Chapter 2 – Chloe: Izaak’s New Roommate


Previous:  Chapter 1 – Violet’s Chaotic Relationship

Here’s the original version if you’d prefer 🙂  If you would like a soundtrack to go along with this, check out my playlist on Spotify or YouTube. This chapter’s songs: “Troublemaker,” “Sweet Disaster,” “Trouble,” “Judgment Day,” and “The Darker the Weather.”


“You scared the shit out of me!” I gasped at the tall, muscular figure as I climbed in from the fire escape, putting a hand over my chest and taking a deep breath. “How long have you been home?”

“Long enough to know what you were doing.” Izaak folded his arms, dark eyes icy in a mixture of disappointment and anger. “You didn’t tell me you started smoking.”

Tossing the half-empty pack of cigarettes onto my bed, which was just a futon in the corner of his living room blocked off by a couple of tall privacy screens, I shrugged him off and started walking towards the kitchen, but he blocked my path. Scowling, I looked up at him. “Am I supposed to confess all of my bad habits to you?”

He didn’t answer, instead trying to read me and figure out his next move. This had become a pattern recently… Any time I let him down these last couple of weeks we’d have a similar confrontation, neither of us comfortable with fully expressing our emotions yet, just trying to find our balance and figure out if being roomies would work.

“Chloe,” he said finally, “sit down. Let’s talk.”

Izaak’s tone sent a chill down my spine, giving me a flashback of six years before, sobbing over his lap with a blistered backside. My heart thumped wildly at the memory of my first punishment, and butterflies began fluttering in my stomach, throat drying up. I pushed the thoughts away, composing myself as I followed him to the sofa, only making eye contact after we sat.

“You dealt with a lot these last years, and I know it will take time to rebuild our friendship after not seeing each other for so long. So I’ve been talking with a friend of mine… a psychotherapist… you would probably like her…” He paused to gauge my reaction, and I tried to keep my facial expressions in check so he wouldn’t be able to read me.

“Why do you think I’d like her?” My pathetic attempt to control the conversation. Talking about the past was not on my agenda. So much to say, yet so little he needed to know.

He sighed, undoubtedly making a mental note of my defenses, then half-smiled. “You both ask a lot of questions,” he said with a sincere chuckle. “I see what you’re trying to do, kiddo, and it won’t work.” But it did. He stopped beating around the bush and moved towards the point: “You’ve been here a month, what’s your plan going forward?”

His honesty helped ease my nerves, and I let a slight smile emerge. “We’ve had this conversation before. I don’t plan.”

“Well then please tell me, what spontaneous act will happen in your life next?”

“You realize that the point of spontaneity is not knowing what will happen, nor when, right?”

He sighed. “Chloe, it’s time to establish…”

“Where does your psychologist friend come in?”

Being cut off mid-sentence caused Izaak’s brow to furrow, and his eyes to change from icy-cold to watery-rage. But instead of entertaining my insolence, he completed his sentence: “… some ground rules.”

“What? Ground rules? What does that even mean?”

“Stop interrupting me,” he snapped in such a sharp tone that it caused me to jump a little in surprise. His no-nonsense glare made me think again of that first spanking.

“It’s no big deal, I’ll make sure we get a good grade,” I’d said with a flirtatious giggle and carefree shrug. I was only 19, used to doing the bare minimum in school and still getting good grades thanks to my charm.

Izaak’s lips pursed and arms folded in annoyance. “Then why bother coming over today?”

A blush spread across my cheeks and I bit my lower lip, not wanting to admit that it was because I had a crush on him. “I promised I’d show up, and I don’t break promises.”

“You also promised to get your work done, what about that?”

My head shook. “I never said that. I said I promise that the work will get done so we get a good grade.”

“How is that different?” His nostrils flared, speaking before I could respond. “You know what you need? A good spanking.”

A nervous giggle came out, much to both of our disapproval. Then without thinking, I said, “I dare you.”

And that’s when he took my upper arm in hand and half-dragged me to the sofa, sitting and pulling me over his lap. I panicked, half-struggling to break free. “Wait, I was joking…!”

“I wasn’t,” he responded in a bored tone, beginning to rain down swats over my thin yoga pants. They were stingy and quick, causing me to squirm. “You’re going to act like a child, I’ll treat you like one.” His hand was so large that it covered almost my entire bottom at once, and within seconds I was kicking and crying out, now feeling like a kid.

