A Financially Arranged Revenge Fuck

Jim had been waiting a few minutes when Laura finally opened the door; he had been beginning to suspect she wasn't ever going to answer the bell.

The young man surveyed the older woman; she was dressed in a simple skirt and blouse with modest heels, and she wore the same make-up she seemed to wear every day. Business-like and subtle, almost enough to hide her age.

"Come in," she said, her voice resigned. Jim walked into the modest home, hands clasped behind his back. The place looked very much the same as the last time he'd seen it, over three years ago. Some of the more ostentatious pieces of furniture and decoration were missing, heavy indentations in the old carpet showing where they had once stood.

Laura closed the door and turned to face him; she couldn't bring herself to look him in the eye. "I... I've never done anything like this before," she said, wringing her hands a little. "I have no idea how to start or what to do..."

Jim smiled at her. "Well, why don't we have a sit-down in the kitchen and make sure we're both on exactly the same page. You know, just like old times."

She winced at that, but slowly nodded. Jim knew the way well; he'd been in the house a lot the scant few months he'd dated Diane, Laura's daughter. Of course, the conversations at the kitchen table used to go another way.

There was a little bounce in Jim's step as he walked through the familiar kitchen and held out a chair for Laura. She seemed to be more uncomfortable with every simple courtesy he showed, and Jim wasn't hating it. He sat across from her and leaned back in the chair; much more comfortable than the last time he'd been here.

The last time, she'd been telling him in no uncertain terms that he was wrong for her daughter, that she was going to tell Diane to stop dating him and that there was nothing he could do about it. There had been a lot about how Jim was never going to amount to a single damn thing in his worthless life. True to her word, Diane had broken up with him the next day.

A lot had happened since then. No longer dating the somewhat demanding Diane, he had been able to devote himself fully first to his studies, then a startup business. Three years had been good to him; he was more than financially secure, he was almost sickeningly rich compared to where he'd been.

Three years hadn't been so good to Laura. She'd been sponging off of her crippled lawyer husband for years, using their joint income to maintain not only the fancy little house but also his expensive boat. Dan, he husband, had passed away around a year ago, and Laura had discovered multiple mortgages and other loans that the crippled but criminally wiley lawyer had concealed from his family.

Diane was living out of state with someone or other, and Laura had run out of places she could appeal for funds. When she'd agreed to this arrangement with Jim, it was literally her last hope.

"Let's lay it all out," Jim said. "No hints or innuendos. Let's both be very clear what we're both agreeing to, here."

"Do we have to?" asked Laura. "Can't you just... just do what you need to do?"

"See, that's what I'm talking about. No ambiguity: it will save us both a lot of time and frustration later. Tell me exactly what you need from me."

Laura didn't like that at all, but despite the heat of the blush rising to her face and her hands nervously running through her hair, she squared her shoulders. "I am a hundred thousand dollars in debt and have over fifteen thousand dollars in payments every month that I do not have the ability to pay. I need you to pay that debt and cover my payments for as long as possible."

Jim nodded solemnly and frowned as though she were talking about a great deal of money. Three years ago it would have been. These days, that was practically pocket change for the young man.

"And what are you willing to give me in exchange for this considerable sum up front, with continuing payments?" He leaned forward, looking her in the eyes even if she kept her gaze down to her lap.

She swallowed and the blush increased. "The only thing I have left. Me. My body. Sex. I'm offering you sex with me."

Jim smiled, almost happy to see the tears forming at the corners of her eyes. She was hating every minute of this, and that made it all worthwhile.

"All right," he said, sitting back and unbuttoning his suit jacket. "Here's how it's going to work; this arrangement is non-negotiable, take it or leave it."

He took a deep breath; he'd been practicing this in his head for a couple of days now.

"I will pay the loan and maintain the monthly payments; you will compensate me my making me cum. Every time you get me to ejaculate, I will remove one thousand dollars from your debt."

He leaned forward again. "That is you making me cum; not you watching me jerk off on you. If I have to finish myself, no pay, try again later. This is not about your orgasms; I don't care if you get off or not."

She winced again as though his words were causing her physical pain; to some degree, they might have. Laura had never struck Jim as a particularly sensuous woman, all angles and business.

