Chloe's Caning

CHLOE’S CANING

I first met Chloe standing on the corner of the street in the rain. She was dressed in high heels, a short skirt and a sleek black top and though she looked wet and bedraggled she was still smiling as she touted for business. Chloe stood out from the other hookers because she was genuinely attractive. About five feet nine, with 36D breasts, long, flowing brunette hair and dark, piercing eyes, she instantly grabbed my attention as I drove slowly towards her. She stood there with one leg bent, provocatively, almost showing off what she had under the short skirt, but not quite.

I wasn’t looking for the same kind of business Chloe was offering to anyone who’d take her up on it, but I was looking for an attractive young woman. As I slowed the car down for the corner I nodded at Chloe and pulled round the corner, stopping about fifty yards further on. I watched in the mirrors as she started strutting towards me and at the last moment I lowered the window to speak. She asked if I was after business and I said maybe. She asked what I wanted and I said I was looking for an attractive woman who had no inhibitions and wanted to earn a lot of money.

By way of reply she asked what I was talking about, so I told her, half expecting her to walk away, giving me a whole mouthful of verbal, but she didn’t. Instead she asked me what I was going to pay, so I told her it was two thousand dollars for the work I’d mentioned.

Chloe thought about it for all of ten seconds and then walked round to the passenger door of the car and got in. Smiling she made a call to one of her fellow hookers, gave her my car registration number and told her she was busy for the next twenty four hours. Having finished the call she told me it was a security arrangement, whereby her friend would alert the cops to my car if she hadn’t made touch with her friend again in twenty four hours. I assured her I was far too well known to risk doing anything stupid and I didn’t fancy a ten stretch for manslaughter or life for murder. She smiled back and asked me what was going to be involved.

Before I continue, maybe I should introduce myself. I’m Ken Brown, and my business is making money on the Internet from porn movies. Actually I specialise in making movies of a particular style as you will see in this story. I expect the best from the girls and I pay them well for what they have to do. I told Chloe the order of events and a rough schedule and told her she could back out at any time she wanted, for a reduced fee of course. She smiled back as I glanced at her for the hundredth time since she’d got in the car. We were driving out of town now and my place was a few miles away in relatively isolated countryside. The last mile or so was little more than a dirt track that led to half a dozen estates. Mine was at the end of the track, set in about forty acres of land with a small river running down the back of the estate.

Chloe was about the twentieth girl I’d picked up for this work and I have to say my judgement is pretty good when it comes to picking out suitable girls. I’ve only had three that backed out and that was simply because they couldn’t cope with the demands of what I do.

Chloe looked at me and said she was concerned about the sheer amount of work I intended to do in twenty four hours so I politely asked how many men she’d usually pick up in an evening. She surprised me by saying she had a target of fifteen men. She went on to explain that probably seven or eight of those would be hand jobs, and take only a few minutes each down some alleyway or in the back of a car. Four or five more would pay for oral, which she usually did in the cars as well, and the men usually were so looking forward to it that they didn’t last more than a couple of minutes. Then, she’d have a handful that wanted to do it properly either up her cunt or her ass. Sometimes, when it was warm and dry she’d do it al fresco in an alleyway or drive to some pull-in just out of town and hop in the back seat, but she had a small rented room she could use close to where she worked and that was the usual place for a full workout.

My cock was throbbing as she went on to talk about some recent clients and their roles in life. I was amazed some of them got away with it but then again having a judge in your panties was probably good insurance against a day in court on charges of soliciting.

We finally arrived at my place and I showed Chloe to the room she could use for rest periods and for changing. It was a double bedroom with en-suite bathroom. It was eight in the evening and I told Chloe to get bathed and dressed into the clothes I’d lay out for her, and then meet me downstairs for some food. She smiled at that and so I left her to wash and dress in the skimpy black number I lay on the bed for her. She was told to wear her own high heels, no bra and no panties. I showed her where the hair dryer was and left her to it while I went and cooked some pasta. No girl can work on an empty stomach and Chloe was going to be working hard later that evening.

When she came down to find me in the kitchen she looked stunning and the little black wrap-over I’d selected for her showed off all the curves and her slender waistline perfectly. We ate and polished off a bottle of white wine. Evidently Chloe was famished for she finished ahead of me and I am not a slow eater. I opened a second bottle of wine and poured her another glass before handing her the standard contract I have for all my assignees. She took it, read it quite quickly and signed the bottom. At least now she knew what she was going to get paid for the various parts of the assignment.

