Penny the Pain Slut Pt. 03

Penelope

Sebastian and I laid there for a little while in post orgasm bliss before he said he wanted some coffee.

"At your service Master," I said as I peeled off him. He groaned and watched me with sharp eyes.

"Do you have any costumes?"

I turned around in the space between my doorway and the bed, blinking at him.

"Costumes? Like for halloween?"

"Yes, any sexy maids, sexy nurses, sexy..."

"Oh," he was making me blush.

"Well?" Sebastian raised a brow at me. I motioned for him to follow me into my closet. All I had was an old waitress uniform I had worn when I was 20, but since then my tits and hips had grown. I don't know what made me admit to this as I could have just said no I have nothing of the sort and moved on with my life.

Instead, I held up the tiny skirt and too small blouse.

"Where did you used to wear that?" Sebastian smirked.

"I was a waitress through college," I explained.

He nodded and motioned for me to try it on. Once again I felt exposed in front of Sebastian. He was expecting me to get changed right in front of him.

"What're you waiting for?" He asked as I hesitated.

"Turn around," I replied.

Sebastian laughed but did as he was told. I began to strip with his back turned. "You know you're being so ridiculous," he chuckled.

"I'm not," I said, pulling the skirt up and onto my body.

"How's this too intimate but being a perverse little slut and touching yourself isn't?" He teased me.

"Sebastian," I snapped at him.

He laughed harder. I was turning beet red. I rushed through putting the blouse on.

"Watch your tone, slut," he snapped back.

I was dressed then. The skirt was just below my ass, tight and black, a stretchy material. The blouse buttons were almost popping over my tits so I unbuttoned them, showing ample cleavage. I wasn't even that busty I was just a late bloomer, and the blouse was tight back then let alone now.

"You can turn around, Sir," I said in a soft tone.

Sebastian turned and when his eyes landed on my body they almost fell from his head. I covered my mouth with my hand, almost as if I didn't want him to see my smile. His eyes met mine.

"I think I'll enjoy ordering you around in this. Do you have an apron?" He asked.

"I have a little white one," I said. "It's in the kitchen."

I began to walk and Sebastian followed me. We walked down the short hallway of my bedroom and into the living and kitchen area of my apartment. It was an open plan.

I stepped into the kitchen and opened the drawer where my tea towels and apron were. I pulled it out and fastened it around me, making it tight on my waist.

"Why don't you make me coffee and some breakfast while I sit and admire you? Okay slut?" Sebastian ordered.

I spun on my heel to see him sitting at my breakfast bar staring at me.

"Is this going to be part of our dynamic? Me doing all the housework and cooking?" I asked, a small frown threatened to escape.

"No, I'll only make you do these things for my pleasure. Make you do the laundry naked then fuck you over the machine. I'll dress you up like a French maid and make you dust my office while I work and suck my cock when I need a break," he said.

I realised then the game he wanted to play. It turned me on to be ordered around but I was worried of being taken advantage of. So, this suited me just fine.

"So this is all part of the game?"

For a moment I wasn't sure if Sebastian caught my meaning but then he nodded. "Yes."

I walked over to the other side of the breakfast bar and bent down so my tits dropped. I was giving Sebastian a show. "Well then, how would you like your coffee Master?" I batted my lashes.

"Do you have an espresso machine, honey?"

"I do, one of the pod ones."

"Could you make me a latte?"

"I can-- and if I do a bad job?" I chewed on my lip.

"I'll have to teach you how to make a good coffee before I take you over my knee and teach you what happens when I am displeased with your service," he replied.

I nodded and spun on my heel. I got to work making Sebastian and myself coffees. I made his first then my own before picking his up and walking it to the breakfast bar, presenting it to him.

"Here is your coffee Master," I said.

Sebastian took a sip and then nodded. "I won't beat you today."

"Thank you Master," I replied. "Can I drink my coffee now?"

"Yes slut. Go get your coffee."

I turned and went to grab my coffee before returning with it. I sat on the stool next to Sebastian. I took a few sips and we sat in silence for a little while.

"What did you want to do today, Master?" I asked.

"I want to see how far I can push my dirty little slut," he replied. A zap of arousal hit my pussy. I was all tingly, ready for whatever Sebastian had planned for me.

***

We finished our coffee and Sebastian turned to me. He watched me the way a predator watches its prey. His hand found a tendril of my hair, tugging at it, hurting me.

"Do you have any toys in the house?" he asked.

"Like what," I replied.

I knew what he meant, but I wanted to hear him say it.

"Do you have a riding crop or a cane, slut," Sebastian asked. Even when he degraded me like that he had an edge to his voice that made me know he didn't mean it in a bad way. On the contrary he was almost praising me through degradation.

