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To Pay Her Debts Ch. 01

By: Whacky



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.

To Pay Her Debts Ch. 02



Lisa rushed home from her first assignment and went to her bedroom wardrobe. Slipping off her dress and pants, she turned to look at the damage in the mirror. The cane or the crop had left red stripes on her backside and the whole area of her bottom and lower back glowed red. Over the next few days she kept examining herself and after a short while, the red stripes turned to dark blue bruises. A few days more and these too had faded, leaving her with just the memory of her assignment. Still her bottom had not been too sore and with £400 off her debts already she thought she could tolerate more next time. But Tom had said he would concentrate on one area. What should she choose next time? Her bottom seemed to be recovering quite well. Her back had born a few blows – could she choose that? He had said 'breasts, cunt or arse'. Also would the marks mean she would have to wear high backed tops for a few days.? The cane and crop had been very painful. Would they break through her tender skin? What about her breasts. They were not particularly large – a 34C bra fitted her well – but they stood up for themselves well without sagging and had quite large prominent nipples. If she chose these, what would Tom want to do? She had seen enough BDSM pictures to know that they could be tied up until they changed colour, or the nipples could be stretched with pegs or clips. What would this be like? She always liked her boyfriends playing with her breasts and nipples. Would Toms treatment also be enjoyable? Finally she considered her cunt. It had quite prominent lips once excited ..... and it had become excited during Toms treatment – could she withstand up to an hour of concentrated action in this area? But it would be so embarrassing to expose herself so intimately. In her present situation £50 was nearly a weeks money, and if she could manage an hour ... and with Tom being so generous last time....?

When a week had passed she made her decision. She texted the single word 'breasts' to Tom and awaited his reply. He arranged to meet her in the same place the following day, and gave no instructions as to what she should wear. So, the next day, she shaved her armpits and cunt as before. She also plucked a few stray hairs from the aureole around her nipples as she wanted them to look their very best. Dressing rather more casually this time, she prepared herself for her ordeal. She was still very nervous walking the few hundred metres to her pick-up, but her nervousness was tinged with excitement. She had already presented herself naked before Tom, so she was slightly more comfortable about exposing herself again. However, the last time she had expected, and received, a bottom tingling experience. This time she could only speculate about what was to occur.

Tom was waiting for her this time, and again wrapped a black scarf around her eyes as she fastened her seatbelt. They drove for a short way with many junctions so Lisa guessed she was still in the town somewhere. She was asked to wait in the car, and heard a garage door being opened. Her seatbelt and blindfold were released and she was lead by Tom into the garage before he quickly lowered the metal door. The garage had a high window down one side and a small door which she thought could lead into the house. The floor had carpet but the walls had various wooden frames and in the middle of the floor was a hard backed wooden chair.

'So, today we are going to concentrate on your breasts' said Tom. 'Do you remember your safe words from last time? I will pay you at least £100 if you can withstand my treatment of them, but please stop me if it is too much – I want to enjoy giving you pain, not do any lasting damage. Please remove your shoes & trousers, and take your top and bra off. You can leave your pants on if you prefer' Lisa nodded and slowly raised her top over her head. She then bent and removed her shoes and her trousers. Finally she reached behind her back and unclasped her bra and added it to her small pile of clothes.

Tom produced a simple felt eye mask and placed it over her head. 

'Can you see anything?' he asked.

Lisa shook her head.

'I'm going to tie you up so you won't be able to move much' Tom said. 'If it gets too uncomfortable, just say "amber" and I will ease or release the ties, though I won't stop the session unless you say "red"'.

Tom gently pushed Lisa back towards a wall of the garage and took hold of one of her wrists, lifting it up and to the side of her head. He took a silky length of rope and wrapped it round her wrist and round a shackle on the wall, before doing the same with her other wrist, so that her arms were now wide open above her head. He then took hold of her ankle and asked her to allow him to move her foot outward. This time he fastened the foot to a wooden bar which had a rope through a hole at each end. He eased her other foot outwards and looped the rope at the other end of the bar round her ankle so that Lisa now had her legs spread wide in front of Tom.

