0 comments/ 127018 views/ 11 favorites Jackie's Punishment By: funinthesun56 Jackie sat at her desk, sorting through stacks of bills, seeing what needed to be paid, and what could be held off for a little while longer. Her bookkeeping job for this small company of three was reasonably boring and didn't keep her busy enough throughout the day. Her mind wandered as she looked out the window at the treetops just below the 5th floor level of her office. If only she could be out there, soaring like the birds who flitted from tree to tree, never looking back. It wasn't that she had a bad life, it was just boring. She and Mark had been married twenty five years, their two boys were almost out on their own, their youngest just having graduated high school and leaving for college in a few short weeks. The older son was already gone. Even though he attended the local university, he lived in an apartment with two of his friends. That would leave just her and Mark alone together for the first time in twenty years. What were they going to do? Watch TV every night? She could knit a thousand sweaters, but she'd still be bored. It wasn't that Mark was the problem, but they had just fallen into a routine. Sex every 3rd or 4th night, but nothing exciting. They even did it in the same position every time, for heavens sake. She had quit giving him blow jobs years ago when they had a major blowup that lasted for months. Somehow, she had just never wanted to again. Likewise, he no longer went down on her, choosing to use his fingers to get her off. It worked, hell, anything would work at this point. But she knew she was missing out on some good times. No one was in the office with her this afternoon, leaving her to her own devices. Work done, she had a few hours to kill before leaving. Sneaking a look around to make sure no one was really there, hiding in a corner somewhere, she turned back to her computer and typed in a few words in her search engine. A site came up with erotic pictures and stories. Feeling a flush of embarrassment, she glanced around quickly, reassuring herself once again that she was alone. Scrolling through the pictures, she was in turn shocked and completely turned on by them. "How could some of those women do that?" she thought. Or, "that's totally disgusting." What really turned her on, though, were the pictures of women with cocks in their ass. She and Mark had tried it a few times years ago, but he never acted like he much cared for it and she was too embarrassed to let him know how much she liked it. Looking at these pictures now, she could feel the excitement build. After getting totally turned on, she then moved on to the stories. What had her life come to? Getting her jollies from going to porn sites! She felt dirty, but it didn't stop her. Looking around yet again, she decided to make sure no one interrupted her and got up to lock the office door. After all, no one was coming in that she knew of, and if someone did need her, they would knock and she could just say she didn't like to be in the office alone. Settling back down at her desk, she hiked up her skirt and felt how wet her panties were. Her nub was already swollen, and as soon as her hand began rubbing it, she felt waves of desire rush through her. Reading intently, living vicariously through the fictional characters, she let her fingers pinch and pull on her clit, rubbing it intently, then letting one of her fingers slide into her soaking wet pussy. Stroking in and out, adding another finger, she felt herself getting close. She knew there was one thing that would quickly push her over the edge. Even though the door was locked, she still glanced around one more time before pulling her wet fingers out of her pussy and leaning as far forward as she could in her chair. Her hand snaked around her backside and she ran her wet fingers over her tight asshole. Her other hand worked on her clit, and as soon as she pushed a fingertip into her ass, she felt the beginning waves of her orgasm wash over her. Her entire body convulsed, squeezing her fingers in her ass, which she didn't allow to slip out until the last shudder faded away. "Oh My God!" she thought. "I can't believe I just did that here in the office!" Getting up quickly from her chair, she rushed down the hall to the restroom and tidied up in the stall, then washed her hands, not once, but twice. She looked at herself in the mirror, seeing a 45-year old woman with the afterglow of sex still on her face. She was still in good shape despite the years. Her brunette hair was straight and cut shoulder length, framing a pretty face that she hoped didn't show too many wrinkles. It was inevitable, though. Time was marching on. Her breasts weren't that large, a B cup, so sagging wasn't much of an issue. Mark had always told her a handful was more than enough anyway. Her ass was small and shapely, she still fit into her size 6 bottoms. All in all, she figured she wasn't an embarrassment to Mark. If only their sex life would liven up a little. Heading back towards her office, she heard the phone ringing and ran the last few steps to catch it. Panting hard, she sat back down in her chair and saw that her computer monitor was at the same