A Financially Arranged Revenge Fuck Ch. 02

Jim had thought that having his ex-girlfriend's mother, Laura, as a sex slave was going to be a satisfying revenge. Laura had been a domineering, almost sadistic presence in the doomed relationship with Diane; she'd never missed a chance to make Jim's life miserable. When Laura showed back up in Jim's life, after he'd built a successful business and amassed a good amount of wealth, the opportunity had seemed too good to pass up.

Looking back on the past couple of months of their "financial arrangement," Jim could only reflect that it wasn't merely a satisfying revenge; it was so, so much more!

Laura had fallen on hard times after her husband died; it didn't help that he'd gone massively in debt without letting her know. She wasn't a well-liked woman in any of her circles; her shrill and adversarial demeanor had burned bridges with her family, her work colleagues, and what few social connections she'd bothered to make. Jim was literally her last hope of not ending up in desperate poverty for the rest of her life, and she'd been willing to offer herself up as collateral.

It wasn't that Laura was any good at sex; she was anything but. Jim couldn't be sure that she'd ever really performed sexually in the past aside from getting pregnant with her daughter, Diane. She was a painfully thin, somewhat angular woman with a body as pointy and sharp as her personality. No, it wasn't her physical appearance or her skills with intimacy; it was how much Jim hated her, deep in his soul, and how very much she hated everything about the arrangement.

Although they'd been at it for two months, she still had the same sour, doomed expression when she opened the door for him on this particular Thursday night. It was always a Thursday; if Laura was lucky, Jim would have come over two or three other days of the week, but he was a busy man.

She was dressed in a plain but expensive bathrobe, black with silver stitching. Pulled tightly closed and tied at the waist, it covered her from calf to neck. "I hope you had a good day," she said, spitting the words. Jim smiled at her as she closed the door behind him.

"Not bad," he said, cordially enough. He loved the look on her face when he was nice to her. There were no illusions of affection in this arrangement; she'd never stopped hating him and wasn't about to. Jim didn't mind one bit; these sessions were good for his deeply vengeful and petty soul. "I'll take a beer, though; I could stand to relax a little."

Laura wasn't the kind of woman who would ever willingly fetch and carry for a man. Nevertheless, she got one of the fancy imported beers she'd bought specifically for him out of her refrigerator, opened it, and handed him the bottle as he hung his suit jacket over the back of a kitchen chair and had a seat. These little conversations were part of the foreplay for him.

She sat across from him, putting her hand on a spiral-bound notebook. "I wanted to talk about the arrangement," she said.

"Absolutely," said Jim.

She opened the notebook to reveal some fairly primitive financial diagrams; she'd obviously been working hard at this. "I don't think, at this rate, I can ever pay you back," she said, eyes lowered. She paused, waiting for a response.

"Walk me through it," he said, smiling and leaning forward.

"Ok," she said. She ran her fingers through her tightly curled hair, picked up a pencil, and started to tick off points on the charts. "The initial loan to cover my debts was a hundred and ten thousand dollars. My... payment... is a thousand dollars ever time I... well, you know..."

"Specify, please," said Jim. "In conversations like this, it's important that there's no ambiguity. No assumptions, no shorthand. Say exactly what you mean."

Laura swallowed uncomfortably. "It's a thousand dollars every time I make you orgasm," she choked out. Jim smiled, nodded, and motioned for her to continue. "Over the past eight weeks, you've averaged three orgasms a week. It's going to take close to a year to pay back the initial loan."

"Correct so far," said Jim. He wasn't even a little surprised that she'd been tracking his ejaculations; it meant a lot to her future.

"But you're also covering fifteen thousand dollars a month in payments," she said, voice trembling a little. "So, in the time it takes me to pay off the initial debt, a larger amount will have accrued in back payments. It will take me more than a year to pay off a year's worth of payments, after which more than a year's worth of additional payments will have accrued."

She looked up at him, tears in her eyes. "I'll never be free," she said. "You knew this, didn't you? This was your plan all along?"

Jim sat back, taking a long pull on his beer. "Let's talk about economics, for a minute," he said. Laura shook her head.

"You can't do this... this isn't right! I came to you for help..."

"Economics," repeated Jim. She looked at him with hatred, then closed the notebook, sat back, and folded her hands in her lap.

