The Mistake Ch. 02

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Ginny does what her boss wants her to, to preserve her job.
6.6k words
4.33
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Part 2 of the 2 part series

Updated 09/22/2022
Created 01/31/2012
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"Great," Doug said, and walked a slow half circle around her, behind her but very close. He went to the chair in which Ginny had been sitting and slid it over in front of her. He then sat down in the chair, and leaning on the front edge of it, he looked her slowly up and down, as if contemplating what to do next. Ginny figured he had some ideas, but she thought she'd probably taken him by surprise, agreeing to his stupid game so quickly. That was fine by her. Maybe without time to plan, he'd be letting her off easier than he otherwise would have.

She'd obviously been sarcastic when she asked if all day was enough time for him, and was somewhat taken aback when he said he'd be finished with her by lunch. Three fucking hours?? How much groping and kissing and gawking could the guy possibly do before getting bored? Still, she was not inclined to back out now. She figured it was the best she could hope for in this shitty set of circumstances, and the sooner she satisfied him, the sooner she could move on and forget about this whole sordid deal. If Doug really wanted to spend three hours rubbing her tits and ass, Ginny was prepared to comply in order to extricate herself from this mess. It would be humiliating, but that would be the end of it, and no one else would ever have to know.

"OK then." Doug's hands had been together in front of his face, fingertips touching, as he looked her over. he dropped them into his lap when he began speaking. "The most important thing I'm going to ask you to do is relax. If you're tense, or frightened, it may ruin it for me." He paused and raised an eyebrow at her.

"I said you might even enjoy this a little," Doug went on. "Perhaps that's wishful thinking on my part. But if you hate every minute of it, it's probably best if you don't let that become obvious.

The unspoken subtext, Ginny assumed, was that she'd better seem to be enjoying herself while her douchebag boss stuck his tongue in her mouth and squeezed her ass. Fine. For the rest of the morning, to save her job and her family's lifestyle, she could submit to Doug's fondling and not be overtly disgusted by the way he'd leveraged circumstance to coerce her into this.

"Do you understand what I'm saying?" Doug asked.

"Yes."

"And you're OK with removing your top, and your skirt, and letting me touch you anywhere? Through your underwear, of course."

"Yes. That's fine."

"'Fine?'" Doug echoed. He sounded mildly skeptical, but also a tiny bit mischievous. Ginny wasn't sure if he was seriously asking her to play this up for him, but she didn't want to take any chances.

"I WANT you to touch me, Doug." She delivered the best fake smile she coud manage, trying not to over-do it. Doug responded with a smile of his own, an obviously genuine one.

"Ahh, excellent!" he said. "Let's begin." The way he said 'begin,' like this was some grand event for which he was host and emcee, caused her nervousness to flare up again, but she suppressed it.

"First I need you to take off that blazer," said Doug.

"Sure, no problem." Ginny was wearing a light wool skirt suit, with a two-button jacket, both buttons done. She turned toward the door as she undid the buttons, and walked over to the nearby coat hooks, taking off the jacket and hanging it carefully on one of the hooks. She turned back toward her boss, still sitting on the edge of the chair, and walked back to where she had been standing. Doug's eyes lit up and zoomed in unrepentingly on her chest.

"Wow. Ginny. Very, VERY nice. I didn't think I'd ever see that."

Under the jacket she'd worn a gray-green silk blouse. It was a very plain blouse, and Doug seemed more excited than she would have expected, considering he'd seen her in just a blouse plenty of times. It wasn't as if she always wore a jacket at work, and--oh, fucking shit. Fuck.

Too late, Ginny realized the reason behind Doug's reaction: she'd been in a real rush this morning, knew she was going to be late. She couldn't find the bra she'd wanted, and the only comfortable one quickly at hand was sheer; no padding. In other words, no nipple protection. She was always exceedingly conscious of not having her nipples show through her clothes, and when she wore a thin blouse like this one, she would be sure to have a thick, padded bra beneath it. When she couldn't find one this morning, she had donned the sheer bra in her rush, and chosen the suit with the most comfortable jacket, so she could just wear the jacket all day. The tumultuous events of the morning had made her completely forget about that. But now, under Doug's gleeful stare, she was all too aware that her bra offered no protection, and that Doug was looking at her very clearly defined nipples through the silk blouse. Judging from his reaction, her nipples had already been hard, and now, standing there facing him, she was sure they were getting harder.

