A Financially Arranged Revenge Fuck Ch. 04

Jim was at a unique crossroads in his life. He was struggling to find a way that things could be better.

His bitchy ex-girlfriend Diane was on her knees in front of him as he reclined in the overstuffed armchair. She was naked as the day she was born, her wrists tied behind her back, her red-haired head bobbing up and down as she voraciously sucked his throbbing cock.

Laura, his ex-girlfriend's even bitchier mother, was also naked, kneeling behind Diane. As Diane slid her pouty lips up and down Jim's cock, Laura was reaching around and fondling her daughter's breasts, gently pinching and twisting her nipples. The extra stimulation made Diane moan and whimper around Jim's big dick as she sucked, adding to his pleasure. The look of disgust and shame on Laura's face was the cherry on the cake.

Diane, supple and curvy, jiggled and bounced gloriously as she slaved away at her task. She sucked Jim's cock like her home depended on it, which it did. It was her mother's poor financial sense and immense debt that had caused this situation. When Diane was faced with homelessness if she couldn't move back to the family house, she fell to the same trap her mother had.

A few years back, Jim had been a struggling college student; nowhere near good enough for Laura's precious daughter. Diane had been all too happy to bow to her mother's insistence that Jim get dumped and dumped hard; she'd always been looking to trade up, apparently.

The much-motivated Jim had not only excelled at college but had created new opportunities and made some sterling investments. Only five years later, he was a wealthy and successful businessman, and the only place that Laura could turn to when the death of her ne'er do well husband left her in the ruinous depths of crushing debt.

"The Deal" was a masterstroke of vengeance; Jim had covered all the debts and continued to cover some extravagant payments for the older woman, and she was paying him back, all too slowly, at the rate of a thousand dollars every time she made him orgasm. The payments were doubled if anal was involved. Until the debt was paid, it wasn't her house... it was his. He held the deed, and would until every last cent was properly paid off.

It hadn't been about the sex; sex, Jim could get. It was about humiliating Laura; about seeing how much she hated absolutely every moment of what they were doing. The was no way, at that rate, she could ever pay off the debt, and they both knew it.

Diane had moved on, moving in with another man in a town to the north. That hadn't lasted; Diane's expensive tastes and tendency to "trade up" often cost her these situations. Jim had seized on the golden opportunity and made Laura an offer; all payments for his orgasms would double or more if Diane was involved as well. Not instead... as well.

The helplessly bound Diane plunged her pouty lips all the way to the base of Jim's big cock, taking him down her throat. She gagged and struggled but kept him in, letting the spasming and choking muscles of her throat milk his over-stimulated dick. Laura closed her eyes and turned her head away, still pinching Diane's nipples, as Jim groaned loudly and blew his thick load down Diane's struggling throat.

Jim came so hard and long that the muscles in his stomach cramped a little, aching all the way down to his properly satisfied nuts. Diane kept up her gagging, sucking action until his thighs stopped quivering, then slowly pulled up, licking and sucking at him the whole way off. The additional stimulation brought more shudders of pleasure, bordering on pain, from the young man.

Laura was not good at sex. Jim was amazed she'd managed to get pregnant with Diane; she didn't enjoy intimacy and hated their every encounter. Diane was another matter entirely; she'd learned early on how to manipulate a man's pleasure for her own ends. The wealthy businessman was enjoying the best of both worlds, the revulsion of his ex-girlfriend's mother and the skills of his ex. The financial domination was working out better than he could have imagined.

Diane looked up at him from between his knees with her big, blue eyes, cum dripping from her pouty lower lip. "That's two, right?" she asked in her best little-girl voice.

Jim took a moment to let his breathing slow down. "That's two," he agreed. "You're actually getting ahead this month, which is good."

Laura released her daughter's aching nipples and slowly got to her feet. "Do... do you think we can keep working it off at this rate?" she asked, eyes to the floor. She could rarely look Jim in the eyes anymore.

"Oh, man, maybe," said Jim. He looked down at the curvy red-headed Diane, still tied up on her knees. His cock tried to stir, but she'd drained him quite thoroughly. "The sessions with both of you are big payouts, but they're also exhausting. I like to think I've got as much endurance as the next red-blooded American male, but there's only so much I can do at a time."

