Jackie's Punishment

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."