story she had been reading when she had her meltdown orgasm. Eyes widening and heart pounding, she checked to see that no one had come in. "Hello?" she heard a man's voice from the phone, as she frantically looked all around. "Oh, sorry! Hello, can I help you?" She quickly exited out of the website and turned her attention to the person on the other end of the line. "Jackie?" "Yes, can I help you?" "It's Darryll. I needed to check on payment for some open invoices." Darryll was part-owner of the computer company that oversaw their network in the office. "I know, I know. I've cut a check for all the unpaid ones through last month, will that work?" Times were slow for everyone, it was hard to pay bills, and even harder to collect. "I suppose it will have to. You can bring it with you tomorrow." "Pardon?" Jackie was confused. Where was she going to bring it? She had no reason to go by their office that she knew of, unless her boss had arranged something she didn't know about. Leave it to him to do something like that and then forget to tell her. "Well, let me put it this way." Darryll smirked. "Were you aware that your boss had me install software on the computers in your office that tracks what websites you visit?" "What?" Jackie shrieked. That little shit! How dare he? Wait until she ripped into him over that one. She knew he was the worst offender of all, he just wanted to see what she was doing, obviously. Which suddenly made her heart stop. "Oh my God," she whispered. "I can see in real-time exactly where you surf on the Internet, Jackie." His voice was way too smug for her liking. "Shit." "So here's what I can do. I can cover this up easily, and you can keep your job." She knew it couldn't be that easy and waited for the axe to fall. "Of course, you will owe me. A lot." "Darryll, I don't have extra money." He laughed, "That's hardly what I was talking about, Jackie." A cold shiver ran through her. "Tomorrow, meet me at the hotel across the street, 1:00 p.m. You can bring my check with you then." "You've got to be kidding! Darryll, there's no way I can do that. I'm a married woman and I've never been unfaithful to my husband," she pleaded. "You don't think what you're doing is a form of unfaithfulness? Does he know you do this?" Darryll demanded. She didn't answer, couldn't answer. Her heart was pounding painfully, and she had no idea how to get out of this mess she had gotten herself into. Damn this man. He was a nerd, a complete computer nerd. She hardly remembered what he looked like, other than he wore glasses and wasn't much taller than she was. "I didn't think so, and I don't think you want me telling him, now do you?" he asked, waiting for an answer that she couldn't get out. "Good, I'll see you tomorrow. Oh, and Jackie?" A short silence followed as she still didn't respond. "Shave your pussy please." "I can't!" she cried, startled into responding. "Sure you can, you'll figure out a way." With that, he hung up the phone. She stared at the receiver in her hand like it was going to bite her, before slamming it down. No. This couldn't possibly be happening. "I just won't go," she thought. "Surely he's not serious." As the rest of the afternoon slipped by, minute by agonizing minute, Jackie sat and stared at the offending computer monitor. Anger at her boss filled her with resentment, more so than it normally would have. She was blaming him for her predicament, when in actually, it was no one's fault but her own. The hands on the clock moved painfully slow until finally they reached 5:00 p.m. Jackie had never been happier to see the end of the work day before. All she wanted was to get home and forget about what had happened. Unfortunately, it didn't work that way. When Mark walked in the door, all she thought about was what she might potentially be doing to their marriage. She was quiet throughout the night, and when Mark asked what was wrong, she complained of a headache. That excuse always worked. She begged off watching their favorite TV show together and went to bed, where she tossed and turned all night. As she was putting on her makeup in the morning, Mark walked into the bathroom and stood behind her, looking at her with concern. "Are you feeling alright? You didn't sleep well last night, did you?" He rubbed her shoulders just the way she loved it. She stopped what she was doing and just stood there, arching her back like a cat, purring her approval. He laughed as he walked back into the closet to get his clothes for the day. "You're fine, you little pretender." "Yes, I'm fine, I just don't want to go into work. Do you know what that little shit, Thomas, did?" Without waiting for him to answer her, she proceeded to tell him about the software installed to track all Internet usage. "So much for my shopping anymore." She very wisely didn't mention any other surfing she did online. "Well, you can't really blame him. It's a major problem in the workplace for employers." "Mark, you can hardly say I abuse it! I get my work done." Jackie complained. "Yeah, but does he know that? Obviously, he thinks there must be some problem." "The only problem is him." With that, she walked into the closet and chose her own wardrobe for the day. Not