The Secretary

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Mr. Spader wanted so much to take out his cock, to stroke it. His secretary's butt hole looked so cute, so naughty, so puckered and exposed.

Maggie wondered if she could become so wet that a drip might actually form on her pussy lips, perhaps even slide down a thigh. This had happened at times when she was making love with someone, or when she was masturbating, but never without anyone ever even touching her, down there.

She fixed her attention on the document, and then she saw it. "I typed 'passed' rather 'past.'" That had to be it! Frankly, she still wasn't sure which one was correct. She always got those confused.

Mr. Spader was disappointed, but that was indeed the final error. "Yes, correct, Miss Gyllenhall." He hesitated before he added, "You can go back to your desk now."

Maggie let go of her cheeks, the curtain protecting her modesty was again closed, but she did not get up. Instead, she returned her hands and elbows to the desk and looked back at Mr. Spader to ask, "You're not going to spank me, sir?"

"No, I believe that is all that is necessary, for today." He turned away from her to make his way over to his orchid garden. Perhaps they needed some attention as well.

Maggie was surprised, and confused. But, Mr. Spader was apparently finished. She pushed herself away from his desk, pulled her panties back up, and made her way out of his office, her eyes fixed on him as she did so.

- - - - - - - - - - - - - - - - - There had been no further errors for the next three days, or at least none that Mr. Spader called to her attention. Maggie didn't know for sure how she felt about that. She had worn some of her best panties the last couple of days, just in case, then sighing with disappointment when she took them off in the evening.

But, she really shouldn't feel disappointed, should she? She had been working especially hard, and careful. Any word for which she had any doubt she would check within a dictionary. He did not object to that, as long as it was a real book and not the internet.

Of course, errors that she could identify were not the real problem. The typical problem was in the concentration, in typing so quickly that she failed to notice a homonym.

"Miss Gyllenhall, could you come in here, please?"

Maggie's heart fluttered. She flipped the switch. "Yes sir, right away, sir." She pulled out her mirror, checked her hair and make-up, applied a bit more lipstick, got up from her desk, checked her outfit, and then made her way into his office.

She almost smiled when she saw the document on his desk, in the usual position, albeit not quite as well centered as it was usually placed.

Mr. Spader was standing beside the desk, gesturing toward the document with his left hand.

Maggie slowly strode toward his large, imposing desk, her heart accelerating with each step. When she finally arrived she began to assume the position.

"No, Miss Gyllenhall, not today."

"Excuse me?"

"No. No, I think the bar needs to be raised. I'm sure you understand."

"Yes sir," she softly replied, although actually Maggie didn't understand at all. There were quite a few different ways to raise the bar.

"If you would, please, get up onto my desk."

"Your desk, sir?"

"Yes, if you would."

Maggie's heart was now racing, for quite a few reasons. What precisely did he have in mind? "Well, yes, of course, sir."

It wasn't that easy getting onto Mr. Spader's desk. There was certainly plenty of room on it, although she wanted to be sure not to disturb the document. The difficulty was her tight skirt and heels. She hitched her skirt up a bit, almost to the top of her nylons and brought her left knee high up onto the desk, providing a rather provocative up-skirt peek. She slid her knee as far onto the desk as she could, gripped tightly the edge with both hands, and then hoisted up the rest of her body.

Once there she wondered how to position herself, but then realized that there was really only one obvious position. She got into her elbows and knees, her feet and bottom thrusting out over the edge of his desk, the document just to her left.

Mr. Spader did admire the position. Her bottom was now at the level of his face, at the level of his eyes, and his mouth. It would be so nice to have her raise her skirt now, and then pull down her panties, as he stood in between her legs. Her pussy would be just inches from his lips, and tongue. But, he had another idea.

"No, Miss Gyllenhall, that will not do."

"No sir?" She was disappointed, in herself. She thought the position would please him. She arched her back and raised her bottom up higher.

He shook his head.

Maggie was confused. Could she be in a more submissively exposed position? "Shall I remove my skirt, sir, and...." She hesitated before she added, very quietly, "lower my panties?"

"No."

"No?" He didn't want her to lower her panties? What could she do to please him, if not that?

"Stand up."

"What?"

"Stand up on the desk."

"Here?"

He didn't answer. He knew she understood and so there was no real reason to repeat himself.