She was now very glad she had been blindfolded as she knew Tom would be getting a view of her freshly shaven cunt through her very thin silky thong.

'So, today we are going to be enjoying your breasts? Let's see just what they are like.'

Tom ran his hands gently over the soft flesh, and his fingers lingered over her nipples. They tightened until he was pinching the nipples quite hard, making Lisa wince in pain. At this Tom didn't squeeze any harder, but continuing his grip, slowly pulled her nipples away from her body until each breast was quite conical in shape. This made Lisa gasp even more and cry out loud. Tom ignored her cries and held the breasts outwards for perhaps twenty seconds before he gently released his grip. His hands then gently stroked the breasts and nipples again, sufficiently hard to maintain the erect state of her nipples, but causing pleasure rather than pain.

Unseen by Lisa, Tom stopped handling her and reached for a short flail whip made with a number of silky strands with a wooden handle. 

'Let's see how they can withstand a whipping, shall we?' he said.

Lisa wanted to say no, but knew that this would reduce her earnings for the session – and she really did need the money.

Tom started gently stroking the strands of the whip across her flesh. Slowly, oh so slowly, he increased the force of the whip so Lisa could hear the ropes of the whip as they hit her breasts. Now Tom added an occasional much harder stroke to the regular flailing. When these harder strokes hit her nipples, Lisa tensed and screamed in pain. After perhaps six or eight scream inducing hits, the whipping stopped and Lisa relaxed into her bonds again.

Once more Tom fondled her breasts and ran his fingers over her now much more tender nipples.

She now felt a clip being attached to each one. Nipple Clamps, she guessed. They felt tight, but bearable.

'I'm going to whip the end of your breasts until each clamp gets knocked off' said Tom. 'Then perhaps we'll try them on again and see how much weight we can add to make them really stretch'

The flailing started again, gently as before at first, before Lisa again experience the harder strokes, this time concentrated on her most tender flesh. It only took three hard strokes before her left nipple was freed from it's clamp. As this occurred Lisa grunted in pain. The right nipple then received five blows, before it too was released and the clamp fell to the floor.

Lisa found her arms were getting tired and the bonds around her wrists very tight as they took some of her weight. Her nipples felt stretched and sore and she wandered whether to use a safe word, at least to get some respite. But Tom seemed to anticipate her needs because she felt her wrist ropes being released, and then her ankle restraints. He also removed the eye mask and Lisa blinked as the unaccustomed light

'Take a moment to rest' said Tom. 'You are really coping very well' 

Lisa stretched and flexed her arms and straightened and flexed her legs and Tom guided her to sit in a hard wooden chair. Lisa rubbed her breasts to try and alleviate the pain in the nipples.

After all too few minutes rest, Tom asked Lisa to stand up. This time he leant her body forward, so that her head and shoulders were resting on the seat of the chair. Once more Tom attached the clamps. This time each clamp had an empty plastic bottle, hanging straight down from is on a short piece of string.

'I'm going to slowly add water to each bottle' said Tom. 'You can stop the water being added at any time by saying "amber" but otherwise I'm going to continue adding weight until the clamps fall off. If you can manage that I'll add £50 to the money you receive.' 

Tom poured a small amount into each bottle, then slowly alternated between each one until there was almost two inches in each. The weight of this was just too much. Lisa gasped as the clamp pulled on her left nipple as the bottle fell. Her right nipple was now being really stretched, as Tom added more and more water. Lisa moved her body to swing the bottle and try and persuade the clamp to release – she really couldn't take much more – but Tom stopped the bottle swinging. Why was this clamp so much tighter than the other? Tom trickled more water until the bottle was nearly half full. Suddenly it fell, and Lisa screamed again as the pain of the release scourged through her poor right nipple.

'Well done,' said Tom. 'You should be very proud of yourself for withstanding that so well. You really are the most perfect masochist.'

'Thank you' said Lisa, as she straightened herself upright again, although really she wondered if her nipples would ever recover.