"Fine," she said. "Economics."

"At the current rate, you are correct. The rate at which you supply the given commodity - my orgasms - governs the rate at which I supply the commodity you're interested in - payments against your debt. Three times a week is actually kind of generous, but I can see it averaging out there."

She stayed silent, just waiting for him to continue.

"There are factors governing how quickly you can supply me with orgasms," he said. "Mostly, the quality of the sexual experiences you give me, but also the overall pleasure of the encounter. Are you trying to act like someone I want to have more sex with? Are you dressing yourself or otherwise maintaining yourself as a desirable sexual partner? Are you offering services in the form of sex acts I can't get elsewhere for less money? No. The answer to all of these is 'no.'"

Laura blushed hard and looked back down at her lap.

"You want the average to go up to a point where you can get ahead? You'll have to work for that. I come over here, you're dressed like a nun in court and you treat me like a necessary evil. I might BE a necessary evil, but it's not a sexy look."

He shrugged and finished the beer. His cock was raging hard in his pants; that look of defeat on her face was the strongest aphrodisiac he'd yet encountered. "Like I said before, a thousand dollars an orgasm is a monstrously high rate. If I was the kind of guy who had to pay for sex, I could get better service than what I've been getting from you for a tenth of the price, from someone who goes all out to make sure I'm going to be happy enough to be a repeat customer."

Laura slowly shook her head. "I... I don't know HOW, Jim. I've never... it's not something I've ever had to do before." She looked up at him. "Tell me how. Tell me how to get my numbers up?"

She was the kind of desperate that Jim liked. She knew exactly how bad her situation was; it was a little surprising that it had taken her this long to work it out. She was desperate enough to start going an extra mile.

"Let's go to the bedroom, and we'll see what we can do."

She nodded, rose, and led him across the hall to her bedroom. Jim sat in the overstuffed armchair in the corner and looked her up and down; the bathrobe was a fine, sheer material, but she had no curves to be accentuated by it. She might as well have dressed in a cardboard tube.

"Take off the bathrobe. Let's see what you wore for me to find under it."

Laura frowned, then untied the tie and opened the robe. Underneath it she was in her customary cream-colored bra and panties, purely no-nonsense function. Jim nodded as she slipped the robe down off her shoulders and placed it across the foot of her bed.

"Sexier underwear," Jim suggested. "You've got a nice, slim figure; just about any lingerie shop will be able to fit you without any problems. Go ahead and take those off, now."

The blush not leaving her cheeks, she nodded curtly and slid the shoulder straps of her bra down her arms and off. Then the twisted the bra around her body, her tiny A cup breasts popping over it as she did so and unclasped it when the clasp was more accessible. Then she rolled her panties down her thighs until they slid effortlessly down her calves and off her feet.

She stood naked before him, arms at her sides, thin body on display. She was looking better than when they'd started the arrangement; stress and money issues had caused her to lose weight she couldn't afford to lose, and she had looked nearly skeletal the first time he'd had her here. Now it was a healthier slim body; not a lot of curves but at least there was enough meat on her bones to hide most of her bones. Her ribs and pelvic arch still protruded, which Jim was starting not to hate.

"You're going to have to start doing that slower. Maybe get a bra that clasps in front, or a top that has ties on the sides. Same with the panties; unwrapping the present is part of the presentation. I'm sure the girls working the lingerie shops can give you some suggestions. Grab a pillow and come over here."

The brown-haired woman grimaced, then collected a pillow from the head of her bed. She stood in front of Jim and dropped the pillow on the floor between his feet. "On my knees?" she asked, knowing the answer.

Jim nodded, smiling. Laura knelt carefully on the pillow, hand on one of his knees to steady herself on the way down. She rested her ass on her heels, eyes down, shaking a little.

"Are... are you going to tie me up?" she asked. "You've usually tied me up by now..."

"Not this time. Not yet," said Jim. "I'm going to give you a chance to make this better for me. Take me out, nice and slow. There's no rush."

Laura looked at the bulge in the front of his suit pants, swallowed audibly, and reached for it. She preferred to hurry; these encounters were unpleasant for her for a number of reasons, and she would much have rathered to have gotten everything done as quickly as possible. With shaky fingers, she unbuckled his belt, unzipped his pants, and unbuttoned the waist band. As usual, he was wearing no underwear for their encounter.