"But, sir, my heels. They might scratch the wood."

That was a good point. The mahogany was over a hundred years old. Would he risk this priceless desk for such a capricious act? "Well, then, take care that you don't."

"Yes sir," she quietly replied, and then very, very slowly, got off her knees and onto her feet, being careful to take no steps, taking no chance of dragging a pointed heel along the ancient, worn, smooth, polished, slick wood.

When she was on her feet, her back to the door, she did shift her feet somewhat to help firmly plant herself, but in doing so being quite careful not to slide or slip a heel along the wood. She could feel her legs tremble a bit, so concerned that she might in fact scratch the wood. The desk was probably worth more than her annual salary; actually, much, much more.

She stood so far above him now, so tall, like a statue to admire, to treasure, to worship. His eyes traveled up her shapely legs, today so wonderfully embraced within peach colored nylons.

He could see a bit beneath her black skirt, but it was so tight, and so dark in there, that he could only just barely make out the sight of the lace at the top of her nylons, tightly wrapping around her thighs.

"Three today, Miss Gyllenhall," he announced with apparent disinterest.

"Yes sir," she replied.

He then made his way around his desk, to his chair.

He looked up again. And, from below, he got a better appreciation of his secretary's breasts. They were not large. They were on the small side. But, when viewed from below, within her tight shiny silk peach blouse they did appear rather prominent, perhaps even a bit majestic. He leaned over the desk, picked up the document and handed it to her.

She bent over a bit to retrieve it from his hands, her pearl necklace falling away from her neck, the cleavage of her blouse briefly opening up, providing a very momentary glimpse of just a bit of her brassiere. It was again, peach; peach lace.

He sat down, to study a few papers of his own.

Maggie looked at the document. It was about 59 pages long! It would contain more than 24,000 words! Does he really expect there to be no errors? Would anyone really expect that?! She began to read, carefully proofing her typing, looking for the errors. She felt a little precarious though, perched up on Mr. Spader's desk. She had no reason to feel perilous. It was unlikely that she would fall, but she often felt unstable, unsteady, when standing near the edge of a cliff. There was little rational reason for her feelings of instability, as it wasn't like it was in any way more difficult to be standing there than anywhere else. The ground was just as solid and flat as it was elsewhere. But, apparently because the potential risk was so much greater if she did fall that it just made her legs and feet feel so uncertain, so unsteady.

"I see one!" She announced with a big smile: "I typed 'grown,' like when you're grown up, rather than 'groan,' like when you moan." She looked down at her boss and smiled, waiting for his pleasure, his praise.

Mr. Spader though did not look up. He continued to be studying his own material. "Yes, that's correct, Miss Gyllenhall. Two more to go."

"Yes sir," she replied, but she did still feel pretty good about finding one so quickly. On the other hand, she felt bad for committing the error in the first place. Those homonyms were just so hard to notice!

It took a while to find the next one: "Oh, yes, 'downside' should be two words!" That was an understandable error. He shouldn't really blame her for that one.

"No, Miss Gyllenhall," Mr. Spader replied, the exasperation evident in his voice. "'Downside' is one word. You did type that correctly."

"Oh," she softly replied. Well, that was good, wasn't it? It's better to have been correct than to be incorrect. But, she was, once again, incorrect in her proof reading.

Mr. Spader did now look up. "Drop the skirt, Miss Gyllenhall," he quietly instructed.

Maggie looked off to the side and softly replied, "Yes sir." She undid the skirt's clasp and then pulled down its zipper. Keeping her eyes averted from his, she let it fall to her ankles.

She began to step out of her skirt but Mr. Spader raised his hand to stop her.

"Just let it lay there, Miss Gyllenhall."

She wasn't happy about leaving such a mess on his desk, but if that was his preference then certainly she would defer. "Alright sir," she replied, and then resumed her reading.

Mr. Spader considered her position, a little smile on his lips as he admired her choice of panties. Maggie's blouse did nothing to hide them as it was a straight hem that only reached her waist. Her peach cotton bikini panties very nicely complemented her blouse and thigh high nylons, being peach-colored as well, trimmed with a little strip of lace, with a full juicy ripe peach embroidered on her mound, seeming to fill out with fleshy fullness with the rising curves of her pussy. Mr. Spader did so like a fresh peach.