"You could just leave me tied up here, for a while," suggested Diane, coyly. "Maybe something will... come up."

Jim regarded her shrewdly. Tied up, on her knees, his cum dripping down her chin, she was trying to take as much control of the situation as she could. As dangerous as that was, Jim also couldn't help but admire the skills.

"How about we all get cleaned up and see if anything happens in the shower?" he suggested. "Not saying it's going to; this was exceptionally good. But you two do have ways of surprising me."

Laura nodded, knelt back down and untied Diane's wrists. Diane rose and stretched, thrusting out just the right parts of her body just the right way. Jim growled a little deep in his throat; this situation did things to him deep in his guts that made him feel good in all the wrong ways. He silently marked off the additional two thousand dollars that he KNEW the ladies were about to earn in the shower and started to consider some dietary supplements to boost his endurance.

It was a few days before Jim thought seriously about going back to Laura's house. There had been plenty of medical checkups done in this deal, he wasn't worried about catching anything from his money slaves. He'd also had a vasectomy shortly after he'd hit it big in business; if he ever met someone he actually wanted to reproduce with, it was relatively easy to get the procedure reversed. In the meantime, anyone claiming that he'd knocked them up to get at his money was going to have an extremely embarrassing day in court. There weren't going to be any health issues from the constant mother-daughter threesomes. He'd even picked up a six-pack from the regular abdominal workout.

No, his concern was the amount of control Diane was trying to exert over the situation. She was good at this; too good. Jim enjoyed watching those skills at play; he hadn't appreciated them fully before, but his business-acumen found them quite appealing. He almost wanted to start properly dating her again; there was a challenge there, something to stimulate him on levels other than the purely sexual.

That was for later, though; he had no intention of letting Laura off any easier on The Deal. For now, he needed to find a way to enforce his control over the situation. Diane was obviously starting to think she could game the system; if Jim didn't think of something, she would be right.

He got an inkling of a thought and let it cook on the back burner for a few days. When he started getting anxious texts from both Laura and Diane wondering if he'd like to come over again, he knew they were just about desperate enough.

He picked a Friday night; plenty of time for everyone to recuperate afterwards. Usually, he showed up empty handed; this time, when Laura opened the door in her slinky evening wear, Jim was holding a bottle of very good wine.

"It's good to see you again, Jim," said Laura, obviously not meaning a word of it. "I was beginning to worry."

"Just needed a little rest after that last time," Jim assured her. Diane was waiting at the kitchen table for them; she was wearing a whisp-thin baby-blue nightshirt that left nothing to the imagination.

"Hi, Jim," she said, smiling. "You brought something? You know we'll take care of you here, right?"

Jim shrugged and set the bottle on the table. "You know, I thought that, for once, I can just do something nice. A friend of mine introduced me to this little vineyard out in the country, and I love their stuff. How about we share a glass, and then go to the bedroom?"

Ever the student of human behavior, Jim made all the signs of making a simple offer of hospitality, bordering on contrition. It had the desired effects.

Laura seized on the opportunity to put off the unpleasant business of whatever sexual deviancy Jim had in mind; she got the bottle opener and a set of wine glasses and set about the task of getting the drinks ready.

Diane, on the other hand, read the situation exactly as Jim wanted her to... it looked like Jim's resolve was weakening. He was acting more like this was a relationship than a business deal, was taking the time to engage in a charitable act. In short, it looked like Jim was getting soft... weak. She was all smiles and giggles as they clinked glasses and toasted a "memorable evening," but there was a sparkle in her eyes that said, "I got him!"

He didn't want them drunk; he wanted them to fully experience everything that was about to happen. They had a couple of glasses each, then Jim corked the bottle and suggested they head to the bedroom.

Laura followed like a woman walking to her gallows. Diane followed like a woman about to accept first prize. He had them right where he wanted them.

While Laura and Diane stood expectantly in the middle of the room, Jim went to the closet and gathered a selection of ties and silk scarves. Laura immediately tensed; she hated being in bondage. Diane, on the other hand, took it in stride; she and Jim had experimented with BDSM when they first dated, and she had more than a bit of a kink for being tied.

"Why don't the two of you undress each other?" suggested Jim, as he set the bundle of binding items on the side of the bed. "But... don't use your hands. Make it interesting."

