Penelope

I laid down in my bed with a peg on either nipple. The pain was sending jolts of pleasure to my pussy. Two of my fingers were on my clit and I was watching this woman have hers spanked hard. I rubbed myself as I listened to the agony in her voice. The sound made arousal spark through me like nothing else could. I wished that was me.

I’d never experienced anything like this in real life. I watched porn a lot, though. Ever since I was a young adult, I knew that there was something different about my sexuality. But as I got into college, I just went out with regular boys and we did regular things. In my second year of college a friend of mine was reading this book that looked like it was from the 1980s or something and it had a woman on the front cover with a leather bodice. I don’t know why but it piqued my interest. I asked her about the book. She told me to read it.

It followed the story of a woman who became a sexual slave for a man that she met in the same city as her. They went through this very tumultuous but a lust filled relationship. The book wasn’t so much a romance because they split up in the end. But the graphic sexual details of their relationship opened me up to a whole new world.

The only problem was I never actually followed through with any of my desires. Started off with me reading a lot more books about the same subject. Then I moved on to pornography. I still read the books but it was far more real to see how it translates into reality.

The woman in the video screamed in agony. I felt my orgasm come on slowly then all that once. It rattled through me. The vibrator was still pressing against my clit. The pegs on my nipples were beginning to hurt so bad. It was a delicious feeling but it felt like there was something missing.

I always thought it would feel so much better if someone was hurting me. Inflicting their will on me. Hurting me for their pleasure.

I discarded the tab and turn the vibrator off before rolling over in bed. I had long day ahead of me tomorrow.

I was walking through the street when I saw a poster for a BDSM club. The reason or part of the reason I had never followed through before because it all just seemed so difficult. I didn’t know where to look. I didn’t want to find someone dangerous. I wanted something real. At least real in a sense that we were on the same page.

I went home and looked the club up online. Their vetting process was vigorous. They checked IDs at the door and you had to buy tickets to get in. This meant that anyone that had caused trouble before wouldn’t be able to get in. Obviously, you can’t stop every bad actor but the fact that the club was trying made me feel better.

It was Friday night and I was free. I’d been thinking about it all week. What I would wear. How it would go.

Now I was just waiting in line to be let in. I was wearing a tight black dress that fell to my midthigh. I didn’t want to go too overboard especially when it was my first time attending.

At the front of the line, the bouncer asked to see my ID. After a few moments he’ll let me in. I walked into the club. It was dark like a normal nightclub. There was a round island bar in the centre. On the perimeter of the club there were couches and booths and other places to sit. Around the bar people were lined up. Between the bar and the seated areas people were dancing. There didn’t seem to be an official dance floor because people were just dancing wherever there was a spot.

The club was bustling with people and I felt a thrill zip through me. I was wide smiled and excited for what was to come. I walked up to the bar where I saw the wristband system I had been reading about online. Behind the bar was a big board with writing explaining it all.

Different coloured wristbands signified different things. I scanned my eyes over the selection of like twenty or so colours then settled on two.

Red: I like pain Pink: I’m here to have fun

I wasn’t sure what the pink one meant but if I could signify that I was here for a good time it couldn’t hurt.

Some of the other wristbands had nothing to do with BDSM either, like orange: leave me alone I am just here to dance.

I did not want to be left alone.

Even if I didn’t leave with someone I hoped to at least make a friend.

“Could I please get a virgin mojito?” I asked the bartender. I thought I should stay sober if I was going to make any sound decisions.

“Sure thing, honey,” the lady winked at me. Her tits were glorious, in this harness shirt contraption. Her long black hair and pretty blue eyes drew me in. I wasn’t even attracted to women but wow, I’d let her bend me over.

The woman made my drink and slid it to me before I paid. I turned around and began to walk through the club. I honestly had no idea what to do first, maybe sit and recuperate now that I was here.

In my reverie I lost some sense in where I was. I was trying to escape the crowd that huddled around the bar as well. I bumped into something hard. I almost fell back on my heels when a hand reached out and grabbed my arm that wasn’t holding the drink. I somehow steadied myself then looked up to see a man half smiling down at me.

His lazy grin was making me melt. He had these sharp dark eyes, and stubble all over his jaw. He wore a tight black t-shirt with some black pants. A simple understated outfit but the way it was all so well fitted made him sexy.

“Hello,” he just said, almost as if he was teasing me.

“I’m so sorry,” I squeaked.

His hand was still wrapped around my arm but I didn’t mind one bit. When he didn’t speak I felt compelled to keep talking.

