Chapter 6 – Chloe’s First Day of Work


Previous:  Chapter 5 – Violet Spiraling

If you would like a soundtrack to go along with this, check out my playlist on Spotify or YouTube. This chapter’s songs: “Perfect Day,” “Favorite Liar,” “Last Nite,” and “Seven Nation Army.”


The subway station was only a block from the apartment, nestled above a cafe where Izaak ordered us both a latte as he smiled at the barista he clearly knew. We climbed the stairs and found a red-headed woman sitting on a bench, arms folded. “How did you have time to get a coffee? I’ve been waiting forever!” Molly half-shrieked with a smile and bloodshot eyes.

“What? I’m on time!” Izaak said, showing her on his watch.

Her mouth dropped, and she glanced at her phone. “Holy shit you’re right. How am I early?” She giggled and peered at me. “You must be Chloe, I’ve heard so much about you! It’s nice to finally put a face with a name.”

I gave a shy smile and wave, remembering Toby’s comment about the spunky psychotherapist. It was obvious why Molly was the only one who could crack Izaak’s tough exterior:  she was like a cuddly teddy bear, permanent smile and gushing with genuine empathy. Her green eyes exposed a kind and gentle soul. No wonder Izaak wanted me to meet her.

“You look exhausted,” he commented rudely, but Molly didn’t mind.

She took a step forward with a nod as the train screeched to a halt in front of us. “Worried and high.”

He gave a mock-gasp and shook his head at her. “Isn’t it a little early to be high?”

I followed them inside the cart, taking a seat at the edge of the bench, Molly dropping to my side. She looked up at Izaak who towered over us, holding onto the bar above. “You ignored the worried part. Violet wasn’t home yet when I left… she was out all night again… she’s got my anxiety up because it’s like she’s a kid running to touch the hot stove even after I’ve warned her plenty of times.”

“But she’s not a child.”

She sighed and rolled her eyes. “I realize that. But she’s like a little sister to me. I’m worried she’ll take it too far and really hurt herself.” Glancing in my direction, Molly explained Violet’s situation until Izaak cut her off.

“Breakups are tough, but she can’t just stay stuck in her pain. She needs to get out and do something fun.”

“That’s what I said! But she took that as needing to go out drinking and getting fucked up.”

He shook his head. “No, she needs good, clean fun. Didn’t we say we would set up a paintball game? Let’s go next Sunday. Invite her along… it’ll do her good.”

Molly nodded, staring into space before agreeing verbally. “Yeah, and Toby could come, too.”

“And Chloe will be there,” Izaak added. They both looked at me grinning.

“Perfect! Cross your fingers that it’ll work for Violet!”

Molly babbled on for a while about other things, and Izaak easily engaged. The two of them had a peppy and optimistic rhythm to their conversation, purely platonic but flirtatious, often engaging in subtle comments related to the spanking lifestyle. At one point Izaak told her in code about disciplining me earlier that day, which caused my face to turn beet red. She playfully smacked him for teasing me, to which he warned her to be careful, or she’d be next.

“My stop is coming up,” Izaak said, pulling out a thick black credit card from his wallet. He placed it in my hand and looked me in the eyes seriously, then to Molly. “I trust you to give her a limit if needed. And Chloe, I trust you not to exceed a reasonable limit, or you know what will happen.”

“Don’t worry,” I said as I snatched the card away and hid it inside my bag.

“Remember, I know where you live.” He smiled and squeezed my shoulder. “Good luck today.” Then gave Molly a fist bump and said, “Thanks for your help.” And he disappeared into the crowd, out of the train.


Ninety minutes, five shopping bags, two mani/pedis, and a cigarette later, Molly and I walked to my new office building.  It stood at least 80 stories high, a modern superstructure with sharp edges and mirrored windows. There was a security guard downstairs who had to call my future boss to let us through to the elevators, though with my sexy business outfit, I could’ve probably convinced him using only my good looks.

We rode to the 46th floor, then stepped into a bright white office area. Three receptionists sat at the end of the hall under gold letters than read Cain, Hamilton, & Specter. One of them nodded at Molly for us to pass and I followed my new friend through the maze of cubicles, hypnotized by the skyline and chic decor. Everything was much posher than I’d imagined, which just made me more excited.  The environment reminded me of old schemes, attending parties with rich dates and pretending I belonged. I can do this!

The desk outside Mr. Gabriel Specter’s door was abandoned, phone light flashing due to unheard messages. Papers and folders had piled up on the corner of the desk, sticky notes strewn about.  “You’ve arrived just in time.” I looked up to see a man with slicked-back sandy brown hair, dressed in a pressed gray suit and tie, shiny shoes. He stepped to the side, inviting us in. Molly nodded for me to go ahead so I did awkwardly, waiting for him to show me where to sit. “You haven’t introduced yourself,” he admonished after closing the door behind us. Molly hadn’t followed me.