Her instinct was to cross her arms over her chest, but she thought that would probably be a bad idea, so she forced her arms to stay at her sides. Just fucking great. It was one thing to stand there in her underwear (which she would of course soon be doing, having agreed to Doug's terms) with her normal padded bra. But if she took her shirt off now, she would essentially be bare-breasted. You could see everything through this bra; it was one of her husband's favorites.

Ginny didn't necessarily think that remembering what she was wearing would have changed her mind about giving in to Doug's deal. But she might at least have put it off until another day. At this point, it would have seemed ridiculous to try and back out, though, so Doug was just going to get a goddamned good look at her nipples, and that was that.

"Just beautiful," he breathed, and sat back and took a long stare at Ginny, soaking it all in. She clasped her hands together behind her back, and ever so slightly poked her nipples toward him, trying to make sure he got the best show she could give him. When this was over, he wouldn't be seeing any more of her, she'd be sure of that. She wanted to look down at herself, to see how visible her nipples were, but she resisted. She didn't really need to, though. She was certain they were as hard as they'd ever been, as she could literally feel them pushing against the fabric.

"OK then, perfect," Doug beamed. "We've got plenty of time, and I don't want to rush things. Believe it or not, I've got a couple of phone calls to make, and some forms to fill out for the Pratchett proposal. And I'm going to do that while you're in here. I'll ask you to take the shirt off in a bit. But first, can you come closer?"

Ginny took a few steps, and they were at normal conversing distance, perhaps a little closer.

"Closer," Doug ordered. Ginny stepped forward until her tits were right in Doug's face, an inch or two away. He was still sitting down. His arms came up and he wrapped them around her, his hands moving over her butt, then back around to her hips, finally gliding down the front of her thighs, over her skirt. He let them drop, but then she felt one hand on her leg, just below the knee. He stroked her leg up and down just a little, squeezing her thigh lightly, then moved the hand slowly upwards under the skirt. He kept going until his fingers found the top of her stocking, and there encountered bare skin. Ginny breathed in sharply, involuntarily.

Doug looked up at her face, and now Ginny looked down, to see him with a small serene smile on his face. Their eyes met briefly, then Doug closed his and began massaging her upper thigh...small squeezes, and rotating his open hand around to the back, then back again. His eyes were still closed, and his face angled up toward hers, his chin pressing against her midsection. He switched hands then, and began to massage her other thigh in a similar manner. He pulled away slightly, just enough so he could raise her skirt a tiny bit with the free hand.

"Do you want me to just take this off??" Ginny moved her hands to her lower back, feeling for the skirt's zipper, trying to move things along a little bit.

"No!" Doug rushed to say. "Keep your hands back there, though. Just rest them on your butt."

Ginny breathed out, a very tiny sigh through her nose, but did as she was told.

"Stand with your feet a little bit further apart," Doug directed.

She repositioned herself. Now she was standing with her feet shoulder-width apart, Doug sitting in front of her holding the hem up with one hand, rubbing her leg with the other. He scooted closer and now moved his right hand up under her skirt and around to grab her left butt cheek. She could feel his hand exploring her ass, under her own left hand. As his hand moved around to the center of her ass, his forearm forced her skirt up higher, and his left hand, still on her inner thigh, became more active. He creeped up higher, continuing to squeeze her thigh, moving back to front, until finally she felt the top of his hand brush against her pussy lips.

Doug paused for two seconds, then repositioned his left hand between her legs. He rotated his wrist to let his palm face upward, and brought his hand firmly up to feel her pussy through her underwear. His middle and index fingers began to rub her lips, moving up toward her clit, then back toward her asshole. After a minute, he again repositioned his hand, up higher, so his fingers pointed up toward her navel, and slid his hand higher so he could rub the top of her slit with his thumb. His right hand was still on her ass, and now he used it to pull her in tighter to him. His left thumb searched for her clit, and quickly found it. She was certain he knew, because she couldn't help arching her back just a tiny bit. Doug began rubbing her clit intently with his thumb, in small circles.