'You can sit down in the chair now' said Tom. 'I wonder if you breasts are large enough to be bound? There's only one way to find out'

He took a length of red cord and wound it tightly round her left breast. He was clearly dissatisfied with the result because it was unravelled again and wrapped it again more tightly before tying the two ends in a reef knot. He repeated the same process with her right breast, this time getting the tension right first time. Standing back to admire his handiwork Lisa noticed his look of admiration as slowly her breasts turned to a darker red colour, exacerbating the redness from the beating they had already received. By the time about ten minutes had passed, her breasts were turning purple. She watched as Tom struggled to untie the two knots and restore circulation.

'Considering your breasts are quite small they were still able to get knotted up very nicely. I love the look of your tightly bound breasts. We might return to this exercise on a future occasion, perhaps with some extra exciting changes. For example, I wonder how far I can stretch them away from your body? We'll leave that for now as I think they have had enough stretching and beating for one day. There is one more thing I'd like to try befre we call it a day'

Lisa massaged her breasts gently as she felt the blood tingling back through them again.

'For your final experience today I'm going to cover your breasts in wax. You'll be able to watch and hopefully anticipate the pain or pleasure that each droplet of wax will bring as it falls from the candle' Tom explained.

He asked Lisa to lay on an old sheet covering part of the floor of the garage and reached for a pair of red candles on a nearby shelf. Using a lighter, both candles flickered into life. Lisa watched as the flames on the candles grew higher. Tom took a cande in each hand and lifted then gently so they were above her chest. Whn a sufficient pool of wax had grown on each one, he tilted first one and then the other, so that the wax droplets landed on Lisa's chest. Tom waited as the wax pool grew on the candles again, then brought the candles lower, so they were only about a foot above her breasts. Aiming for the nipples, he poured the small pool of wax onto each in turn. This time the wax felt really hot. Lisa flinched, squealed and moved her body to avoid the worst of the assault, so some of the wax ran down her side onto the sheet. 

'Was that too much?' asked Tom. 

Lisa was surprised, as Tom never normally seemed too concerned about her reaction.

'It was just the sudden shock' said Lisa. 'I'll try and stay still for the next one'

Tom was equally surprised that Lisa was showing such fortitude and seemed to be almost enjoying the experience. 

Tom lifted the candles rather higher before pouring a third little message of wax onto her body with each candle. Either this was less painful or else Lisa was now getting accustomed to the hot droplets. So the waxing continued until almost the entire nipple and sides of each breast was covered in the cooling red candle wax.

Once it had completely hardened, Tom helped Lisa back to her feet, trying to keep the red covering intact. 

'It's not part of the deal, but that looks fantastic. Can I take a picture of them? asked Tom.

Lisa paused for a moment, and then shook her head.

'I don't want anyone to know about this and I'm frightened somebody might see the picture and recognise me' she said.

'Not to worry' Tom replied. 'I'll just have to remember the fantastic sight of you with red tits. Leave the wax on them and get dressed. You can take it off at home as a reminder of your time with me.

Lisa eased on her bra and then the rest of her clothing. Tom took out his wallet and counted out five £20 notes. 

'This is for you, as you've done so well again. I'll pay you another £200 into your debt account as agreed. If you are ready we'll pop on the blindfold again and return you to the car park. I look forward to seeing you again. The bits we have left to work on mean that we'll have to get more intimate next time. Send me a text next week when you are ready.'

Blindfolded, Lisa was helped into the car. She arrived back at the car park, and, released from her blindfold, she walked slowly home. What would Tom think of next? Getting more intimate? That could only mean one of two places. Still, with another £300 off her debts she was over a quarter of the way towards the £2500 that she owed. But could she withstand whatever Tom would want to do next? Well, he did say she had a safe word to use if necessary, and Lisa had never used it yet. She would just have to wait and see.



