemed unlikely the headstrong redhead would ever consent to anything as demeaning as helping her mother sexually pay off her ridiculous debt. He went back to his day-to-day of managing a growing business empire, figuring he'd go back over to Laura's in a few days for a quick fuck or two.
He was caught by surprise when Laura sent him a text... "Diane's here and wants to talk."
Responding that he'd be over that evening, Jim ran over some possibilities in his head before deciding that he'd just roll with whatever happened. He held the deed on the house, among other assets, until the debt was paid off; it was always nice to talk to an ex from a position of strength. He had a light dinner and went over to Laura's with an amused curiosity.
Laura had started to dress a little more pleasantly for his visits; she was in a peach-colored silk robe when she answered the door. Diane was waiting for them at the kitchen table in her usual jeans and t-shirt, along with a sour expression.
Jim smiled and extended a hand. "D! Been a while! How's it..."
She shut him down with a glare. "You're a sick fuck. I just want you to know that."
Jim let the hand fall back to his side, but the smile stayed. "Yeah, hit the nail on the head, there. I absolutely am." He'd gotten pretty good at reading her in the past... he'd known she was breaking up with him before she did. He was even better at it now; reading people was a large part of how he'd gotten as successful as he was. She really wanted him to believe she had some control in the situation, but it was obvious to him that she did not.
Laura put a hand on her daughter's shoulder. "I told her about our arrangement," she explained. "And about your offer."
"I figured. Mind if I sit? It's been a long day."
Laura nodded while Diane glared, so Jim sat down after pulling a chair out for Laura. The three sat in an uneasy silence as Laura composed her thoughts.
"Diane needs a place to stay," she finally explained, as Diane looked away. "The break-up; it wasn't good. Some bridges got burned."
Jim was entirely unsurprised. Like mother, like daughter.
"So, if she wants to stay here, she has to help me pay the debt off. It's that simple."
"I do NOT believe this bullshit," said Diane, her face going red from shame, anger, or a combination of both. "How the FUCK do you have the kind of money to cover this debt, anyway?"
Jim shrugged. "Turns out I'm good at a few things after all. Made some better choices, invested in the right markets, bought the right properties when they became available. All in all, covering the debt was pretty much pocket change."
He didn't need to be good at reading people to see her suddenly doing the math. Diane wasn't good with money on her own, no more so than her mother. She was more than likely starting over from scratch after the disastrous breakup, and she'd be looking for a source of the nice things she was accustomed to. Enter an old boyfriend who'd hit it big. The fact that the old boyfriend was screwing her mother and trying to get her into a three-way with them wasn't as much of a problem as she'd thought.
Jim wasn't entirely sure how to play that angle; his interests in his old flame was purely part of the sexual power trip he was enjoying. It would be fun to string things along, though; it might spice things up.
"If this thing is going to happen," said Diane, "I have some rules."
"I see," said Jim. "Do they involve how you're going to pay off the debt on your own?"
"What?" she said, caught off guard. "No. Why..."
"Because that's what you'd have to be doing if you wanted to make any rules, here. This isn't hard... we do it my way, or we don't do it. That simple. Until I'm paid off, you're not in your mom's house... you're in mine. So, this thing is going to happen... with you living here and involved, or you not living here. I'll give you a few minutes to make up your mind, I know it's a big decision."
He sat back casually as she looked at him aghast.
"How the FUCK did you get like this?" she asked. "You didn't use to be such a prick..."
Jim shrugged. "Yeah, I know. I used to try to bend over backwards for everyone, especially my girlfriend. Turns out that doesn't get you anywhere but dumped. I'm a lot happier now that I bend other people over backwards."
Laura looked on, absolutely beside herself. If this thing didn't work out, she might be paying Jim off with her body for the rest of her life... or worse. Her only real chance of getting ahead and escaping the debt was arguing with the man in charge of the entire situation, and at any moment he could simply decide to have her evicted from the property rather than endure any more of Diane's ire.
Diane looked at the ground. "Would it help if I said I was sorry? I made a mistake."
"I appreciate hearing it," admitted Jim. "But the deal isn't changing."
The curvy redhead winced, and Jim could see her mind racing. She was looking for her way out, for any loophole or opportunity to seize just a little control. Her obvious desperation was getting Jim painfully erect.
"Ok," she said after a minute, defeated. "I just hope you don't expect me to enjoy this."
Jim shrugged. "Oh, I don't," he said. "Not what this is about, anyway."
She looked up at him, then between him and her mother, tears dripping down her face. "So, what now? How do we do this thing?"
Laura choked back a sob; she was torn between the relief that things were going to work out and the inescapable fact that she was now, effectively, pimping out her daughter.
Jim could see that both of them were distressed and upset. He had a momentary thought of going a little easier on them, loosening up the terms of the deal or forgiving a large part of the debt to sweeten things. It didn't last long.
"How about we go into your mom's room and figure it out?" he said, standing up. The two women also stood, and they walked across the hall together into the large, well-furnished bedroom.
Jim left his suit jacket on the back of his chair in the kitchen and sat in the overstuffed armchair in the corner of the bedroom. He unbuttoned his collar and cuffs, looking over his nervous, mostly unwilling partners.
"Why don't the two of you start by undressing?" he suggested.
Laura nodded and started to untie her robe, as Diane spat a "fine" and began to lift her t-shirt over her head.
"Hang on a second," said Jim. "How about you undress... each other?"
They both looked at him in shock for a moment.
"Jim," said Laura, pleading, "no... you can't..."
Diane, on the other hand, was realizing how the game was going to be played. "Fuck it, mom. Just do it so we can get it over with."