wanting to even think about what might possibly happen, she carefully chose a business suit that was as far from sexy as she could get. She pulled on a camisole over her boring bra, hose over her boring underwear (no thongs for her today), donned her suit and a pair of pumps. Bo-ring, and just the look she was trying to achieve. "Bye!" she called out as she headed out the door. "See you tonight, honey." Mark was still reading the paper and drinking his coffee as she left for work. The morning flew by, the clock's hands in fast motion, speeding toward 1:00 pm. The closer the time came, the more nervous Jackie got. She still had no intention of going, but even so, she was worried that Darryll might possibly have been serious. Surely not. At exactly 1:00 pm, the phone on her desk rang. "Hello, this is Jackie, how can I help you?" "I sincerely hope you haven't forgotten." Darryll's quiet voice sounded threatening across the phone line. "Uh, uh, well..." "Jackie, I think I made myself completely clear. Your boss will have the information on his desk by 1:05 if you're not over here. Now. And after I send it to him and you lose your job, I'll send it to your husband and let him know why." "Fine, I'll be there." "Room 405. I'll be waiting." She slammed down the phone and grabbed her purse. Sticking her head around the door of Thomas's office, she waved to let him know she was leaving for lunch. He waved his hand as he continued talking to someone on the phone. She knew he didn't have a problem with her taking a long lunch occasionally. He was leaning back in his chair with his feet up on the desk. She took the stairs down to save time, then, walking as quickly as she could, she crossed the street, almost forgetting to look for traffic, not that she cared if she got hit right now. "Hey," she thought, "there's an easy way out of this." Not ready to jump out in front of a car, though, she safely made it across the 4-lane highway and ran into the hotel, hoping beyond hope that anyone who saw her would think she was eating lunch in their restaurant. She crossed the small lobby, nervously waiting for the elevator, feeling eyes boring into her back from the desk clerk. "He must know what I'm doing," she fretted. Relief coursed through her as he turned away to help someone at the counter. The hotel had gone through a major renovation a few years ago, the décor contemporary, mirrors lined the wall of elevators, allowing Jackie to watch the people coming in the front doors, walking to the desk, or entering the restaurant, and fortunately, she saw no one she new. No one else was waiting for the elevator as it finally announced its arrival and the doors slid open. Alone in the car, she watched the floor lights signal its rise, praying that it would take her beyond the fourth floor, but she was having no such luck today. The doors opened with a swish, and there was nothing left for her to do but walk down the hallway until she found Room 405. The carpet muffled her footsteps, and as she reached the door, her hand hesitated as she raised it to knock. "This is it, do or die," she muttered. Taking a deep breath, her knuckles rapped on the smooth, wood door, and her heartbeat sped up when she heard the latches open before the door swung wide. Darryll stood just inside the door, staring at her intently as she hesitated. Jackie had never looked carefully at him before, he came in the office, worked on the computers, and left. Looking him over now, she realized he really didn't look that "nerdy". The glasses weren't in sight, and she suspected he only wore them for close up work, just as she had to do when sitting in front of the computer for very long. His wavy brown hair was a little long, but acceptable enough by today's standards. He wasn't much taller than her 5'7" frame, and she could see he actually had defined muscles in his arms and guessed he worked out to offset the time he sat doing computer work. "Come in. Nice to see you made the smart decision." He stepped back, sweeping his arm to indicate she should enter. Jackie wanted to slap him, but chose to hold back, at least for now. Shoving the envelope with his check at him, she held her head high and walked past him through the tiny hallway and into the room. There was one king-sized bed, lucky her, a tacky painting hung above it, a dresser with TV on top, a round table in the corner with two chairs scooted up to it. A standard hotel room, she knew what the bathroom looked like without even seeing it. There were thousands of identical hotel rooms across the country. She wasn't sure what she expected, but it wasn't Darryll walking past the bed and pulling out a chair at the table instead. Maybe she thought he was just going to strip her clothes off, take her right there and then and be done with it. Sitting down, he looked very much at ease with himself and looking forward to their encounter. "Darryll, why are you doing this?" she broke down and asked. "Please, don't do this to me." "It seems to me you brought this on yourself. You shouldn't be visiting those kinds of websites if you are such a prude." He sounded impatient. "But we both know you're not a prude, don't we. Tell me, Jackie, what do you do when