“Okay, okayyyy!” I pleaded. “You can stop now!”

But he ignored my cries, and the swats became more intense. “It’s time someone teaches you a lesson about responsibility.”

“The reason I mentioned my psychologist friend is because I want you to meet her,” Izaak said, snapping me back into the present moment.

“Talking to a shrink and having another person analyze and judge me? As if you being an FBI agent isn’t enough already? No, thank you.” My voice dripped with annoyance, though my palms were sweaty and I was ready to run. All this drama for a stupid cigarette?

“She won’t judge you… much.”

“Uh-huh… sure she won’t. It’s not like that’s her job.”

“I’m not trying to convince you to be her patient. I think you would benefit from having someone to talk to and help you deal with this… transition. And she has good job connections.”

“I don’t need help.” My arms folded in a pouty huff, and I glanced up at him to see what he would do about it.

He frowned. “We’ll see about that.” Breaking eye contact for the first time, Izaak cleared his throat. Whatever he was about to say seemed to make him uncomfortable, though he excelled at hiding it. “I’ve noticed that discipline and positive motivation have been lacking in your life for some time.” He chose his words with caution, careful not to offend. “And I think it would be valuable for someone trustworthy to guide you towards a healthier lifestyle, even if it requires you hate the person sometimes.”

My blood started pumping and body trembled. I could guess where he was going with this, and not sure if I was more excited or scared.

“When there was structure in your life, you thrived. You had dreams and were motivated to achieve them. Remember, you were so determined to go to art school?”

Of course I remembered, and I still kinda had that dream, but so much had happened in the years that Izaak and I hadn’t seen each other. Now it made more sense to stay off the grid. “I was never good enough. And art school takes too much time and energy.”

“It’s been hard for you dropping out of university and taking care of your grandmother… And with absent parents… Life and people have let you down again and again, and you’ve lost hope. But now there’s a light at the end of the tunnel… You have endless possibilities and opportunities in New York City. You can accomplish anything!” His face lit up as he spoke, smiling inside. But then he became serious again, leaning in towards me and giving a stern, matter-of-fact look. “Chloe, don’t mess this up.”

I knew Izaak was making me feel a certain way on purpose because his job is basically manipulating people to get what he wants. But I wasn’t one of his FBI cases. I wasn’t just some dumb criminal for him to play with my feelings. He wouldn’t control me that easily, so I told him just that.

“I realize you aren’t one of my cases. You’re my friend, and I care about you.” He kept an even tone, suggesting that he had expected my minor outburst. “I see so much potential not being used while you’re lying around all day, apparently smoking cigarettes and who knows what else.”

“Where are you going with this?” I snapped, rolling my eyes. “Just spit it out already!”

“You won’t tell me details of what’s happened with you these last few years, and I’m giving you space to tell me on your own instead of pushing you to confess everything. But you’ve lied to me about more than smoking—don’t look so surprised, as you said, it’s my job to read people. For example, have you applied to one single job since you’ve been here?”

I looked away in shame, wondering what else he suspected.

“Certainly you haven’t, but you’ve made me believe otherwise. Am I happy you’re smoking and slacking off? Of course not, but it bothers me more when you blatantly lie to my face.”

Still staring at the floor, tears formed in my eyes. I wasn’t sure how to answer him.

“You like to push my buttons and see how far you get before I react.”

“That’s not true,” I argued, wanting to say more, but Izaak interrupted me this time.

“And I think you need a hard, bare bottom spanking.”

“W-What?! N-no!” I’d tried to shout my answer in anger, but it came out hoarse, nervous, afraid.

“I would also like to propose that we make a plan to change your lifestyle. It’s possible to drop unhealthy habits by enforcing a system of rewards and consequences. My gut is sometimes wrong, but I sense that you’ve been pushing buttons for years, crossing lines to see what you can get away with, and instead of being challenged, people have given in to your big blue eyes and pouty lips.” He stood now, all six feet five inches looming over me. “You’ve wanted someone who will fight back, establish boundaries and not take any of your bullshit.”

He left me speechless, ashamed to admit that he was spot-on… nobody had ever read me so clearly. That’s part of the reason I’d come to New York, anyway. Maybe with Izaak’s guidance, I could stay out of trouble.

