An Assistant
Bdsm Story

An Assistant

by Toddyesplease 17 min read 4.8 (11,400 views)
office age gap personal assistant edging female orgasm denial male dominant female submissive chubby
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The garage around me was dark, but my phone screen glared. I was staring at the photo that my new personal assistant, Molly, had just posted online under her username 'your_perfect_girl.' It was a selfie that showed her lying on her back in bed, cropped square from nose to bellybutton to reveal her gently parted lips and full breasts, which were squeezed together by her outstretched arms and clad in... Well, what would you call it? A bra? A bustier? It looked decadent on her, the black lace setting off the pink flush of her skin, the white billow of the duvet, the golden curl of her hair. The caption on the photo read: "Bought myself a present for passing my probation at work!! Do you think my boss will like it?"

"God, yes," I breathed to myself, alone in the front seat of my car. I liked it a lot. I couldn't tear my eyes away from the photo, even though it was already... "Shit."

It was already 10 minutes to 10. I was going to be late for the weekly Monday morning strategy meeting. How long had I been sitting there? With one last longing glance at the photo on the screen, I flicked my phone off and swung the car door open. A few moments later, I was watching the little light above the elevator doors count down the floors towards 'G1' and smoothing the leg of my suit pants with the palm of my hand anxiously. My cock was still uncomfortably hard. Was it visible? What were people going to say when I walked in late, and looking like

that

?

Molly was not just one of the prettiest women I had ever known, she was also far and away the kinkiest. Her dirty posts had shown me as much, and I had learned a lot more at the end of the day on Friday, when I had confronted her with what I had found on the internet. While I was stroking her clit on my office couch, she had basically begged me to treat her the way 'your_perfect_girl' treated herself in her photos: to edge her and deny her, to tie her up and spank her, to fuck all three of the perfect holes she offered up to whoever stumbled across her profile. The lingerie selfie that had me transfixed moments before in my car was probably the chastest thing she had ever posted...

And as I edged her in my office that night, her arousal-addled brain had suggested another fantasy, that she would have to do whatever filthy thing I wanted to keep me from showing everyone these pictures, not to mention to keep her job. We had been interrupted by the janitor before we had discussed exactly what our relationship was going to look like going forward, so I had spent the weekend alternately fretting and frothing at the mouth with desire. This was the craziest thing I had ever done, a total fantasy, and yet terribly real. Was I going to lose

my

job? Would anyone believe that she wanted me to fuck her? To blackmail her? But how could I resist? And the caption this morning... What more encouragement could I need?

The elevator door pinged open and I heard a tittering, whispered conversation stop abruptly as I stepped in. I recognized the two young women as junior analysts working under my colleague Sandra, the only female executive at our firm. I liked Sandra fine, but she had a habit of hiring decades-younger members of her college sorority that I found... Well, maybe it was that they all had the same slim, blonde, high-ponytailed look... Or maybe just Sandra's insistence that these girls half her age were her 'sisters'...

"Good morning, Mr. Andres," I heard one of them say behind me as I turned to face the closing doors.

"Hmmm?" I responded distractedly, and their

sotto voce

conversation recommenced. I was still thinking about Molly.

'Do you think my boss will like it?' God, what a question...

I was blearily aware of the little numbered buttons lighting up in turn as we made our way towards the eleventh floor, where the boardroom was located. One, two, three, four, five... My office was on the fifth floor. Did I need anything from my office?

Oh, shit!

A sudden, panicked thought as my fingers rose to the 'Open Door' button.

The weekly reports!

I had been so distracted...

The doors opened before I could hit the button. Head down, I bundled myself out and directly into... That perfume...

"Sir!" Molly squeaked as we collided. Her body was soft against mine for a moment before she stumbled back, clutching a bundle of file folders tight to her chest. "I was just coming to find you! You're going to be late!"

"I know, Molly," I said, pulling her inside the elevator with a hand on each shoulder. The conversation behind us had stopped suddenly once again, but something roared inside me, chasing away my anxiety in an instant. Molly looked fantastic in a crisp, white blouse and slate-grey pencil skirt. She was wearing a slightly taller heel than usual, just tall enough that we stood eye-to-eye, and she had her hair pinned back, opening up her face, except for two escaped ringlets that she pushed behind her ear as the elevator rumbled back to life. "Are those the reports?"

