To Pay Her Debts Ch. 01

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Debtor is offered an unusual way to pay her debts.
2.5k words
4.25
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16

Part 1 of the 3 part series

Updated 09/22/2022
Created 01/25/2013
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Whacky
Whacky
12 Followers

Lisa looked sadly at the financial statement she had drawn up. Income - £67 per week on her jobseekers allowance. From this she had to find her food and clothing, water, gas and electricity. It was impossible. She had never been very good at budgeting and now she was in a crisis. Why had she approached Wonga for money? It had all seemed so simple at the time. A quick phone call, a few questions and the money was into her overdrawn account in just a few hours. But when her next benefits cheque arrived and she could not afford the repayments, the problems started. And she owed money elsewhere. She totted up her total debts. Nearly £2500. She had to seek help.

Later that day she met Tom, a recently retired ex neighbour outside Fareham jobcentre. He chatted about what she was up to now and in her usual way, Lisa confessed her problems to him. He seemed sympathetic. They parted on good terms and Lisa went on her way to buy food for her evening from the market. Did she have enough gas left to cook? Better not risk it..

Next day she awoke to find an unstamped letter from Tom through her door. It said there could be a possible solution, but they would need to talk it through. Lisa contacted the number given and they agreed to meet up that evening in a local bar. After a general chat, Tom launched his proposal. Lisa was in debt. Tom was a wealthy man. Tom said he was not really interested in sex. He could get that from his wife. However, he had always been excited by the prospect of putting an attractive young lady such as Lisa through some training exercises. These could involve spanking or caning on her naked or semi naked body, torturing her breasts, nipples or cunt lips, or intruding on vagina or anus. Lisa had a nice plump rounded bum, which looked ripe for a spanking. How about if he paid to allow her body to be used? Lisa had always enjoyed spanking games with her boyfriend, but had obviously never thought of being paid for it. The thought of being spanked, caned or sexually tortured by a man old enough to be her granddad both revolted and excited her. She really couldn't take it all in as he suggested the practicalities to her.

He would pay money, not to her, but directly to her loan accounts. That way she could continue collecting her benefit and looking for employment. However, it was the way his tariff would be constructed that most intrigued Lisa. If she were to be naked she would get the rates suggested. If she kept her panties and bra on, the money would be one third of his proposal. Tom suggested a rate of £1 per stroke a light hazel switch or light multi tail flail whip, £2 per whack with a table tennis bat or plywood bat, and £5 per stroke of the cane or riding crop. After she had received 50 blows, these rates would be doubled, if she could withstand the pain. For hurting her breasts, nipples or 'games' with her anus or vagina, she would be paid at the rate of £50 per half hour. Tom suggested that he she select one part of her body as the focus of his activity each time they met. Tom also suggested that for her safety they use red/amber/green safe word system as at the fetish club he attended. Red would stop everything whilst amber would call a temporary halt to proceedings, with a chance to review why she had asked for a pause.

Lisa could hardly believe her ears. Her emotions were a complete mess, torn between excitement at the possible torture, the fear at what she would go through and revulsion at the prospect. Tom added that he would enjoy some proceedings out in the open air, away from prying neighbours and with the added frisson that they might be discovered.

Tom bid goodnight and left Lisa sitting at the bar considering her options.

Two days later the arrival of an unpleasant debt collector at the door precipitated her action. Once she had got rid of the bailiff she texted Tom with the single word 'yes'. Minutes later a return text appeared ...'Tomorrow 11.00 outside Wallington Village Hall, wear stockings' Lisa giggled as she wondered what Tom would say if that was all she wore, but then started to think of her outfit. She decided on a knee length full pleated black sleeveless dress with a jacket top and a pair of black heels. Beneath it she wore a lacy black bra but chose a pair of boxer knickers -- if she was going to keep them on she wanted some protection for her bottom -- should she perhaps try two pairs? The only stockings she had were hold ups -- she found they had a short ladder, but they would have to do. She was in no position to go and spend yet more money. That evening and night her mind was in a turmoil as she anticipated the next day. Her heart thumped in trepidation.