"To make sure the arrangement is followed," he continued, "when I pay off the first two mortgages, I will retain the title on the house. When you finish paying your debt, I'll turn the title over to you."

The tears were flowing freely now, and Laura tried to speak through a throat choked with regret and despair. Jim handed her a Kleenex from the box on the table; when he'd broken down her a few years ago, he'd had to pull his own tissues.

"I don't... just a thousand? I was thinking more like five..." she said, waving her hands, trying to find reason.

"You're lucky I'm giving you a thousand a shot," said Jim. "I don't generally pay for sex, and if I did, there isn't a pussy in the world that I would spend five grand on. You're going to have to work pretty hard to make yours worth one grand, let alone more."

Defeated, Laura just nodded. "I'll never be able to make it all..."

"Tell you what," Jim said. "You do a really good job, you give me some very good times, and we'll look at ways you can earn more, maybe get a percentage taken care of. But that's strictly depending on performance."

She nodded again, wiping her eyes. Then she took a deep breath and set her shoulders straight. "So, now?"

"No time like the present," said Jim. The situation and conversation had him rock hard in his suit pants. He stood up and held out a hand, helping her to her feet.

She turned and walked across the hall to her bedroom, Jim following casually.

It wasn't going to be the first time he'd had sex in that room; Diane had enjoyed the occasional rebellion of fucking in her mother and stepfather's bed when they were away. Jim had a feeling this was going to feel better.

Having moved with grim purpose into the bedroom, Laura stopped and turned around, looking a little lost. Jim had suspected that Laura's marriage to Dan had been more a business arrangement than anything else; the diminutive, crippled lawyer had most likely not had much in the way of function below the waist. After her divorce from Diane's biological father, she probably hadn't had much need for physical intimacy; she was practically in new territory.

"What do you want me to do?" she asked.

Jim sat down in the armchair in the corner. "Take off your clothes. All of them. Slow. Strip for me."

The look of mortification on her face almost made Jim cum right then and there. He hadn't thought he had a sadistic streak, but apparently there were exceptions.

He could see that she wanted to hurry through it, to get it all over with so she could get on with her life until the next time. He wasn't about to let her off easy; this was going to be a difficult night for her.

She unbuttoned the striped blouse and slid it off, revealing a no-nonsense cream-colored bra. She kicked off her heels and unzipped her pencil skirt, letting it slide out of her hands and onto the floor. Clad only in panties that matched her bra and thigh-high stockings, the tears started to flow again.

"Turn around, let me see you," said Dan, his voice tightening with lust and excitement. It had been a while since he'd been with a woman; running a big business took a lot of his time. He was going to get some mileage out of this arrangement.

The slim woman slowly turned around, hands at her sides. Jim had to admit there wasn't a lot to see; he liked a woman to have some curves and Laura was almost painfully thin. The bra was more of a fashion requirement than a physical need; Laura's A Cup breasts barely strained the fabric.

Jim stood up when her back was turned to him, and stepped up close behind her, dropping his jacket as he went. She gasped when he wrapped his arms around her from the back, pinning her arms to her sides.

"It might help if you relaxed," he hissed into her ear, "but I understand if you don't."

Then he was kissing the side of her neck, sliding his lips from the back of her ear to her shoulder, and she shuddered against him.

"Oh, god, I can't do this," she said, not struggling, but her whole body tight.

Jim loosened his grip, only to slide his hands up her arms to her shoulders and slowly slide the shoulder-straps of her bra back down her arms. "Of course you can," he said. "You don't really have a lot of choices, do you?"

She shook her head and wept quietly as Jim deftly unfastened the clasp at her back; doing that one-handed was a skill he'd worked on in this very room. As Laura's bra fluttered to the floor, he slid his hands onto her soft little mounds, capturing her large and already erect nipples between his fingers.

She gasped again, pressing back against him. His lips kept working at her neck as he played with what little breasts she had. Eventually, he felt her hips starting to press back against him, her tight little ass rubbing his throbbing bulge. He let her feel his teeth on her neck then, making her yelp a little.

Her hands came up to his, clutching his fingers as they played with her breasts. He allowed her to set a rhythm of rolling her tits and squeezing her nipples, making her breath come in pants.

He pulled his hands free, then, slid them down her sides, and worked her panties down her thighs. She began to cry again as they slid down her legs to the floor.