With the meal finished I took her to my den. I had the lights in place and the cameras set up and told Chloe exactly what I wanted her to do. With the camera rolling she stood in the middle of the floor and treated the camera to a long, slow look all over her body. She teased the skimpy material over the outer edges of her firm breasts, forcing them out into view of the camera, so the viewer got a perfect view of her dark areolas and the leathery coloured nipples that were stiff and almost looked like they were going to burst from the middle of the dark circles on which they were mounted. Then she slowly raised the hem of the very, very short skirt, first with her back turned to the camera so I saw her perfect, taut young buttock cheeks and then, she turned to reveal her shaved mons and her pouting pussy lips. God I wanted to cum on the spot but I had something better planned.

“So why are you here?” I asked her, as per the script she had read through quickly before we had got started.

“I’m here to be spanked and fucked,” she replied demurely, letting the skirt drop back down so her pussy was tantalisingly just out of view.

“And why do you want that?”

“Because my partner says I am a naughty girl and I need to be taught a lesson,” she said and flicked the long eyelashes at the camera as she put one finger up right on the dimple on her left cheek. She smiled and licked her lips.

“Okay, well we’d better see if we can teach you a lesson then, hadn’t we?” I said and switched off the camera. I had four video cameras positioned round the room, and a stills camera that was set to take a picture every few seconds. I was going to miss nothing, and never had done. The fun part was always in the editing. In addition the couch I was going to use for the spanking had two very powerful microphones hidden behind it so her every gasp and cry would be heard as well as the sounds of the spanking itself.

With the push of a button on a remote control unit, all the video cameras came back to life. I sat on the couch and Chloe came and lay across my lap with her pretty, firm ass cheeks right on top. I was damned sure she could feel my massive erection pushing into her stomach as she lay there. I checked the four small screens on the wall to check all the pictures were being recorded okay and then I proceeded to hand spank that lovely bottom. I started off gently at first and made small talk while I warmed her cheeks up. At this stage Chloe could reply quite easily, as I was not trying to hurt her much. With an, ‘okay, now we’re going to get harder’, I increased the pace until within a few swats Chloe was gasping and complaining it was starting to hurt. That was when I chided her quite seriously and told her that a spanking was of no benefit to her unless it did hurt and, for her information, things were going to hurt a lot more before I was done.

So far her skirt had been covering her bottom, but once Chloe was gasping with every fresh smack on her firm, pert bottom, I stopped for a moment and lifted the skirt up to reveal two very pink orbs. Up to this point Chloe had dutifully kept her arms in front of her. Her left arm was pinioned by her position over my lap anyway, and Chloe had been using the right hand to prop her up and stop her falling on the floor.

I continued the spanking apace and Chloe realised now that this was a very real spanking and not some fake session. I’d told her this would be the case but until now, when my hand was stinging her bottom and her cheeks were starting to turn bright red, I don’t think she’d fully realised what was going to take place.

“Ow, ow, ow,” she kept on moaning as the spanking continued.

“Okay,” I said after a few minutes, “let’s see how you are progressing.” I stopped the spanking and made a big play of examining her very red bottom, gently pulling the cheeks apart so the camera directly behind her got a good shot of her pussy lips between her legs. “Coming along nicely,” I said after a good few seconds. “Are you beginning to wish you hadn’t been a naughty girl?” I asked, reaching behind me and retrieving the ping-pong bat shaped paddle from behind the cushion supporting me. Made of two pieces of thick leather, the paddle was a short but painfully powerful device.

“Yes, I think I am,” Chloe sobbed, and the tears I could see on the monitor screen looked real enough.

“Good, well I am going to drive the message home now,” I said and Chloe knew it was time for more pain.

“No, please, I really have learned my lesson,” she pleaded, still remembering the essence of the script.

“Of course you have, but we don’t want you to forget it,” I said.

Splat! Splat! Splat! Splat!

“Agggghhhh,” Chloe cried out as I landed four solid strokes of the paddle, two on each of her bright red cheeks. “Jeez that stings,” she moaned through her sobs.

I continued to paddle her bottom with medium strength strokes for a couple of minutes. When I stopped, Chloe was sobbing loudly and crying out as each stroke landed. Her groans and cries were real, as were her tears. Her bottom had gone from red to crimson and purple and in places it looked puffy from some bruising.