"I have a riding crop," I said. I hadn't actually bought it to play with. Especially considering I had no one to hit me. But I had bought some lingerie and it came with it as a free gift. At the time the shop assistant thought it was hilarious that they were giving those out. As I put it in my bag, I wondered if I would ever be able to use it.

"Go get it," Sebastian told me.

I stood up off my stool and scurried back to my bedroom. In my closet I began rifling through my lingerie drawer. I found the riding crop right at the back. I don't know why I was basically hiding it. No one was going through my stuff. I lived alone. Yet I guess I had just the smallest bit of shame for my desires buried deep inside me.

I grabbed it and walked back out to Sebastian. When he saw me his eyes raked up and down the length of my body. He made me feel so beautiful. It was hard to explain. I close the distance between us and presented the crop to him.

"On your knees slut," Sebastian commanded.

I dropped down to my hands and knees just like I was told. It was so demeaning to be down here on the floor. Sebastian stood over me then. He cracked the crop against my ass.

"Crawl bitch."

"Yes Sir."

I began to crawl through the apartment towards the living area and away from the kitchen. I figured over here we'd have more room to play. Sebastian cracked the crop against my ass again and again as we moved through the apartment. I stopped mid crawl with each and every smack. The pain zipped through me transforming into pleasure. I was practically panting by the time we reached my couch.

"Sit on the couch, legs spread, arms to your sides. I want to see just how much my pretty little slut can take," Sebastian said to me.

I bit my lip as I started to stand. A crack landed against my thigh and then another.

"Did I say you can stand?"

I shook my head. "No but..." how the hell was I meant to get on the couch. I pouted up at Sebastian.

"Crawl onto the couch, like a good little slut," he told me.

I couldn't help but frown. "Yes Master."

Sebastian smirked down at me as I leaned back so I was kneeling then I put my hands on the seat of the couch and started pulling myself up on it. It felt unnatural to move this way but after a few seconds I managed to get onto the couch. I situated myself so I was sitting back with my legs spread.

"We're going to play a kinky version of this or that," Sebastian said to me.

I looked at him with knitted brows. I'm sure he could sense my confusion.

"I will throw out two kinky practices and you will reply with the one you prefer," he said.

I nodded. Sebastian took a seat on my coffee table. It was quite sturdy, luckily for us both. He was directly in front of me, wielding the riding crop in his hand. I followed it with my gaze, anticipation growing inside me.

"Spanking or flogging?" Sebastian said, before smacking my inner thigh.

"Spanking," I yelped.

"Mmhm, flogging or caning?"

"Caning," I said. Another sharp hit landed on the opposite thigh.

"Vibrator or dildo?"

"Vibrator."

Two sharp smacks landed on either of my thighs.

"Why are you hitting me?" I gasped. I didn't mind but I had to know if the hits were because I was giving unsatisfactory responses.

"I just enjoy hitting you. Don't you enjoy suffering for me baby?" He cooed.

I felt myself lull into a submissive state. I was always submissive but sometimes I felt like I had fallen into a hole I couldn't get out of. When I was inside the hole my brain was in an altered state. My submissive mind was more powerful than my logical mind here.

"Oh..." I finally replied. "Yes, I enjoy suffering for you."

"That's good."

I couldn't read Sebastian's mind no matter how hard I tried. He had a calm content look over his angular features, and his lips were almost quirked up into a smile. I was sure he was pleased with that statement at least. But there was not much else I could gather.

"Back to our game, shall we?"

With that I received five sharp slaps. Each came in quick succession, on alternating thighs. Sebastian was nailing me right on the softest spot of the inner thigh where it was so hard for me to gain muscle. This was so much more sensitive than any other part of my thigh.

"Yes Master... back to the game."

Sebastian's eyes sparkled as his gaze bore into mine.

"Giving or receiving?"

"Receiving," came my quick response. I even shocked myself with a small gasp. Sebastian laughed and whipped the side of my tit with the riding crop.

"Receiving pain or pleasure?"

"Both," I burst.

"You can't say both," Sebastian replied with a laugh.

I shrugged.

Sebastian smacked me twice, one on each tit this time. But he aimed right for my nipples.

"Pull your tits out of your shirt," he said.

"Yes Master," I replied.

I unbuttoned one more button then popped my boobs out. The shirt stretched around my breasts. Sebastian groaned as he saw them.

"Degradation or praise?" Came his next question.

"Depends," I found myself saying.

"On?" Sebastian quirked an eyebrow.

"My mood? Or sometimes praise can be degrading," I explained. I wasn't even sure where these responses were coming from. Except maybe that they were buried deep in my subconscious. I had been dissatisfied sexually for a long time. So it made sense.

It ppp

"You like a bit of everything huh?" Sebastian said in a low teasing voice.

"I guess..." I blinked up at him.

"You guess who?"

"I guess, Master."