you're looking at those pictures, or reading those stories? Do you play with yourself? Do you make yourself cum?" Red suffused her face, she wanted to die of embarrassment. "Tell me," he demanded, not letting her out of an answer. "A little," she murmured. "A little? How do you make yourself cum "a little"? You either do or you don't. Do you think you'll cum today "a little" or a lot?" His eyes were greedily running all over me. "Take off that god-awful suit. Are you trying to look like a nun?" "Nnnooo." She stammered. "No what? You're not trying to look like a nun?" "No, I'm not. These are just my work clothes." He snorted, seeing through her ploy. "Take them off. Now, Jackie. The threat hasn't gone away and won't as long as you don't do what I want." "I've never stripped for anyone before." "Get used to it. Now start." His voice brooked no more argument. He sat back, waiting for the show. Slowly, she unbuttoned her jacket, hands shaking a little. As she reached the last button, she slid her arms out of the sleeves and carefully laid it over the back of the other chair. Stepping out of her shoes next, she then pulled the camisole up, breasts pushing against her bra as her arms lifted up to pull it over her head. The bland and boring bra looked just what it was. A utility bra, she was ashamed at the way it looked, though why she should care made no sense at all. Darryll's breathing was coming a little quicker as he watched her intently. She could see the bulge in his pants as his cock grew, straining to get out. She reached behind herself and unzipped her skirt, letting it puddle around her feet before bending over and picking it up, laying it carefully with the jacket and camisole so it wouldn't get wrinkled. Her bland and boring underwear looked like something an old lady would wear, and Darryll's reaction didn't disappoint her in that regard. "That's enough to make me lose my hard-on. Good God, woman, is that what you really wear under there?" He laughed. "Does your husband ever fuck you? With that stuff on, I sure as hell wouldn't. But then, I know you have another side to you, don't I? Continue on." He waved his hand at the rest of her garments, signaling he wanted them removed. Sitting down on the edge of the bed, she took off her hose, not trying to look enticing, just pulling them down and off. Reaching behind her back, she unhooked her bra and let it begin to fall forward, before crossing her arms in front of her breasts, attempting to cover them for a little while longer. A snap of his fingers had her pulling the straps down her arms and dropping it on the floor, her breasts falling free, the dark nipples puckering as he watched them. "Come here," he grabbed her by the wrist, pulling her closer. His hands reached out and squeezed her breasts tightly and painfully, before pulling one towards his mouth and licking a nipple. His teeth nipped at the tip, pulling it out tautly, causing her to gasp, half in pain and half in excitement. She couldn't believe she could react to this, but apparently she was, as she felt dampness spread between her thighs. Letting go of her nipple, he pushed her away and pointed towards her underwear. "Please, get those things off. Burn them tonight. Don't ever wear them again." "Oh please, what does it matter to you?" She was pulling them down and let them fall around her ankles before stepping out of them. When she looked back up, she was surprised to see real anger on his face. "What did I specifically tell you to do?" He demanded. For the life of her, she didn't know how to answer. She frantically searched her mind before realization dawned. "I couldn't! Don't you think my husband would think shaving myself was a little suspicious? I've never in my life done it before, he's going to wonder what in the world would make me start now." "Listen to me, Jackie, and listen carefully. This is not the one and only time we will be doing this. As a matter of fact, I'm thinking every Friday afternoon would suit me just fine. So I don't really care how you do it, but by this time next Friday, you're cunt had better be shaved clean." Jackie's Punishment Ch. 02 Tuesday morning arrived with little fanfare, the sun rose as it always did, the alarm clock sounded at 7:15am, just as it always did. The next door neighbor's car door slammed just as it always did at exactly 7:20am. Jackie rolled over and buried her head under the pillow, not wanting to greet the day quite yet. She wasn't going in to work this morning, having used one of her vacation days to stay home and wait for the computer repairman since Mark had an important meeting today, of all days. Sleeping late was a luxury that didn't happen often, she wanted to take full advantage of it. The squeak of the bathroom door alerted her to Mark moving around the room, getting showered and dressed for the day ahead. The aroma of coffee wafted up the stairs from the automatic coffee maker, clearing her head and pulling her from dreamland. She stretched, raising her arms high above her head, and as she did so, the sheet fell down around her waist, exposing her naked breasts. Mark chose that moment to walk out of the bathroom, pausing on his way to the door and stopping by the