Den of Iniquity Ch. 06

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Sir_Nathan
Sir_Nathan
1,659 Followers

"For um.."

Slap!

"Mmmmm... oooo.... that's... that's better... for me Sir, for me."

I felt like I woke from a dream. I stopped for a moment and leaned down, looking closely at Josephine's ass. It had blushed pink and looked warm. I could make out a couple of hand prints. I traced them with my fingertips.

"Wow look at that."

I slowly made my way around her whole ass very lightly, touching every hollow and curve. I slid my other hand up to her exposed back where the skin was cooler. The contrast was intoxicating.

"It warms up nicely, doesn't it."

"God... your hands feel so good, Sir."

"It looks really good you know... can you feel how hard my cock is?"

"I can... it's against my hip... and it turns me on even more knowing you are pleased."

I smiled. It was time to try something different.

"Okay, I can see the enjoyment derived from spanking; now let's try something else."

"But I was just starting to warm up, Sir..."

"Let's finish warming you up with a crop."

She trembled.

"Y.. yes, Sir."

Josephine giggled and raised herself until she was standing. She started to pull down the hem of her dress.

"No. Take it off."

She grinned and grasped the hem of her tight dress in her hands and slipped it off over her head. As she did, her panties fell to the floor and she giggled again. I smiled at her as she kicked them aside. She was such a show off.

"Pinch your nipples for me."

"Mmmmmm."

She did and then let go of them.

"Don't let go."

"Y.. yes Sir."

"Turn around."

As she slowly turned around, she spoke.

"You know Sir, you have to start off very softly with a crop..."

Her ass was a lovely pink colour, contrasting nicely with her golden skin.

"I'm listening."

"Because a crop is a stinging toy, and it can really sting."

"Okay."

"And um, that's why it's good to be very gentle with um, sensitive spots, okay?"

"Yes, I think I understand... you mean if I choose to crop your breasts or pussy then I should do it gently and be guided by your reactions."

"Yes Sir." I watched as her left thigh started shaking. "That's r.. right."

"Are you okay Josephine?"

"Yes, just um... very excited is all."

"Is this situation getting to you?"

"My pussy is throbbing, Sir. I'll be okay though."

"Your can release your nipples now."

"Thank you, Sir."

"They are very hard."

"Yes Sir."

"Is your clit hard too?"

"Y.. yes Sir."

"Hands behind your head Josephine."

I marveled at her acquiescence. She brought her hands behind her head, lacing her fingers together.

"Elbows out Josephine."

"Yes Sir."

"Feet eighteen inches apart."

She moved them apart.

"Good girl. Just stand there."

"You are good at this Sir."

"Did I say you could talk?"

"No Sir. Shutting up Sir."

I picked up my champagne and sat back in the couch. I could get used to this. I looked her up and down. That telltale glisten of perspiration had appeared on her top lip again. She was so beautiful I swear she could have been a model. Actually, something wasn't quite right. Maybe music. The lights were bright too.

"Do you have some music that is appropriate for this situation Josephine?"

"Maybe something heavy Sir?"

"Hmmm..." Heavy? I shrugged. "Whatever you choose is fine by me. Do you think we could afford another glass of champagne?"

She stood comfortably, understanding my silent permission to relax.

"I would love one more glass Sir, or maybe just a half a glass."

"Put on some music, and are you able to turn the lights down a little? It's very bright in here."

"Yes Sir."

She moved straight to one wall and fiddled with a switch and the lights came down. Then she trotted into her room with a giggle.

I picked up the bottle and poured a half glass for Josephine and a full glass for myself. I was going to enjoy this as much as I could. The adrenaline pumping in my veins had me so clear headed, I could allow myself another glass. It was intense, being able to do just about whatever I wanted. The weirdest thing was, I wasn't thinking ahead. I was just winging it. No that's not right. It felt comfortable. I really liked the timing aspect. Most of the 'couplings' in my life had been either frantic, or 'get it over with' type scenarios. I liked setting the pace. And changing it. I was loving it!

Josephine came around the coffee table and stood before me, taking up exactly the same stance as before. Just then, AC/DC came on through the speakers and she grinned. I smiled up at her and nodded. AC/DC had been one of my favourite bands when I was a kid. I had to stop myself from tapping my foot as 'Highway to Hell' started its thumping beat. Fortunately it wasn't too loud to talk over.

I picked up Josephine's glass and nodded to her as I passed it up to her. She relaxed, took the offered glass and stood self-consciously with one arm across her stomach.

"Thank you Sir," she said, sipping her champagne. I took my own glass and sat back in the couch admiring her.