"Wait... what?" asked Laura. "How are we supposed to do that?"

Diane turned to her mother, exasperated. "Like this, mom," she said. Kneeling down, she tugged at the tie of Laura's robe with her teeth, pulling it loose. The older woman was naked under the simple robe, and gasped as she was exposed. Then Diane slowly stood and clasped the lapel of Laura's robe between her full, red lips. As Laura closed her eyes and trembled in shame, Diane slowly dragged the robe off of Laura's shoulder and down her arm. She then walked to the other side of her mother, looked Jim in the eyes, and repeated the process on the other side.

Laura's robe slid off of her, bunching at her feet on the ground. Then Diane lifted her arms over her head and stood in front of her mother.

"It'll go easier if you start from the bottom," she said, quietly.

Laura swallowed audibly and looked at Jim as if there might be some form of reprieve from the shameful act. Jim merely finished taking off his jacket and unbuttoning his shirt cuffs, grinning like a maniac. With no choice but financial ruin and homelessness before her, Laura knelt in front of Diane, took the hem of her nightshirt between her perfect teeth, and slowly stood.

The front of Laura's thin, angular body dragged deliciously along the front of Diane's soft, curvy form, the friction arousing both women as the baby-blue nightshirt was pulled up. Diane bent down a bit so Laura could get the hem of it over her head and off her arms.

The two women, now naked, slowly hugged; it was the only form of comfort Laura could find in these sessions. The fact that seeing the two women embrace fueled Jim's lusts kept the blush of shame burning on Laura's face.

Jim stripped himself completely naked; while it was nice to have one or both of the ladies take his pants off, he was going to need to keep himself calm and collected for the next parts. This was going to be one of the longer nights.

"Laura, I want you on the bed. On your back."

Laura and Diane reluctantly broke their embrace, and the thin older woman started to crawl into the center of the bed. Jim stopped her as she started to assume her normal position.

"With your head down at the foot of the bed, this time," he said. Laura stopped, and both women looked at him.

"Why? What are you doing?" asked Laura, nervously. Jim shrugged.

"That's just how I want it."

She thought about questioning him further and thought better of it. Too many questions, too much resistance, and he'd simply leave. He'd already been gone for most of a week; they were still ahead of the payments, but only barely. If they didn't have the chance to make him cum tonight... worse, if he got upset with them and stayed away for a while longer, she'd fall so far behind that she'd never be able to pay the debt off.

She quietly turned in the bed and laid on her back, head towards the footboard.

Diane looked on with interest as Jim used the silk scarves to tie Laura's wrists to opposite ends of the footboard. Then he gently spread her thighs wide and wrapping the scarves around her legs just above her knees, tied them to opposite sides of the bed frame. Laura struggled a little, testing the scarves. It was worse than when he tied her by the ankles... with the scarves higher up, there was absolutely no closing her legs at all. She was fully exposed and more vulnerable than she had ever been with him.

Jim took a moment to enjoy watching her struggle. "Diane? I want you on top of her, the other way. Sixty-nine your mother."

"Oh, JESUS," moaned Laura.

Diane looked at Jim with a hint of surprise and a sweet smile. It looked like her victory was complete... first a nice bottle of wine and now she got to be on top of her mother in this arrangement. Giving her shapely ass a little extra wiggle, she slowly crawled on top of her helplessly bound mother.

"It's ok, mom," she whispered as she settled on. "This isn't my first time doing this; we'll be ok. Just relax; this can be good."

Laura's response was muffled between Diane's curvy thighs, but it didn't sound reassured.

Diane planted her knees on either side of her mother's head, and on all fours, arched her back just right. Her hot, moist cunt settled on Laura's face, and she looked Jim in the eye. "Like this, Jim? Is that what you want to see?"

Jim picked up the silk ties. "I want to see both of you getting off. You may need to talk your mom through this; it's probably her first time with a pussy in her mouth."

Diane nodded, and wiggled her hips, getting her sex in a good position. "Mom? It's ok... you have to lick me. You can do it... just push your tongue in, right at the top."

Laura, starting to sob loudly, began to crudely tongue her daughter's cunt. Diane moaned a little; a tongue was a tongue, even if it was in the wrong place. "Close, mom... find my clit. I know you can find a clit... right there near the top..."