With considerable reluctance he returned his eyes to the report he received from Mr. Ellsberg.

Maggie wondered how Mr. Spader felt about her panties. She had gone through her best pairs the previous few days. She so wished he had alerted her that today would be the day he would be seeing her panties. But, a secretary can't always know what her assignments will be before she arrives at work. Rolling with the punches is part of the job. In any case, there wasn't much she could do about it now. She focused her attention on the document.

Quite a bit of time passed before she proposed another error. She didn't want to make an additional mistake, partially out of concern that she would disappoint him but, of course, worried as well what she would have to do next. She had identified a couple of possibilities but wasn't confident enough to propose them.

With a deep breath she finally committed herself. "Um...I typed 'for quite a while.' Should I have typed 'for quite awhile;' 'awhile' being one word?"

Mr. Spader looked up at Maggie. A girl dressed only in her panties and blouse looks so cute, particularly from this angle. Her feminine mound looked so prominent, so full, admiring it from below her thighs. But, his secretary was about to become even cuter. "No, Miss Gyllenhall, I'm afraid that's not it."

"Oh, well, um..., sir?" What was she to do now?

Mr. Spader felt that Maggie should really figure that out on her own, but he didn't want to put any undue pressure on her. After all, she had not worked for him for very long. "The panties, dear." He gestured with his right hand, indicating that her panties were to come down.

"Yes sir," Maggie softly replied, hooking her thumbs into the waistband of her panties, bending over just a bit as she slipped the cotton off her bottom and down to her thighs.

She hesitated, looking down at her boss, her necklace again hanging away from her neck. She let Mr. Spader see her bottom the other day. This would be letting him see her cunnie. This was embarrassing on a number of levels. There was nothing more important to her than making a good impression on her boss. She wondered if perhaps she should have shaved down there before she came into work. She understood that lots of guys like that. But, of course, he might have found that to be rather perverse.

She pulled her panties down a bit further and then let them slide down the rest of the way. As they came to rest at her ankles she stood back up straight, her hands clasped demurely behind her, resting against her now naked bottom, one knee turned a bit inward, as if that might help protect her modesty at least somewhat.

Mr. Spader showed no emotion on his face, but his dick swelled hard within his slacks. Miss Gyllenhall had a very attractive cunt. He would have preferred that she kept it shaved but he could hardly count that against her. It was certainly not appropriate for an employer to require his secretaries shave their pussies. It did at least appear that she trimmed and managed the curls with some consideration and care. That was impressive. This clearly demonstrated an attention to detail, a quality he much admired.

Plus, her cunt was just so darned fetching. She had rather thick, fleshy lips that clearly suggested a very warmly receptive and engaging home for a hungry, hard, thick cock. In fact, he felt he could even detect a bit of moisture on the lips.

He reluctantly took his eyes away from her cunt to look into her eyes, albeit that feminine moist peach was still well within his field of vision. He could see the uncertainty, the anxiousness, within her eyes. He reassured her. "I'm sure you'll soon find the next two, Miss Gyllenhall. Now, please, continue."

"Yes sir," Maggie replied, and resumed her search. She kept the document between her eyes and his, not wanting to know if he was just sitting there staying at her cunnie. She so hoped that he hadn't noticed the moisture. She studied the material very, very hard.

Mr. Spader's eyes left hers, but paused at her peach panties gathered around her ankles. He hadn't noticed before how pretty were her ankles, so delicately feminine, so awkwardly perched on her high heels, and so lovingly draped by her undies and skirt.

"Oh my," Maggie quietly exclaimed as she stared at the page. "I misspelled Poconos. I spelled it with a 'k,' didn't I."

"Yes, yes you did," his eyes still on her panties. He turned back to his work. "Only one more to go," he announced. He hoped the third, and last one, would take her a while.

'Only one more to go,' thought Maggie. She hoped it wouldn't take too long. She glanced over at the door. Even if someone knocked it would be difficult for her to get her panties and skirt back up before they came in. In fact, she might just fall off the desk if she had to do so hurriedly. Of course, that assumed that Mr. Spader would even let her pull her panties back up. Goodness, she wondered, he wouldn't require that she keep them down! She glanced down at him, trying to read that recondite mind. She squeezed her thighs together. She felt such a sense of urgency, of heat, of lust.