I looked her up and down. She was freshly shaved and seemed to push her hips forward as my eyes passed over her pussy. Sure enough, when my eyes flicked up at hers, she was watching me intently.

I looked back down. Her pussy was one of those tucked in ones. Almost nothing showing but the lips of it.

"Come here."

She moved towards me.

I reached out for her and slid my fingers along her cute pussy. She moaned softly.

"Mmmmmmm..."

"You have a pretty pussy."

"Thank you S.. Sir..."

She tipped back her last sip of champagne and put the glass down on the table. She stood a little back from me and took up her original stance, hands behind her head. My fingers continued to play over her little cunt. I looked up into her eyes. She was ready to go.

"You are such a fucking showoff."

"I know," she grinned.

She pushed her hips forward once more, but I withdrew my hand. I sat back in the couch again and finished my champagne.

She whimpered.

"Ohhh..."

"You might be the teacher Josephine, but you are not the boss, okay?"

"Yes, Sir."

"Good girl."

She smiled at me and blushed strongly. I wondered what was going through her mind.

I finished my champagne and moved back to the edge of the couch. I put the glass aside and moved my case in front of me and opened it. I looked up at Josephine and she was rocking back and forth on her heels, clearly impatient.

"Stay still. And I mean 'still'."

She nodded and made like a statue.

I looked over all my choices and stuck with my original plan. I picked out the crop and held it across my hands.

"This is a beautifully crafted thing, isn't it?"

I looked up at her.

"A little Dubbin from the shoe store will keep it supple, Sir."

"Anything else I should know?"

"Only that it should be disinfected now and again, Sir. Keep it clean."

"Understood. Something from the drug store?"

"Yes, even a rubbing alcohol would do the trick."

"You say I should start gentle then..."

I looked into her eyes as I took hold of the handle and slapped the crop in my palm. I wondered if Josephine would flinch like Annie had.

She didn't.

She just smiled.

"Step back into the centre of the room... can I move this table?"

"Yes Sir," she said, "whatever you want Sir."

She moved into the centre of the room, still holding the position I'd originally asked her to take, while I pulled the coffee table over to one side of the room. Once it was moved, I stood up straight and turned toward Josephine. I was completely clothed and Josephine was naked. It was surreal.

The crop hung stiffly from my hand but I wasn't really aware of it in the sense that it was an addition. I didn't think of it at all, except as a way to touch her.

I stood and walked toward Josephine until I was a couple of feet in front of her. She held her position but her chest was heaving. I raised the crop and watched as I ran the tip of it down her side.

Josephine closed her eyes and moaned over the music.

"Mmmmmm..."

She moved her hip away from the crop as though it tickled and I struck her softly with it. Right on her hip. Well, I'd told her not to move.

Pap!

"Uhhh..." she shuddered. "Sorry Sir..."

I smiled.

"Try not to move Josephine."

"Yes Sir."

I walked over to the table and leaned over with my back to her. I picked the handcuffs out of the case and noticed the small key in the cuffs and unlocked them. I slipped the key into my pocket and turned to face her.

Josephine's hands were still behind her head and her eyes were closed, with her head down. I approached her and stood before her with the cuffs loose in my free hand. I gently caressed over her hip and up her side with the black leather crop. I moved it over her skin deliberately and her enjoyment of the situation was obvious. Her eyelids fluttered as I caressed the underside of each perky breast. Her nipples were crinkled and tight. I touched each one with the crop. She moaned softly.

I walked around her and trailed the crop around her waist.

"Put your hands behind your back."

"Yes Sir."

She did.

While behind her, I put the crop in my teeth and cuffed her wrists.

My cock throbbed as each cuff ratcheted closed. I could only imagine how Josephine felt. No, I could do more than that.

From behind, I reached between her legs and ran my fingers over her pussy again. When I realised she was so hot, and so moist, I leaned into her ear and whispered.

"I can't believe how fucking wet you are."

She groaned.

"Having fun Josephine?" I whispered.

"Mmmmmm..."

"Bend forward a little."

She did.

I looked down over the curve of her ass.

"That's nice."

She moaned again softly.

"Mmmmmm..."

I gritted my teeth. I had much to do.

"Keep with the program, Josephine."

"Y... yes Sir."

I stood back from her and looked down at her wonderful pink ass with the tan lines. I wondered if she could stay still if I tried using the crop on her ass.

"Remember, stay still Josephine," I said.

"Yes Sir."

Then I popped her. On the side of her right ass cheek. She didn't move but her ass cheek did. Her thigh muscles were tight, but her cheek vibrated like a tuning fork.

