Jackie's Punishment

Her mouth dropped open, anger rising in her. "How dare you! You have no right to expect me to do this more than once. That wasn't the deal!"

"I don't recall making any deal with you. I told you to be here, period. I never told you it was just this one time." For a computer nerd, he was pretty forceful, she thought, anger and frustration rising in her.

"You will do it, or you know the consequences. And now, I have more I can tell your husband, like how nice that little freckle is just above your tit." He was deadly serious and she knew she was in way over her head.

She moaned, hugging herself with her arms, sitting back down on the edge of the bed, realization hitting her that she would be blackmailed as long as he wanted and there was nothing she could do about it. Mark would never believe her, she knew.

The snapping of his fingers brought her attention back to the present.

"Earth to Jackie, I said come here." She evidently hadn't heard him the first time, but now she stood slowly and took a few steps to stand in front of him. She couldn't hide her nakedness and was shaking inside as his eyes slowly traveled the length of her, then his hands followed suit. He ran his fingers over her breasts, stopping to pinch each nipple hard and then rub them between his thumbs and forefingers. An ache spread through her groin, and she knew her pussy was getting wetter.

Hands traveled down over her flat stomach, making their way down to the cleft between her legs. Pushing her legs apart with his hands, he felt the wetness and laughed.

"You like this, you little slut."

No response was required, and she couldn't speak anyway, as he roughly shoved a finger inside her, twisting and turning it before pumping it in and out a few times.

"You're soaked, I can smell you from here. You smell like a bitch in heat." He sniffed the air and grinned up at her from his seat on the edge of the chair.

"Turn around," he demanded as he grabbed her hips and twisted her around until her ass was facing him. "Nice," he murmured. His hands gripped each ass cheek, pulling them apart to expose her wrinkled, tight hole.

"We're going to have some fun today, aren't we?" he asked. "But for now, I want you bent over my knees. There has to be a price to pay for not doing what I told you to do."

Before she could pull away, he yanked her down and flipped her so that she was bent over his knees, ass in the air, her head hanging down to the floor on one side and her feet on the other. A sharp smack landed on first one ass cheek, and then the other, making her jerk uncontrollably.

"That was two, you have eighteen more to go." His arm rose again and his hand landed over and over on her ass, first one side, then the other, sometimes in the same spot again and again, making her cry out in pain. When he was finished, she just laid there, exhausted, unable to move and in pain.

"That was twenty smacks. Will your pussy be shaved next week?"

"Yesss," she stuttered, tears pouring down her face, her ass on fire.

His hand rubbed the spots he had so recently spanked, soothing them to a small degree.

"I love the way your ass looks right now, all bright red, I can see my handprints all over it. You're going to find it hard to sit this afternoon, so you'll be able to think about this the rest of the day while you sit at your desk, or on your ride home, and when you're sitting next to your husband tonight." There was a definite smirk in his voice.

She moaned, shame running through her at the position she was in, literally, and because despite the pain in her ass, she knew her pussy was even wetter than before. She felt a throbbing between her legs, getting stronger and stronger.

A finger ran down the crack between her cheeks, continuing on between her legs that he nudged farther apart. She grabbed onto one of his legs and pressed her face into his calf, holding on tightly. She pushed her ass up instinctively. Hearing a chuckle, she was beyond caring. There was a fire in her that desperately needed release.

His finger dipped into her pussy, spreading her juices around, quickly joined by a second finger, and then a third. Fingers thoroughly coated, he pulled out and teasingly circled her clit with his forefinger a few times, sending shockwaves coursing through her. The hand resting on her ass now spread her cheeks apart with thumb and finger, totally exposing her asshole to his view. The other hand moved up to lazily play with her hole. He spread her pussy juices around the rim, lubing it well, before going back to dip into her again for more.

She felt a fingertip push against the tight hole, forcing its way inside where no one but her had been for years. Feeling her orgasm build, she wiggled and pushed against the intruder, trying to pull it in further. He complied, ramming the one finger in as deeply as he could get it, without waiting to see if she was ready.

"Ohhhh!" she cried out. Her ass began wiggling back and forth on his lap as he began fucking her with his finger. Her clit was rubbing on his hairy thigh, giving her just enough pressure to bring her to a crescendo. She yelled out as he rammed two fingers in deeply and twisted them around, feeling her muscles clenching tightly as she came explosively.

Shudders ran through her, she was soaked with sweat, her pussy was dripping, and she lay there with her ass sticking up in the air and two fingers shoved deep inside. She didn't care, she had just had the best orgasm she could ever remember.

Coming back down to earth, she felt Darryll pull his fingers out and his hand patting her still sore behind.