Her body was reacting in ways it probably hadn't in a while, and she was as confused as an inexperienced virgin. Jim slid a hand around to softly fondle her sex, the fuzz-covered mound hot and moist against his palm.

"Oh god... what are you doing to me?" Laura asked, eyes tightly closed, tears slowly rolling down her cheeks.

"Just examining my investment," Jim purred in her ear. Still massaging her mons with one hand, Jim undid his tie and pulled it off with the other. He'd rehearsed so much of this in his head over the past couple of days, he didn't want to miss any of the things he'd planned to do.

Releasing her throbbing pussy, Jim gently pulled Laura's wrists behind her and crossed them at the small of her back. Laura's eyes opened wide as he looped his tie around both her wrists and carefully pulled it tight.

"Jim? Jim, you don't have to do that," she said, squirming. "I'll do whatever you want, you don't have to tie me..."

"I know," said Jim, as he fastened a simple slipknot. "But what I want is I want to tie you up a little."

He pressed up against her again, now feeling her bound hands struggling slightly in their bonds, pressed tight to his hard cock. She stopped stock still and carefully felt up and down the bulge in his pants, as though measuring.

He proceeded to kiss the side of her neck again as she began to stammer. "J... Jim? Is... it that YOU? I mean... is that all... is that your..."

"Yes, Laura," Jim said. "It's my big, hard cock. More than you thought you'd have to deal with?"

"I... I had no idea," she said, more than a little fear in her voice. Jim stepped away from her, and grabbed a pillow from the bed.

Taking her by the shoulder, he walked back over to the armchair and threw the pillow down in front of it.

"On your knees, Laura. Let's get you introduced."

"Oh my god," she said, looking down at the pillow in disbelief. Jim slowly unbuttoned his shirt as she considered her position, then sat in the chair and helped her balance as she knelt.

"I've never done this," she said breathlessly as Jim unbuckled his belt. "I... I don't know how..."

"Think of what it's worth to you," said Jim, as he unbuttoned his slacks and slowly pulled the zipper down. He was glad he'd decided to fly commando for the occasion; the look of disbelief and fear on her face as he pulled his thick eight inches out gave him an extra tingle deep in his balls.

Truth be told, he knew he wasn't exactly huge. Compared to anything she'd had to deal with in recent years, though, it was probably big enough to be a problem. Jim didn't hate that.

"You've never sucked cock before?" he asked, reaching out to stroke her hair.

"No, never," said Laura, eyes still locked on his turgid member. "Stan... Diane's father... he wanted me to, but..."

"Well, you're going to suck mine," Jim said. He slid his hand to the back of her head and started to gently, but firmly, pull her head down to his lap.

She didn't resist, exactly, but she also wasn't moving down on her own. "I... I don't want to do this," she whimpered as her lips came closer and closer to the head of his prick.

"Yeah, I know," said Jim. "Does that matter, though?"

Laura squeezed her eyes shut, shook her head slightly, then bent down the last few inches and took the tip of Jim's cock between her thin, tight lips.

She obviously didn't really know what to do; she sucked on the head of Jim's cock and lapped her tongue against it in her mouth, but it wasn't anything like a proper blowjob. Jim took her head in his hands and guided her, gently bobbing her head up and down, sliding more and more of his thick, hard meat into her hot, wet mouth. She complained around his cock a little, bringing more little thrills to Jim's raging member.

"That's it... up and down. In and out. Just let it slide in, then suck when you're coming back off of it. You can do it."

Laura felt as helpless as she ever had; the financial arrangement was crippling all on its own. With her hands tied and his hands in her hair, she was well aware that Jim could just force her to do what he wanted. Instead, he was instructing her, guiding, her making her an active participant. She hated herself for appreciating the kindness, even for a moment.

Jim's cock began to ache with the need to cum; he could feel his pulse from the tip of his dick all the way up to his teeth. He started to thrust up into Laura's mouth as he guided her down on it, not going into her throat but coming close. He could finish like this, he realized. He could just get a few more thrusts in, maybe force it down her gullet and let her tight, violated throat milk him out. It was an effort of will to pull her head up and off of him, breathing hard.

Laura looked at him in confusion. "I... was I doing it right? Give me another chance, I can do it better..."

"Oh no, that was a really good first effort," said Jim. He stood up and walked behind her. "There's just more I want to do."