"Yes, sir," Molly responded. She was blushing hard as she handed over one folder, then another. "And Carl's... He asked me to print his, too..."

"You need to stop letting men take advantage of you like that, Molly." I heard one of the girls behind me stifle a laugh. Molly looked down at her shoes.

"Why were you so late, sir?" She asked in a whisper.

"Something came up," I answered at a normal volume. "You had a busy morning, though?"

"Yes, sir." Her blush was deepening. Fuck. How was I supposed to resist that? "Two calls for you from Hong Kong..."

"And it'll be the middle of the night there, when I'm out of the meeting..." I mused, trying not to sound thrilled. So we'll have some free time, then... "Anything else, Molly?" No response except her furious blush. "Are you

sure

, Molly?"

"Sir?"

"I'm not sure we should talk about it here, but..." I looked around at the girls behind me, whose faces were glowing with some sort of curious shared emotion as they steadfastly refused to meet my gaze. They couldn't know about Molly and I, surely? Was I running too much of a risk? But what could they say? "What about that special project we started on Friday?"

"Sir?" Molly squeaked again. Her voice was still tinged with anxiety, but I could here a little bit of arousal softening it now, too.

"Did you finish over the weekend?"

Molly hesitated for a moment. I had just gotten her to the edge of orgasm when the janitor had interrupted us. I looked up from her face to check our floor. We were almost there. "No, sir."

"Good," I nodded. "I don't want you finishing without me."

The doors pinged open as Molly responded. "Of course, sir."

A beat of silence as I stepped out of the elevator. Her picture from this morning was still dancing behind my eyes. "Oh, and Molly," I said, turning back. Molly looked up from her shoes. The two blonde girls were staring gleefully at the back of her head. "I saw your question..." The doors were closing. I couldn't suppress my grin any longer.

"Sir?"

"The answer is 'yes.' Yes, I like it very much."

The last thing I saw as the doors slid closed were Molly's eyes, first wide and confused, then suddenly wider with shocked comprehension.

***

She had the same eager, anxious look in her eyes when I saw her again a few hours later, after the meeting. It was lunchtime, so the floor was quiet enough to hear her chair creak back as she stood up behind her desk, which was placed just outside my office door.

"Any calls, Molly?" I asked as I strode up.

She shook her head and hurried around her desk as I continued past. "No, sir."

"Good." She followed a step behind me as I crossed into my office. "Let's see if we can catch Hong Kong," I announced, in a slightly louder voice than strictly necessary.

Molly's voice sounded confused, but she didn't question me. "Do you need lunch, sir?"

"No, just a coffee. And lock the door, will you?" She obeyed wordlessly, and she was already finishing up at the coffee bar by the time I had thrown off my suit jacket and tie, rolled up my sleeves, and settled half-sitting on my desk's front edge. I was too full of energy to sit down properly.

With the door closed, all I could hear was the click of her heels and the coffee cup rattling in its saucer with each step. She was clearly not yet fully comfortable in these taller shoes. Not wanting to seem too eager, I pulled out my phone. Her photo was still open when I flicked past the lock screen.

"You aren't actually going to try and call Hong Kong, Sir?" Molly asked trepidatiously as she placed the saucer down beside me on the desk.

I didn't look up from my phone. "No, I'm not Molly. I just wanted to make sure we weren't disturbed."

"Oh, okay." She rocked on her heels awkwardly in front of me as I took a sip of coffee, still focused on the screen. I could tell she was not sure exactly what was coming next and I wanted to wait for her to break the silence. "How did the meeting go, Sir?"

I looked up. Molly's brow was furrowed slightly. The same two ringlets had come loose again, only now she kept her hands clasped behind her back nervously instead of pushing them behind her ear. "Not well, Molly," I answered, more or less truthfully. The meeting had been a blur. "As you can imagine, I was very distracted."

"Oh, Sir," she cooed bashfully.

"And I think I've already made clear why I was so distracted." Molly nodded. "But would you like me to show you?" She nodded again, her eyes wide and a subtle, coy smile creeping across her lips. With a slow, casual circle of my wrist, I flashed her the image.

"I'm sorry, Sir," Molly said, barely looking at the screen. Her spreading smile undercut her words.

"I'm no good with lingerie, Molly. What do you call this?"

"Oh?" This was not the question she had expected. "A bra... A longline bra, Sir."