"Uhhhhhh..."

"Is that too hard?"

"N.. no Sir."

Pop! On the outside of her left cheek.

"Ohh... It's ri.. ridiculous, Sir."

"Tell me. I'd like to be amused too."

"Well you really don't need to be told what to do Sir. I mean, you are good. Really... " Pop! Other cheek. "... g.. good. I could get used to this."

"Okay, enough talking."

Pop! Same place.

"Mmmmm."

Darker pink welts were rising on her skin.

I moved a little to the side to improve the angle.

Pop! Pop!

Such a pretty ass.

I wanted to make it that slightly darker pink all over.

Pop! Pop!

So I did.

Pop! Pop!

Pop!

"Mmmmmm..."

Pop!

"Ooohhhh..."

I stopped and moved around to the other side. I used the crop like a tennis backhand, but with more of a flicking action. I wanted to get the tops of her thighs...

Pop! Pop!

...Where her ass met them...

Pop!

...Yes...

Pop! Pop!

"That's pretty."

I stopped.

Josephine groaned and emerged from the trace-like state she had entered.

I moved directly behind her and leaned down a little. Reaching out with the crop, I slowly brought it up between her legs.

I touched her, then brushed it back and forth, sawing it gently over her pussy.

"Ohh.. Ooooo..."

"Spread your legs a little more."

She did.

"Tell me if this is too hard."

Tap.

"Mmmmmm."

Tap. Tap.

"Ooh.. t.. that's s.. so good Sir."

Her left thigh started to shake.

Tap!

"OOoohhh... oh... oh God..."

I stopped and straightened up, smiling, but I spoke in a low, stern voice.

"Don't you dare fucking cum."

Though I was standing behind her, I could tell Josephine spoke through clenched teeth.

"Nn.. no S.. Sir..."

I was pleased.

"Good girl. I'll un-cuff you now."

I took my handkerchief from my pocket and wiped off the tip of the crop. Walking over to the table, I slid the crop back into its place and nestled it into the red foam. I glanced over my shoulder and Josephine was biting her lip, looking down at the case longingly.

"Is something the matter?" I teased.

"Um, no Sir, I was... um.. just wondering.. can you crop me more later?"

"We'll see."

"Yes Sir."

I stood and faced her.

"Come to me."

She looked up into my eyes and smiled a slow warm smile. She stepped close to me. I slid my hand into my pocket and retrieved the key to the handcuffs. I put my arms around her and slid the key into the locks and unlocked each handcuff.

"God, Sir," she whispered.

"Are you okay?"

"Yes," she smiled, "and it's wonderful that you keep asking that."

She put her arms around my neck and kissed me impulsively. I slipped the cuffs and key into my pocket and kissed her back, pulling her into me with my arms around her waist. Quick hot movements of her tongue betrayed her excitement and added to mine. My cock had been thick in my pants for over an hour now. Her tongue played over my teeth and teased my own tongue. I hardened considerably while kissing her back.

"Mmmmmm..." I breathed out in a whispered moan.

Reluctantly I broke the kiss, opened my eyes, and whispered to her.

"I want to see what happens when I put those clamps on you."

"Okay."

"Do I have to be careful?"

"I don't know. Let's see what kind they are."

I nodded and we slid from each others arms and took the couple of steps over to the coffee table I had pushed against a wall. Turning the case around, I picked up the box of clamps and looked at it for some sort of instructions. Finding none, I shifted my gaze to Josephine, who was still looking down into the box.

"What are you thinking?" I asked.

"Um... sorry Sir. Just um... just daydreaming about being flogged."

"I see," I smiled. "Well there are no instructions on the box." I opened it and took out the lengths of long thin silver chain with what looked like small tweezers attached to them. In the centre, the ends of chain all met and were held together by a small silver ring.

"Oh, I like that kind!" Josephine exclaimed.

I looked at her with mock surprise.

"Yes, I guess you do."

She blushed almost the colour of her ass.

I leaned down and put the clamps loosely on top of everything in the case, picked it up and headed for her bedroom.

"Come with me," I said looking over my shoulder.

Josephine giggled and ran right past me into her bedroom and leapt onto the bed. When I came in she was kneeling on the edge of it, facing me, with her hands behind her back. She was smiling and biting her bottom lip.

"Okay, now I'm sure you do."

I winked at her and sat on the bed beside her. Josephine just grinned and turned a little toward me, sitting back on her heels with her knees together. I put the case down on the other side of me, near the foot of the bed. I retrieved the clamps and pretty chains and closed it again.