“Chloe Patterson.” I thrust my hand out to shake his, nice and firm like they teach in etiquette class.

His shake was also firm, hand warm and strong. His hazel eyes scanned me, trying to figure out if I was trustworthy. “You can call me Gabe. Have a seat.”

I did as told, finding the cushioned blue chair very comfortable, despite my nervousness.

Sitting behind his large desk, Gabe sat up straight and cleared his throat.  “Why should I hire you?” His expression was strict and serious, an attempt to intimidate me.

“Well, it looks like you’re too busy to find anyone else, so I think it’s me or keep that pile of work on the desk out there.”

He smirked, approving of my answer. “Do you even have any experience in this field?”

“I have experience in management, I think I can handle a little secretarial work.”

“This is a fast-paced environment, a lot of detail-oriented work, and I don’t have time to train you. But I provide adequate compensation.” He printed out a page and shoved the paper towards me, showing a generous salary that was quadruple what I’d made at my previous restaurant job.  Wow!  “You’ll start off-the-books as a contractor.  If after a month we mutually agree this is the job for you, I’ll hire you full time.”

Trying to keep the enthusiasm out of my voice, I said, “I’ll take it.”

“Molly said you can start now, so go ahead. Get to it.” He dismissed me and I stood, taking a deep breath as I stalked to the cluttered desk outside his office.

Throwing myself into work was easy, and actually felt good.  For the first time in months, I didn’t feel haunted by memories of my past.  I stayed focused on the tasks at hand, organizing my workplace, filing away paperwork from weeks ago, and returning phone calls to set up appointments on Gabe’s calendar.  If I was unsure about something, I always sweet-talked my way to a person who could help me.  

As promised, my new boss didn’t micromanage me, out of the office much of the day and leaving me to my own devices until evening.  It was nearing sunset when the phone intercom buzzed and he called me into his office. 

“Set up a meeting with Bill Winters ASAP, and you screwed up the calendar — the deposition is supposed to be before the hearing next Tuesday… Are you even listening to me?” He snapped his fingers angrily.

“Sorry, I forgot to bring a notebook to write…”

“Then what are you waiting for? Go get it!”

I scampered away and took a deep breath. That name had sent a sharp shiver down my spine: Bill Winters. What are the chances, though? There must be plenty of wealthy New York businessmen with that name.

Gabe cleared his throat loudly, signaling that I should hurry, so I grabbed my notebook and came back, writing as I walked. He pointed out more errors that I’d made with the schedule and followed up about assignments that’d been left on the desk, until finally, I gave him a pathetic look, wishing to die.

“Be here tomorrow morning at eight o’clock sharp. Early is on time, and on time is late. Remember that.” He stood suddenly and gave me another handshake. “Good job today.”

Smiling at the sincerity in his voice, I managed to squeak, “see you tomorrow,” and hurried out of there.

Day one of work was over and suddenly every ounce of me swam in trepidation.  I bummed a cigarette from a stranger, my second of the day, as I walked through the crowded, trash-littered streets.  What if Bill Winters is the same guy? 

A fleeting thought about my old partner in crime, Sage, came as I found the subway station, stepping out my half-smoked cigarette and descending into the murky underworld. Both of us had agreed that it was for our own good to stay out of touch while she was on house arrest, but I couldn’t get rid of the guilt that came with letting her take the fall unless I knew she was okay.

Before my thoughts turned into a panic attack, I plugged my ears with music and breathed in the musty air, shutting my eyes for a moment. I’m a new person now, I’m Chloe Patterson.  And I’m great at faking it til I make it and not getting caught.  I can do this.


The aroma of spice and onion filled the living room and my stomach growled when I entered. Music blared from the stereo, classic rock, and Izaak sang and danced along, not realizing that I’d come in until the door slammed behind me.

“Oh, hey kiddo, how was your first day?” He reached to turn down the volume, then returned to stirring something in the pan.

Tossing my bag into my half of the room, I heaved a sigh and plopped down at the kitchen table. “I’m not cut out for this type of work,” I grumbled.  My mood had taken a turn for the worst during the commute home, exhaustion and hunger causing me to regress to the mindset of a sulky nine-year-old.

“It’s only the first day, how can you say that?”

“Really, Izaak? I’m an artist, not an office person.”

“You’re adaptable. Just do this to work your way through college. Look,” he grabbed a couple of brochures and handed them to me, “I picked up these applications.”

“This is all virtual now, ya know.” But I appreciated the sentiment. “My own family didn’t even help me with the college stuff.”

“And because of that, you’re stronger. And yes, I realize it’s virtual now but we have tons of those lying around at the office.” He turned back to the stove, and I glanced down at the papers. Somehow I doubted he just stumbled upon them at work. They were from art schools, Pratt Institute and the School of Visual Arts. Wow, he really thinks highly of my artistic ability. “Did you smoke today?”