“It’s my first time at a place like this. I didn’t realise how crowded it was going to be,” I said.

He nodded.

“My name’s Seb, well Sebastian but they call me Seb,” he replied, instead of letting me go.

“I’m Penny, well, Penelope but…”

“I understand,” he said, smiling.

Sebastian still hadn’t let me go. His eyes bore into mine and I was turning into a squirmy mess.

“Well, it was nice meeting you.” I pulled my arm and it slipped from his grip without any force. I shuffled sideways and he eyed me.

“Where are you going?”

“To go sit,” I said.

“Can I come sit with you?”

A nervous quiver bubbled in my stomach. I found myself chewing on my bottom lip and nodding. Sebastian was a good looking man. I was just not sure how to go about our interaction, which is why I tried running away. He made me nervous. Not just by his looks but by his presence. It filled all the empty space around us.

“Yes yes,” I choked.

Sebastian gave me another smile and I began to walk. I could feel him hot on my tail through the club. I found an empty booth and slid into one side. Seb slid into the same side.

“So, what brings you here?” He asked.

I didn’t know what to say and I felt shameful saying my kinks out loud. Ironic, I know. I lifted up my wristbands which earnt me head tipped back barking laughter from Sebastian.

My cheeks went hot under my makeup.

“What?” I scowled.

“You’re so cute you used their wristband system,” he cooed.

I pouted at him and he moved closer to me. Sebastian made me feel electric. Our thighs were almost touching now.

“What’s wrong with them?”

“Nothing in principle,” he said.

“I thought they made a lot of sense,” I continued.

“So you’re a masochist? That’s why you’re here?” His voice dropped an octave.

“I like pain… I want to explore my sexuality properly.”

“Can I hurt you Penelope?”

For some reason the request made me pause. I knew I wanted it but it felt like a rash decision somehow.

“How?”

“Well, tell me, how do you want me to hurt you right now?”

Another tough question.

“I’ll take my bra off… and you can pinch my nipples through my dress,” I finally said.

It felt weird and a bit slutty to allow a man I just met to do that. But, it seemed like the most safe option. I almost asked him to slap me across the face but I knew from my reading online threads that it could be dangerous if they missed your cheek. I would let him slap me across the face eventually but we needed to build some rapport first.

“You read my mind. But I don’t even need you to take off your bra,” he said.

“Won’t the padding stop you?”

Sebastian didn’t reply. His hand found my tit, cupping it over my bra. Within a second he found my nipple through two layers of fabric and began to pinch it. Pain shot through me. It quelled into pleasure deep in my core.

Something about the unexpected nature of how he did it was better than anything I could inflict on myself.

“Fuck,” I groaned.

“You like that?”

I nodded.

Sebastian grabbed my other nipple, and twisted it. The electric shock pain pressed through my tits before fizzling out into the rest of my body. He continued his tirade on me for a minute or so before finally stopping. Sebastian's eyes caught mine, glistening.

“I like hurting you,” he said in a thick voice. I nodded.

We fell back into a regular conversation but my head didn’t stop spinning. Arousal was bubbling up inside me.

The people in the club began to waver as the night went on and people paired off. Sebastian and I swapped numbers as the club was beginning to close for the night and last drinks were called.

“Can I walk you to your car?” He asked.

“Yes please,” I replied. “How did you know I drove?”

“You haven’t been drinking,” he said as we stood up.

We walked through the club and out the front door. I started walking in the direction of my car and Sebastian came with me. I parked in a lot about a block away from the club. We walked in a comfortable silence. After talking to Sebastian all night I felt like I’d known him for weeks. We reached the lot and I scanned through it.

“Which one’s yours?” He asked.

I pointed at a small red hatchback. He pulled me along, holding my hand. Once we reached my car Sebastian walked me to my driver's side door. I stood with my back against it. He stepped forward until his body was flush with mine and he was gently pinning me to the door. I almost moaned in delight but held it together.

“When can I see you next?” He asked.

“I’m free all weekend,” I replied.

“Good, I’ll text you and we can finalise things.”

I nodded and Sebastian smiled before pressing his lips to mine in a chaste kiss. As he retracted he bit my lip, making me sigh.

He pulled his body off mine and let me get into the car. I turned to watch him walk away before driving off.