"Warrmmm..." he said slowly and quietly. He tilted his head up, to watch her face. Ginny was looking at him, but couldn't maintain eye contact. She directed her gaze over Doug's head, and looked at his computer monitor, still turned backward so she could see it, still displaying the email from Dan Greaves demanding her dismissal. Doug squeezed a little tighter from behind, and his thumb, still making circles on and around her clit, began to rub faster, and push harder. Ginny was feeling a surreal combination of anger, desperation, and, she had to admit, turned on. She knew there was a significant wet spot growing on her panties.

Very suddenly, Doug stopped and pulled away from her. He sat back in the chair now, and appeared to be trying to catch his breath. It was as if he knew he was getting too worked up and didn't want to continue along that path at the moment. Ginny couldn't help noticing a respectable bulge in his pants. He stood up and walked back to his desk, began opening drawers and closing them.

"Are you looking for something?"

"Pencils. I was going to have yoyu sharpen some pencils for me."

"What??" Ginny was puzzled. "We use mechanical pencils. And pens."

"I know, but I had this weird idea," Doug laughed nervously. "I wanted to watch you sharpen pencils in your underwear. Is that weird?"

Ginny didn't know what to say. "Ah, never mind," said Doug. "We can do that tomorrow." The phone rang.

"Doug." Ginny said.

Doug picked up the phone "Yea, Doug here," he said quickly, then listened on the line.

"DOUG." Ginny almost yelled.

"Hang on," Doug said into the phone, and pushed the hold button. "Hm?" He looked at Ginny, questioning.

"There is no tomorrow, Doug," she said, very deliberately.

Doug looked confused.

"This ISN'T an ongoing arrangement. Don't fuck with me, Doug. We made a deal. You have me in your perverted little game for the morning. Today only. Then we go back to normal. RIGHT?"

"Oh, yes," Doug's eyes unclouded and he seemed to snap back to reality. "Sorry, of course. I was just distracted for a minute, didn't know what I was saying. Listen, I need to take this phone call, OK?"

"OK..." Ginny said.

Doug held his finger over the hold button. "Ginny, I'd like for you to take that shirt off while I'm talking on the phone. Just there. Stay right there. I'm going to deal with this, and while I do, I want you to unbutton your shirt, and take it off. Not too quickly, OK?"

Before Ginny could ask for any clarifying instructions, Doug pushed the hold button and had the phone back to his ear, already talking about proposals and transfers and some details for an account that Ginny didn't know anything about. He leaned against the side of his desk and talked intently, looking down at the floor. She wasn't sure if Doug was really still paying attention to her, or if the conversation had absorbed him, so she just stood there, fingering the top button on her blouse with one hand.

Finally, Doug looked up. "Hang on. Just a minute." he sounded annoyed. He held the mouthpiece of the phone against his stomach, to muffle sound, but he didn't actually say anything. He raised his eyebrows then made a turning motion in the air with his other hand, as if to say 'let's get on with this.' Ginny shrugged, shifted her weight to one leg, cocking her hip out, and rolled her eyes. But she unbuttoned her top button.

"Sorry about that," Doug was back on the phone now. "I just had to get something started. Yeah. Yeah, it's going now." He looked pointedly at Ginny as he spoke.

Ginny started in on the rest of her buttons. Doug wanted her to go slowly, she knew, but she felt stupid. She was NOT going to give him a suggestive striptease. She went as slow as she could, but soon had all of the buttons undone, and stood looking at Doug, her blouse hanging open. She didn't have huge tits (they were 34C), but they weren't small, either, and when held in by a bra, they forced her shirt outward some, so there was a several-inch gap now in her shirt, through which Doug could see her bra clasp and the inner curves of both of her breasts. Doug was still talking, but he was paying attention to Ginny now, and he made another 'get on with it' motion, telling her to take the shirt all the way off. She took a deep breath, grabbed her blouse above her chest, and pulled backward. It was impossible to do this motion without sticking her chest out, and it was immediately obvious that Doug enjoyed that very much. He was getting hard again, apparently, because he adjusted himself with one hand. Ginny let her blouse fall down her arms and off, catching it with one hand. She stood there, looking at Doug, holding the shirt she had just removed. Their eyes locked for a few seconds, and Ginny tried to look as bold as she could. She was sure she failed, but no matter, because Doug's eyes were already lowered, scanning her nipples. This time she allowed herself to look down, and she saw her nipples, rock hard, and poking out as they rarely had before. The sheer gray fabric did nothing to hold them back, and it did very little to conceal them. Not only could Doug see their dark color, she was pretty sure he could also see every little bump, and every wrinkle that came from squeezing her boobs into a bra which was perhaps just a little bit to small.