"It seems you like things shoved up your ass, Jackie." He appeared to find this amusing. "We'll have to see if anything else will fit in there."

With that, he pushed until she rolled off his lap, letting herself land on the floor next to him. She wasn't ready to move anywhere quite yet.

"Unzip me," Darryll commanded.

With shaky arms and legs, Jackie pushed herself into a more upright position and leaning over him, unbuttoned and then unzipped his shorts, pulling them down and off as he raised his hips off the chair.

"Now my shirt." She reached for the hem of his polo shirt and pulled it up and over his head while he leaned forward in the chair. She had been right, he was ripped and must spend countless hours in the gym.

All that was left was his boxers. He stood up and she could the large bulge just hiding out of sight. She tucked her fingers under the elastic waistband and pulled them down, releasing his engorged cock, which sprang out at her, a drop of pre-cum on the tip.

On her knees at his feet, with his cock right at face level, she couldn't stop herself from leaning forward and licking the drop off. She tasted it, savoring the flavor, before letting her tongue come back out and lick up and down his shaft. It jumped as she touched the sensitive underside, she ran over the spot a few times before licking her way down to his balls. He was au natural down there, and she ran her tongue over the wrinkled sacs, down to the ridge below, as he spread his muscular legs to give her more room to explore. Her tongue licked the spot between his balls and his asshole, pressing hard on it before moving back to take one sac into her mouth, where she rolled it around and let her tongue run circles on it.

Opening her mouth wide, she took both balls into her mouth, feasting on the musky taste, very gently sucking on them. It occurred to her she had him in an extremely vulnerable position, and the thought must have occurred to him at the same time, for he reached down and entwined her hair around his hand. Pulling back slowly, she let his balls pop out, then moved back up to take the smooth, rounded head of his cock into her mouth. She began a rhythmic up and down motion, sucking hard and pressing her tongue into the side of him. His hips began pumping and his cock hit the back of her throat on each thrust.

Her hair was suddenly yanked as he pulled his cock out of her mouth. He was breathing heavily and was holding onto the table to stay upright.

"I don't want to cum in your mouth. Actually, I do," he panted, "but I really want to fuck your ass and I don't have time to do both today, so hop up on the bed...on all fours, please." He grabbed a few pillows and piled them high, then patted them to show her where he wanted her to be. She got up off the floor and on her knees, crawled to the pillows and positioned herself so her ass was pointing up in the air and her head was cushioned on her arms.

She felt his weight on the bed behind her and his hands pushing her legs farther apart.

"Ah, what a sight to see. Your asshole and cunt wide open and waiting for me." She hated his crudeness, but found that it also stirred something within her.

His hands began kneading her ass cheeks, pulling them open and closed. She whimpered, the spanking he had given her hadn't been forgotten and she was still hurting, aware that he had been right when he said she would be feeling it all day long. Every time he squeezed, she moaned, so of course he continued, enjoying the sounds of her discomfort.

Finally, tiring of tormenting her, his hands began to explore. Fingers dipped into her pussy, circled her clit, pinching and pulling on it, sending electric shocks through her. She squirmed, searching for a release to the dam building again inside. Two, and then three, fingers entered her, pumping in and out, over and over again, sending thrills through her, until suddenly they were gone and she was left feeling empty.

She felt him leaning over to the edge of the bed, and laid silently, waiting impatiently for whatever was to come. Within seconds, she felt cold gel being squeezed over her asshole, then the tip of the tube inserted and a cold sensation inside as he squeezed more into her. It was soon replaced by his finger, which slowly slid in and out of her, teasing her, making her beg for more.

"Do you like that, Jackie?" he asked.

"Yes," was her whispered response.

"Do you want more?" Two fingers inside, sliding in and out.

"Yes, please."

"Tell me what you want, Jackie." He demanded. Three fingers inserted, embedding themselves deeply.

"Please, Darryll, fuck me in my asshole," she begged.

"With pleasure, my dear, all you had to do was ask."

His fingers pulled out with a sudden pop and she felt the head of his cock push against her tight opening. He moved slowly, pushing forward as she pushed backwards, letting it slowly slip past her tight inner muscle. Once his cock stretched her enough to slide all the way in, she sighed her pleasure deeply and relaxed while he hovered over her.

His weight was balanced on his arms, his chest against her back, she could feel his breath on her neck, as his hips began pumping. The long, smooth strokes became harder and faster, his balls slapping on her ass, the wetness making slurping noises as he thrust again and again, building to his peak.

Needing help to reach her own climax, her hand pushed underneath herself and pinched her clit, then she began rubbing it frantically back and forth as he fucked her. He pulled back suddenly, bringing her with him, and sat back on his heels, she ended up straddling him, sitting on his thighs. She was impaled on his swollen, engorged cock, and had never felt anything so large before as he held her up.

