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As he ran his fingers over it, the pain and the humiliation rushed to Ellen's face. She turned her anguished expression downwards, but a finger under the chin lifted her gaze up to meet hers. He was so close. The look in his eye was strange. It wasn't lust. More, curiosity. She held his eye contact as he stroked her wound, trying and failing to keep the pain off of her face. Then, mercifully, he withdrew.

He paced around her slowly, cain in hand. Once he left her field of view, there was only the sound of his footsteps, and her pain. Then the footsteps stopped. He must've been right behind her.

The whistle of the cain warned Ellen of the strike a split second before it hit home. This time, it took her on the arse.

There was no respite. This time the blows came thick and fast and hard. Each blow felt like it had the man's full force behind it, smacking unpredictably anywhere between the top of her arse and the back of her knee. The pain was ferocious and ever building, but Ellen managed to bite her lip for the first few blows of the cain. That didn't last long. After half a dozen blows, she was squealing. After twenty, her cries became long and agonised. Don't cry, she thought, as the cain rained pain upon her arse. Don't you dare cry.

After fifty strikes, or near enough as made no matter, the man relented. Ellen had not cried. Her head hung limply though, and her breathing was ragged. Sweat beaded on her forehead and in her hair, and a drop of it hung off her nose. Being caned was hard work. The pain was intensely sharp, and her entire thighs and arse were red hot and throbbing. She didn't realise that the man was standing in front of her until she felt his finger under her chin again, and raised her head to look him in the eye.

How long has it been? She wondered. If it's been ten minutes, then I've paid for my textbooks for next semester one and a half times. This didn't have the savour it had had a short while ago. But it did sharpen her resolve, which was all it was meant to do. I can get though this, she reminded herself. I can. And when I do, all those problems will be gone.

She let out a heavy breath of exertion as she looked into the mans eyes, which were as impassive and neutral as they had ever been. He didn't break eye contact a he began to slither the cane up her inner thigh. Neither did she.

He gave the cain a testing tap against the inner thigh, halfway up. Ellen's legs were trembling as much as they were able, situated as she was. Otherwise, she did not react. The cain tapped the inside of the other thigh. She did not react. Then, he began to whip the cain back and forth between her legs with deft and rapid flicks of the wrist. The cain didn't have to room to build up as much speed between her legs, but the blows were fast and concentrated on her upper inner thigh. Ellen gritted her teeth. Neither of them broke eye contact.

I can do this, she realised. I can do this.

As is often the case when you have realised you can deal with something, it got worse. The man leaned in and, with his free hand, took one of the nipple clips and twisted, hard. Ellen cried out, then bit her lip again, pain exploding across her little tit. Despite herself, she felt moisture spring to her eyes as the rapid slapping between her legs continued its interminable rhythm.

Then the cain struck her pussy.

Cleanshaven and unwarned, there was nothing to protect Ellen's naked sex. Every instinct she had was telling her to close her legs, but her knees squirmed helplessly against the bar at her ankles. Her body flexed and her arms bent, rattling the chain as pain exploded through her core. Her nipple and arse and legs and stomach, all forgotten in an instant. There was only her clitoris, and the burning pain that consumed it. A sob racked through her body, and a tear fell.

Again. Again.

He was whipping it now, almost delicate flicks of the wrist. Each one felt worse than anything she could have ever conceived of. The most sensitive part of any woman. It was not long before she was crying. It was not a delicate single tear moment. Her face was screwed up as hot tears streaked down her cheeks, loud cried tumbling from her mouth like song. She struggled as every instinct in her body commanded, but she was immobilised so effectively that she could do little more than jiggle. A finger under the chin. Must keep eye contact must keep eye contact.

She raised her red and teary eyes to those neutral ones, and the caning stopped. Ellen was still crying. It was the only sound in the big, empty room. The man stood there, looking at her a moment. Then, he went to his knees and, one by one, released Ellen's ankles from the straps on the bar. As he did so, her feet swung down limply, the knuckles of her toes scraping ineffectually against the ground. Her hips ached as they were released from their wide stress position.

Then, as she dangled limply, the man went to where the chain was affixed to the wall. It was only when she was lowered that she realised how weak her legs felt. Instead of supporting her, they slowly crumpled as she was lowered inch by inch to the ground. He kept lowering her until she was lying, bruised and broken on the hardwood floor. All of her stung.

Ellen barely noticed when her handcuffs were removed. It was only the man's voice that caught her attention.

"Hands and knees."

