An Assistant
Bdsm Story

An Assistant

by Toddyesplease 18 min read 4.9 (3,000 views)
office age gap personal assistant edging female orgasm denial male dominant female submissive chubby
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The following Monday was the first hot day of spring. After my morning meeting, I was back in my office with my top three buttons undone, my sleeves rolled up, and my stocking feet up on my desk. My assistant, Molly, had cracked the window just before I got back so that sweet, cool air now washed over us. Molly was standing on the other side of the desk, holding up one of my shoes and brushing it dry with a rag. The other sat dirty on a sheet of newspaper spread out on the desk between us, beside an unopened tin of shoe polish. She had decided to go for spit-and-polish to avoid messing up her pretty white sundress.

I was a very lucky man. I knew that cleaning her boss's shoes before a meeting--even an important client meeting like I had that afternoon--would have been above-and-beyond for most personal assistants, but Molly was more than willing. In fact, she volunteered. Then again, Molly was no ordinary PA. She had only noticed my scuffed shoes when she was on her knees in front of me, first thing that morning...

We had unfortunately run out of time before I could deposit a weekend's worth of pent up arousal onto her eager tongue, so for the second week in a row I had spent the weekly strategy meeting uncomfortably erect under the boardroom table. In the fantasies that Molly and I were spinning out together, her 'special responsibilities' were supposed to relieve me of sexual tension and corresponding workday distractions. In actual fact, the opposite was happening. It had been decades since I had felt this... Well, there was no other word for it than 'horny.' The more encounters we had, the more I craved her. And it was increasingly clear that there just was not enough time or privacy at the office to have nearly as many encounters as either of us wanted. At least I knew for certain that Molly had it worse.

Molly had not had an orgasm for over three months at that point, a state of affairs that I was now complicit in, but that she had initiated entirely on her own. Orgasm denial was just one of her many submissive fantasies, which were among the reasons--and I felt a little tinge of shame admitting it--that I had originally hired her. As far as I knew, Molly had only ever explored those fantasies online before we met. My suspicion was based on her online profile 'your_perfect_girl,' which she had accidentally revealed to me in her job application by slipping up and uploading one of her many nudes, instead of a headshot. I had made sure that HR never saw that photo and half-heartedly resisted going back to profile... Well, I held out for a few minutes. Her username was right there! Perhaps I shouldn't have... And then telling her, right as she finished her three-months probation... I told myself that I was giving her an out, that she deserved to know that I knew if we were going to keep working together, but I knew that was a lie. I didn't want to protect her. I wanted

her.

And she had just... Given herself to me. The 'her' that I received was still the same fantastic personal assistant I had known through her probation period--diligent, intelligent, much more of an adult than I expected from a pretty twenty-something--mingled completely with the, ah,

adult

version that I saw online. I knew that Molly had challenged herself not to orgasm for the whole three months of her probation, so when she handed over the responsibility of ending her denial to me, the implication was clear that she did not want the end to come too soon. I had generously set a date, the now upcoming Friday, April 26, when she

might

be able to cum, but the emphasis was truly on 'might.' Some cruel, dominant impulse that she brought out of me had also set her a near-impossible challenge to earn that long-awaited orgasm: 250 edges, completed somewhere at the office, over the 8 intervening workdays, 9 to 5.

On that warm Monday morning, there were now only 5 of those workdays left. To her credit, Molly had completed 72 of her 'tasks' by end-of-day Friday. And now, by locking herself into my empty office while I was at my meeting, she had managed to reach 85. That was still just shy of the 30-plus she would need each day to meet her goal. I had been fantasizing a little bit about what would happen at the end of the week if she did not get to 250. Would it be good enough to just set a new date, a new target? Or something more? In business, there were usually

consequences

for missing a deadline. I had spent the weekend putting some plans in motion, practicing some new skills, just in case...

And 30 edges a day was not an insignificant number. Molly and I had not discussed it--it was not our style to break the veneer of office professionalism--but I could tell that the near-constant masturbation was effecting her. Each look was more significant, a bit more eager. She kept finding little reasons to come into my office when I was alone, or to put her body close to mine. And, while her work was still getting done, it was getting done a lot slower. The only job that seemed to interest her was the one I had her performing on me that morning on her knees, as if feeling my orgasm in her mouth would somehow soothe her own aching denial.