His hands reached around in front and pushed her hand away from her clit, taking over the task, quickly bringing her over the edge as he squeezed one of her breasts roughly and rubbed her nub unmercifully. Unable to keep quiet, she cried out, convulsing, muscles spasming around the cock embedded deep within her ass, and the fingers that had slipped into her pussy.

She was still coming and groaning loudly, when he suddenly rose up on his knees and with a hard thrust, lifted her high in the air, held up by his cock and his hands on her hips. She fell forward across the pillows and he followed, pounding in and out of her until he too, cried out, shooting his load deep inside her canal.

Spent, he collapsed on top of her and they both lay quietly for a moment, catching their breath. Grinding his hips against her, she could feel his cock still deep inside, even though it wasn't nearly as hard anymore.

"So tell me, Jackie, have you ever been fucked this way?" She was pinned under his weight and knew he wouldn't let her up until she answered.

"Never like this," she replied, sensing his satisfaction.

"And when was the last time you came like this?" he continued.

"Never like this," she repeated, just knowing he was gloating.

He pushed against her again, "You love to be fucked in your ass, don't you, Jackie?" She hated it that he kept saying her name, it somehow made it more personal. He reached under her and found her clit, which was super-sensitive still. He pressed into it, making her jerk. "Answer me, Jackie. Tell me how you love having my cock shoved up your ass." He pinched her clit hard.

"Yes," she cried out, "I love having your cock up my ass, Darryll!"

"I know you do, you're so wet, and I have to apologize for ignoring your pussy today. We just don't have time right now, but next time, we'll make sure that's taken care of." With a final tweak of her clit, he pulled back and let his cock slide out of her ass. She felt his cum running out and puddling between her legs.

"What a sight, I wish you could see this, Jackie. Your ass is sticking up in the air, your asshole is stretched wide open from my cock, and my cum is running out. It makes me want to fuck you all over again." He swiped a finger down her crack and brought it around to her mouth. "Here, taste me."

She struggled to turn her head away, but he held it motionless as he forced his finger in past her closed lips. Her teeth were gritted, so he rubbed his finger across her inner cheeks and gums. "For that, you can have more," and his finger entered her ass this time, rubbing around the edges before he brought it back and shoved it in her mouth again.

"Lick it," he demanded. "Suck it clean, or I'll make you suck my cock clean." Horrified, she forced herself to relax her jaw as his finger pushed its way into her mouth, rubbing across her tongue so she could taste a mixture of them both. She fought not to gag.

"Jackie, Jackie. You're more of a prude than I thought." He stood up from the edge of the bed and smacked her ass one more time, before going into the bathroom. She heard the sound of running water and rolled off the pillows. He returned and tossed a wet towel to her, "Here you go, you'd better clean up. I'm sure you have to get back to work sometime today."

There were ten minutes to go before she had to get back to the office, she jumped up from the bed and took a tentative step towards the bathroom. Her ass was killing her, how was she going to walk normally? Trying her best, she walked into the bathroom and cleaned herself as best she could, and when she walked back out into the room, Darryll was dressed and holding her clothes out for her.

"Thanks," she muttered, taking them and starting to dress as quickly as she could. "Where are my underwear?"

"Gone. They were the worst things I've ever seen, so I got rid of them for you." He pulled them from his pocket, torn in two pieces, holding them up for her to see. There was no hope of saving them.

"Just wonderful." She dressed, hoping that nothing leaked out the rest of the afternoon onto her skirt, but knowing the possibility was pretty slim.

They walked out the door together, but split up once they reached the lobby, he to go into the restaurant, she to head back to the office. "I'll be in touch," were his parting words.

Not much work was accomplished the rest of the afternoon, she was too distracted, and she was so sore. The end of the day couldn't come fast enough, and before the clock struck five, she was out the door and headed home.

That night over dinner, Mark asked her about her day, not paying much attention when she mumbled that it was okay. He talked about all that was going on with his job, his clients and how he wanted to golf the next day.

"Whatever," she didn't really care if he golfed or not. What she really wanted was to be left alone.

"Oh honey, did I tell you we're having computer problems with the desktop in the den?"

"No, what's wrong?" she looked up from her plate.

"I don't know, but it's beyond my capabilities. I called a company here in town, one of the owners is coming out on Tuesday morning to work on it. I have a meeting that morning that I can't miss, could you take the morning off work?"

A shudder ran through her, "Who did you hire?"

He named the company, confirming her worst fears. "I talked to a guy named Darryll, he offered to come out personally..."