Laura closed her eyes and faced the chair, starting to tremble. He was going to take absolutely everything he could from her, and there was nothing she could do to stop it.

He knelt down behind her, his hard cock coming to rest in the crack of her ass. He put his hands on her shoulders and started to push them forward.

"Bend over, now, Laura," he said. "Keep your butt in the air for me."

"Oh my god," she said, as she bent down and rested her chest on the seat of the big leather armchair. Behind her, Jim got a knee between her thighs and spread them wide apart. Her posture presented her tight, little-used sex to him, and he ran a fingertip through her glistening pink.

"You're soaking wet," he said, smiling. "That will help a lot. Now just relax."

Helpless, humiliated, totally vulnerable, Laura began to weep into the seat of the chair, her quite sobs gently wracking her body. Jim grasped his turgid cock in a tight fist, then brought the tip of it to her slightly parted outer lips.

It wasn't exactly easy going. It had been a long time for her, and Jim's cock was thicker than any she'd had before. He rubbed it up and down her outer lips, feeling the hot wetness on the tip of his prick, then placed the head against her opening and slowly leaned into it.

"Oh... GOD..." said Laura as he gradually forced her open. "Oh... OH... Oh Jim, it's too big... please, I can't take it..."

Jim declined to answer, focusing all of his attention on penetrating the older woman. She shrieked a little as he got the throbbing head of it inside her. Then he backed off a little, gave her a moment, and leaned in again, pressing inches deeper.

He could see her hands struggling to be free of the tie around the wrists, and he kept a hand on one of her shoulders to stop her from trying to rise. As she gasped and started to cry, he pulled out all but the head, and then rammed his eight inches home, burying it to her depths!

The hard intrusion took her breath away, and in the moment of quiet, Jim leaned down and put his lips to her ear.

"This is happening," he said, flexing his cock in her too-tight quim. "There's nothing you can do to stop it. You're going to take it, now and every time I want. Deal with it."

Then he had one hand on her shoulder and one hand on her hip, and he started to slide it in and out. Laura gasped and moaned, crying out when he started to use his grip on her shoulder to pull her back onto him as he thrust.

Soon, the sound of his hips slapping into her bony ass filled the room, along with her agonized whimpers and groans. He got both hands on her hips and fucked her hard, driving his cock deep again and again. He could feel that they would both have bruises in the morning, and it only made him fuck her harder.

"Please... Jim PLEASE... oh GOD..." moaned Laura, as her nipples were rubbed mercilessly against the cushion of the chair. Then she felt it well up inside her; all the sensations, the attention unlike any a man had ever given her, the stimulation, the penetration, the hard, throbbing cock bottoming out in her poor, abused pussy again and again...

"Not like this... no... NO... I'm CUMMING!" she called out as the orgasm took her.

Her pussy bathed Jim's rampaging cock in hot slickness and the walls of her cunt rippled and gripped him just right, and as her voice descended into long, low moans, Jim grunted and slammed in hard. He felt his nuts pull up hard to his body over and over as he launched jets of hot semen into her helpless pussy, pounding hard and deep to get every last drop into her.

Eventually he slowed, his balls thoroughly emptied into his ex-girlfriend's mother. He slid out of her as he gradually softened and pulled the slipknot on her wrists loose.

"That's... a thousand," he said, sweat rolling off his body.

Laura got her arms under her, braced herself, and pulled herself into the armchair as Jim sat across from her on the edge of the bed. She was pink with sex-flush, looks of shame and lust competing on her face.

"Did... did I do a good job?" she asked, curling slowly into the fetal position.

"Just right," said Jim. "We can go to the bank tomorrow and sign all the paperwork."

Laura nodded. "Are... are you going now?"

"I might," said Jim. "Unless you had another idea."

She looked at him from her position, curled on her side in the armchair, knees pulled up to her chest. "If... if you want... you can sleep here, tonight. Maybe... could I make another payment in the morning?"

Jim could feel his spent cock stirring a little as she looked at him. He'd been doing the math in his head for two days. Even if he spent all his time in this house, fucking her day and night, it would take months for her to pay off the initial loan. During that time, the monthly payments would keep accruing, putting her deeper and deeper in debt. By the terms that they'd agreed on, she'd never be out from under him.