Ellen looked up at him through bleary eyes. £2,000, she remembered groggily. She tried to do some maths with that, but couldn't hold the numbers in her head. All there was, was the prize. All there was to do was to earn it. With aching joint and stinking flesh, Ellen climbed up to her hands and knees.

Her head was down as she heard the faint sounds of a wardrobe door opening. Footsteps brought the man back to her. He knelt down beside her. He reached underneath her, and the sting at her nipples redoubled its sharpness. Looking down, Ellen saw a fine linked chain connecting the two ever-present file clips. On the chain was a little metal weight, pulling firmly downward. Her small pale tits were tented triangles, tipped in scalding pain.

Ellen didn't protest. It seemed she had been through so much already. This was all or nothing, and she hadn't endured that caning for nothing. No. It would have to be all.

When the man came around her front, she looked at what he had just retrieved from the wardrobe for the first time. There were three items, and she didn't recognise any of them. The first was a strap with an empty plastic ring in the middle of it. A weird collar perhaps? Next was something that resembled a toothpaste tube, but that couldn't be right. The final thing was the strangest: It was a Y shaped rope. The two ends both had what looked like heavy duty clawed hair clamps, but metal and with heavy springs to hold them closed. The single end had a large metal hook on it, except that it had no point; instead, it had a stainless-steel sphere, about the size of a tennis ball.

A finger peeled gently at Ellen's bottom lip, and she took the cue to open her mouth. The man put the plastic ring of the collar in her mouth and fastened it behind her head, beneath the plats. A gag. The thing was large and uncomfortable. The plastic ring sat just behind her teeth and held her jaw uncomfortably wide. It was already beginning to ache, and a thin rivulet of saliva was dribbling helplessly from its edge.

Ellen was on her hands and knees, obedient and gagged as the man took up the strange device with the clips and hook. Opening the first clip, he clamped it to one of her plats. Then, the other. She was still and quiet as he did it, still unsure what this thing could be for. He moved behind her then, and she didn't want to risk looking back at him. She would have to not know.

That was hard. The suspense and uncertainty had her wincing and tense. She heard a spurting sound; something being squirted from that tube most likely. She felt her braids moving as something was being done at the other end of that Y shaped rope. Ignoring it, she looked straight ahead and sniffed.

A finger stroked up the back of Ellen's thigh. She winced as he passed over raised red welts. The hole in the ring meant she could still make noise through the gag, even if she couldn't move her jaw to talk. The finger traced up, gently, painfully, until it reached the cleft at the top of the thigh. Then, it traced inward. This was inevitable, Ellen thought. This was always what I was getting myself into. The finger circled at the edge of her lower lips, still sore and stinging from the caning. Then, however, the finger went higher, and Ellen felt it force its way into her arsehole.

She jerked forward out of instinct, letting out a shapeless squeal as she did so. That set the weight at her tits to swinging, pulling the nipples so fiercely she thought they might come off. The pain redoubled as he slapped her sore caned arse and pulled on the rope at her hair, forcing her back. His finger entered her again, and this time she did not resist, though she let out a long low groan, and a stream of saliva. She had never had anything in there before.

At first, she could feel her hole tight around the finger, but as the man gently worked it she felt it begin to loosen. As soon as it was loose enough that it was no longer uncomfortable, a second finger joined it, Then again with a third. After what felt like an eternity to Ellen on her knees, three fingers were working their full way in and out of her newly stretched arsehole. She moaned gently on occasion, but didn't move for fear of another slap, or that she would shake her weights again. Or worse than either of those things, that I might not get my money.

Just as Ellen was beginning to loosen to the three, the fingers withdrew. She felt empty and open, cool air making its way inside her. The man pulled at the rope, hard. There was pain, and her head shot backwards, her back arched inwards as far as it would go. The, something cold and hard pressed at her arse.

That metal ball on the hook, she realised as it eased open her hole. It seemed too big, impossibly big, and yet, millimetre by millimetre, her arse yielded to the metal invader. The pressure built and built as it eased deeper and deeper. Ellen whined a long, high whine. Then, as it felt as though she couldn't stretch any wider, the whole ball popped inside her. It felt like a whole fist had been shoved inside her. She made the closed thing to a shriek she could with the gag, and received another painful arse slap for it. Ellen whimpered, and then fell silent.

Ellen stayed as still as she could. Any movement would hurt one way or another. Her back was arched painfully inward by the rope, and if she relaxed it even for a second it would pull painfully at her hair while forcing that great metal ball even deeper inside her. It was all she could do to keep that damned swinging weight still. The throbbing of her little tits had become an ever present, ever painful white noise.