"Three points of contact..."

"Yes Sir."

"This should be fun too."

"Shall I show you how they go on Sir?"

"Okay but just the first one. I can't see them being too complicated."

Josephine nodded.

"It's pretty easy."

I passed the tangle to her and she straightened out all the chains. She then proceeded to take one of the clamps between finger and thumb and closed it with her nipple between the ends. She moved a slider into place and looked at me.

"All done."

She grinned.

"That's it?"

"Yes Sir."

"Are they tight?"

"No Sir."

"How do you make them tighter?"

"You move the slider closer to the tips, Sir. Just a little at a time though."

"Show me."

"Yes Sir."

She bit her lip again as she moved the slider up a little.

"It doesn't look very tight."

"Try tugging on it Sir."

"Okay."

"Mmmmmm."

"So that feels good."

"Yes Sir."

"How about we get you comfortable. Lay back on the bed, feet on the floor. Wait a minute, stand up and let me put a couple of pillows under you."

"Yes Sir."

Josephine stood and I placed her two pillows where I would have her sit before lying back. I put them one on top of the other.

"Sit on the pillows, then lay back, feet apart on the floor."

"Yes Sir."

Josephine arranged herself as I requested, and my cock throbbed at the sight. The single clamp attached to her right nipple looked very pretty. But the other chains and clamps strewn across her body from her laying back were breathtaking. The stainless steel glinted in the golden wall lighting and the effect was extremely erotic. I could hardly wait to see what she looked like "all clamped up". She smiled up at me with pink cheeks. With the pillows under her ass, her pussy was a few inches above her head.

"Pretty as a picture Josephine."

"Thank you Sir."

I smiled.

I picked up the clamp intended for her other nipple and stretched the chain across her chest. I inadvertently tugged it.

"Ooo..."

"You like that, huh?"

"It's good, Sir."

I smiled at her and fixed the remaining clamp tightly to her other nipple.

"Ohhh..."

"Too tight?"

"N.. not it you want it tight, Sir."

"I want it tight."

"Yes Sir. Um... the other one isn't that tight."

"Thank you for telling me."

I winked at her and she blushed.

I reached across to her other nipple and tightened the clamp.

"Oooooo...."

She didn't complain so I was pleased. I picked up the loose chain with the clamp on the end of it and lifted it up. It looked like an upside down Y. I tugged gently on it and Josephine closed her eyes and cooed.

"Mmmmmm..."

"While I hold this up, I want you to open yourself, Josephine."

"Y.. yes, S.. Sir."

She reached down and with her fingertips, she opened her steaming wet pussy.

"Control yourself Josephine."

"Sorry Sir... it's just... it's like having your nipples constantly and firmly pinched Sir. It's maddening."

"It lifts the erotic base."

"You are s.. so good with words Sir."

"Must be all the novels I've read."

I chuckled to myself and laid the chain down the middle of Josephine's torso. Now it looked like a real Y from where I was sitting.

"Open a little more Josephine. Push your hips forward. Pull the hood back a little."

She did.

"Good girl."

I put the tips of the clamp on either side of her firm pink bud, just behind the tip of it, so the clamp itself would hold back the hood when she let go. I adjusted the slider into position and Josephine moaned softly.

"Is that too loose?"

No words came out of Josephine's mouth, just stuttered breath. Her eyes were tightly closed, her mouth open.

"Nnngggg.. oohhh... mmmmmm..."

"I'll just check. You can let go now, hands by your sides."

She did as I asked.

Her pussy closed back up but her clit stood proudly beyond the tips of the clamp.

I picked up the chains where they met in the middle of the Y and lifted them up a few inches above her body. They grew taut and Josephine's thighs tightened and her hips rose to follow the increasing tension. The clamp on her clit held fast. To make sure, I tugged at the chain a little.

"Uhh.. jje.. mmmmm..."

"Okay, that seems good for now."

"Godddddd.... it's ...it's been so long since mmmmmmm..."

"Since what?" I smiled and tugged at the chain a little again.

"S.. si.. since I uhhhh..."

"Answer the question, Josephine."

I tugged the other way, pulling at her crinkled and clamped nipples.

"F.. fu... ohhhh... since I.. since I've been clamped.. clamped like this... S.. Sir..."

I thought she looked beautiful. She had a lithe and youthful body with barely a blemish and not a tattoo in sight. I let the chain drop to her skin and brushed my fingertips upward gently and slowly, starting from her pubic bone. She was really quite flawless and I was starting to feel quite bold.

Sir_Nathan
Sir_Nathan
1,659 Followers