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The Assistant

Chapter 17

Ch. 18 / 28 Jan 07, 2026

The list of tasks Jon sent me seemed innocuous at first, at least until I got to the last one telling me where I could find several credit cards, a ridiculous amount of money to just have lying around, and the instructions to have the driver take me shopping for tonight. It felt wrong to take it from him, but he refused to change his mind and insisted I go have fun and we could talk about it later. I relented eventually, once he told me where we were going for dinner and I realized I had nothing in my closet that would feel fancy enough for theAugustine.

The restaurant booked reservations more than a month in advance, but apparently, Jon knew the head chef and pulled strings to get us in. Money talks, especially in a city built on the foundation of earning it at any cost. So, I went shopping and I refused to look at price tags or totals – if he wanted me to look nice, then I was going to look fucking fantastic.

Patrick had called while I was shopping, frantically trying to make sure I was okay because Jon had emailed him about my little outburst. I felt stupid for my sudden emotional bout, but I couldn’t say I didn’t like the way the two of them immediately started fussing over me like I was the most important thing in the world.

Speak of the devil. My phone vibrated and I grabbed it off the marble counter in the bathroom, my heart caught in my throat from sudden excitement and anxiety.

8:29 PM

Are you running on Standard Time or Lydia Time?

I rolled my eyes. I wasn’t always late, just most of the time.

8:30 PM

You’re so funny. I’m leaving now, I’ll see you soon.

I tucked my phone into the glittery clutch beside my makeup palette. Glitter was my theme tonight, I wanted to stand out. From my royal-blue wrap, bodycon dress with shimmery thread adding a starry night feel, to my black rhinestone coated platforms, to the matching clutch, and finally, my hair pulled to the side with black glittering flower clips – no one could miss me.

I took one last glance in the floor-length mirror before taking the elevator down to the garage. The driver was already waiting to pick up Jon and nodded at me in greeting. I carefully slid across the leather seat and daintily crossed my legs as I debated the best pose to be in when he got in the car.

The drive was short, my foot bounced the entire way and I fought the urge to pick at my fresh manicure - the pink polish was too cute to ruin. When we pulled up in front of Bower & Rosing’s I was pretty sure my panties were about soaked through from anticipation, which did not bode well for us making it through dinner. The door across from me opened and I jumped to attention, stretching my legs in front of me elegantly and arching my back to push my tits out.

Jon’s eyes roamed over my body slowly, his gaze searing into my skin as he sat down next to me. “Look at you,” he said huskily. “Is this all for me?”

I grinned and leaned in for a deep kiss, letting my new nails scratch through his stubble. “Is there someone else here?” I asked after pulling away.

“We should skip dinner, that dress is doing more for me than Viagra ever could.”

I laughed as he pulled me into his lap to make out, I ground down on his cock, feeling it harden under me and wanting to tease him for as long as I could. Jon tried to slide my dress further up and I slapped his hands away. “First base only,” I whispered close to his ear.

He growled in annoyance but relented, though his mouth did find its way down to my cleavage. Extracting ourselves from the car was a bit of a chore, I was flushed and stumbled slightly as we made our way into the restaurant but he had a very self-satisfied smirk as he adjusted his jacket and wrapped his arm around my waist.

The Augustine was stunning; white stone-tile walls reflected the warm chandelier lighting beautifully, dark wood floors made the room seem smaller and more intimate, the walls were lined with rounded booths and massive gilded mirrors above them, there were tables scattered around the space with off-white silk linens and shimmering china sets. The whole space had an old-world feel, especially with the soft classical music adding romantic ambience. It was mostly empty as well, which was welcome as I tried to hide how close I had gotten in the car to coming just from necking like teens.

As the maître ‘d showed us to our booth in the back, I caught two women gaping at us, I smirked to myself and leaned into him while I ran my hand up his chest as they watched. I gave exactly zero shits what they might think, but hey, if they wanted to be outraged then I would make sure they had something to be outraged over. Which is why I pulled him in for another long kiss before even glancing at the menus.

The menu was overwhelming, and I just passed it off to Jon to handle, I trusted him to find me something good. What the fuck is spätzle? I had no idea how to even pronounce it, let alone what it would taste like.

“You’re upsetting the patrons,” he whispered to me while we waited for our drinks.