Over the next few weeks Sebastian and I went on several dates. They were normal and nice and we were mostly getting to know each other the way people do. What was different though was sometimes Sebastian would hurt me in subtle ways. I also came to find out he was quite dominant. So, he would on an occasion order for me. It was what I wanted anyway but he told me in the future he might not be so nice. Food was never a sexual thing for me but for some reason it sent a thrill through me. It was almost like the physical masochism I was used to but different.

Tonight I was to go over to his house for the first time.

I had strict instructions on my outfit and presentation. Sebastian told me to put on a tight black mini skirt, my brightest panties, and a corset style top. I told him I didn’t have a corset style top and he gave me a hundred dollars to go buy one. He told me to have red lipstick on and leave my hair loose.

I did everything to his specifications. I pulled up to his street and found parking. He lived in an unassuming suburb on the outskirts of the city.

We had already discussed safewords on a previous date so we were into the swing of things by the time my arrival at his home was even planned.

When Sebastian opened his front door everything said for me for what was about to happen. I wasn’t quite sure what he had planned. I just knew that we had discussed what was allowed and what wasn’t allowed. We had started this little thing slowly and surely so I trusted that he was normal. As normal as a sadist could be.

It was funny actually he was a little bit protective, which is almost ironic. And I know those are two different things, sexual pain and other kinds of pain, but it was still amusing and quite romantic if I was being completely honest.

“Come in,” Sebastian said motioning for me to come inside.

I stepped into his house and he closed the door behind us. Next thing I knew he was pinning me against the closed door, pulling my skirt up.

“You are so well-behaved,” he said. He pushed my skirt down and then pulled me so I was in front of him. I began walking into his house. It was a very normal well furnished suburban dwelling. He had art on the walls, photographs of friends and family, a vase in the corner, and a couple things out of place like any normal person would. His home had a warm feeling like a candle or a blanket.

“Have you eaten dinner?” Sebastian asked as we turned into his dining room.

“Yes Sir,” I replied. He had told me to eat before I arrived so we could get right to it. But sometimes he couldn’t trust whether I had eaten or not. Through no fault of my own I’d forget or get too busy, which seemed to be a sticking point for Sebastian.

“What do you have planned for me?” I asked. Nerves were getting to me.

“I want to see what you can take and how well you can submit,” he replied. “Come on, slut,” Sebastian then said in a playful tone. I never thought I could deal with such degrading language let alone be turned on by it. But when Sebastian called me those names I was slack jawed and tingly.

He walked back out of the dining and kitchen area into the living room where he sat me on the couch and asked me what I’d like to drink. I said something sweet like lemonade or juice if he had any. I wasn’t one to have sweet drinks all the time but I found that the pain would go to my head so it’d be good to have one on hand. Sebastian returned with our drinks and sat beside me on the couch.

“I heard that you were bad today,” he said. It was game on and we were playing. I turned to face him on the couch and my skirt rode up.

“Who told you that?” I gasped.

“Your boss, she called me and said you were on your phone, mouthing off, bad bad little office worker,” Sebastian continued.

I backed up on the couch and he grabbed me by the waist, pulling me down so I was laying flat. He spread my legs making my skirt ride up.

“Sir,” I gasped. “I’ll be good.”

Sebastian pushed my panties aside and plunged three fingers into my wet cunt. I went slack jawed and moaned as the feeling rushed through my body. He pulled his fingers out then tsked at me.

“You’re so misbehaved that it turns you on when you’re bad, huh?”

“I…”

“We’ll have to fix that. I can’t have my slut out there running amok,” he chastised.

Then Sebastian grabbed me by a wad of my hair and pulled me up so I was sitting, before standing and dragging me with him. He dragged me through his house like a rag doll until we were in his bedroom. He pulled me over the bed, letting me go. I turned around and started scrambling up onto the bed backwards whilst watching him.

He went into his closet and pulled out a riding crop. The idea of it was delightful. I knew those things hurt much more than anything I could do to myself. I’d watched women and read about them being smacked around with those things countless times now.

“Sir,” I said in a low tone as Sebastian approached me. I wasn’t sure where I was going with it.

“Yes slut?” He replied.

“I did leave work early today, so I could get ready to come here. No one saw me leave,” I admitted. It was the truth. I was hoping somehow it would make this whole thing feel more real.

“Oh you have been bad,” he chastised, but his smile gave him away. It made me melt all the same.

“Yes I’m terrible,” I just said.

Sebastian grabbed my ankle and dragged me beneath him. Next thing I knew he flipped me so I was face down. He smacked the back of my sensitive thighs with the riding cropped as he kept me pinned to the bed. I groaned. Pain and pleasure washed over me. I was aroused beyond belief within five or so smacks. Sebastian pushed my skirt up and shoved my panties aside then plunged into me without warning.