bed. Sitting down on the edge, he reached over and gently fondled one breast, giving her a kiss on the forehead before rising. "Looking good, as usual, Jackie." He smiled. "Wish I could stay, but I've really got to get going. I'll give you a call later today to find out how the repair went. Maybe tonight?" The question hung in the air between them, they didn't make love often enough, so she smiled up at him and agreed. "Absolutely, we'll go to bed early." With that, he was gone. Jackie threw back the covers and padded towards the bathroom to get a shower. But the smell of coffee drew her to the kitchen first to pour a cup and take back with her upstairs. She walked through the house naked, not worrying about anyone seeing in, their property was large and private. Back upstairs, she showered and dressed for the day, not sure what to wear...not sure what Darryll expected her to wear. She was pretty sure he had an opinion, but she didn't know what it was, other than it had better look sexy. Choosing a thong and nude lace bra, she found a short skirt and t-shirt that looked like they'd do the trick. She left her feet bare as she went downstairs to the kitchen and cleaned up from last night's dinner. Trepidation filled her; Darryll was the computer repairman who was blackmailing her into sex as payment for his silence over catching her visiting explicit porn sites on her computer at work. He had threatened to tell her boss, as well as Mark, if she didn't meet him on a regular basis. So far, they had only had one encounter. But that encounter had taken days to get over. Her ass still tingled at the memory of the resounding spanking she had received and the thorough ass-fucking he had given her. She wondered if he knew who's house he was coming to today, and suspected he did. It was just her luck that Mark couldn't be here and had specifically asked her to stay home. She spent the morning catching up on laundry and making phone calls that always got put off, like the scheduling of dentist appointments for her two boys. Nervousness grew as 11:00 am neared, the time Darryll was showing up. It made her angry when she dwelled on the problem. First, it wasn't right that Darryll should be blackmailing her, and second, why, oh why, did she respond to him? She never would have believed she liked her sex a little rough, but she had not one, but two, orgasms when she was with him and that wasn't even in a full hour's time. She was getting wet again, just thinking about it, and became determined to not allow herself to let go this time. Damn him, she wasn't going to let him get the upper hand. All too soon, the doorbell rang. She left him standing outside for a few minutes while she stood in the kitchen, wondering if she could pretend not to be home. No, Mark needed his computer fixed, and it didn't matter if she wasn't here, because if not today, then just another day, as it wasn't going to end. Head held high, she opened the door and stepped back, not greeting him and not meeting his eyes. "Good morning to you, too, Jackie. What kind of a way is that to greet me?" He leaned over and buried his head in her neck, taking a deep breath. "Ahhh, the scent of a woman." The door reverberated as she slammed it shut, pictures rattling on the walls and a vase on the table in the hallway threatening to fall off before she caught it and set it back upright. The little display of anger only encouraged him, she realized, as he laughed. Setting the case he carried down on the floor, he reached under her skirt and shoved his hand under her thong, seeking her wetness to confirm how turned on she was. She felt a finger enter her, and knew he was satisfied by what he felt. The finger came out and he ran it around her lips, "Taste yourself, Jackie; you're ready for me, aren't you?" She kept her mouth closed, but could faintly smell the musky odor of herself on his finger, and now on her lips. Seeming to tire of the game, Darryll stepped back, picked up his case and headed down the hall, "Where is it?" She directed him into the den and pointed out the computer that was giving them problems. He sat down behind the desk, opened up his case and pulled out his laptop, setting it on the desktop and firing it up. "Come here a moment." She had been standing in the doorway, leaning against the jamb and wondering whether or not to stay. His quiet command brought her to his side. "Sit down," he patted his leg, so she sat down on his lap, stiffly at first, wondering what he could possible be planning. He placed an arm around her waist, pulling her back against him. "Relax." He picked up a flash drive and placed it in the USB port of his laptop. "Watch this." Her heart came to a complete stop as she saw a picture of herself completely fill the screen on his laptop. A slideshow began, starting with her standing at the open door of the hotel room last week. The next picture was her fully clothed, standing in front of him as he sat in the chair at the table, then standing in front of him completely nude. Next, she was across his lap getting spanked; she could actually see the red handprints on her ass. From that, the slideshow moved on to the moment when his fingers were in her ass and it was