Millions of thoughts raced through my head as my roommate went to the kitchen to retrieve a straight-backed wooden chair. He placed it in the middle of the living room and came towards me, taking hold of my wrist and helping me to my feet.

“It’s clear you’re running away from something, trying to start a new life. If you truly want that, I can help.”

I’d been waiting for a spanking since moving in with him a month ago, but now a surge of anxiety washed over me, causing me to sink into an awkward silence and become hyper-aware of my senses. Izaak’s bronze-colored fingers were warm and sticky clasped around my wrist, and I breathed in the earthy scent of his cologne. In the distance, the clock’s ticking made the hairs on the back of my neck stand up and my heart pump at full force.

I looked up and studied my friend. His red tie was slightly loosened, shirtsleeves rolled up to his elbows and exposing his strong forearms. His thick black hair had a light layer of gel holding it in place and beard was neatly trimmed. It took a few deep breaths before I mustered the courage to look into his eyes, immediately noticing a hint of vulnerability. He’s as nervous as I am.

I gave a slight nod as if probing him to continue. The insecurity that had been present quickly faded, and now his dominance took over.

Izaak sat in the chair and grabbed the belt loop of my jeans, pulling me towards him. “Young Lady,” he said in a low and stern voice, “I don’t know how long it’s been since someone gave you a good spanking, but I can guarantee that it’s been too long.”

He tugged at my pants, then I heard my zipper opening. Izaak’s fingertips brushed against my belly as he moved my shirt away and pushed my pants and panties to the floor, leaving me vulnerable. I started panicking inside, screaming at myself to do something to make this stop, but then I heard: “Quitting smoking will be tough, and I intend to be with you every step of the way to help in your moments of weakness.” A gentle breeze caressed my thighs and goosebumps formed on my arms. “Moving forward, you will be spanked any time you smoke, do you understand? Ten swats with the hairbrush for each cigarette.”

I shrugged.

Without missing a beat, Izaak slapped my left butt cheek, and hard. I hadn’t been expecting that! “Owww! What was that for?” I whined, reaching back to rub the sting away. He gave me a look, so I allowed myself to submit enough to say, “I meant, ‘yes Sir, I understand’.”

He gave a half-smile, happy that I was willing to join his spanko game and play the submissive role.

Izaak’s fingers enclosed around my wrist again, and he jerked me forward to lie across his lap. I wiggled myself into a moderately comfortable position, his warm hand resting on my cool naked bottom. Izaak’s legs felt calm and confident underneath me, unlike my own body that quivered with fear. The dry taste of nervousness in my mouth mixed with the disgusting flavor of Marlboro Lights as I listened to our next-door neighbor’s laughter, idly worried about how much they’d hear of my punishment.

“As I was saying earlier,” Izaak began, circling my waist with his left arm and tensing up as if he were getting ready to deliver the first swat, “your routine is about to change. No more staying up all night, no more sleeping until late afternoon. The first step towards a better life is taking care of your physical health. We will structure your days to include healthy meals, exercise, and a good night’s sleep.”

Grrr… He’d waited until I was over his lap to tell me all of that because he’d suspected my resistance. “Wait, what? Don’t I get a say in this?!” I asked, looking back angrily, not able to move as freely as I would have liked.

“Not until we’ve established good habits, which will take about a month, the same time I’ve given you to do this alone. Since you have made no progress doing things your way, we’ll try mine.”

“What if it doesn’t work?” I asked weakly, wondering if it was too late to run away.

“Then we will have another discussion to figure out what will.” With that, he tightened his grip on me and landed the first sharp smack to my bare bottom. It didn’t take me entirely by surprise, hurting about as much as expected, though my tolerance was higher than I’d given myself credit for. Maybe it won’t be too bad.

Izaak followed up with another slow, precise swat, so hard that my bottom jiggled afterward. I blushed profusely at that thought when he landed the next, beginning to develop a rhythm. My goal was to take the punishment with little noise, but as his pace quickened, it became more challenging to stay quiet.

“I didn’t think I’d need to punish you like this again,” Izaak commented, delivering an especially hard swat to my right sit spot, then another to my left.

“Me either,” I lied, biting on my hand to keep myself from shouting out in pain.

“I’m going easy on you today since it’s only the second time I’ve spanked you.”