She suddenly gasped and plunged her hips harder against her mother's face, slowly thrusting her clit against her mother's inexpert tongue. "FUCK, mom, yes... just like that... please... just keep doing that..."

As her weeping, humiliated mother kept tonguing Diane's sensitive clitoris, Diane dipped her head down, slipped the tip of her talented tongue between her mother's pussy lips, and began to gently lap at her mother's sensitive nub.

Jim's cock was throbbing, aching for stimulation. Laura's sudden groans of unwanted pleasure from her daughter's oral attention added fuel to his lusts; the scene was one of the best things he'd ever witnessed. He knelt next to them on the bed, silk ties in hand.

Gently, almost lovingly, Jim brought Diane's wrist in full contact with Laura's thigh, and tied it firmly in place. Laura, trapped between crushing humiliation and orgasmic rush, barely noticed. Diane purred into her mother's pussy, enjoying the tightness.

Making sure that his ties were secure, Jim bound Diane's other wrist to Laura's other thigh, then tied Diane's thighs, widely spread, to Laura's upper arms. Diane enjoyed the wider spread, as it allowed her to press her pussy more tightly to her mother's licking mouth. Laura was able to briefly look up pleadingly from between Diane's shapely ass-cheeks as Jim tied them, tears running down the sides of her face.

"Keep licking Diane," he said, running a hand through Laura's hair. He then stood up and walked to the bedside table.

His cock screamed for attention. He stood at the side of the bed, next to the nightstand, just watching them for a few minutes. Every so often, a shudder would start at Laura's belly and ripple through her whole body; Diane's talented tongue making her mother cum again and again.

Not quite as often, Diane's back would arch harder, rubbing her cunt against her mother's face, as Diane whined and shrieked into her mother's pussy. Diane was cumming too... not as often, but good and hard.

That was perfect; he wanted them focused on their pussies and their pleasure and using their tongues, their eyes and minds full of the other's sex. He wanted Diane thinking she was on top of the world, getting everything she wanted out of the deal.

Slowly and deliberately, he opened the top drawer of the nightstand and pulled out the lube.

Laura hated the anal; it doubled her payout, but she hated every moment of it. The pain, the violation, the unnatural penetration, it was all more than she was really willing to tolerate. Jim had gotten her a good lube to make the process easier, but it was still her least favorite thing in a world of unfavorite things.

Jim had never had Diane in her ass... she'd always told him flat out that it was a non-starter. Almost anything else, but not the ass. It was time Diane found out just how much control she really had in this situation.

Looking down at her as she lapped at her mother's clit, Jim popped the top of the bottle, squeezed a good portion into his palm, and started rubbing the cool, slick gel up and down his raging shaft.

Diane, barely registering the noise, glanced to the side to see Jim lubing up. Even in her pleasure addled state, she could put two and two together. She started to panic, raising her head and lifting her mouth from her mother's sex.

"Jim, no. NO. You can't do that... anything else, but we're not doing that."

Jim remained silent, continuing to stroke the lube along his shaft. As Diane watched with widening eyes, he added another dollop and spread it evenly.

"Jesus, no! What the hell? You know I don't do that..."

"So, should I untie you and leave? Because it's this... or that. Your call," said Jim.

Laura, uncertain of what was happening but unwilling to miss out on a payment, started protesting from between Diane's thighs. Diane looked at Jim in growing fear. She tested the binds on her wrists and thighs, but she was stuck. Jim knelt on the bed next to her, hand on the back of her head.

"Here's how it goes, Diane," he said, voice quiet but firm. "You can stop this. You can make this not happen. All you have to say is that I need to stop. But if you do, I leave. I untie you, I leave, and I don't know when I'll come back. Maybe a week, maybe a month. Maybe it's not me, but a Sheriff to throw you two off my property. So... do I stop, Diane? Or do I finally get your tight little asshole?"

Tears started to drip down from her pretty blue eyes, running her dark mascara. Her lips began to tremble as she looked first up at his eyes, then down at his glistening, throbbing cock. It was long and thick and it was straining for release, and Diane slowly realized she'd pushed things too far.

"Do. You. Want. Me. To. Stop?" Jim asked, slowly... deliberately.