The Assistant Part Sixteen [F20s,f30s][semi public][consensual humiliation][penetration][dildos][double penetration][restraints]

DULCIE

The previous night, once I had gotten home, had been fine. I’d fed myself exactly what I wanted– lots of hot black tea, roasted greens and rice. Something cozy to warm myself up. I slept fine, but I woke up too early. Which was fine. I had a lot of work to do, and some catching up that needed to happen. 

When I heard the clatter of Andy coming in for the day, I gave a start. Like I was going to get up out of my seat and go to greet her. But a reticence stopped me. Unsure of how I’d be received. And a bratty sort of “let her come to me” stoppage because of how I’d felt like I’d been treated the previous evening.

And she did come– I heard her putting down her things, hanging up her jacket, the quiet burble of the kettle being turned on to make my tea. The hushed near-pneumatic opening and closing of the dorm refrigerator. 

“Good morning,” she said, breezing in. Carrying both my tea and a small tote bag. My eyes narrowed. She didn’t carry a purse or briefcase or anything. Just whatever she could cram into her jacket or breast pockets. The last time she brought in a bag it was with my repaired clothes and lotion for after care. 

She set my tea down and stood in front of my calendar.

“Only thing up today is that meeting at like… twenty to five about the proofs,” she said. 

“Right,” I agreed with a heavy sigh. “It’s what I’m working on today and I specifically left the day empty just to buckle down on that.”

“Yes, I noticed you had some catch up to do today,” she said, back still to me. Another black suit. A slate gray button up. High shine oxfords. She smelled good when she brushed by me. Hair oiled, one little lock over her forehead being very distracting. Remembering her hand on my lower back and– “I am prepared to harshly turn away any interlopers today,” she added, breaking into my stupid reverie.

“That would be much appreciated,” I said, already feeling relief. She was very good about heading off interrupters, taking calls and making sure no one bullied their way to me. Much better than I was.

“And I am also prepared to make sure you stay the fuck in your office and get shit done,” she said.

I perked up now. She didn’t really curse unless we were going to play. And I wanted to play. 

She snapped at me twice and I actually slid out of my chair and onto my knees. She laughed and I even exhaled a single giggle. So ingrained to just go “wind up dog” even when I hadn’t been directed as such.

She shook her head, snapped her fingers again and said, “no, ma’am, your clothes.”

“My clothes?” I squeaked. All well and good to play a little at work. That one brief (and oh-so exhilarating) sprint nude in the office. But it was nine in the morning– there were actually people here now. 

“Your clothes, yes,” she said, all impatience. “If you’re naked, I sincerely doubt you’ll go rocketing around the C-suites. You’ll just stay like a well-behaved little dog, getting her little dog work done. And I’ll be on the other side of your closed door to, one, make sure you stay put and two, make sure nobody sees your little fuck-toy body but me.”

I inhaled shakily. I liked the idea. So I started sliding out of my tweed dress, throwing aside my jacket. She took my clothes from me, folding them up and setting them aside.

“I’ll give them back before the meeting,” she said, as if to reassure me.

I stood shivering, naked but for shoes in front of my desk now. For the first time, feeling my arms rise, to cross over my chest or torso. I didn’t usually do that while naked. I didn’t mind being naked. I didn’t have the time or the energy any more to be ashamed about rounded tummy or upper arms or chubby thighs. Anyway; I’d been told by a number of people that their favorite part of me was the softness. 

“I’ll give you something else to focus on,” she said. “Bend over your desk, hands flat on the top.”

I braced my hands on the edge, sweaty palms instantly sticking to a few glossy sheets in front of me. I shoved them aside, still shivering. Not cold, just excited. 

She rested a hand on my lower back, pushing me deeper. Another hand on my stomach, easing my hips upward. I fell instantly into the position she wanted– backside vulnerable, chest to the table. Wriggling a little, as if I’d be able to get either of her hands to slide lower, in between my legs. She just laughed at me. 

I heard and then felt her spitting in between my legs. Another moment of humiliation and ambivalence, the way she could always make me feel. Disgusting and sexy and unworried about being either disgusting or sexual. I grunted and shook under the light weight of degradation.

She rolled her finger tip over my clit and I moaned and then bit my lip. 

“Don’t get excited now,” she said. “Just hitting my toy’s lube button to get her prepped.”

Then I was penetrated– not by her fingers, and not by the strap, but something in between those two sizes. More shocking, however, after that penetration was the slickness of some sort of actual lube, something jellied, being pushed into my anus.

I started forward a little, body knocking into my desk, making the tea in my glass shiver. 

“You can take it just fine,” she said. “You’re perfect, don’t worry.”

So I relaxed– I’d never been penetrated like that before. It was new and not necessarily arousing on its own, but certainly of interest now that both holes were filled. 

I shifted a little, deciding how I felt, knees rubbing together. I felt… well, filled. Almost in the same way that you’d grasp your stomach while experiencing cramps, but without pain. Just… filled. 