obvious she was climaxing. As she sat transfixed, she felt his hand move up to cup her breast, his thumb rubbing against her hardened nipple, causing the dull ache of need to spread through her. She gasped as she saw herself down on her knees with her head between his legs, which must have been when she was licking the spot behind his balls. Another shot of her with his cock in her mouth, her eyes looking up at him. His hands were on her waist, positioning her so that her legs straddled one of his thighs. She found herself slowly rocking back and forth against him, applying pressure to her clit, her breath a hiss, as she watched the show unfold before her. Shot after shot filled the screen, leading to her spread across the pillows on the bed with her ass up high in the air. There he had three fingers in her ass, the shot of her face showed nothing but desire. Another one of his cock entering her ass, more while he was fucking her, and finally, the picture that the slideshow stopped on and didn't change from again, a picture of her all alone, sprawled over the pillows, ass high, with his cum dripping out of her gaping asshole and running down into her pussy, leaving a puddle of fluids between her legs. "What do you think?" he asked, nuzzling her neck. "You...you...you had cameras?" "Sure, I set them up discreetly around the room before you got there. These are just snapshots from the videos I have from four different angles." "You bastard!" she cried, trying to break free of his hold on her. He held on tight to her until she stopped fighting, but tears threatened to run down her cheeks as she thought of how her life was ruined. "Don't worry, no one will ever see these but you and me. I'm not that much of an ass." His words didn't reassure her completely, though. What if he changed his mind someday? "I have some presents for you." Reaching down into his case, he came back with a small brown bag and handed it to her, then reached back down and bringing out something else, he held it by his side so she couldn't see it yet. "Open it," he nodded at the bag. A little worried at what was inside, she stuck her hand in the bag and pulled out a box; looking at the picture and words printed on the outside, her mouth dropped open. "An enema? That's your gift?" She set it down on the desk in disdain. "You're out of your mind." "It's entirely up to you whether you want to use it or not, but it might make you more comfortable knowing that you're cleaned out and have nothing to worry about." She considered that, and then set it aside to think about later. Leaning over to see what was in his other hand held just out of sight, her pussy rubbed roughly against the hair on his leg, causing her to stop for a moment and allow the little electrical shocks to run up and down her insides. A moan escaped through her parted lips, her eyes closing, as she rubbed again. "You shameless slut, Jackie," Darryll teased. "Do you want me to lean you over the desk and fuck you right now?" Actually, the answer to that was a wholehearted yes, but she couldn't bring herself to give him that satisfaction. Instead, she stopped and sat up straighter, primly smoothing the front of her skirt down to cover herself. He couldn't stop from laughing at her attempt to appear like she wasn't turned on. He decided it was high time Jackie saw her other gift, and as he lifted it up to show her, what she saw made her gasp, for he held a riding crop in his hand. It was 2 – 3 feet long, covered entirely in leather, thick at one end where he held on to it, tapering as it extended out before ending in a flat leather tongue that she was sure would hurt when it came in contact with bare flesh. She pushed against him, shaking her head back and forth, "No, no, no." "Yes, yes, yes. You're going to like it. The way you like to be spanked, I know you'll like this, too." He was right, she had loved being spanked, but this was going too far. A moan came from deep inside, half in fear and trepidation, the other half from pure lust. She was so wet, she guessed that his leg was soaked. She knew he could feel it, she could feel his cock pressing hard against her. "Go upstairs, take the enema with you and use it, and while you're there, Jackie, shave the pussy." "How am I supposed to explain that?" she cried. "You tell your husband when he comes home that you're hot for him and have been thinking about him all day, that's how. Now go do it, or I'll have to try this out now, rather than later." He snapped the riding crop against the desk; the sound sent her hustling out the door and up the stairs to follow his orders. A little under an hour later, Jackie stepped out of her bedroom, all her pubic hair gone, her ass "cleaned" out, and freshly showered. Not bothering with any other clothes, she had slipped on a short robe. Taking a deep breath and gathering her courage, she started down the steps, holding tightly to the handrail, slowing at the bottom for only a moment before moving across the hallway and entering the den. Darryll was staring intently at the computer monitor, glasses perched on the tip of his nose. "Good timing, I'm just re-booting this. It was just a little conflict in the software running on here. You