Doug stared for a long time, quiet. Then he spoke into the phone.

"Yeah, yeah, I'm here, I'm listening...was just writing some of this down." He started to move back toward his desk, but turned and kept looking at her. Despite everything else, Ginny was still conscious of getting her blouse wrinkled so she walked back over to the coat hooks by the door and hung it up carefully next to the blazer. She walked halfway back toward Doug, who actually was writing down something now, and got his attention. She turned halfway, sticking her butt out at him, looking over her shoulder with a questioning face, her hands coming up to the zipper on her skirt. Again, he waved her off: keep the skirt on for now. He motioned for her to come closer, and she returned to her original position.

Now Doug stopped writing, but kept talking on the phone. As he did so, he walked slow circles around Ginny, getting closer with each one. For a long time he stopped behind her. She stood, looking straight ahead. It was several minutes, Doug behind her, talking, talking...reassuring his client, offering financial advice, laughing about something related, though she couldn't tell what. She waited, not turning, shifted her weight back and forth a few times, until finally she could tell from the sound of his voice, and then from his breath on her neck, that he had come very close. His mouth grazed the back of her neck during pauses in the conversation, and he eventually got so close, pushing his pelvis up against her, that she thought she might fall forward, but then he wrapped one arm around her to prevent that, and his hand stroked her stomach briefly and then moved down, rubbing her crotch through her skirt and pushing her ass back into him. He was definitely hard, she could feel that now without any doubt. For a full minute he was listening to the phone, and he was so close that Ginny could hear a man's voice on the other end. As the phone chattered with unintelligible (to her) garble, Doug's hand came up and then slipped down again, this time underneath her skirt. His hand went straight down between her legs; he had to move partially around her to get it as far as he wanted it to go. He was now mostly behind Ginny, still holding the phone in one hand, while his other hand rubbed her pussy hard. Yes, on top of her panties, but she was so wet now, and could feel it, that she knew Doug was getting her juices on his fingers as they soaked through the thin fabric. He rubbed more vigorously, and she could begin to feel his cock bounce rhythmically against her backside as he moved his hips into her and back out again. Goddammit, she was getting light-headed now. She wouldn't have said she was having "fun," exactly, as she couldn't completely forget why this was all happening. But as long as she had to do this, she let herself give in just a little, and each time Doug brought his hips and his hard cock back into her, she arched her back just a touch, and pushed her ass back at him.

"Just a sec," Doug said. He was talking into the phone, but he was so close to her ear that it startled her, brought her out of her warm thoughts. "Ginny-" Now he was talking quietly into her ear, not quite whispering. "-I want you to bend over as far as you can. Grab your ankles if you can." She hoped he was somehow covering up the phone with his other hand, but couldn't be sure. "Just grab your ankles, or as low on your legs as you can, and hold onto them."

He must have thought because of her age she might not be limber enough to grab her ankles. She'd admit she could be in better shape, but she did all right, thank you. She was a regular attendee at her yoga clinic, and she could damn sure grab her ankles! She'd show her boss. 'Jesus, what the fuck am I thinking?' she asked herself. Am I getting into this now, trying to impress this ass who was bullying her into being his slave for the morning. Well...yes, she guessed she was. Doug had backed away a few steps to admire her body again, and was back to talking. Ginny bent forward slowly, wrapping her hands around the backs of her knees, sliding them down her calves, pausing to let her muscles know they were being stretched, then sliding them down to her ankles, and beyond. She heard Doug exhale as she kept going down and wrapped her hands under her feet, just in front of her three-inch heels, knuckles scraping the carpet. Her legs were still perfectly straight. She felt the hardness of her nipples touching the tops of her knees.

"Bill? Bill. Hey, I--they need me for something here, I gotta go. Yeah, we'll pick this up this afternoon, if that works? OK. Great, we'll talk then." She heard the beep as Doug turned the phone off, and heard him set it down on the desk.

"You're doing great, Ginny. Are you too uncomfortable?"

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