Jim's rock-hard eight-inch cock sprang up, the head already purple with blood and shiny with tension. Laura looked up at him, a lost expression in her eyes. He was usually taking her head in his hands by this point, making her suck him. He was sitting back, now, just watching.

"Feel it a little. Run your hands over it. Get to know it some," he said.

Looking like she was touching a venomous snake, Laura wrapped her cool, thin fingers around his hardness, finding that she could get both hands on it. She fought her feelings, but the look of disgust on her face was impossible to hide. Keeping her eyes focused on the throbbing cock in her grip, she slowly and inexpertly ran her fingertips over it, sliding her palms along the sides and across the top.

"I... I don't know what to do," she said, voice high and tight. "Am... am I doing this right?"

Jim reached out and ran a fingertip along her arm. "There are hands on my cock; it's hard to do that wrong. Just keep the touch light, for the moment. I'll let you know when you need to do something differently."

Her confusion and stumbling were almost as good as her humiliation, Jim decided. She treated his cock with caution and no small amount of fear, and that made tingles run all the way through him. Eventually, he took one of her hands in his, and wrapped it around his cock.

"Just one hand on my cock, now. The other one should be holding my balls, nice and soft."

Tears running down her face, Laura complied, cupping Jim's heavy nuts in the cool palm of her left hand. Jim guided her other hand to begin stroking him.

"Up and down... you know the action. Same as in your mouth or your pussy. Fuck my cock with your hand. Slow."

Laura complied, picking up the action quickly enough, even when Jim took his hand away from hers. He settled back in the comfortable chair as his ex-girlfriend's mother gave him what had to be her first handjob ever.

Diane, Laura's daughter, had been very good at handjobs; she was especially good at them when she didn't feel like being fucked. In comparison to Diane's expert treatment, Laura's was unrefined and clumsy. It was, however, a hand stroking his cock. The fact that it was the hand of a woman he hated who had no choice made up for a lot of skill.

After a few minutes, he reached out to modify her grip a little bit.

"That's a good start... really good. Now, loosen up a little bit. You don't want to drag the skin up and down; you want the skin to slide through your grip. And take your thumb... like this... yeah. Along the underside, so you're rubbing the cleft of the head."

He moaned as she followed his instructions, and again took his hand away to let her work. It was almost too good. As long as she kept it slow, it wasn't going to make him cum, but it was getting him most of the way there.

"Ok, this? This is how you treat a cock... and in particular, MY cock."

Laura focused on his dick, getting immersed in learning the skill. She might not have been good with money, but she was good with her hands. She gently rolled his balls in the palm of her left hand, noting how it made him moan thrust his hips a little.

"Will... will this make you cum?" she asked. "If... if it does... will it count?"

"It might, and it would," admitted Jim. "As far as our deal goes, an orgasm is an orgasm." An evil thought brought a twinkle to his eye. "Well, except for one case, where it might count as two..."

Laura perked up at hearing that, unconsciously pausing her stroking for a moment. "What would count as two?"

Jim looked at her disapprovingly, then down to his cock and her motionless hand. She "eeped!" a little and went back to stroking and fondling.

"I'll have to show you," he said. He paused, looking down into her questioning, even hopeful eyes. "You aren't going to like it."

"That's ok," she said. "Show me. I want to know."

"All right," said Jim with a resigned tone. "Get on up, let's go to the bed."

Laura stood, shakily, all too happy to release Jim's hard, throbbing cock. He was glad for the break; he'd gotten too close too fast. He wanted to cum, but he wanted her to really earn her thousand dollars... or more.

Laura sat on the edge of the bed, surprise on her face when Jim walked past the bed to her closet. He'd been in here a few times over the past few weeks; he was pleased to see she still hadn't gotten rid of her deceased husband's selection of silk ties.

"What... what are you going to do?" she asked, a little frightened, as he returned with a colorful handful of the ties.

"You'll see. Lie down, now."

She nodded uncertainly and laid flat on her back. Jim knelt next to her on the bed, running a hand over her tiny breasts.

"On your stomach," he said.

Laura's eyes widened, and for a moment she considered objecting. Desperate and powerless, she rolled over onto her stomach.