shouldn't have any more problems with it." With that, he pushed back from the desk and turned to look her over. "Very nice, come here and let me look at you." Tentatively, she walked over to stand in front of him, allowing him to untie the knot in her robe and pull it back to expose her body for his examination. He ran his hand over her mound, feeling its smoothness, then explored farther, urging her to spread her legs for him. His fingers ran over the outer edges of her labia, checking to see if she had gotten everything, then even moved farther back to feel around her asshole. "Jackie, I'm so proud of you, you got it all, didn't you? And the enema, did you use it?" He looked up at her face as his fingers continued their exploration. She nodded, not trusting her voice to come out as more than a squeak. "Tell me, is there any chance Mark will be coming home?" "No, he never comes home during the day, it's too far to drive and I know he has meetings scheduled all day." "Good. I don't have to leave for a few hours." A finger thrust deeply into her, twisting around before coming back out to rub across her nub. She felt him pull on it, then push back the outer covering, exposing the most sensitive part of her and rubbing his thumb hard over it. His hands moved non-stop, either a finger or a thumb in constant contact with her clit, the rest moving in and out of her pussy, one, two and even three fingers at a time shoving hard in and out, in time with the rhythm he was playing on her clit. Her legs grew weak, threatening to collapse under her, as her breath started coming in gasps, an orgasm building to an explosive end. She felt a wave hit her hard, and after that, all she remembered was her entire body convulsing as her hands came down to grip his hand, holding it tightly against her in order to extend her climax as long as possible. Pulling his hands away, he grasped her hands and drew her closer so he could lean forward and lick the still-swollen, hyper sensitive nub. She cried out, wrapped her hands through his hair and tried to bury his face in the cleft between her legs. "More of that later, but for now, I have something I want you to do for me." He stood up, unzipping his pants. As he stepped out of them, he kicked them aside. "Something nasty, something that you want to do for me." Turning away from her, he placed both of his hands on the desk and spread his feet apart. "I want you on your knees behind me, and I want you to lick my asshole. And I don't want any arguments, or I guarantee you, we will try out that crop right now." His voice brooked no argument, and knowing he was deadly serious, she dropped to her knees, facing his backside. His cheeks were firm, muscles solid as they ran down the backs of his legs. She settled in behind him, and tentatively reached out to part his ass cheeks. Hearing him sigh, she leaned into him and let her tongue lightly rim him. She was beyond humiliation right now. "Don't worry, I'm clean," he panted, having her in this position obviously greatly excited him. Her tongue began licking in circles around his hole, teasing it, leaving it to travel down to his balls hanging between his legs. She nuzzled them before moving back up and running her tongue back and forth across the outer edges of his puckered hole. "Fuck me with your tongue, Jackie," he commanded. Without question, she pointed her tongue and pushed at the very edges, barely parting him. "You can do better than that." Her tongue pushed harder, slipping in, until she had to swallow and pulled it back out, then pushed it in again, a little farther this time. The taste was faintly bitter, she quit trying to swallow and let her saliva run down his crack and her chin, as she pumped her tongue in and out of his ass. He pushed back on her, and she reached through his legs to cup his balls in one hand and grasp his cock in the other. The sac surrounding his balls was stretched tightly, they were heavy and full in her hand. She guessed he was ready to come because he quickly stood up straight and turned around, shoving his cock into her ready and waiting mouth. Thrusting hard only three or four times, he held her head still while he shot his cum deep into her mouth. "Ahhhhhh." Leaning back on the desk that had so recently supported him; he held her face tightly in his crotch as he ran his hands through her hair, letting his breathing slow down, occasionally thrusting forward as she sucked a few times on his softening cock. There was nothing else to do but swallow the cum filling her mouth. She had never swallowed Mark's before and didn't want to start now, but she had no choice. The taste wasn't nearly as bad as she had thought it would be, but not necessarily something she wanted all the time. She had a feeling that she'd be doing a lot of this with Darryll. "Your turn." His cock slipped out from between her lips, he lifted her by her arms to stand on her shaky legs. The brown leather couch on the other side of the room beckoned as he steered her in that direction. "Lay down and spread your legs wide for me." She obeyed, laying her head back on the cool cushion, her right leg up and over the back of the couch, her left hanging off the side. He sat down