As if

... I could not help thinking.

But servicing me

was

an outlet of a sort, and over the weekend, with that outlet unavailable to her, the pent-up desperation needed to find somewhere else. Naturally, she had returned to her old haunts online, and returned with a vengeance. Leaning back in my chair, I had my phone out in my hand, scrolling through the dozens of pictures that she had posted to her account in just 48 hours. "This is quite the photoshoot you did," I mused out loud.

Molly just blushed back at me. "Yes, Sir." Coming back from the meeting that morning, I had caught her lying on my office couch, one heel on the carpet, the other on the flat leather armrest, and her fingers working furiously under her skirt. She had scrambled to cover herself again when I opened the door, clearly embarrassed at being discovered, and even quickly volunteering to clean my shoes had not cleared that feeling entirely. I shook my head and grinned. It was funny what got a reaction out of her. The photos she had willingly posted online seemed so much more compromising.

"I like this one." I flashed Molly the picture I was looking at. Although she had carefully cropped out her eyes, this picture showed much more of her face than she had ever posted before. She was framed in profile in front of her bedroom mirror, with a teal dildo stuck to the glass by its suction cup base. Kneeling, Molly had the whole silicon length down her throat so that her nose was scrunched against the mirror's surface and her pretty face was blotchy and contorted with exertion. A long string of frothy white saliva dripped out between the sex toy's tight, molded scrotum and her bruised lower lip. Some previous drool had landed on her chest, where it had turned the white shirt translucent to reveal the pink curve of her breast, the black ridge of her bra.

Molly glanced quickly at the picture on my phone, then looked away and back down at my shoe just as fast. At first I thought she had not seen it, but then, wordlessly, as if to mimic the image on the screen, she let a tendril of saliva dribble out between her lips and onto the black leather of its toe. If this was supposed to tease me, it worked. I felt something hard and angry throb in my lap. "I wanted to practice for you, Sir," she said, rubbing the saliva in vigorously with a rag. "You know... I want to take all of you."

I nodded and read the caption. "'Training my throat for Daddy.'" It was hard not to let a little tenderness colour my voice. She was so good to me. "But I..." I hesitated. Molly and I had talked about deepthroat training, but I had not set her any in the end. "But I

like

it when you gag on me."

"Really, Sir?" For the first time since I had caught her on the couch, Molly looked me in the eye, a little bemused, a little eager, needy.

"Yeah," I mused. "So enthusiastic and... But innocent at the same time, you know?" I studied the photo again for a moment. "Too innocent to keep up with your fantasies. I like that."

"That's very..." Molly's voice was soft with happy surprise. The rag sat still against my shoe for a moment. "Thank you, Sir." She considered my shoe silently from a few angles, then judged it finished and picked up the dirty one.

I kept scrolling and settled on another picture that showed a daring amount of her face. This one had her lying in bed, wearing nothing but a black choker necklace, knees together and pulled to one side, almost demure. Her body was covered in writing, thick black letters against her rosy skin. I smiled at 'EDGE' and 'SLUT' written upside-down across the top of each of her thighs. I had first marked her with those words myself, a week before. 'WHORE' across her face also stood out, with her parted, lipsticked lips standing in for the 'o.' The rest of the words were written in smaller letters--'cum on me' on one breast, 'smack me hard' on the other, 'pin me down' on her round, smooth belly, and a dozen other little phrases all over her body--but I found myself looking back again and again to one single word, written in the smallest print of all, just 'daddy's' in dainty rounded letters below the soft pooch of her tummy, with an arrow pointing down through her golden pubic hair.

"'Daddy's'..." I read softly. Molly's only response was a smile directed down at my shoe. After a moment, I smiled too and scrolled to a third photo. She was still in bed. The camera had moved down her body, zoomed in, her knees were parted, and... "Oh, Molly," I said softly. I could still read 'daddy's' above that tangle of hair, but her newly spread thighs revealed the base of her suction-cup dildo, the blue-green silicon standing out against the white bedsheets. It was clearly pressed right up inside her. I looked up across the desk. You could hear my cock's painful, jealous pang in my voice. "Were you fucking my cunt without permission?"