I was fearfully excited at the prospect of knowing what a “real” spanking would be like if this was going easy on me! He was doing such a thorough job, covering every inch of my bottom. It was tingling and stinging all over, and each spank made the pain more intense.

“And in the future,” he said, increasing the intensity of his smacks, finally causing a whine to escape my lips, “I expect you to be more honest with me.”

I groaned in response, not totally sure that I was on board with his expectations, but not wanting to argue given my current position.

He must have suspected my noncompliance because he increased the speed and intensity of the swats, so much that I was squirming and whining even more. “After this punishment, you’ll have a clean slate. Now is a good time if there is anything else to get off your chest.”

The spanking stopped for a second and Izaak rested his hand on my warm bottom before pulling my chin so I’d look into his eyes. He was silent for a moment, only studying my face, checking for any clue that I had more to hide.

“Let go, kiddo. Let go of your past and the guilt, cry it out.”

“I can’t,” I whispered.

He helped me up and my hands flew to my bottom to rub out the sting, but instead of letting me, Izaak held onto my upper arm while walking me to the couch, delivering a smack with each step. “I see that I’ve been too nice.” He let go of my arm and I looked up, noticing that his icy glare had come back. “Bend over,” he said, pointing to the armrest on the sofa. His cold words pierced something inside of me… maybe it was my submissive side. I obediently bent over, raising my bottom high into the air, and turning my head so I could see as he unbuckled his belt. It was black leather, thick and wide, the kind of belt that’s associated with a “good butt-whuppin’.”

“Is there anything else you need to tell me?” He folded the belt over once and held it casually to his side, waiting for my response.

“No, Sir.”

He nodded, seeming to believe me. “This will not be over until you’re able to let everything go, or at least some of it.” Then he raised the leather and crashed it down onto the center of my bottom.

“Owwwww!” I cried. Earlier, the spanking had hurt about as much as I’d expected, but now it was much worse! And to top it off, Izaak didn’t give me much recovery time before delivering the second lash, and then the third. “Ohhh Izaak, please!” I begged, now feeling his disappointment loud and clear.

He was satisfied with my cries, convinced he was getting through to me. Now I was getting proper discipline rather than just a slap on the wrist.

“Okay, okay,” I howled, now trying to squirm my way off the couch. Izaak’s hand pressed against my back, gently pushing me back down as he delivered a deafening lash across my bottom. “Owwwwww, I’m getting the message!” I told him. But now he’d realized that to get his message across, actions were more important than words, so he remained silent. “Izaaaaaak!” I howled, now burying my face into my hands and letting the first real tears slide down my cheeks. “It hurts too muchhhh,” I said, kicking up my right foot, only to have it pushed back down before another lash.

“Be still,” he commanded.

His firm, yet calm voice mesmerized me.

“Put both feet flat onto the floor and stick your bottom out. And do NOT make me tell you again.”

“But Izaak,” I cried, now letting the tears flow more freely. I was almost ready to let him win.

I locked my feet into place and stuck my throbbing, red bottom into the air as if I was asking for more punishment. “These last ten will be hard and fast. If you get out of position, we will start over again. Do you understand?”

“Yes, Sir,” I said, squeezing my hands together and clenching my butt cheeks. I heard the jingle of the belt buckle, then the loud cracking sound of the leather meeting my flesh. The stinging sensation spread through me, and I cried out just in time to receive the second one, inches below the first. I recited to myself each of the lashes, only losing count when struck on my sit spots. That was when my tense body relaxed and I collapsed into the couch, crying softly. I was finished resisting and now only focused on my tears and physical pain.

Izaak finished up the swats and stood behind me, allowing me to cry. I could feel the heat radiating from my bottom, and even through my tears of embarrassment and shame, I wondered what it looked like. Was it cherry-red? Were there stripes from the belt?

The floor creaked as Izaak walked towards me, stooping down to my level and moving my hair out of the way until he could find my face. I looked up, eyes red and puffy, the tears still coming. I was sniffling and hiccupping and confused.

“Nothing else you need to tell me?” he asked again, with tired and friendly eyes.

“No, Sir,” I answered as he scooped me onto his lap with a bear hug. My face pressed into his chest, thoughts racing about everything I wished I could say.

But I couldn’t, not with him being an FBI agent. Because once you confess, there’s no taking it back.


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Continue Reading:
Chapter 3 – Violet’s Defeat

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