However, I grunted, bopping my head painfully off my desk top when the sensation became bigger. A hsst and phew noise from behind me. I looked over my shoulder, seeing her standing there with something like a blood pressure pump in her hand.

“Filling my toy with balloons,” she said, as if that answered anything. Both toys inside me swelled slightly, increasing that almost-a-cramp feeling. Then she stopped. One hand on my stomach again, the other lightly flicking my clit a few times. Nothing near to getting off. More like trying to relax me with stimulation. And it did. 

She tossed a cushion into my desk chair from her tote bag and then put my clothes back into the bag. Clearly intending to actually take them from me. 

“What page are you on now?” she asked.

“Um… ah… hm–” I stuttered, still bent over the desk, still getting used to the toys inside me. Horny and distracted. She snapped and I stood up, everything shifting inside me. More and less comfortable in different ways standing than bent in half. 

“Ma’am?” she snapped.

“Eleven,” I said, the way you’d answer a question when snapped out of sleep. “Shit… no, nine, nine.” 

She shot her sleeve, checking her onyx watch.

“If you can get to nineteen by 10:30 I’ll come back in and give you some relief.”

It took me a good ten minutes to settle back into work. I understood why she’d tossed the cushion down on my seat. Partially just to protect the leather, but without some little extra fluff between me and the seat, the bottoms of the plugs would have likely hurt. Sitting was another all new sensation though. Pleasantly and awfully reminding me of riding strap the other night. Thankfully, whatever was in me was neither as wide or long as her monster strap, but having my body weight press and keep them inside me was still distracting. 

And of course, the sensation of nudity in my office was very strange.

And yet… once I let my eyes drift back down to the pages in front of me… work just came easy. 

I’d shift sometimes, feeling the toys inside of me. And I was wet– though blessedly not dripping– although I was sure I’d be leaving a mark on her pillow. Oddly it was all more akin to doing a task in an unusual place. Like if you did your sewing in a bathtub, or your makeup in your car. The thought of “this seems strange” quickly surmounted by the simple routine of whatever process you were doing.

So while I was headily aware of rock-hard nipples and my doubly filled holes, the simple routine of work superseded it. 

And it was easy, until I heard someone in the outer office. Talking with Andy. Andy clearly turning them away, offering a return call or something. My skin went all goose-pimples– nipples drawing even harder and tighter, hands cold, face pale. The idea of being naked and only one general-issue pressboard door between me and some stranger brought me back to that roller-coaster feeling I had when Andy and I played. Contained danger.  

For a moment I pictured that wicked grin she had; when I wasn’t around, or she thought I wouldn’t hear it, I sometimes eavesdropped on her talking to the other guys in the company. About girls. No one ever said anything truly reprehensible, but I heard some ribald jokes. And now I helplessly pictured her saying “I’ve got the boss’s juicy little pussy waiting for me next door” and–

There was a knock, and I almost shrieked. Leaping out of the chair, shocked I hadn’t lost the toys– but they were too big and too well lodged to fall from me. Not like the hairbrush.

“Just me, ma’am,” she said, all obsequious assistant. I laughed at the mimicry. She heard my laughter and came in, rapidly closing and locking the door again behind herself.

“Page, ma’am?” she asked.

I looked down and paid attention for the first time.

“Twenty-one,” I said, genuinely surprised.

“Good work,” she said. “Since you’re ahead of schedule, and I am sure you’ll remain so, perhaps we can take a little extra time with that promised relief.” 

“Yes, I think so,” I agreed. 

“Do me a favor and lay out all the pages you’ve already done across the floor,” she said. I noticed the tote bag once more. 

So I did. Getting up, gathering them together, laying them edge to edge out on the floor. Now I was aroused again. Clit slick and huge and I was sure pulsing under the overhead lights. 

“All right, you go ahead and lay down on your back in front of them,” she said.

I did. Office carpet scratchy under my skin; far more than it should have been– I was overstimulated and tended to sensitivity because of it. She came over with that bedamned tote bag again. Lifting my legs up, pressing my thighs to my chest, folding me in half. My labia felt all bloomed outward, toys obvious and pulsating. 

She strapped me in that bent-in-half position, with a series of canvas belts, just something quick and handy to tie me tight. Knees pressed into my breasts, thighs to my tummy, feet in heels parallel to the ceiling. Then she sat on the back of my thighs. She turned me into a short little chair, my calves the back of the ‘chair’ for her, my thighs and torso the seat. 

I exhaled hugely– it certainly felt like she was sitting with her full weight on me. Grunting again when her finger once more lazily flicked at my clit. She didn’t stop touching me, but neither with much speed or much pressure. 

“You go ahead and finish while I double check your work,” she said.

I moaned. Realizing it was easy enough to release my breath, but not so easy to bring any back, not with her weight on me. Now that I was crunched in half, the toys also had a horrible… escaping sort of feeling to them. Everything was compacted, and I felt even fuller than I had earlier. 

I could feel myself spasming particularly around the toy in my vagina, buried deep behind my belly button, by the feel of it. It wouldn’t take me long at all to finish.