"Maybe, Sir." Molly's voice was raspy. She kept her eyes away from mine and kept blinking, like she had to keep pushing some thought out of her mind to stay focused on the task at hand. The cloth moved across the leather of my shoe without the same decisive precision as before. I checked the clock on my phone as my cock throbbed again impatiently. Yes, we had plenty of time before the meeting. I had some prep to do, but I could put Molly under my desk at the same time, which meant I could keep teasing her a little bit longer while she finished her shoeshine job. Perfect. I swung my feet off my desk and replaced them with my phone, face down, swivelling in my chair to face Molly directly.

"I think you need a reminder," I continued, still in that stern growl. I could feel my eyes narrowing hungrily as I looked at her."Of who owns that little pussy."

Her response was quick, breathless, the words all a-tumble. "

You

do, Sir." Her breasts were rising and falling, hot, heavy, panting breaths escaping her open mouth. The complex bodice of her dress, with its puffed nearly-off-the-shoulder sleeves and low neckline held tight with a tie across her cleavage, left little to the imagination.

"That's what you wrote." I gestured at the phone. "'Daddy's.' But I'm not sure that's good enough, if you're going to keep playing with yourself and posting pictures all over."

"No, Sir." Punctuation, more than a contradiction. There was no 'no' in her voice at all.

"If you're really giving it to me to keep," I continued, leaning forward across the desk. "Then I'm going to need to mark it."

"

Yessss

," she breathed, the long sibilant 's' hanging in the air until the clunk of leather on wood interrupted it. Molly was staring into space, focused entirely on the fantasy. My shoe had slipped from her grasp onto the desk in front of her.

"Just writing 'Daddy' on it isn't good enough. I could barely see where that arrow was pointing. Here's a new rule..." Molly's eyelids fluttered. "

My

pussy... You're sure it's mine, Molly?"

"Yes, Sir."

"And I can use it however I want?"

"

Yes

, Sir."

"But all that hair is in the way..." I leaned low across the desk, my heart beating hard.

Molly gasped gently, caught my eye, unblinking. "You... The new rule..."

"Smooth, bare," I replied, holding her gaze. "Just so you remember who owns it."

Her eyes were so wide, her voice, so soft. "Yes, Sir."

"And I mean 'smooth.'" I thought back to some of her older posts. "No stubble..."

Molly nodded once, a deep, full acquiescence. "Of course, Sir." She was still feet away, but I had never felt so connected to her. "I'll go get it wax--

ah

!"

A single, sharp knock on the door interrupted her, followed immediately by the click of it opening. My eyes swung up over Molly's shoulder as I froze with shock.

Fuck, fuck, fuck, fuck, fuck. Why hadn't we locked it?

In walked Carl Boehner, the gregarious blonde Midwesterner who led the sales team that shared our floor. He had a laptop clutched under his arm awkwardly, more focused on the half-finished apple he kept tossing and catching as he walked towards us.

"Hey, Dan," he said, spraying pulp. He swallowed and his tone softened slightly. "Molly." She sighed and glanced at him quickly as he reached the desk. "Whatcha getting waxed?"

Shit.

Molly didn't miss a beat. "His car," she said casually, flicking her chin towards me with her eyes locked on my shoes. She set them straight beside each other on the newspaper and brushed the cloth lightly over their surfaces, as if chasing final flecks of dust.

Carl grinned and looked down at the motion of her hands too, then looked significantly at me, eyebrows raised. "Ahhh, he's letting you take the roadster out? An honour."

With panic still dry in my mouth, I could not exactly read Carl's tone. "I have a lunch," I spluttered. Now Molly shot me a look. "Ahh, ahh, Molly's taking my car while I'm out."

Molly looked away with a tiny shake of her head and pushed my shoes towards me across the desk. I got the impression I had said something wrong, but there was no criticism in the perky voice she put on. "Two birds with one stone!"

All for Carl's benefit, clearly. He took a final, thoughtful bite out of the apple and tossed the core--there was still plenty of meat on it--into the wastepaper basket. I doubled over gratefully to retie my shoes. "That's a big deal, Molly," I heard him tease, with my head under the desk. "The Miata's his

baby

."

I could almost hear Molly roll her eyes. At least he seemed to be buying her story. "What can we help you with, Carl?"

Carl was nodding and pulling open his computer as my head came up from under the desk. "Yeah," he started. "I've got some numbers to..."

"Can it be an email?" I stood up. I could pass off my nerves for impatience, right? "Molly, our coats?"