To Pay Her Debts Ch. 03



Lisa passed through the doorway of her flat and stood before the mirror in the bedroom. She eased off her top and unclipped her bra to view what Tom had done. Some of the wax was already coming off but her breasts still looked outrageously prominent with their red covering. Should she have allowed Tom to take a picture? Using her phone she took an image of her reflection. She could always relent and send it to Tom. No wonder Tom had wanted to do the same – they did look pretty good. However, with bits of the wax falling everywhere, she laid out a towel on the floot. Leaning over, she peeled the wax from her breasts until they were almost back to normal. There remained red marks and blue bruising in the places to mark where she had been whipped. She could also feel a dull ache around her nipples. This ache was to remain and only wear off when several days had passed.

Tom had said to text her next week when she was ready, but he had said the next session would be more intimate. That could only mean her cunt, or possibly her arsehole would be receiving his attention. He had said he wasn't going to have sex with her? So what could he do? Perhaps he would treat her cunt flaps to the same stretching as her nipples? Would he try to insert things inside her? It would still be embarassing to have his eyes so focussed on her most private places. She was very unsure whether to procede. In a sense she liked being told what to do. The money she was receiving gave her an excuse to allow her body to be misused. The last session had certainly been painful, but had left her with mixed feelings of real excitement, fear and arousal all at the same time. 

More than a week went by and she was still unsure whether to procede. The decision was really made for her when Tom sent her a short text. "Are you ready for more?" She felt she had to respond, and deliberated for some time. The money was good, and Tom had not done any pemanent damage. Indeed the dull ache she had felt for a few days after the last session had almost been a welcome reminder. After half an hour of agonising she replied with an "OK".

Tom was back very quickly. "Looks like a good forcast for the afternoon tomorrow. If you are free, you can make your money outside again. I'll meet you at the usual place at 14.00." So, the scene was set for her third encounter, and Lisa could hardly contain the mixture of excitement and trepidation she felt.

After the same preparations as before, Lisa met Tom as arranged the next day. Once belted and blindfolded, she was driven away. When the car stopped and the blindfold removed, Lisa realised she was probably at the same place as on her first session. Tom said that the mud had now eased and they would not need boots. He picked up a holdall, and taking a zipped up bag in his other hand they made there way to the hidden clearing in the woods. It was a beautiful day and the sunlight filtered through the trees onto the warm sheltered mossy glade, with the old dead yew tree in the middle.

The two bags were placed together on the ground and Tom said.

" The same conditions apply. You have a safe word to stop procedings and one for a pause. However, you have shown that you can withstand pain and I am sure you won't need them. I'm going to try and put you in control of what happens today, and the money you can earn will depend upon what you manage to achieve. Firstly, you must remove your clothes. With all this sunshine you may even start to achieve an all-over tan."

Lisa slowly removed her top then unclipped her bra, placing them beside the bags. She then stepped out of her shoes and trousers and finally her thong. She stood with her hands by her sides whilst Tom looked admitingly at her naked body.

'Beautiful' said Tom. 'I think I may as well take advantage of the sunshine as well'

With that, Tom removed his shirt to show a tanned chest with quite a mass of short dark hair. He then removed his shoes and took off his shorts to reveal his cock. 

Lisa couldn't help looking, though she tried not to let Tom see her doing so. His cock was hanging down at an angle from his body, semi hard and uncircumcised. Lisa had seen cocks before, but never before one which had no hair around the shaft or balls. She did not feel she could make a comment about this, so remained silent and obedient.

'Right' said Tom, 'to business.' 'I said I would try and give you control over the money you make today, so I am going to set several little tasks. The better you perform these, the more money you will make.''In the holdall are a few samples from my allotment. Open it up and see what you find.'

Lisa went over to the bag, being careful not to bend with her back to Tom so that he could see her bottom as she did so. Opening, it she took out a long, straight yellow gourd which looked about penis sized, but with a very large bulbous end. There were also seven green courgettes of diffent sizes.

'I want you to put the courgettes into size order' said Tom. 'Then I want you to sit down and spread your legs wide open in front of me and put a courgette up inside your cunt as far as they it go.' I will pay you £1 for the smallest one and then double that for each bigger courgette, so that if you can manage the biggest, you will get £64. Having tried them in your cunt, you can then use them in your arse. I will pay you one and a half times more for that, so if you can get the largest one up your arse, you will get £100'.' You will find a tube of lubricant in the bag as well.' 

