by Jamie Knight
There was no longer any question or indecision about the clothes I wore. It was sexy all the way—cute sneakers, short skirts, and skintight blouses that showed off my assets. I didn’t know for sure if Max was interested in me, but I wanted to wave my interest in him around like signal flares.
At least he seemed to appreciate the improvement in my performance. I still had a lot to learn but getting rid of the heels solved many problems like tripping over my own feet and dropping things. There hadn’t been a major spill or spillage in a few days, and I gained confidence in myself and my job.
I got to work early, as had become my habit. Elsa and Max were already there because, of course, they were. They were always there before everyone else, sometimes even the security guards, or so I’d heard.
“Morning, sunshine,” Elsa said, not looking up from her crossword.
“Morning,” I replied.
I stopped off at the watercooler for the day’s first bit of refreshment. Max had insisted on at least eight cups a day.
Properly hydrated, I went to my office and smiled at the brown paper bag on my desk. I shouldn’t have been surprised. Putting bags of food on my desk was something he’d started doing. Maybe he got Elsa to do it. Either way, I knew the meals were from Max. He had commented before how light I was and asked if I was eating.
I confessed I hadn’t been eating much. It wasn’t on purpose. I just never honestly thought about it until I was so hungry it hurt. Food always seemed like fuel and was never the initial thing on my list to do every day. But I had to admit, I’d started to feel stronger since Max had insisted that I eat. My hands were steadier, and my mind was clearer, making it a lot simpler to learn what I had to.
The breakfast bagel was delicious, and I ate too fast, feeling full but satisfied when I tossed the empty bag into the wastebasket.
The knock on my door made me jump, pulling me out of my happy little world. Elsa stood in the doorway like the goddess she was.
“Did you enjoy breakfast?” she asked.
“Very much so.”
“Good, Max thought you would. It was from his favorite bagel place. Be sure and tell him.” She grinned and drummed her fingers against the door. “He wants to see you.”
“Of course.”
Straightening my clothes and checking for stains, I went to Max’s door, not even bothering to knock.
“I enjoyed the bagel,” I said, closing the door behind me. “Thank you.”
“Great, sit down, please,” Max replied, not looking up from his papers.
I obeyed my master’s orders and sat.
“I—”
He glared at me.
“I don’t recall asking you a question or giving you permission to talk.”
I shut my mouth so fast it made a noise. I watched him, taking in his every move, trying to gauge his mood. I couldn’t get anything except that he was very busy. Though busy with what, I could only begin to imagine.
He lowered the paper to his desk and leaned back. “I like you, Charli,” he said, the sound of my name on his lips soaked my panties. That was the first time he hadn’t used my full name. And was I in a dream? Had my fantasy man actually said he liked me?
“I-I—”
“Silence,” he replied again, more gently that time.
“Yes, sir,” I said, hanging my head.
“I like you, and you have been doing a lot better. You are still rough around the edges, mostly due to a lack of practical experience. But I see genuine potential in you. I think you could do really big things, even become an assistant editor if you want to, but you are going to have to go through some discipline.”
“What kind of discipline?” I asked before I could stop myself.
“Some very serious and strict training. I am willing to undertake this endeavor if you are interested. I won’t lie to you. It could get harsh, but I think it will be of a significant benefit to you and your future career.”
I swallowed hard, imagining the type of training I’d like to receive from him.
“What does it entail?”
“We will work very closely. You wouldn’t be in your office anymore. I would set up a desk for you here so I can keep an eye on things. You will do what I say when I say it. If you screw up, you get punished swiftly and severely, but if you do well, you will be rewarded in the same manner.”
“Punished and rewarded how?” I asked, my voice quiet and small.
“If you’re bad, I will spank or paddle you. If you’re good, I will fuck you.”
The world around me turned hazy, and it took a few seconds for me to understand what he’d said.
“Y-you’ll spank me?” I asked, trembling at the thought, though more with pleasure than fear.
“Yes, but only when needed for correction. I will never harm you.”
I grasped the armrests, my fingers digging into the soft leather.
“What’s the difference?”
“Harm leaves a permanent mark.”
There was a long pause. I tried to make it look like I was thinking his offer over. In reality, I was trying to catch my breath and, with it, regain my ability to speak. My heart pounded against my rib cage, and my pussy ached with desire, longing for the unknown pleasures being offered by this sexy, strong, and commanding man.
“Yes,” was all I could manage.
“Good. I am still working out the details, but it won’t take long.”
All I could do was nod. Every muscle in my body trembled at once, making it difficult to form words. I couldn’t stop thinking about it—about him.
I imagined him standing behind me while I was on all fours. Imagined him spanking me, then fucking me. Pounding his big, beautiful cock into me and bringing me to previously unimagined levels of pleasure.
“You are excused,” Max said, picking up his paper again.
“Y-yes, master,” I blurted out.
I covered my mouth, and my cheeks flushed, burning hot. I wasn’t sure where the words had come from, but I had said them and couldn’t take them back. But I’d meant them. I rushed from the room before he had time to say anything. It didn’t matter if it was good or bad. The cat was out of the bag, and it was up to him to make of it what he liked.