Jim took one of her wrists in his hand and wrapped a loop of silk around it, then used it to tie her wrist to the corner of the headboard. As Laura quietly wept into the remaining pillow, he went to the other side of the bed and tied her other wrist to the other corner.

He picked up the pillow from the floor in front of the armchair and knelt on the bed again.

"Lift your butt up for me," he said. Bracing with her knees, Laura lifted her butt into the air and Jim slid the pillow under her hips.

"I don't like this," she said, as Jim walked into the connected bathroom.

"See? I told you," he said. He found what he was looking for; a bottle of baby-oil on the side of the bathtub. He set it down on the nightstand next to the bed as Laura watched. As he shed his clothing, she pulled experimentally at the bonds on her wrists. She was well and properly tied.

"This is wrong," said Laura, as Jim pulled her knees apart. He settled onto the bet between her spread thighs and picked up the bottle of baby-oil.

"Oh, I know. So wrong," said Jim, as he uncapped the oil, filled his palm with it, and rubbed it's smooth, scented slickness over his raging member. He had to be careful; Laura's inexpert handjob had him throbbing; even the few minutes of preparation for the next act hadn't calmed it much. He wasn't going to be able to last long, here.

He placed the bottle back on the nightstand and got on top of Laura. She was crying openly, now; her mascara staining the pillowcase as it ran in rivulets from her eyes. Jim got a controlling grip on his cock and started to guide it to its destination.

His knees between hers, he pressed them even further apart as the head of his slippery cock glided between her scrawny butt cheeks. Her whole body jerked in reaction when he pressed it up against her virgin anus.

"Don't," she wept as he ground his hips down. "It's... its wrong... you can't! Please, don't!"

Jim put his lips next to her ear. "If I stop now, I'll just leave... and I'll come back next month."

Her eyes went wide again. "NO... no please... let me use my mouth, or just fuck me, don't do this..."

"It's this, or nothing," said Jim, trembling from the effort of holding back. "Two thousand dollars, or zero. What's it going to be?"

Laura screwed her eyes shut and took a deep breath. "Ok... just... just please, don't hurt me..."

Jim grinned like a maniac, and slowly lowered his hips. Laura squealed as his thick eight inches sank into her tight, unwilling asshole.

He could feel her body trying to fight him; the tension in her arms as she struggled against the ropes, her thighs trying to come together against his own, her whole core trembling with the effort of trying to hold him out of her rectum. He got his hands on her hips and continued his long, slow push to sink his whole length into her.

She yelped when he hilted it, his hips pressed tight to her bony ass, his balls draped on her moist, fuzzy pussy. Jim rested there for a moment; it was heaven. His cock was wrapped in hot tightness, her anus holding him just a bit too tightly, throbbing with her pulse, and her struggling body sending ripples through her guts which stimulated every inch of his straining manhood.

He laid along her back and braced his hands on either side of her, sweat starting to drip down his body. She gasped as he slowly pulled himself out, withdrawing until only the head was still inside her ass. Then he drove it back in, just as slow, just as hard.

"It hurts," she managed to squeak out. "You're hurting me..."

"Try to relax," Jim hissed between clenched teeth. "Push out with your ass. It helps."

It wasn't the first time Jim had done the anal sex thing, but it was going to go down in his history as the best time. Laura struggled to comply with his suggestions as he slowly plowed her back door. He could have brought himself off in her quivering butthole with a few hard, fast thrusts, but this was so much better. The blood pulsed through his cock and his whole body with a thundering rhythm, his senses acute and his breathing heavy.

She squirmed and writhed and whimpered as he fucked her ass long and slow, making sure she felt every moment of it. Eventually she went limp under him, mind and body surrendered to the unnatural act that was being forced on her.

Jim slowly picked up speed, his hips crashing into her ass with loud slaps that filled the room. Before too long, he was fucking Laura's poor abused asshole with all his speed and strength.

When he came, it was like a stream of fire that erupted from his balls and through his groin, the searing pleasure tearing a yell from his throat as he gushed cum into her bowels. He pounded his hips down into her as his cock pulsed out its sticky payload, his nuts yanking up against his body four, five, six times as rope after rope of jizz filled Laura's violated rectum.