'If you look at the long gourd, that has numbers marked every centimetre or so . Each number represents the amount of money you will receive if you can prove to me that number is embeddeed into your cunt. So the deeper inside you can get the gourd, the more money you will receive. At 15cm, or 6 inches you will get £20, but if you can manage 20 cm, or about 8 inches you will get £70. The numbers do go even higher if you can cope with that. I will pay you a similar amount if you can get it into your arse in the same way. 

Lisa was horrified. She had not imagined that something like this would happen. The small courgettes looked very manageable, but she knew that she would not be able to cope with the largest. And to have to do this in front of Tom. How degraded she would be. She could feel herself getting excited at the prospect. No one else need know, and after all, she was doing it for the money.

So, Lisa sat onto the mossy ground and reached for the tube of lubricant. Spreading her legs, she squeezed the lube onto the lips of her cunt, and then put more onto the smallest of the courgettes. She rubbed her clit gently and then more firmly for a few minutes, not caring about being seen to masturbate in front of Tom. Easing apart her cunt lips, she nosed the courgette gently into her vagina, and continued pushing until it was firmly embedded and she could only hold one end. She pulled it our ready for the second. This was slightly shorter and only a little fatter. She didn't worry about lube for this one and again squeezed it inside her cunt with ease. The third was rather longer, but she still managed to get it inside her until a bend in the vegetable stopped its progress. The fourth and fifth looked about the diameter of a penis. She lubed these up more carefully and also rubbed her clit again for a while. Slowly, she managed to push first one and after removing that, the larger into now well stretched cunt.

The final two looked a much more daunting proposition, but if she was going to make any money from this exercise, she would have to manage at least one of them. She lifted her knees higher and looked up at Tom. He was staring at her, open mouthed.

'Well done so far, Lisa. That's quite a show you're putting on there. I'm looking forward the the last two.'

The sixth courgette had quite a curve, and it really stretched her cunt apart as she eased it into the opening. She twisted it round and back a little as it forced her lips apart. She then pulled it out, but Tom said that it would have too go further if she was to receive her reward. Adding yet more lube, she tried again. Grunting with pain, she inserted the giant dildo sized vegetable about four inches into her cunt.

Tom said 'Well done'.

Lisa took that as her cue to remove the courgette, but not before noticing that Tom was showing his enjoyment of the procedings all too obviously.

'I don't think can manage the last one,' said Lisa. 'The sixth one was too big. I might have a try with it at the end'

'Try the gourd next, then' said Tom. 'After that you can try your sexy arsehole for size'

Lisa took the gourd and squeezed lube on the tip and along its length. She had used nearly half a tube already. Taking the fatter end in both hands at first, she nuzzled it up to her cunt lips. Spreading these apart with her fingers she started sliding the long vegetable inside. Tom knelt down and peered short sightedly at the progress that she was making. She reached the £6 mark quite quickly and then squirmed on her bottom and she very slowly twisted the gourd in deeper. She laid her body back on the ground and kept gently pushing away, aware that Tom was now only inches from her cunt. She could no longer see the numbers as the gourd eased its way deeper inside. Lisa grunted with pain and pulled the gourd back slightly, tried once more and then quite quickly removed it.

'How deep did it go?' asked Lisa.

'Nearly seven inches' lied Tom. 'You must have a very deep cunt. Lets call that £60 for trying so hard'

Lisa decided that she would have another attempt and asked Tom if she could try it again. 

'Of course' said Tom. ' I did enjoy watching your last effort'

Lisa didn't like to say, but she had actually quite enjoyed displaying herself so intimately to Tom. She had not expected to enjoy being an exhibitionst quite so much.

She laid herself down on her back again, and eased the long protuberance into her cunt. She twisted it very slightly from side to side as it went deeper. She then started to move the gourd gently in and out, each time managing just a few millimetres more, before with another grunt of pain, she pulled it back from her now very stretched opening. 

'How far that time?' she asked.