I grabbed the key to the staff bathroom from the receptionist’s desk drawer and practically ran there.
Locked in the privacy of the single-occupancy bathroom, I yanked down my panties and pressed my fingers against my soaked pussy. I slammed back against the cool tile wall, moaning with relief.
Gently as I could, I worked my fingers along my delicate pink folds, paying close attention to my swollen and throbbing clit. Getting into the rhythm of things, I closed my eyes, losing myself to the pleasure coursing through my body.
The bathroom door opened again, the hinges squeaking like the door of a haunted house. I could smell Max’s cologne. The musky scent wrapping around me like a cocoon.
Peering at me with his molten gaze, he removed my hand from between my legs, and one by one, he sucked my fingers, groaning as he did.
Lowering his hand, he slipped two fingers inside me. “I can’t wait to slam my cock inside your tight hole, Charli. I can’t wait to fuck you again and again and again.”
I couldn’t stop the moans falling from my lips.
“Shush, pet. We don’t want anyone to know what we’re doing here.” To keep me quiet, he clamped his palm over my mouth and deftly worked me to a head-spinning orgasm. My cries of pure joy muffled by his gentle hand clamped over my mouth.
When I had nothing left to give, he put his fingers in my mouth and had me suck them clean. Not one to leave a job unfinished, Max got to his knees. Holding the front of my skirt up, he buried his face between my legs, again muffling my yelps and screams.
His lovely tongue worked my sweet little pink cunt with the skill of a master. It was the right decision to have him train me. I had a hard time imagining him hurting me even in the case of an incurred punishment.
He stru
ck me as the type who knew what he was doing in all things, be it giving pleasure or pain. The line between the two was thin, as I was soon to discover.
He got to his feet and lowered his lips to mine, his breath smelling of my arousal.
“I should spank you. It was very naughty, running out like that. I don’t mind what you were doing, but the way you left was unacceptable. Still, it was my mistake, not yours. I should have seen how excited you were getting. Usually, I’m a lot more sensitive to the needs of my pets. From now on, though, if you pull a stunt like that again, your ass will be the color of a fire truck. Understand?”
He grabbed a handful of my naked ass and squeezed hard.
The feeling was so beautiful it made me squeal and ache and want.
“Yes, master,” I murmured when I regained my senses.
“Good, pet.”
With that, he washed his hands and left.
I slid down the wall, spread my legs, and brought myself to another soul-shaking orgasm.
Chapter 6 - Max
I could still taste her pussy, clean, and sweet on my tongue like delicious candy. I wanted more, so much more, but there would be time enough for that. For the moment, I held myself back.
I savored the thought of being with her again and of taking her virginity. She hadn’t been with a man before—something my time finger fucking her had confirmed. I would punish her when needed but also help her reach her full potential. I hadn’t been lying about that. I saw great things for her. If only she could learn to be more refined and less clumsy.
I got dressed in a hurry, not even noticing which suit I took from the closet, and, once dressed, I gave a moment’s thought of taking the car into work. But even I had limits in terms of moral compromise.
***
“That’s not your Thursday suit,” Elsa said, sounding shocked.
“It’s not?” I looked down at myself, doing my best impression of befuddled.
“What tie did you bring?” Elsa asked, digging through my backpack, my bike still standing between us.
“I really don’t—”
“Oh, Max,” Elsa groaned, pulling out far and away the ugliest tie I owned
“It was dark,” I explained.
“Are you actually going to stick with that story?”
“Until my dying day,” I confirmed.
She shrugged.
“Suit yourself.”
Elsa slipped the tie around the collar of my shirt and started on a fancy double-Windsor knot. Her long fingers moving with practiced deftness. I had little doubt she knew about Charli and me. Whether she approved was another matter.
I realized she was younger, but not by much. Just sixteen years. She was nineteen, and I was thirty-six. It was hardly cradle snatching. I saw our arrangement as a legitimate mentoring opportunity despite my burning desire for her. It was common in the BDSM world. Particularly in certain subsets. While we would do sexual things, it would all be for the greater purpose of nurturing Charli.
“Be gentle with her,” Elsa said as if reading my mind, “she’s delicate, and I don’t just mean her body. I think she led a very sheltered and protected life. From what I can gather, her parents were old fashioned and controlling.”
“Understood,” I said, a silent understanding passing between us.
Elsa finished the tie and lay her hand over my heart. It was her subtle way of giving me her blessing, something that was still important to me. Elsa had served as my conscience for longer than I remembered.
“The pandemic is getting worse,” Elsa said, returning to her desk, “it looks like there could be a state-wide lockdown soon.”
“Keep me posted,” I said, heading for Charli’s office.
I was all the way there before I realized I hadn’t brought her any food. My forgetfulness was funny. Until I’d met her, I’d never forgotten a single thing. If I didn’t know better, I would have said I was lovesick. Still, it wasn’t too bad. For every problem, there was a solution, as Elsa’s mom used to say.