"A longline bra..." I nodded. "When did you take this picture, Molly?"

"Last night, Sir."

"But you waited until this morning to post it?" The tinge of frustration in my voice was only half in jest.

"Yes."

"And then you lied and told me you hadn't done anything this morning?"

"Sir?" She tried to force her forehead into a confused furrow, but the giggle in her voice told me she knew exactly what game we were playing.

"Are you wearing it now?"

"Of course, Sir."

"Show me."

Still blushing and smiling, Molly complied, looking down at her toes as she began to unbutton her blouse. I settled back against my desk. The erection that had been throbbing off-and-on all through the meeting was returning again.

With three buttons undone, Molly's face froze and she glanced over her shoulder towards the door. "No one is going to interrupt us this time, Molly," I lied confidently. How could I be sure? But I needed her.

We had not undressed at all on Friday night, and while I had seen every inch of Molly's body in her photos, this was my first chance to appreciate her like this in person. It was only a moment before her hands were clasped behind her back again and her blouse was completely unbuttoned, untucked, and pulled open to hang loose from her shoulders. Her eyes searched for mine as I took in her body, here in front of me for the first time. The black lace hugged all her curves and her breasts rose and fell deliciously with each quick, excited breath. I felt my own breath quicken sympathetically.

"How does it make you feel to show off like this, Molly?"

She blushed and smiled and broke eye contact--all the answer I needed. "There's more, Sir."

"Oh, is there?"

"Mmmhmm," Molly nodded. Now I got to watch a full-body wiggle as she shimmied her skirt up her thighs.

"It's a matching set," I mused. The panties were French-cut and nearly sheer, in the same black lace. Their high waist covered her nearly to the base of the bra and gave a smooth curve to her belly, with a inviting indentation around her middle where they dug slightly into her skin.

"Do you like it, Sir?" Molly's voice was eager and earnest.

I took another sip of my coffee as I considered this. Truthfully, the set was only one part of the whole stunning display: the blushing young women with her hair and clothes all dishevelled, showing off the expensive-looking lingerie she had bought just to be that little bit more attractive to her boss, a man over twice her age. I knew how much she made. How much had she spent? Half a paycheque maybe? Just for

me

? The power of it made my heart pound in my ears. But telling her as much would ruin the game...

"That's not what we need to talk about, Molly," I responded, affecting a severe tone. Molly squeaked in surprise. "We need to talk about this morning. I was late for my meeting because you decided to tease me with this photo online."

"Tha-that's not..." Molly started stammering.

"I thought I made it very clear on Friday night when I passed your probation," I continued. "I need a diligent, reliable personal assistant. And one of your chief responsibilities is to maintain my schedule."

"Yes, Sir," Molly stammered, looking at her toes. She was blushing again now.

"And then I had to sit through the whole meeting, distracted by my throbbing cock, with no one there to help me." A pause. No response from her but a slight shake of her downturned head. "I thought you had what it took," I continued, shaking my head in turn. "It seems like it's a good thing we were interrupted on Friday... I was just about to let you cum..." Molly groaned. She had started to shiver slightly and I could see that her thighs were squeezed tight against each other. "I thought you had earned it, but now it seems like..." I eyed her carefully. Was I pushing her too far? Had she been denied for too long?

She looked up through her lashes at me, chin still lowered. "Oh, Sir, I want to be good for you... Ohhhh..." It was a perfect, impassioned moan that brought a smile to my face. I was pushing exactly far enough.

"What about those girls in the elevator this morning?" I asked.

"Sarah and Becca, Sir?" As before, the change of topic seemed to disarm her momentarily.

"What do you know about them?"

Molly shrugged. "They work for Sandra. Both Epsilon Upsilon Alpha at USC. I've seen their reports..."

"I think I've seen their reports, too," I lied. "Very good work. And they're very pretty..."

"Oh-h, yes, Sir," Molly stammered.

"Do you think they realized what a filthy little whore you are?"

"N-no, Sir."

"Do you think they would ever do anything improper, like making their boss late for an important meeting?"

"No, Sir."

"Or post dirty photos of themselves online?" Molly just squeaked in answer. Her face was screwed up in a look of agonized arousal. "Here's what I propose, Molly. You have a choice to make. You can just be my plain old PA, keep your slutty ways on the internet and out of the office, and I will ask Sandra which one of her juniors could use my, ah,

mentorship

..." I trailed off--a sudden, wicked thought. "You wouldn't mind helping with that, would you, Molly?"