I glanced at him at caught the way his eyes glittered mischievously. “I hadn’t noticed,” I replied dryly. As our drinks were served, I took the glass in one hand and let my other find its way to his cock, feeling the rigid line straining against his trousers.

Jon stilled but spread his legs slightly as he warned me, “Don’t start what you can’t finish.”

I pulled my hand away innocently and sipped away at the wonderful glass of red wine he had ordered me, the bottle of which sat beside us and I planned on drinking copious amounts of as he went to town on scotch. We leaned against each other and chatted quietly about work while we waited for our food, I wanted to know that his day hadn’t been entirely shitty after my outburst, especially because he had worked almost thirteen hours again and I worried about the stress that could bring on.

He seemed alright though, and it felt good just to be able to sit and talk about the mundane stuff. As we ate, I slipped my shoe off and gently ran my foot up and down his calf, his hand seized my thigh and I jumped in surprise at his sudden movement, jostling the table slightly and making him chuckle.

“Don’t draw attention to yourself.”

I nodded almost imperceptibly and continued quietly telling him about my day as his hand slid higher. This is oddly familiar. “We’re in a restaurant…”

“Do you want me to stop?” He stared at me expectantly, his hand frozen mere inches from my pussy.

Never. “No,” I whispered as heat crept up my neck.

Jon’s fingers pushed the lacy material of my panties out of the way and sought out my clit, my breathing became shallow and I struggled to keep talking and not draw attention to us. The restaurant was still pretty much empty, just the other two women that had gawked at us, and even now they were packing up.

My back arched as his fingers moved faster and I tried not to squirm even though my skin was flashing hot and cold the closer I got to my finish. My heart was pounding in my ears and I rested my head against his shoulder, trying to hide my panting. I gripped his thigh again suddenly as my hips bucked against his hand and gasped. He stopped instantly and I whimpered, trying to bite back the words on my tongue.

Jon’s mouth met my ear and my eyes rolled back at the warmth and intimacy. “Pull my cock out,” he ordered.

I didn’t even think about it, just worked to unzip his pants and struggled for a minute as I got his cock out. It throbbed in my hand, the head an angry red as I stroked up and down. I revelled in the silky feeling of his shaft, the hardness of it as I squeezed gently and twisted my hand while I pumped up and down. My body was on fire and his touch was ice melting over my skin, raising goosebumps and sending chills through me.

He went back to working my clit and I bit his shoulder to stifle my moan. “Sit up straight, you can’t look like you’re getting worked over at the table,” he warned me.

It was a struggle, but I braced my forearm on the table as I tried to keep a straight face and just look like a normal couple. I took a shaky sip from my glass, my third or fourth by this point, and almost choked as he grasped my clit between his thumb and forefinger.

“Daddy,” I whispered frantically. “I can’t— I’m going to—” I stopped again and fought to keep myself upright as I came, one hand squeezing the stem of the glass and I tried desperately not to death grip his cock as a full-body shudder ran through me.

He laughed quietly and just rubbed harder, I shivered, and my chest heaved with my laboured breathing. His hand came up to cup my cheek and turn me to him so he could kiss me, his mouth was warm and spicy from his drink. “Again,” he murmured against my lips. “Come for me again, baby.”

Releasing his cock I clutched his hair tightly in my fist as I went over the edge, trying to keep his mouth glued to mine so I wouldn’t scream. When he pulled away he moved his hand from my pussy as well but his wet fingers still rested on my thigh.

Jon placed a quick kiss on my cheek as he watched me closely, looking even more self-satisfied. “You’re such a good girl that I can have you wherever I want, can’t I?” he asked as his thumb stroked over my cheekbone.

My lips parted and I wanted to protest, tell him to go fuck himself and that I would decide where and when, but I didn’t. I nodded and removed my hand from his groin so he could tuck himself away again. I was sweaty, flushed, and still nowhere near sated –I wanted him in me. Or touching me. I had no fucking clue, I just wanted him to do more to me. This did not bode well for trying to keep up my Ballsy Lydia shtick.

After the waiter came and collected our plates, Jon ordered dessert, which was cruel considering I just wanted to get my mouth on a certain body part and not wait for souffle. Once the waiter had left, I threaded his fingers through mine and brought his hand to my mouth, I held his gaze as I kissed his slightly moist fingers and then the signet ring. Glacial blue turned dark as he regarded me through heavy-lidded eyes, watching me with a mix of predatory desire and interest.