In the morning she prepared with extra care, taking a long shower and shaving her pubic hair afresh. She still had not decided whether to strip completely for Tom, but at least she would be well prepared. Slipping on a coat as the morning seemed colder than expected, she walked the few hundred metres to Wallington Village Hall. Tom was already waiting in his car for her and greeted her cheerfully. How could he seem so calm and relaxed? He made sure she was belted in safely, then took a piece of black cloth and bound it around her eyes. 'Can't have you knowing where we're going, can we?' he said.

Lisa tried to remember her route by the movements of the car, but after only a short while she was completely disorientated. The car soon bumped to a halt on a rough verge, and Tom released Lisa from her belt and removed the blindfold. He also took out a pair of boots for Lisa and put on a pair himself. He put their shoes into a holdall, which had a length of plastic drainpipe across the top, sealed with tape at each end. Together they walked down the road for a short distance, before taking a narrow path into a wood. The path grew increasingly muddy, and Lisa staggered to keep her footing as they walked deeper into the shade. After only a short distance, Tom lead her away from the path, past some low holly and down to a tiny stream. Thank goodness her stockings were not a new pair, thought Lisa. A steep bank uphill and they were in a small clearing with a bright green mossy floor, surrounded by dense holly and shaded by a huge oak tree. In the middle of the clearing were the stark remains of a yew tree, now bare of any vegetation

'Right' said Tom. 'To business. Take your coat and dress off please. You can also remove the boots'. Lisa slowly raised the dress and folded it neatly on the ground beside her. She then took off the boots and her feet were cooled by the damp moss beneath. 'What have you selected for today?' asked Tom. 'My ...... bottom, ' Lisa whispered, almost too afraid to speak. 'And would you like to earn more by being naked, or would you like to keep your bra, pants and stockings on' he asked.

Lisa had not decided what she was going to reply to this question. She was standing a secluded glade in a forest. She had never been naked in the open air before. 'Could I just take my bra off and leave my knickers on, and get three quarters of the money?' she asked. Tom laughed and burst into a line of song from Oklahoma '"With me, it's all, or nothing, is it all or nothing with you?" No deal, but the original choice still stands. What is it to be? Butt naked or bra and pants?. You can keep the stockings on.' Lisa had no idea what she should decide, but in her excitement, her hands moved slowly to the clasp of her bra, and she slowly unclipped it and let it fall to the ground. Covering her breasts with one arm, she turned her back on Tom and lowered first one side, then the other of her knickers, before using both hands to ease them down and step out.

'Right, bend over and rest your hands on the tree' said Tom. Lisa did as she was told, but Tom was dissatisfied with her position and asked her to raise her bum higher into the air. 'Spread your legs wider' he instructed. 'Comfy? Good, then we'll begin'

Ripping the tape from the end of the plastic tube, Tom removed the items concealed inside by tipping the contents onto the ground. 'We'll start with these', he said, taking out a light hazel switch and a flail made with a wooden handle and what looked like a cluster of thin nylon ropes. The switch whipped through the air and landed with little noise on Lisa's naked behind. Nine more followed, with a pause between each strike.

' That's £10 you've earned then' he said. Lisa was surprised that, though the hazel looked intimidating, it's light weight had caused sharp sting but nothing too severe. 'We'll move on to the flail whip now'

Tom wielded the flail onto her bottom and backs of her thighs, then onto her back. Lisa thought that her bottom was to be the only target today, but was relieved, as the blows on her back were less painful and at least, they provided some relief for her reddening arse cheeks. Though the flail, like the hazel, did sting, its impact was quite bearable. '£20 off your debts, well done. Now we'll move to the more serious stuff. I want you to count the strokes of the paddles, so you can keep track of how much I owe you' he said.