The curvy redhead untied her mother's silk robe and opened it, revealing Laura's white lacey lingerie. As Laura stood still, shivering, Diane peeled the robe down off her shoulders, then unfastened the frilly bra and let it fall to the ground.
Laura, now only in her panties, swallowed, and lifted Diane's t-shirt up and over her head. With trembling hands, she unsnapped her daughter's tight blue jeans and unzipped the fly. Dropping to her knees, she dragged them down to Diane's ankles, where the redhead stepped out of them.
Standing again, Laura slid her hands around her daughter's sides and unclasped her plain white bra. As Diane's full, round breasts bounced free, the two women, tears on their cheeks and now clad only in their panties, slowly embraced one another for comfort.
Jim's cock was rock hard, and his mind raced at all the possibilities. This had turned into a much better investment than he had ever counted on; truth be told, he'd figured early-on that he'd get bored with Laura and forgive the majority of the debt just to be done with her. Now? He watched his nearly naked ex-girlfriend hugging her nearly naked mother as tears streamed down their faces, and he didn't think he could ever get enough.
Slowly, Jim stood. "Look, I can see this is a bit much for you both. Why don't I leave and we can work on this another time..."
"No!" said Laura, snapping out of it. "No, it's ok, we can do this."
Diane was taken aback by the desperate tone in her mother's voice. "Mom, he's giving us a break, it's ok..."
"If he leaves, we can't pay down!" said Laura through tears. "It will never end!"
"Shit," said Diane, shaking her head. "This... this is fucking sick, Jim. Is this what you really wanted?"
"Leave him alone," said Laura. She dropped to her knees in front of Jim and started to unbuckle his belt. "This is the deal... I made mistakes, a lot of mistakes, and Jim is the only person who can help me out of them. If it wasn't for him, you wouldn't even have this house to come back to... your stepfather left me SO far in debt I'd never get out! The bastard bought a BOAT! So if you want a place to stay... help me with this. Help me with him."
Jim didn't resist as Laura opened his pants and pulled his slacks down his legs. Staring at the ground, Diane slowly dropped to her knees next to her mother, and helped Jim step out of his pants. She was well familiar with the cock that stood hard and proud before them.
"All we have to do... is make you cum?" asked Diane, as Laura gently wrapped her thin fingers around his throbbing rod.
"That's it," said Jim. "Might take a little more effort than you remember, but that's basically what it takes."
Diane slid her hand up the inside of his leg and slowly cradled his heavy balls in her soft hand. He watched as her mother stroked his member softly and lovingly, surprised that the harsh woman could do anything with a gentle touch.
As Laura's stroking hand brought fiery tingles of pleasure through Jim's cock, Diane leaned forward and gently kissed the tip. As much as it galled her that Jim had turned her mother into a sexual slave, there was a burning ember of old grudges deep in the redhead's heart that got a perverse pleasure from watching her ever so lilly-white-puritan mother giving a handjob to a man she'd hated.
It was just enough guilty pleasure to bring Diane's free hand down across her own belly and into the waistband of her panties. She softly groaned as she began to finger her hot slit, and as she caught Jim's eyes, she opened her mouth and took his cockhead inside.
Jim moaned in pleasure... it had been a while, but that mouth was still as pleasurable as ever. It was one thing to instruct Laura in every little thing his cock liked, but it was another thing entirely to have Diane's talented lips and tongue finding every good spot and exploring for new ones. She suckled expertly on the head of his dick while Laura continued to stroke it softly, a smile on her face to please Jim, but tears dripping down her cheeks as she watched her daughter degrading herself.
"Laura, lick my balls," said Jim, eyes slowly closing so he could focus on the delicious sensations in his cock.
Diane helpfully lifted Jim's heavy scrotum towards her mother's mouth, and Laura obediently released her grip on his shaft, bent down, and began to stroke the underside of his swollen orbs with her soft, warm tongue.
With more room available on the shaft of Jim's cock, Diane started to bob her head back and forth, slowly taking more and more of him into her hot, wet mouth. Jim couldn't help slowly thrusting his hips as mother and daughter teased and pleasured his throbbing, sensitive member. In the back of his mind, he fully understood that if he let things keep going like this, he was going to be paying three thousand dollars for this blowjob. As Diane slowly dragged her lips and tongue back from midshaft to head and just as slowly took him back inside, he figured that was a fair price.
Diane braced herself against Jim's muscular thighs, both for balance and so she could judge how close he was to cumming by the trembling of his legs. Her mom might have picked up some key skills very quickly, but Diane knew a lot more tricks. She wriggled her tongue along the underside of his hard dick, pausing at the frenulum to draw little, hot, wet circles. Her lips puckered tightly at the end, kissing the very tip. Then she was plunging back down on him, drawing another gasp of pleasure.
For her own part, Laura was in mostly new territory. Still, she lapped at the underside of Jim's balls slowly and gently, while wrapping one arm around her daughter to make it easier to share the space in front of him. She could tell that Diane was pleasuring herself, and since she couldn't conceive of any reason that her daughter would be taking genuine pleasure from the situation, Laura assumed it was something that would please Jim more, and maybe make him cum faster.
With her free hand, Laura reached down the front of her silky, lace panties and began to gently finger her own sex. This was something she rarely did on her own, and she didn't really associate her own pleasure with these sessions; she was occasionally aroused when Jim had sex with her, but it rarely resulted in an orgasm. As she slipped a finger between the outer folds of her pussy and began to tease the pink flesh within, she moaned quietly and started to tongue Jim's balls more enthusiastically.