Tom lied again, to encourage her 'Just over seven inches, so even further than last time. It looked just fantastic. Next time we meet I think I'll pay you to masturbate in front of me.' 

Lisa was shocked and excited to hear that. Displaying herself so wantonly in front of Tom was surprisingy easy and she did enjoy watching his reaction. Would she be able to bring herself to orgasm with him watching?

'Now, have you ever tried putting anything inside your arse before?' asked Tom. 'The best way is to slowly increase the size of what goes in there, so it stretches to fit. I'm sure that with lots of lubrication you'll be surprised with what it will take. Make sure you hold the end of each courgette though, because otherwise your bum will swallow them inside and you'll have to shit to get them out again.'

Lisa was shocked and excited by what she was being told. Did he really want he to try and put things inside her bottom? Tom was obviousy vey much enjoying watching Lisa display herself so intimately. In turn, Lisa was actually quite enjoying being told what to do and being forced into performing such degrading acts in front of Tom.

Tom handed her the smallest courgette. Lisa turned onto her side and bent her legs slightly. She put more lube onto the green shaft and teased it gently round her arsehole to make the edges good and slippery. Pushing the vegetable gently, she was surprised when after a short effort it popped past her sphincter and almost disappeared into her arse. She was just able to retain a hold on the end.

'Well done' said Tom. 'That looked quite an easy way to earn £1.50' Try the next size up now.'

Lisa pulled the courgette out and took up the next that Tom passed to her. This one was only a little fatter and much longer. Again, after some hesitation whilst pushing against her sphincter, the courgette was quickly swallowed up inside her arse, though this time Lisa kept rather more sticking out.

The third courgette was considerably fatter. Lisa twisted it round and eased it backwards and forwards, before deciding to try and keep a steady pressure. She could make no progress for a long time, but then, with just a small extra push, the green tube went inside. That was £6 she had earned. If she could get the next one in, it would be worth double that.

She put some more lube onto her fingers and, not caring for Tom whose nose was very close to the proceedings, spread more lube around her arse and even poked a finger up inside. Taking the fourth courgette she pushed it into the crack between her legs and pushed steadily as before. The edges of the vegetable felt very sharp against the sides of her arsehole. She continued, twisting the courgette backwards and forwards. After struggling for nearly a minute, she pulled it back. 

'I don't think it will go' she said.

'Never mind,' said Tom. 'Do you want to try again?

'All right' said Lisa.

She pushed the courgette against her sphincter again. But no matter how hard she tried, she could not make it go into her bottom.

Tom said 'No worries. If you want to do better next time, try plugging your bum with things of increasing size back at home and see if it will stretch it. Slowly you will be able to take more. I'm sure your boyfriend will appreciate that, when he decides that he wants to use your ass instead'

Lisa didn't have a boyfriend at the moment, but wasn't going to tell Tom that.

Tom said 'You've earned about £100 for your wanton display so far. I'd now like to try and put your cunt lips through the same trial as you nipples experienced last time. Stand up, put your legs apart and put your hands behind your head.' 

Lisa did as she'd been asked. Tom went to the other bag. He took out a couple of black and silver metal clips of the type that are used to hold papers on a clipboard. He knelt down in front of Lisa and pulled her right cunt flap downwards and slightly outwards with his fingers. With the other hand he gently attached the metal clip, so that quite a long and thick section of her flesh was clamped between the blades of the bulldog clip. He then took hold of her other lip and did the same, so that the two clips rattled together as Lisa trembled slightly, not so much with the pain as with trepidation. She knew what was likely to happen next. Tom took a short stretch of elastic strap, which had a hook at each end. He attached one end of the strap with the hook through one of the handles of each of the clips on her flaps. He put a large, empty, five litre plastic container on the ground between her legs.

''Right' said Tom. 'I'm sure you've seen a snatch lift in weightlifting. I have a real snatch lift for you to try. I'm going to put water into the container and then you will bend your knees, we'll ll hook on the container, and you will lift it up. The more weight you can lift, the more money you will get.'