“What does that symbol mean?” I asked after a moment.

He glanced down at the ring for a second before stroking his thumb over the back of my hand, electricity shot up my arm and for a fleeting second my eyes fluttered shut. “There’s no set meaning, just an identifier to other people that are looking for it. Originally, it came from The Story of O, but the design is a lot different than it is in the book. We don’t use the same rules as Roissy did, but we issue the signets to all members.”

That better be the only thing from the book that you want to replicate. “Not to be a stick in the mud, but I draw the line at having you whip me bloody – O might have liked that, but I’m not down for it.”

Jon choked on his scotch and started coughing through his laughter. “I wasn’t planning on it, I like seeing bruises, not blood. I’m also not asking you to get branded or tattooed in case you have any other body mutilation concerns.”

“Oh, well thank you, I do appreciate that you don’t want to brand me like cattle,” I said with a dramatic eye roll.

His arm snaked around my waist, trapping me against him and bringing me close enough that he could kiss my shoulder. “Roll your eyes again, see where it gets you,” he warned.

I smirked and tucked my head against his arm. Dessert was amazing, almost worth making me wait for the real main course, I certainly liked taking turns feeding each other ice cream. We rushed through it though, because we were both starting to get worked up again and there wasn’t much stopping me from just crawling under the table and going to town. The ride home was even more rushed, and I was almost certain he had just told the driver to floor it.

Just as we stepped into the foyer Jon seized my upper arm and kissed me hard, his tongue invading my mouth and feeling like he was searching for my soul. I moaned and melted against him, my hand braced on his chest as my nails dug into his jacket. His hands were in my hair, tearing the clips out and letting them fall to the floor in a harsh sound that echoed around the empty room.

He led me up the stairs, back into the playroom and stripped his jacket off before undoing the buttons on his shirt but still leaving it on. I watched him closely, following his graceful and calculated movements. He sat on the chaise again and I clasped my hands behind me to emphasize my tits, he crossed his legs, his ankle resting on his knee as he stared levelly at me. A slow smile spread across my face as I met the challenge in his eyes – I wouldn’t move until he told me to, I already knew my ass was getting wrecked tonight, I refused to give him more reason to punish me. After a moment, he smirked and pulled his phone out, soon the sound of smooth electric guitars and slow, sexy rock filled the room.

“Strip.”

Every step I made was thought-through and slow, turning around so I could peel myself out of my dress and bend over in the process so he could get a nice view of my ass with my legs completely straight and tight together. My lingerie was all black lace and crystal embellishments, with straps and details glittering like diamonds against my light tan. It didn’t cover anything but my slit with a wider band of lace, everything else was more like a harness. I slid my hands over myself, grabbing my ass as I turned back toward him then reaching to cup my breasts. I noticed immediately that his belt was undone and his cock was tenting his pants. My mouth watered and heat spread through my abdomen rapidly. I daintily worked the shoulder straps down and held the front closure - toying with it as he watched.

He chuckled and retrieved his wallet; I took a few slow steps toward him as he pulled out several bills and I flushed. I perched myself on his lap, my knees braced on either side of his legs, took the money without question and slipped it in the sideband of my thong. It was two hundred dollar bills.

I nipped at his ear lobe playfully. “You think I’m that cheap?” I teased as I kissed the junction between his throat and shoulder.

His chest rumbled as he hummed thoughtfully. “You’re going to bankrupt me for that cunt, aren’t you?”

I giggled as his hands kneaded my ass suddenly and I started to grind on him in response. “Don’t get ahead of yourself, you haven’t even gotten to my tits yet.”

Without another word, Daddy pulled out another wad of cash and held it just out of reach. “Take the top off.”

I unsnapped the clasp and tossed the bra to the side before sinking my fingers into his hair and pulling him to my chest, he groaned and slipped the bills in my back waistband. His hands quickly found my tits, his thumbs brushing gently over my nipples and sending little sparks throughout my body at his touch. Suddenly, his mouth latched onto one sensitive peak and I moaned loudly, my head tipped back in ecstasy as his tongue swirled around my nipple. My pussy was getting wetter by the second, and as his teeth grazed my flesh I almost came right then, until he bit harder than I expected and I yelped in shock.

