To Pay Her Debts Ch. 03

Story Info
Lisa submits to some intimate intrusions to earn money.
3.8k words
4.27
49.5k
9

Part 3 of the 3 part series

Updated 09/22/2022
Created 01/25/2013
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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
Whacky
Whacky
12 Followers

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.

Whacky
Whacky
12 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
AnonymousAnonymousalmost 10 years ago
Keep on Going!

D4D7his is a fun, yet erotic, series! Hope you will consider further money-earning trials for Lisa with her endurance of various enemas, sybian/vibrator orgasms and various strenuous bondage ties against time durations, reactions to various types of whips, paddles & belts, pony girl challenges, and electro and/or breath play, etc. - all sorts of tests for her to earn more cash to pay off the rest of her debt! Maybe even invite Tom's wife and a wealthy friend to also play with her. Great continuity between the chapters so far - keep it up!

SubSandySubSandyover 10 years ago
when is part 4 coming out?

This has been great! I really want to see more

AnonymousAnonymousover 10 years ago
sweet!

I felt you could have put all this into part 1 and it would have been a successful introduction. I wanted to read more breast bondage but you flew over it with candles.

I like the story and your writing but it was a bit rushed :-).

AnonymousAnonymousover 10 years ago
More is sometimes less

The excitement here is that she is told she is getting more control whilst actually it is revealed in the end that she is getting less. I envision her juices flowing from her womanhood and running down her elastic labia to form long droplets that increase in size before slowly falling to the floor and form a small puddle.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Accidental Gangbang Wife-to-be ends up fuck-slut at her fiancé's bachelor party.in Group Sex
My Wife at the Holiday Party Wife plays party game with her husband's coworkers.in Loving Wives
Filling up Amy Devoted wife will do anything for hubby.in Loving Wives
Jennifer, the Cumbucket 19-year-old nearly drowns in cum.in NonConsent/Reluctance
Wife's Fantasy Threesome Wife finally gets the threesome she's always wanted.in BDSM
More Stories