Sebastian pulled the crop back until it made a noise then slammed it against the top of my thigh. He repeated his reign down onto my other thigh. Smacking me a handful of times each. Small noises started escaping me. The pain was beginning to escalate now. The more I took the worse I was faring.

"Pussy or mouth?" He clipped. What kind of question was that?

"Pussy," I replied.

"Ass or pussy?"

"I've never..."

"Oh?" A smirk laid across Sebastian's face.

I shook my head. He smacked the crop down directly onto my nipple. I sucked in a sharp breath. My nipple stung but at the same time arousal zipped down to my pussy. My body was buzzing between pain and pleasure. I looked up at Sebastian with dark eyes.

Sebastian shot out a few more questions to me. I was answering just barely. He kept smacking me with the damn riding crop. My mind was in a spin trying to think of the right answers to the questions while being smacked over and over again on my thighs and tits. Then Sebastian came and sat down on the couch beside me. He pulled his long thick cock out of his pants. It was standing tall and hard waiting to penetrate something. I was hoping to penetrate me.

He started wordlessly unbuttoning the rest of my blouse and pulling it off my body. I helped him remove it, freeing my tits further for him to do as he pleased.

"Panties," he mumbled.

I pulled them off and he pointed at my skirt which I removed as well.

Without a word, Sebastian lifted me up and lowered me down on his cock.

"We can finish like this can't we?" he asked in a teasing manner. I could barely think straight to answer him.

"Yes Master," I replied. My tone was so breathy. I was struggling to focus between being so full of his cock and the tingling sensation that was running through me from what we had been doing.

"Humiliation or degradation?" Sebastian asked me. He hadn't even started moving me on his cock yet. I was just sat there staring into his eyes.

"If I had to pick, I guess it would be degradation. But, I'm not 100% certain on what the difference is."

Sebastian took hold of my hips in his two hands and started to bounce me. It wasn't too fast or too slow. I held onto his shoulders for balance and then when he finally removed his hands, I continued to bounce all on my own accord.

"Humiliation is like me making you feel embarrassed. For example, I could make you masturbate in front of me. Degradation on the other hand is being making you feel small, degraded, less than me. Like for example, you not being allowed to sit on furniture. Or me I making it clear that you are below me at all times. That you're just a dirty little slut and I'm completely in charge of you."

Sebastian explained this all to me calmly and coolly as I continued to fuck myself on his hard cock. I could barely believe the kind of self-control he seemed to have. I held tight on his shoulders trying to concentrate on what he was saying.

"Can something that's degrading also be humiliating and vice versa?"

"That's a really good question slut. Yes I think there can be a lot of overlap," Sebastian said to me.

He reached to the side and picked up the riding crop. I braced myself for what was to come next.

Sebastian started spanking me with the riding crop as we fucked. He kept one hand wrapped around my throat. While he wielded the riding crop with the other hand. Sebastian's eyes born to mine he had this deep intensity that made my breath catch in my throat. It wasn't even the pain that I couldn't handle. It was everything else that he brought. His dominance was all-encompassing. It surrounded me completely, enveloping me and it's warm but strangling me at the same time.

He continued to shoot this all that questions at me. My mind was in a spin. I was struggling to say what I wanted to say just answering him that face value. He started hitting me harder and harder. The more we fucked the worse the pain became. He was whipping that crop through the air before smacking it in a loud stinging slap against my raw skin.

I cried against him, leaning forward and burying my head into his shoulder. Now Sebastian wasn't even speaking anymore. He was only grunts and curses. I was completely encased in the moment. I bounced harder and faster as he hurt me over and over again.

At some point Sebastian dropped the riding crop. He just grabbed me by the hips instead and made me bounce at his own pace. I tipped my head back as my moans filled the room.

"I need to come," I called out.

"Come for me, slut," Sebastian replied. His words made the muscles in my cunt spasm and contract into an orgasm.

My head spun.

"Sir," I gasped. "Oh my god."

Sebastian smacked the outside of my thigh with his big hard hand as I was coming down from my high. I slumped against him and he came deep inside my wanton pussy.

We sat there like this for a little while just basking in each other and trying to catch our breaths. Then Sebastian lifted me off him and laid me down on the couch. Before I could even think to move he was pinning me down with his body.

"Let's lay here for a little bit," he said.

I hummed in response and Sebastian began to mindlessly play with my nipples. He was hurting me even now in this small moment and I loved it. Then he tangled his fingers through my hair, tugging it painfully.

I tipped my head back into the couch cushion and let myself relax. Soon, I tangled my hands into his hair and ran my fingers through it as he stopped hurting me and began to sooth my nipples.

"If I make you sore everywhere we'll have to take a break," he said. "Can't have you bruised and battered unable to play for days."

I couldn't help but laugh and Sebastian joined me. He hugged his arms around my body and held me tight with his stubbly cheek on my bare skin.