Clearly his expectation of my ability to quit smoking was lower. I glanced up at him and shrugged. “You can’t expect me to work in a law office and not plead the fifth right now.”

“We’re not in court, the fifth doesn’t work with me.” He took a taste of the food, then turned off the burner and came to the table, wooden spoon still in hand. “I guess a more appropriate question would be, how much did you smoke today?”

I felt intimidated, seeing how tall he stood over me with his serious face. Gulping, I whined, “Why does this have to be part of the deal?”

He shook his head, breaking eye contact to reach for two bowls out of the cabinet. Without a word, he filled them with a red, eggy substance, placing the bowl in front of me as if I were a child.  Ew. It didn’t look as appetizing as greasy takeout.

“It’s shakshuka, a traditional Egyptian meal. After my parents died and I moved to Holland, my aunt made this to give me a little taste of home.”  He peered at me now to notice my scrunched up nose. “You’ll eat every bite, or you know what will happen,” he threatened in a low voice.

My heart thumped as I thought, he wouldn’t! But I knew he would. Or would he? Instead of pondering the question, I stood and reached inside the fridge for a beer, only for him to almost close it on my hand.

“Water or juice only for dinner.”

“Seriously?? Izaak, come on, I don’t need you treating me like a kid.”

“I will not keep reminding you of the thirty days we’re doing this.” His tone was kind yet firm, and he gently pushed me back into my seat. With the expression of a stern big brother, he withdrew two pitchers: water or grapefruit juice.

“Twenty-nine days now,” I huffed, confused and irritated. I’d never been in this kind of predicament… people always gave in to my demands, even as a child. But Izaak was playing the strict guardian role, unfazed by my big adorable puppy eyes. “This isn’t fair!” I whined, settling on water.

His expression softened when he sat beside me, pouring our drinks and complimenting my new clothes.   “It seems you and Molly hit it off. She’s happy to have you as part of our ‘spanko family’ as she calls it.”  

“She’s cool… I like her vibe.”  I took a bite of my food, humming with satisfaction as I remembered Toby the psychiatrist again, his smirk and cocky attraction to me.  “You have a lot of friends in the lifestyle.”  

“Most of it is thanks to Molly… She introduced me to everyone, though I met her through Violet.  Sometimes we have social events: we meet at Molly’s apartment and administer spankings in ‘public’.”  He paused to study my body language before asking, “what do you think about that?”

With a shrug and nervous gulp of water, I said, “I’m down.  Could be fun.”

We continued the conversation, discussing my new job and his day at work.  The food was tasty and Izaak’s humor had me back to a good mood in no time, all thoughts of Bill Winters and cigarettes far from my mind.  But when we finished the meal and I began washing the dishes, Izaak interrupted me with the dreadful words: “We still need to have a discussion.”

“What do you mean?” I asked, shifting from one foot to the other and chewing on my lower lip, feeling myself regress again.

He waited till I finished then led me to the couch and sat down, pulling me to sit on his lap. I blushed profusely, wanting to squirm away, but he held me in place. Looking into my eyes he asked, “Why does quitting smoking have to be part of the deal?”

I searched for the answer in his face, any clue about what he wanted to hear, finding it a little too easy. “Because we’re doing things your way for a month so you can ‘help me’.”

“Why else?”

Glancing at the ceiling in annoyance, I muttered, “because smoking is dangerous and causes cancer and yada yada.”

“Exactly. It’s addictive and harmful. I’m not trying to make too many big changes at once…”

My snort cut him off. “Sure could’ve fooled me.”

“Not smoking is important, #1 bad habit to change. #2 is your circadian rhythm… you need to sleep at night and be awake during the day. Having your job will help with this.”

“Ugh, I hate my job, can I change that?”

“If you find another job, sure. But be practical. It’s good money and also prestigious. It will be beneficial for you, especially if you want to aim high and achieve your dreams.”

My shoulders slumped, a little sad at the reality.

“And it’s never easy to make money unless you’re doing something illegal, which I don’t think I have to remind you, isn’t worth the risk.”

I glanced up at him to see if there was any trace of him knowing my past, but it didn’t seem to be there. It was just typical concerned Izaak, looking out for me. “I’m not stupid enough to take that risk.”

“How many cigarettes did you smoke today?”

“Two,” I admitted.

His eyebrows raised in surprise, not doubting the sincerity of my answer for a second. “Is there anything else you need a spanking for tonight?”

“Of course not!”

“Are you sure about that?” I nodded. “What was the penalty we agreed on for smoking?”

With a grumble, I said, “Ten swats with the hairbrush for each cigarette.”