in the space between, lifted her leg and pushed it back up towards her body, exposing every inch of her to his exploring eyes and hands. Watching him look at her, she felt herself quiver, then begin shaking all over as his head dipped and his mouth closed over her sensitive nub. It began sucking, nipping, licking, probing, sending waves of ecstasy throughout her. His tongue fucked her pussy, then licked the tight hole of her ass, before fucking that, too. He was holding both of her legs up and wide open, she grabbed the back of his head and pressed it deeply into her crotch, all thoughts and feelings centered there, her head was turning back and forth as she cried out over and over. He took her swollen clit in his mouth again and sucked on it until she began screaming and came violently. Slowly, so slowly, her climax began to fade, and she settled back down into the couch, her legs coming down to rest, her arms falling at her side. She felt Darryll's lips move up to her stomach, up farther to her breasts, the wetness on his mouth and chin spreading over her. His tongue lapped at her nipples, which were hard to the point of hurting. His fingers replaced his tongue, pulling her breasts taut, causing her to flinch at the same time as she groaned. He let them go, rubbed them, then pinched them hard, squeezing them between his thumbs and forefingers, rubbing them back and forth, never easing up on the pressure. Her moans turned into pleading as he continued to abuse her breasts, causing her both pain and intense pleasure. "Do you like that?" She didn't answer, couldn't answer, because she was too ashamed to say she did. Grabbing her by both of her wrists, he pulled her up, led her over behind the club chair next to the couch and told her to bend over the back of it, spread her legs and grab the arms. He nudged her legs farther apart, pushed her farther over the back, and walked behind her back towards the desk. He returned a moment later and stood behind her quietly for a moment. She was weak from anticipation, not knowing what to expect. A soft brush against her skin caused her to jump, another brush against her thigh, another across her back, one between her legs. She didn't know where the next spot would be, jumping each time she felt it. He was teasing her with what she was sure was the leather tip of the riding crop and she felt her juices start to drip down her legs. A sudden whistle through the air didn't give her enough time to prepare for the sharp pain when it landed on her right cheek. She jumped and yelled, but another quickly followed, and another after that. Realizing it didn't hurt as badly as she thought, she stopped fighting it and let her head fall forward and gripped the arms of the chair as hard as she could, bracing for more. The whip moved from one leg to another, one ass cheek to the other, eventually she felt it land on her pussy, which sent a searing pain through her. Tears sprang up, constant moans came from between her lips. At least two dozen strokes fell on her ass and legs before finally ending. She couldn't get up, she felt him kneel down behind her and run his hands over her, gently rubbing the spots he had just beaten, kissing them gently, licking her from ass to clit, driving her insane. Jackie's Punishment Ch. 02 He stood and his cock pushed against her pussy, seeking entrance; she wasn't surprised to feel how wet she still was. A mixture of emotions ran through her, deep shame, intense lust, a measure of fear. All combined, she was left uncertain, but knowing that what she really wanted, desperately needed, was to feel him inside her. As his cock found its way home, she pushed back against him and sighed deeply, matching him stroke for stroke as he pounded into her waiting pussy. She could tell his orgasm was intense, he cried out as he thrust deeply, spilling his cum into her, which sent her spiraling into another orgasm of her own, causing her muscles to spasm around his cock, gripping it tightly. He pulled back, letting his cock fall out of her, and again rubbed over her throbbing ass. "The red will fade by tonight, I didn't hit you hard enough to leave any bruises or marks. It will hurt to sit for awhile, though." "Why did you do that?" she asked as she still lay sprawled over the back of the chair. "I wanted to see how much you could take, and what you are capable of. You loved it, didn't you, Jackie? He pulled her up and turned her around to face him. "Look me in the eye and tell me." She did look in his eyes and was afraid not to tell him the truth, "Yes, I did love it. But I hated it, too." "It's okay, you'll get used to it." He patted her cheek, then turned to go find his clothes and put them back on. Gathering up his equipment, he put the laptop back in the case, the riding crop back in beside it and pulled out a sheet of paper. "Here's an invoice for the work I did. Now, walk me to the door." She didn't argue, just followed him to the front door and let him squeeze a breast and pinch a nipple, then fondle her pussy one more time before opening it to let himself out. "See you Friday at lunch," were his parting words as he stepped off the porch. 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..."