“You’re right,” she said quietly, finger still swirling on me. “That original tagline was no good– your’s is better.” 

I had an interesting dizzying panic buzzing in my head. I was horny, and steadily climbing toward orgasm but my breath was very constricted, my heart was beating heavier than it did ordinarily, even for sex. It seemed she’d be able to feel my great thudding heart pounding up into her spine. 

She paused, briefly. I moaned, but it didn’t come out sounding like that, more like a broken squeak toy just going hueh. I felt her fiddling with the toys, and I didn’t know if I was disappointed or relieved by the idea of her withdrawing one or both. But instead she was just reconnecting the hose, reapplying that bulbed pump to the toy in my pussy.

“Can’t,” I said. 

“Yes you can,” she sighed impatiently. “Do you know how big it even is in you, you dumb whore?”

I clenched tightly around it– it certainly felt big to me. 

“Well?”

“I um… Well, I–”

She pinched my clit hard between her thumb and index finger and then twisted. I clapped both my hands over my mouth, squealing breathlessly into my sweating palms.

“Big as a fist, at least,” I panted out. 

She spit down on my splayed open genitals again, rubbing it into my clit, and I felt that coiled tension of orgasm come nearer. 

“Nowhere near,” she said, touching gently now. “But you’re right… I should be training you up for my fist. So exhale,” I did, really trying to relax. “And take whatever I pump into you, fuck-hole.”

I grunted, tears springing to line my eyes and I cramped sincerely now. Feeling her slowly compress the bulb and force more air into the toy. I felt like my belly must be distended with it now, grotesque. 

“Pretty thing,” she murmured, going back to work in earnest on my clit. 

There was a popping sensation in my lower spine. A shocking orgasm. I was used to a build up and release and this just sprang from me. No unrolling ribbon of relief but instead an explosion. One that left my ears ringing, tongue lolled out on my lower lip, almost nauseous. 

“There we go,” she said. “Good girl, good work.”

She unstrapped me and I unfolded with a heavy flop to the floor. She started gathering the pages together for me. 

“All right, I’ll leave you to your work,” she said.

“Oh!” I cried. 

She looked down at me from about a mile away, one eyebrow raised in question.

“Oh, please,” I said, grasping my belly. The odd sensation of drained clit and labia, grossly deflated after all the blood rushed away after orgasm, and my puffed out vagina in stark contrast.

“You really can’t take it?” she asked sardonically.

I rolled my eyes upward in thought. I wanted to bravely say “oh wait, I’m fine” but I really didn’t think I could sit with this much longer. 

“I’ll switch you out with something else,” she sighed. “Assume the position.”

I turtle-rolled off the floor. I didn’t think I’d just be able to hop up. I felt like I hobbled to my desk, like my inner thighs were wet down to my knees. Like I’d start dripping cum into my shoes. 

The awful hose of the toy dangled between my legs, softly thwudding in a figure-eight sort of clock work between my sticky thighs, like a disgusting tail. 

Once I finally reached my desk I bent over again, hands on the edge. 

She started rocking the toy in my pussy gently back and forth in her palm.

“You’re being a lazy little breeder again, work with me here,” she chastised. “Come on, you got those strong, dick-sucking pussy muscles. Help me here. Go ahead and push it out if you don’t want it any more.”

I watched two tears, one then the next splash onto my desk in front of me. I settled lower onto my forearms and spread my legs further apart. Genuinely trying to do as she said, while she also worked it. I started to feel it ease past my inner labia, and then she pushed it back in with one finger, laughing. 

I started crying in earnest, feeling a shiver go down both my legs and not stop. Just quivering and crying and giving up. 

“Worthless,” she said. “You were so easy to break. Cheap toy.” 

I sniffled then focused when she plucked at the hose. She started to work it again, and I started pushing again. Finally feeling it slide out. But it took so long, and felt so enormous. It was a relief to be free, but I felt like I was gaping afterward. Walls still clinging to emptiness. 

She reached over my left shoulder, hooking her index finger into my mouth, stretching my cheek back into a rictus grin. Forcing me to crane my head around, chin almost past my left shoulder. Pushing inch after inch of the now-deflated rubber toy into my mouth. It wouldn’t have fit while it was still full of air. But it was like having a hard tubular balloon stuffed into my jaws, keeping them cracked open. The rubber was hot still from having just been inside me. 

I just sort of melted into the desk, breasts flattening into the top, waiting for whatever she was going to do next. 

Stringing some rough, hempy rope in between my legs, around my waist, between my lips and buttocks. A heavy, itchy little knot pressed against my clit– too tight around my waist and rubbing rashy into tender skin. 

She pulled the toy out of my mouth, dumping it back into her bag, presumably right on top of my clothes. 

“Can you work like that, bitch?” she asked. 

It was bad, but better than feeling like I was going to crack open. Even the toy still lodged in my anus was more comfortable.

“Mhm,” I said, wiping at my face with both hands.

“Then work.”