She nodded once to me, smile softly, and turned on her heel. Carl closed his laptop again with a click as I rounded my desk to follow her. "Yeah, absolutely, uhh." He sounded a little off guard. "What time are you going to be back?"

A very good question. I looked at the lockscreen of my phone as I walked away and made an exaggerated little shrug. "I mean, I don't..." My 2 o'clock was back here at the office. It was 11:30 now.

My hesitation allowed Carl to regain his composure. "And who's the lunch with?" I grinned at the little competitive note in his voice behind me.

Salesmen.

"Wouldn't you like to know?" Molly teased back. She ducked out of the doorframe to let me out, with her purse slung over her shoulder and our jackets bundled under her arm.

Carl gave a good-natured laugh behind us and we were off together, Molly keeping pace with my longer strides down the hall towards the elevator. She looked back up at me when I looked down. She had a faint little smirk on her face.

"So," I said once we were alone together in the elevator.

"I don't think he did, Sir," Molly said, answering my unspoken question.

"Carl?" I looked at her again for confirmation.

She shook her head. "So where are we getting lunch?"

"I think the question is, where am I getting lunch? You volunteered to get the car washed."

"Oh." Her voice had suddenly shrunk down to a whisper. "Yes, Sir." Silence through the rest of the elevator ride, the click of her heels a pace behind me through the garage, until we were walking up to my car, when Molly hooked her arm through mine and pulled her body close against my side. "Sir?"

I looked around anxiously. Thankfully, there was no one else in the garage. "Yes, Molly?"

"I don't think I can take your car."

"Why's that?"

"I..." She hesitated. "I can't drive."

I laughed out loud. "You can't

drive

?"

"I

mean

..." Molly huffed, disentangling herself from my arm and dropping back again to stop a few feet away from my parking space. Laughter was maybe not the right response. "I have my license, but..."

"You

can't

."

"I just never

do.

I live in the city! None of my friends drive either!"

I looked at her for a moment, then turned to consider the Miata. It had been steel grey when I bought it, then dark blue, then yellow, and now a cherry red that I still was not satisfied with. It was a sexy colour, sure. It just drove home the clichΓ© a little too hard. But what else was a bachelor in his fifties supposed to spend his money on?

I turned back to Molly, hesitated a moment more with the keys in my hand. She caught them with little effort when I tossed them to her. "Let's skip lunch."

"What?" She asked incredulously as I walked around to the passenger side.

I grinned at her over the roof as I opened the passenger door. "You need a driving lesson."

***

Molly's anxiety proved a bigger hurdle than her inexperience. It took us twenty minutes to get out of the parking garage, but twenty minutes after that we had left the city centre and were gently cruising down one of the wide, leafy boulevards that led out to the suburbs. We had perfect conditions for a driving lesson. At this time of day, there were not many people out on the roads, which were bone dry and clear after a week of sunny weather. A red light turned green in front of us and I felt myself wince, but it was premature. Molly was finally getting the feel of the car beneath her and accelerated smoothly into the intersection. I smiled, relaxed, looked over at her. "You're doing great."

"What was that, Sir?"

"I said, 'You're doing great.'"

Molly whipped her head over to look at me as we cleared the intersection, smiling the biggest, easiest smile that I had ever seen on her. "Thanks, Sir, I..."

"Eyes on the road, Molly," I said, happy to assert some authority. "Take this next exit on the right."

I watched her eyes follow the sign nervously as it whipped by. "But, Sir, that's for the interstate!"

"I know, Molly," I said. I put my hand on her knee reassuringly. "You've got this... Now you're coming up to speed... Good girl."

"Sir, what are you doing?" Now her eyes darted down to follow my hand from her knee to the dash as I leaned over.

"Don't worry, just pay attention to the road."

I admit to sharing Molly's obvious trepidation as she merged cautiously onto the freeway and the little electric motor whirred behind us, but it could not last. When the retractable roof made its final clunk into place and the nearly empty road opened up in front of us, the wind whipping through Molly's copper curls seemed to carry the last of her nerves with it. I grinned, looked at her, and she flashed a smile back, a huge, exhilarated smile, her laugh lost in the rushing air around us. The air pressed her dress back against her body too, showed every perfect curve tight under the rippling white fabric, made me thrum along with the engine.

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