“Sir.”
It was like the gentle coo of a dove. I turned to see the most beautiful girl in the world standing behind me.
“Charli,” I said with a nod.
“W-were you looking for me? Am I late?”
“No, no, of course not.”
It took a second for me to realize I’d reached out and placed a hand on her hip. Not that it mattered much. Other than Elsa, we were the only ones in the office. I could have put Charli over the desk and fucked her as long as we did it quietly. Still, discretion was the better part of valor and all.
“I thought we could go out for breakfast today,” I said.
Her doe eyes widened.
“Don’t you have work to do? A deadline to meet?”
“Yes, but I can do it at my own pace, and you as my assistant need to be with me. So that lets you off the hook.”
Her lips lifted into a wide grin.
“You’re the boss.”
I fought the urge to take her hand. It was much more vanilla than I was used to being. Charli affected me differently than most women. Not that I didn’t like them. I never fucked anyone I didn’t at least like. It was one of the few moral standards I had. However, there was a big difference between like and love. I felt weird, even thinking about it. My mom and Elsa were the only women I had ever loved, and that was vastly different. What I felt for Charli was practically a pain deep in my stomach. The feelings I had for her both thrilled and terrified me.
My brain barely noticed what my hand was doing as my fingers laced with Charli’s. She looked at me in surprise for a moment before smiling and squeezing my hand. I squeezed back, loving the warmth and the nearness of her.
I had found Lucia’s café a few years before. It was one of the few establishments that kept hours similar to mine, so I became a regular. The owner liked to joke I was the main person keeping her in business.
“Max, how ya doin’ dis fine day?” Lucia asked from behind the counter, her Italian accent coming through.
“Not so bad,” I said as I always did.
“The usual?”
“Yep, times two.”
“Ah, gotcha,” Lucia said with a wink.
It wasn’t the first occasion I’d brought a woman in, but it was the first time I’d done so at that hour and that I was holding hands with said woman.
“I’ve been thinking it over,” I said, putting my briefcase on the table and taking out a manilla file, “and I think I have everything all laid out.”
“You wrote up a contract?” Charli asked, taking the file from my hand.
“Non-binding,” I explained. “It just lays everything out, so you know what you are getting into.”
“Oh, okay.”
Charli flipped through the printed pages, nodding occasionally. Everything seemed fine. Right until she gasped.
“What?” I inquired.
The look on her face was a mixture of surprise and curiosity. “Is this true?”
“Is what true?”
Too shy to say it out loud, she turned the paper in my direction and pointed at the paragraph in question. “This.”
I skimmed eyes over the words that had embarrassed her so much. I smiled to myself. She wasn’t the first woman shocked about the size of my dick. “That’s true.”
“Wow. That’s big. And I’ve never even heard of half the stuff in here.”
“I wanted to go through all the options, but I don’t want to push you too far. That’s why we’re doing this now.”
“I want to! I mean—I just—wow. I didn’t even realize that some of the things were, you know, possible.”
“Possible and very fun,” I said with a wink.
Though she smiled, her eyes were wide and glassy, and her cheeks cherry red. She read on in silence, not objecting to anything.
She firmed her lips and nodded. “I’m in.”
I handed her a pen, and she signed next to where I had printed out her full name. Returning my pe
n and the contract, I signed too. We both signed a second copy, just so we both had one. Charli seemed even more relaxed, which was fair. The contracts were a form of protection.
“So, when do we start?” she asked.
“Right now,” I said, stowing my copy of the contract in my briefcase.
“Yes, master,” Charli whispered with conviction.
I reached across the table for her hand, but just as I was about to touch her, a sound cut through the cafe like an air raid siren. Everyone’s cell phone went off at once. It was a city-wide message.
We were going into lockdown. Everyone had twenty-four hours to get home, and until further notice, no one would be permitted to leave except for emergencies.
Chapter 7 - Charli
He was amazing. I felt so safe and protected by my master. People all around us freaked out, but Max kept calm. He called the office and told Elsa to get home before sending out a companywide email confirming that everyone could work remotely and that their jobs were safe. He then called for a car.
The biggest, fanciest vehicle I’d ever seen pulled up to the curb by the door of the café. It wasn’t a limo but as near as. There was even a driver in a uniform who opened the door for us.
I thought we would go straight to his place in Montauk. Max clarified that we would be doing the training there away from the city and the panic the lockdown had brought, but I was surprised when the car stopped in front of my building.
“Get anything you need,” he said. “You have one hour.”
That was way more time than I needed. I got a bag packed with essentials and was back in the car within twenty minutes—one of the few advantages of not owning much.
“Ready?”
“Yes, sir,” I said, as he’d instructed me to do when around others.
During the drive, he seemed to ignore me. I didn’t know if it was part of the training, or if he was just thinking. Either way, I remained silent and waited for him to speak first. It wasn’t long until I got used to the silence.
Closing my eyes, I listened to the hum of the engine as we sped out of the city, managing not to get stuck in traffic.