"Sir?"

"You know, booking tables for us for lunch, running her things to the dry cleaner if there are...

Stains

." Molly moaned again. She was rocking on her heels again and grinding her thighs together sensually. After subjecting herself to three months of rigorous online exhibition, teasing, and denial, it was clear that my words had a stark physical effect on her. "Oh and maybe... Well, of course, you would need to clean my cock with your tongue after those lunches, too, wouldn't you? Imagine that... The only time you get to have me in your mouth is when I taste like another woman. You would do that for us, right?"

"Oh, Sir, yes, I would!"

"After all, I would still have all your photos..."

"Ohh,

Sir

..."

"Well, that's option A," I continued. "Option B would be that you keep all your responsibilities as my PA, so long as you accept thorough punishment and training so that we don't have any more slip ups like this morning. Which do you think you'd like, Molly?"

"Ohhhhhh..." Molly was incoherent, her eyes pressed closed. "I don't... I don't... Ohhh, Sirrrrrr, don't make me choose!" Her head slumped forward again and her shoulders began to heave.

I sprang forward onto my feet. I thought she was crying when I wrapped my arms around her, but it was just her deep, shuddering breaths. Her whole body pressed into mine, overcome with the power of the twin fantasies I had woven for her. Perhaps I had gone a little too far...

"Don't worry, Molly," I consoled gently, stroking her cheek as her head lay on my chest. She reached one arm under mine and hooked it over my shoulder for support. "I was just teasing."

"You were?" Molly murmured into my chest. I could feel her breath steadying.

"It doesn't feel good to be teased, does it?" I felt her shake her head 'no.' "I know you still want to be my assistant. I think your body knows what it wants. Here, there's a simple way to find out..." Molly said nothing as I bent her limp body at the waist so that she was supporting herself with her hands on my desk. Stroking her newly upturned ass, I continued. "If I have you aroused, if your perfect little pussy is all wet for me right now, then I'll know you want to continue as my special assistant, with all the special responsibilities. Does that sound good?"

"Uh-huh," she agreed. Her voice was small and I could barely hear her, now that she was bent over.

"Good girl," I said gently as I slid aside her panties. No surprise, a perfect string of slick, translucent arousal stretched from the lips of her sex as I lifted the wet fabric away from her body, but still I said out loud: "I'm going inside you now, just to test."

Not only was she as wet as she possibly could be, but her canal seemed to suck my two fingers in as soon as the tips caressed her entrance. We both made separate noises of arousal in the back of our throats, hers the breathy moan that I was coming to expect, and mine a short, sharp grunt as my erection twinged enviously. Slowly, fighting her hot, tight grip, I slid my fingers in and out.

"That's it..." I cooed at her, using my other hand to stroke the small of her back. "I'm so proud of you, Molly. You've made the right decision."

"So you'll keep me, Sir?" It was a small, pathetic question, as her hips began to buck back against my fingers.

"Of course, Molly," I replied gently. On the out stroke, I slipped a third finger inside her, which she took eagerly. "Good girl."

"G-good

girrrrl

..." Molly repeated, arching her back to meet my fingers, raising her head and looking over her shoulder at me with her wide, blue eyes. "D-does... Does that mean..."

"No, Molly, you don't get to cum just yet." I heard her groan as her head collapsed back down, defeated. "No, your unprofessional behaviour this morning has earned you another week of denial, at least." She groaned again, and I felt an electric shiver ripple through her body and up the arm that was still pistoning slowly in and out of her. Her body relaxed and leaned forward, letting me work deeper and deeper in, and she groaned a third time, deeper and more animalistic, as I bottomed out with a gentle tap on her cervix. I grinned, not just at her unconscious response, but also because my fingers had felt something else: the telltale strings at the mouth of her womb.

An IUD? In that case...

"However," I continued, trying to keep my tone cool despite my excitement. "I have a little treat for you." And here I reached for another fetishistic turn of phrase that her posts had taught me, timing it for maximum impact as I pulled my fingers out of her. "I'm going to breed your cunt, Molly."

"Ohh,

Sirrrrrrrrrr

," Molly squealed, her hips fucking her empty pussy back against the air.

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