“Get ready for bed, then we’ll address it.”

I nervously changed into a pair of thin cartoon pajama shorts with a black tank top, then scurried to the bathroom to brush my teeth, taking my time. When I emerged almost ten minutes later, Izaak sat on the sofa, waiting patiently.

“C’mon kiddo, let’s get this over with.” He patted his lap, somehow convinced that I’d come to him on my own. My legs stood frozen in place, and I considered ways to talk him out of it.

“I only had two cigarettes today though, and it was such a stressful day… I really wanted more! You should be proud of me for not smoking like… ten of them.”

“I am proud of you, but you’re not getting out of this, kiddo.”

Taking a mini step forward, my eyes teared up, and I pleaded even more. “Tomorrow I won’t smoke at all.”

“Let’s hope not. Now get over here.”

When I didn’t move, he reached for my wrist and pulled me towards him. I dared glance into his eyes to see a no-nonsense glare, right before I fell over his lap. Without another word he swiped down my shorts and panties, not giving me enough time to process everything before tapping the plastic paddle brush against my bare bum.

The first five swats landed on my right butt cheek, not as painful as I’d imagined, but prompting a squeal. Izaak delivered the next five to my left cheek at the same intensity.

“Owwwie!” I squawked, kicking a little and reaching my hand back to block.

“Is there anything else you need to tell me? Last chance.”

I glanced over my shoulder at him and shook my head. “Noooo! I’m a good girl.”

“Uh-huh. So we’re halfway done. Move your hand.”

Instead of obeying, my eyes welled up with tears and I pouted, trying to guilt him into ending the punishment. It didn’t work. He seized my hand in his, restraining it against the small of my back, and lifted the brush again. Biting my lower lip, I braced myself for the next ten smacks that came hard and fast, alternating between sit spots.

“The agreement is ten swats per cigarette, and that will not change, kiddo. Do you understand?”

“Yes, sir,” I cried.

He set down the brush and replaced my clothes, standing me in front of him. My hands flew to my bottom, rubbing furiously to ease the subtle pain as I watched Izaak. His eyebrow was cocked but eyes sparkled with content. I put on my most pathetic face to make him feel sorry for me and he softened a bit, smiling and pulling me forward in a hug, and finally to sit on his lap. “You take advantage of being cute too much.”

With a giggle, I claimed, “I can’t help it!”

His head shook. “Bedtime in one hour, kiddo. TV until then?”

My eyes brightened and mouth dropped in exaggerated, sincere excitement. Mindless family sitcoms helped us both cope, and cuddles are always nice. “With popcorn and beer?”

“Don’t push it,” Izaak said, face turning semi-serious again.

“Just kidding!” I snuggled up, settling into his lap and sighing happily. For a moment my cheeks flushed with gratitude, thoughts of work problems evaporated from consciousness. Izaak actually cared about me, wanted to help me make something of myself. It was my ticket out of the past, and so far it was working. I had a great job, new friends, and had only smoked two cigarettes in the whole day.  Even if the worst-case scenario happened, he’d help me.


We fell into our new routine:  Running each morning at sunrise with Toby and others, back-to-back showers, silent commutes together to work, then meeting again in the evening for dinner and discussion of our day.  My smoking ceased after a while, but often we found some little infraction for him to spank me over. Then we cuddled and watched tv until it was “bedtime” and Izaak tucked me in with a kiss on the forehead.  

It was overwhelming to live the “little” fantasy that I’d idealized in my mind for so long.  Almost too good to be true. I’d always wanted a guardian who would lead by example and enforce healthy habits.  Izaak easily slipped into that role for me. Staying on the straight and narrow was boring but so far had kept me out of trouble.  Just a tiny part of me was starting to feel rebellious, ready to be on my own again.

Work became monotonous.  Gabe was strict but fair.  I got used to being yelled at (because I really wasn’t that great at my job) and he gave me credit when it was due.  At least my past work in the service industry taught me how to keep my boss pleased. I dressed as sexy as our formal office environment allowed, brought him coffee when he needed, sweet-talked to angry clients until they calmed down, and weaseled our way into important events.  I’m sure that’s the only reason he didn’t fire me from the beginning.

As my first full week at work ended, I focused once again on my new social life.  Friends: something I didn’t have much of in Michigan. Now I chatted with Molly frequently throughout the day, and jogged next to Toby every morning making small talk.  Vanessa and I didn’t vibe well, but I considered her an acquaintance. And Izaak was the mentor I never thought I’d have. The “spanko family” as Molly called it. A piece of me worried of disappointing them, but the rest of my puzzle felt secure, comfortable, complete.

My life as Chloe Patterson in New York City will work out.  I can feel it!


All likes. ratings and comments are greatly appreciated! 🙂


Continue Reading:
Chapter 7 – Violet Meets Chloe 

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