“Sebastian,” I moaned, without thinking.

“That’s Sir or Master to you,” he snapped before smacking my ass hard. He pulled me up by the hips and then started laying into me with the riding crop. I was crying out every few moments. The feeling of his cock ramming deep inside me along with the smacks of the riding crop had me in heaven. This is what all my dreams were made of. I’d thought of moments like this in bed with my fingers on my clit and I somehow made it a reality.

Pleasure surged through my body. My ass was on fire.

Sebastian was fucking me deep and hard. He was reaching places I never even knew possible. If he wasn’t holding me up by the hips I’d be completely collapsed onto the bed.

I cried out in pleasure as my orgasm started bubbling up inside me. I was barely able to keep quiet for a few seconds at a time. Sebastian was ravaging me like I never had been before.

I came with a moan that came out so breathy it didn’t even make a sound.

Sebastian continued to beat me. I’d fallen face flat onto the mattress. He rammed his cock so deep inside me as he continued his abuse on my ass and thighs. Now he dropped the crop and just smacked me with his hands.

“Where do you want me?” Sebastian demanded.

My head was spinning. I was on birth control so it didn’t matter.

“Inside me,” I gasped. “Sir…”

Sebastian grabbed me by the hair and fastened his pace. He groaned then collapsed over me, swearing under his breath.

We laid like that for a little while, Sebastian on top of me. I was sandwiched between him and the mattress. Then he rolled us over so I was on top. I’d never had such a good first time with anyone before. But with Sebastian it felt completely natural.

Sebastian kissed me and I melted. He tangled his fingers through my hair tugging on it before we finally pulled apart.

“How was that?” He asked.

“Amazing,” I replied.

A self assured smile spread across his handsome face. I cupped his cheek.

“Why don’t we go have a snack and sit before starting again?” Sebastian asked me.

I’d already planned to stay until morning. But I understood now that this would be a very long night.

Sebastian and I were sitting in the living room. We’d just finished an episode of a new show we started together. We promised not to continue watching without the other.

The screen went blank and I turned to Sebastian with questioning eyes.

“Have you ever had your tits beaten?”

I shook my head without thinking. If that had happened it would surely be memorable.

“Would you like me to beat you?”

“I didn’t know I’d have to ask for it,” I simply replied. “I thought you wanted to beat me.”

“Sometimes I’ll even make you beg for it,” he then said.

The idea made me completely aroused. Sebastian stood up and then left the room when he came back he was holding a riding crop and a tasseled whip.

“I think I’ll have you naked for the rest of the night,” he said almost as if he was just musing to himself. I chuckled and sat there waiting for Sebastian to make his next move. He came over and I sat up on the couch. “Strip for me, slut.”

Sebastian was sitting to my side, the toys were on the coffee table in front of us. I eyed him. He was watching me like a hawk. I peeled my clothing off slowly but surely, the corset was the first to go– painful thing. Then my skirt then my panties. I sat naked with my clothes in a pile on the floor. Sebastian reached out and took one of my nipples in his fingers. He rolled it back and forth painfully.

“I’ve been meaning to ask,” he said as he grabbed the other nipple. His expert fingers hurting me every step of the way.

“Yes?”

“How would you feel about me having carte blanche to slap you?” “Like across the face?” I gawked. The idea felt more demeaning than painful.

“It wouldn’t be hard just…”

“Extremely degrading,” I finished for him. Sebastian was still pulling on my tits, pinching them even harder now.

“Yes precisely,” he replied.

I thought about it for a few moments, how would I feel if he slapped me across the face.

“Yes but I reserve my right to revoke that privilege,” I said.

Sebastian came closer to me so the front of his body was up against my side. He gave my cheek a chaste kiss as thanks, which felt funny given the circumstances.

“On your knees, whore, face me,” he then commanded.

“Yes Master,” I replied.

We had been going by Sir up until then but the way he spoke to me it just made the word slip out of my mouth. I was facing him, on my knees. He seemed pleased with my omission.

“Am I your Master, slut?”

“I…” I stuttered, searching his face.

“Mine to dominate and torment, mine to do with as I please?” Sebastian asked.

“Yes Master, you are,” I finally said. I pushed my chest out a little, drawing attention to my tits. Sebastian smirked.

“Are you ready for your beating?” he asked.