Ellen was jerked back into the present by the press of the man's cock against her pussy. Though it was probably inevitable with all the nipple stimulation, Ellen was still ashamed to realise she was wet. That didn't mean it wasn't painful when he pushed himself inside of her though. Her clit was still sore and tender, and the first stroke felt red hot.

Most of the thrust was slow, but as his hips were an inch from her arse he sped up in an instant. Hips slammed into a wounded arse and caused an open mouthed, salivating shriek. Her weight bounced and her nipples burned. Then the man accelerated his whole thrusts, pushing into her deep and hard and fast. There was no helping it now, the weight was swinging and pulling and tugging, each thrust knocking her head down, pulling her hair and filling her arse.

He slapped her arse. Again. Again. Each slap burned worse than the least. With his other hand, he grabbed the rope and lifted. Ellen squealed as it tightened at both ends, and burning slaps still rained down on her. Not for the first time that day, she began to sob with the pain of it all. Only this time, she couldn't bite down on her lip to help keep it in. The sobs sounded strange and guttural with her wide-open mouth, but the tears rolling down her cheeks were unmistakeable. Tears and saliva mixed in a puddle beneath her chin as she was fucked. All the while, the rhythmic 'Slap, slap, slap,' kept her arse aflame.

It was as though the cain on the clit had dulled it and sharpened it at the same time. It was sore and sensitive, but nothing more. There was a pleasure there, somewhere under all that pain. It was hard to find though.

Another pull on the rope, harder this time. More pain. Another loud sob. A harder slap. Everything was speeding up, getting harder, faster, louder, more painfully. every part of her was aflame. Then, the man slowed. Then he stopped.

Ellen's panting was fast and ragged as she was held still in place by her rope. Her head was held up high, so she had no choice but to watch the door the man had come in through as he calmly walked over to it, and left. He didn't say a word. As she watched the door fall shut, another hot tear rolled down Ellen's red and sweaty cheek. Was that the end? Was he just leaving her here? What happened now? The room was big and quiet and empty with only her in it, immobilised and in pain.

Ellen heard the door behind her open. The staff door. She heard footsteps, and then a man was stood in front of her. This man was tall, wearing a suit. Tony. Gagged and tied, she looked imploringly up at him, and he crouched down.

"We just got the green light from our client," Said Tony, as he reached behind her head to unfasten the gag. "Congratulations." The gag came out with a dollop of saliva. Ellen stretched her aching jaw as Toy attended to the clips in her hair. When they released, all the tension in her back went. It felt brilliant to finally be able to flex her spine again.

"Sorry about this," said Tony as he pulled at the hook in her arse. Ellen let out another little shriek, as Tony tried and failed to remove the hook. "Can you, umm," He started nervously. "Can you push for me please?"

If Ellen hadn't already been red from exertion, she would've gone red with embarrassment. Wearily, she squeezed the big ball out as Tony pulled, and finally the thing came clean with a gentle popping sound.

"There we are. Can you stand?" Ellen wasn't sure. Shakily, she managed to lift herself to her feet. Her arse still felt strangely like there was something inside it; as though it were holding its self open out of habit. Her legs and back were sore and cramping, her skin covered in red hot welts. Ellen opened the file clips on her nipples and removed them together. She thought it would be release, but they had been on so long that the blood rush ushered in a new wave of pain. She gasped as she looked down at her red, stinging flesh.

It was then that she realised there was cum running down her thighs. Tony saw her looking down at it. "Don't worry about that, we have a morning after pill for you. You can have a shower here, then we have some fresh clothes you can go home in." He smiled. "It's done now. The secretary is transferring you your money as we speak. It'll be in your account by the time you get home."

"My money," Ellen echoed softly. She had almost forgotten about the money, forgotten what this whole thing was about. She had made it. She had the money. Her books, her rent...

Everything was going to be just fine.

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9 Comments
middie17middie17over 1 year ago

Excellent! Exciting story, well-written.

msspnnrmsspnnrover 2 years ago

I really enjoyed the writing style. Hopefully you do a second chapter when she goes back for more.

AnonymousAnonymousabout 4 years ago
Very moving

Will she do it again and like it more next time

AnonymousAnonymousabout 4 years ago
Well written

One of the best written stories I have read recently. Easy read with nice details. Hope to see more stories.

AnonymousAnonymousabout 4 years ago
Great writing style

and a good, and slightly different, story line. I would have liked to see her get some reluctant pleasure from the session, but that’s not everyone’s style I know. First one of yours I’ve read so I’m going down the list now. Typos are annoying, particularly ‘cain’ for ‘cane’, though it should probably be the same as ‘pain’ !! Thanks

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