He laughed darkly, the mean sound reverberated through me and I shivered. “How much for the bottoms?” he demanded. He gazed up at me expectantly, the stunning blue of his eyes practically glowing in the dim room.

“If you have to ask you can’t afford it,” I taunted, leaning back and rocking my hips against him, my hands holding the back of his neck.

A muscle in his cheek jumped and this time he pulled out his AMEX black card, holding it precariously between his index and middle fingers. “How about this?” he asked with a devilish smile.

My eyes had to be the size of dinner plates as I stared at the most exclusive credit card in the world, and my name was on it. “That’s…” I trailed off, my mouth was suddenly bone dry and I had no idea what the fuck I was supposed to say.

“Well?” he asked with a cocked eyebrow. “Do you think it’s enough?”

My eyes were starting to water and my heart ached. “You trust me that much?” I asked finally.

“Of course I do,” he replied instantly. “I trust you more than anyone else.”

Ohmigod. I was going to cry, just start absolutely sobbing. “Daddy, thank you,” I whispered as I kissed him. He handed it to me and I held it gingerly, my hand shaking badly. “Hold on to it for a few more days, I don’t want to feel like you’re actually paying me for sex.”

Jon laughed and tucked it back in his wallet before reaching for the waistband on my thong and tearing it into scraps. Rhinestones skittered across the floor and the money fluttered around it. “I’ll have to get a real stripper pole in here soon, I’m sure it’d get a lot of use.”

Wicked fantasies wove through my mind and I made a mental note to look up pole dancing classes in the area. He urged me onto the floor over the mess and covered me as soon as I was sprawled out, I wrapped my legs around him and he pinned my hands above my head while probing my waiting pussy with the head of his cock. I arched against his chest and moaned as he bit and sucked my throat.

“You’re always so wet for me,” he said with a guttural moan.

I groaned and writhed under him as his cock stroked my entrance. “Only for you, Daddy.”

The floor was cold, my skin hot, my back sweaty, his body pinned me to the hard surface and in one thrust he bottomed out inside me. I cried out at the intrusion and desperately fought his hold on my wrists. I wanted to touch him, to feel his warm, hard body under my fingers. My cunt was filled completely, and with every thrust, I pushed back on him. My wetness was dripping onto the floor, coating my thighs and his as I mewled and whimpered from his brutal onslaught.

His hand left my wrists and came to grip my throat, I swallowed unintentionally and gasped as he squeezed gently, his other hand gripping my hip tightly. I threaded my fingers through his silky locks, revelling in the way it curled around my fingers. He kissed me hard and frantic, our teeth gnashed and his tongue stroked mine sensually.

“Daddy,” I mumbled against his lips. “I love you.”

He groaned and his eyes met mine just as he thrust in again, my heart stuttered as I gazed up at him. “I love you too, baby.”

His grip tightened another fraction of an inch, my eyes rolled back and my pussy tightened around him as bright spots blossomed in my vision. I came hard, crying out against him and feeling a burst of white-hot fire spread through my abdomen before dissipating quickly and leaving me wanting more.

“Oh, fuck.” Daddy groaned and shuddered against me, his other hand releasing my hip and slamming hard onto the floor by my head as he filled me completely – his come was warm and soothing in my battered pussy.

He kept himself from fully collapsing on top of me but I wouldn’t have minded if he did, I liked the way he felt when he was pressed against me – it was protective and warm. I ran my hands up and down his arms, back, chest, anywhere I could reach while his head was bowed to my chest. He rolled over without warning and pulled me on top of him, I giggled in surprise but nuzzled into him anyway.

“I love when you wear stockings,” he said quietly, his hand toying with the lace top of the aforementioned undergarment. “And heels, and basically anything if I’m being honest.”

“How about nothing at all?” I asked as I kissed my way across his stubble covered jaw.

Jon smiled warmly and stroked my back as he relaxed further on the floor. “Even better.”

I raked my nails through his short chest hair and watched with fascination as his chest quivered at my touch. “I believe I was promised a proper whipping.”

“Eager for me to give you some welts?”

Is the Pope Catholic? “Duh.”

He slapped my butt cheek hard and I wiggled against him in response, trying to hide my growing smile. “Bring me the crop, then get on your knees and beg for it like a good whore.”

Oh, fuck yes. I was only too happy to oblige.