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.