Tom poured about an inch of water from another bottle into the large container. He then told Lisa to bend her knees He took hold of the hook at the end of the strap and hooked it through the large container. 

'When you are ready, straighten your legs. I suggest you do it as slowly as you can. We don't want you damaging your back!'

Lisa did as instructed and the weight stretched her lips, before the container swung free of the ground.

'Keep going' instructed Tom.

Lisa straightened her legs until her knees were locked. Once this had been achieved, Tom lifted the container upwards and released the hook.

He added another inch of water to the weight, and Lisa squatted down once more for Tom to make the attachment again. This time, very slowly, she straightened out without needing further encouragement from Tom. She could not see the lips of her vagina, but Tom was all too obviously enjoying the sight of their distended appearance. 

Lisa lowered herself again. Tom lifted the container free and poured yet more into the bottom. Lisa sqatted down for the third time and Tom hooked her up to the container. She slowly straightened up again, but before she could do more than raise the water off the ground she quickly squatted to take the weight off her poor, abused cunt lips. 

'Try again' urged Tom. ' You look really sexy when you are straining and in so much self inflicted pain.'

With this encouragement, Lisa attempted the third weight once more. She screamed in agong as her lips were stretched to the limit, but still managed to straighten her legs, before very quickly bending them back again to rest the weight back on the ground.

'I can't take any more' said Lisa. 'Surely you've done enough for one day now?' 

'Yes' said Tom. 'You should be very proud of yourself. Though after that last scream we may need to try a gag next time. Perhaps next time I could try making you lift a bag of coins. Then you could get to keep all the money you can lift. Now that would be fun!'

Tom asked Lisa to sit down and he released the clips from her vagina. As the circulation returned to her lips she groaned and rubbed the area between her legs. She looked down but although her lips looked red and stretched, she could see no lasting damage.

Tom said ' You have made me feel so horny, Lisa. Your sexy show has already earned you £200 for the exercises you have completed today. I loved looking at your naked body in such pain and so openly displayed.. I'm going to have to masturbate not to release the ache in my balls you have given me. You can have an extra £30 for me to come on your face. If you scoop it all upp with your fingers and swallow it, you can have another £30.'

Lisa nodded, unable to find words to express what she was feeling. It would be so degrading to watch him, though his erection had been on open display since the start of the session. The to have an older man cum on her. How shaming that would be?. She didn't like swallowing cum. Would that be worth £30?

Tom proceeded to run his cock in front of her, and after a very short while moved it closer to her face. Breathing heavily now, Tom moved close to her and sprayed the cum from his penis over her face. Lisa closed her eyes and mouth. Tom stood back to admire his handiwork and Lisa slowly opened her eyes. Slowly she raised one hand to her face. She scraped her fingers over her cum stained forehead and cheek and placed each finger in turn into her mouth, sucking the cum from each as he did so.

'You still have some on your chin' said Tom.

She ran her fingers over her face and chin and again licked them off.

'That looked great' said Tom. 'If you've finished cleaning up we'll head back now. '

He pulled on his shorts and top. Lisa took this as a cue to do the same, and she also took the opportunity to use the inside of her top to wipe over her face.

Tom gather up his allotment produce, together with the now nearly empty tube of lubricant and put them back in the holdall. Emptying out the water from the containers, he put these away as well, togther with the clips and strap. With a last look round to make sure he had collected everything, he lead the way for Lisa back round the screen of dense holly that protected them from prying eyes and up the path back to the road.

Back at the car park Tom again said how much he had enjoyed the session and told Lisa that she had earned £300 off her debts from the hour or so they had been out in the woods together.

'I will enjoy deciding what we will do next' said Tom. ' I hope you'll enjoy it too'

Lisa wasn't sure just what she felt. It wasn't perhaps enjoyment, but she did feel excited and like a moth in a candle, she knew she would not resist whatever Tom asked her to do next. She was now £1000 better off and after only three sessions. Though her bum hole felt a bit sore and her cunt lips had been stretched, she didn't feel the pain had been as bad as her very first session. What would Tom want to do next? She would just have to wait and see.