Whilst the whip and cane had been quiet, the table tennis bat made a hefty thwack as it landed on Lisa's cheeks. Though Tom paused between each stroke Lisa said little at first except to whisper a number. As the pain in her cheeks grew, she began to cry out on each stroke. Switching to the plywood batton, shaped like a short cricket bat, Tom continued the beating. After ten strokes with each, Tom stopped and asked Lisa to stand up straight.

' Well done, you've earned £60 so far. We'll give you a two-minute break and then move on to the serious implements. Don't forget your safe words, and in ten more strokes, the money you earn each strike will double.'

Lisa was already beginning to tremble, whether from fear and trepidation about what was yet to come, or from the beating she had received so far, she was not sure. Tom told her to get back in position -- surely two minutes could not be up so soon - and took up a blue riding crop. At first he used this fairly lightly, but Lisa found this more painful as the leather tip of the crop reached round her butt cheeks to give a sting in the tail of each blow. After five fairly gentle blows of the crop, Tom moved on to the cane. Her bum was getting sore now and she shouted with pain at each blow, no longer remembering to count.

When the caning stopped. Lisa was amazed to hear that she had only received five cane blows, and Tom said he had been very gentle with the riding crop. Gentle? What would it be like to be hit properly? He asked Lisa to stand again and if she wanted to continue. She had £110 towards her debts. It didn't seem like much for the pain that she had so far endured.

'From now on the stakes are much higher. Shall we set £200 as a target for the first session?' Tom asked. 'I have one more implement that I have not yet shown you. It is more extreme than anything you have experienced so far, but should speed up the progress towards clearing your debts. Before we move on to that, I'd like to warm you up a bit more.'

With that, Tom asked if she wanted to continue. Lisa was now trembling and apprehensive, but was also almost excited about the pain she had so far received and withstood. Without replying, Lisa turned her back on Tom and slowly bent over once more. Ten harder blows with the riding crop had her reeling and screaming in pain and she struggled to maintain her position. Her bottom was getting very raw now and again Tom called a halt to assess the situation.

'Right, I' show you my secret weapon. You can stop now, carry on with the cane or riding crop or move to this'

'This' was a short length of wooden carpet gripper, with a handle of gaffer tape wound round one end.

'If I use this on you, your bottom will undoubtedly start to bleed as the spikes bite into your soft flesh. Shall we say £50 for each strike, I will try and aim for a different area of your bum each time'

Lisa looked closely at the wooden implement he held before her. It didn't look like the blows would be very hard, but the spikes looked evil. She shook her head and said 'I don't think I can take any more. I've never experienced anything like this before.'

Tom didn't question her decision and put his arms around her, saying that she had managed very well and that he was impressed by her fortitude. He picked up her clothes and held them in his arms whist Lisa slowly, with trembling hands pulled on her underwear and dress. Squeezing her stockinged feet into the boots, she waited whilst Tom packed up his implements. Slowly, following Tom, she staggered up the hill and along the road to the car. After sitting down gingerly, on went the blindfold, and Tom drove her back to the same spot she had left. It seemed like many hours had passed but they had been gone less that two.

'You've done well today' said Tom. 'If you'd like to continue I'll pick you up again at the same time next week. Shall we say £300 for today's effort?'

Lisa knew that this was much more than the total she should have earned, but just agreed that this would be enough.

'To give your bum time to recover, I suggest that we work in a different way with a different area next week. Let me know by text which you'd like to choose.

Off went Tom, leaving Lisa in a complete turmoil of emotions.

Whacky
Whacky
12 Followers
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4 Comments
AnonymousAnonymousover 7 years ago

Plleeease make a chapter 2!!

AnonymousAnonymousover 10 years ago
This sets the stage for a wonderful continuation.

It will be exciting to see how this continues and evolves.

Miss_JenniMiss_Jenniover 10 years ago
a warm feeling

a lovely and warm story about a true masochist slut

AnonymousAnonymousabout 11 years ago
Very HOT

Loving this story. It is so hot can not wait to see what happens next.

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