She looked upon the page with desperation.

"'Skydiving' should be two words," she suggested.

Mr. Spader shook his head. She really should know better than that. It was almost as if she was being wrong intentionally. He leaned back in his chair. "Step over here, Miss Gyllenhall, squat down a bit and present your bottom to me."

Maggie's eyes and mouth opened wide with shock. "Mr. Spader!" She couldn't believe she had heard him correctly. He certainly couldn't be serious.

"You don't have to squat all the way down," he explained. That was hardly much consideration, Maggie felt. Squatting down above him like this would be frankly, well, entirely obscene! She instinctively covered her cunnie with one hand, and the more personal part of her bottom with the other, still holding onto the document. "Mr. Spader, I don't think I should do that. I don't think that's right."

"Miss Gyllenhall, you don't think I know what I'm doing?"

"Oh, no sir, I mean, of course, my goodness. It's just that, well...."

"Do you wish to continue making these mistakes, Miss Gyllenhall?"

"Absolutely not, sir."

"And, you do realize that all of this is to help you become as accomplished a secretary as I am a lawyer."

She suddenly realized how confrontational and argumentative she was becoming. This was not good. "Yes sir," she softly replied, releasing her hands from her body. She looked down. How was she going to shift position with her panties and skirt wrapped around her ankles, while still in her heels, standing on his antique desk?

It would be easier to just slide along the desk, decreasing the likelihood of having a heel catch on her skirt. But, that would very likely scratch the wood.

Maggie gingerly lifted up her right foot, being sure to pick up her panties and skirt with her foot, and then slowly, carefully, reached out to firmly plant it a few inches away, and then as carefully, cautiously, followed likewise with her left.

Mr. Spader appreciated his secretary's care. He smiled with approval, and pleasure. Somehow, watching his secretary gingerly make her away along his desk, with her panties and skirt at her ankles, her cunt and bum fully exposed, was really quite endearing. Her cunt was now glistening, providing little stars twinkling above him.

When she got close enough she turned so that her back, and her bottom, were facing him. She began to slowly squat.

This felt so, so lewd, so crude, so profane, like she was going to pee on him, or something even worse, and she knew in doing this her cunnie and anus were coming into a fully exposed view, as if she was squatting down so that he could look at them both real, real close. It just felt, and must look, so gross and raunchy. She covered her face with her hands.

But, she didn't have to travel far.

Thwack!

"Oh my!" Maggie threw her hands out, trying desperately to maintain her balance, her eyes wide with shock. She hadn't been expecting that, although perhaps she should have been, given what happened the previous day. It was just that she was so preoccupied with how shamelessly she was exposing herself that she was caught by surprise, and what a surprise it was, a smack right on her bare naked bottom.

Plus, as before, he didn't just provide the more common spank. Once again his hand still rested on her bum, his big meaty masculine hand now firmly fully clutching her right cheek in its grip.

"Mr. Spader, please." This just felt so wrong, yet so good.

Mr. Spader was duly impressed at how round and soft was Miss Gyllenhall's little derriere. Few things felt better within one's hand than the taut perky pliant cheek of a young lady's bottom.

With considerable reluctance he took his hand away.

Maggie reached back to cover her bottom, and her personal spots.

"Just one more spank, Miss Gyllenhall," Mr. Spader instructed, "and then you can resume your proof reading."

With considerable trepidation Maggie slowly pulled her hands away and squatted down even further.

Mr. Spader would have to agree that the sight of his secretary's squatting ass was rather obscene, but that was also what made it so appealing, so lovely. He could in fact place his face right in between those delicate feminine cheeks and give her rosebud a little kiss, perhaps as well taking the opportunity to slip a figure up her cunt.

But, of course, that would be taking advantage of the young lady.

Thwack!

Maggie grimaced, but this time she didn't move, or squeal.

"Alright then," Mr. Spader instructed, his hand still clutching her bum, "You can stand back up now, and find the remaining error."

"Thank you, sir," Maggie responded, pleased that she was only going to get a couple of spanks. Of course, she had previously only received one spank for each error, but it's understandable that there would be more this time, with the bar having been raised. She stood back up, her bottom pulling away from his hand.

1...345678