“Yes Master.”

Sebastian picked up the tassel whip and swung it, hitting it against my tit. It didn’t hurt all that much so I imagined he was building his way up.

He hit me at a steady pace aiming for my right tit then the left one and back again. I let my head fall back as the feeling started to get stronger. It was a different sensation because it felt almost soft at first but as time went on and you got hit in the same spot over and over again it started to sting and ache.

Then the feeling of the hits changed and I knew in an instance he had switched to the riding crop. I looked up to see Sebastian whip the crop against my nipple. It stung and I yelped without any control in the matter.

He continued on my other nipple, then back again. I was yelping and panting between hits. He was smiling at me like he loved every minute of my suffering.

Sebastian dropped the crop and grabbed both my nipples at the same time. He squeezed them, rolling them back and forth between his fingers as I cried out. When my whimpering died out he stopped. I looked down at him with lustful eyes. The pain bloomed arousal inside me. I could feel myself almost dripping onto his couch. He looked back at me with the same face. Sebastian’s hand wrapped around my throat.

“You want this cock, don’t you?” he said, teasing me.

I nodded, desperate.

“How badly would you degrade yourself for it right now?” he then asked. He was wicked.

I frowned. “Badly…Master.”

“Beg for it, slut.”

“Please, I need your cock. Please,” I whined. He slapped my tits with his other hand as he held my throat.

“I don’t know if you even deserve it.”

“Master, please,” I cried.

Sebastian’s hand went from my neck to my hair. He pulled me down by it until I was lying beneath him. I lost my senses for a moment and when I looked up he was removing his shirt, before pulling down his pants. His cock sprung to life and that’s when I was seeing it properly for the first time. It was long, thick, and had a vein up the side. I loved the look of it.

My eyes glazed over. My pussy clenched as I waited for Sebastian to fuck me. He pushed my legs apart and ran his cock up and down the length of my slit, concentrating on the bundle of nerves at the top. Pleasure burst through me. I was desperate to be filled up.

“What a needy, needy little cunt,” Sebastian said.

“I am not,” I couldn’t help but pout.

He burst out with a laugh but then shook his head and pointed at my puss. “No not you, sweetheart, your little cunt.” He patted my mound condescendingly.

“Please fuck me Master,” I begged. I just needed him inside me already. Sebastian pinched my clit so hard I screamed as he plunged his cock deep inside me. I reeled as the mixture of pleasure and pain burst inside my body. I was already primed and halfway to my release.

Sebastian tortured my clit with one hand while he had the other right beside my head as he thrust into me. He looked down at me, capturing me in his gaze as pleasure took over my body. He rolled my clit back and forth between his fingers and pushed into me, the angle of his cock hit my g-spot and I came with a gasp. There was no warning and I couldn’t have asked for permission even if I wanted to. Sebastian ripped orgasms out of me like he already possessed them. My eyes lulled into the back of my head and my pussy constricted around him. He smacked my tits, one then the other, then back again, as I came down from my high. I loved the way he toyed with my body.

“One day I’m going to make you come until it hurts,” he told me.

I whimpered beneath him. All the things he would want to do to me washed over. Sebastian groaned then as I constricted around him and he thrust harder. He pulled his cock out and I felt his come dripping out of me.

“I should make you lick up the mess you made on my couch,” he said, sitting up. I laid there dazed, a dopey smile on my face.

“No…” I just replied. “You wouldn’t.”

Sebastian gave me a wicked grin and winked. I smiled back and sat up on the couch and as I did his fingers laced through my hair and he pulled me down so I was hovering just above the couch.

“Master,” I whined.

“I’m glad you know your place,” he said before pushing me down. “Lick, slut.”

Degrading as it was, I licked our wet patch just as Sebastian had told me to. The taste was standard, I’d had cum in my mouth before. What wasn’t standard was the way he was holding me by the hair and making me lick it off a couch. I moaned as he pushed me down harder.

After a few endless degrading minutes he let go of my hair. Unsure what to do I continued licking the couch.

He pulled me up by my hair and looked at me almost curiously. “You didn’t tell me to stop, Master.” “What a good little slut,” he praised. I smiled and Sebastian grabbed me, pulling me into his lap. I laid my head against his shoulder and wrapped my legs halfway around his waist.

“I hated that,” I admitted. “But, it sort of turned me on.”

Sebastian chuckled. “I’ll enjoy forcing you to do things you hate then.”

I couldn’t help but laugh because that was exactly what I wanted him to do.