Sy Pays the Rent

Sky woke to the front door being closed, it took several moments for her mind to clear, she was on the sofa and the TV was on. I fell asleep on the sofa she thought to herself, after a moment she looked over at the clock, it was 2:42pm, SHIT, she thought, but it was too late, Rob was standing in the doorway looking at her.

'Well, you have been very naughty, but at least you are trying to make up for it by giving me a good view,' he said with a smirk on his face.

Sky looked down, the gown she was wearing, the only thing she was wearing, had fallen open while she was asleep, and she was fully exposed. Sky quickly wrapped the gown back around herself.

'You fucking pervert,' she spat at him!

'That will add a few extra,' he mumbled to himself.

'A few extra what?' she asked, suddenly feeling nervous.

Rob was looking around looking a little absent minded, and said, 'what?' still distracted.

'A few extra what?' she said again.

'Oh, lashes,' said Rob as if that explained everything.

'Lashes? What the fuck are you talking about?' she said as she tied up her gown properly and started to get up.

'Yes, don't be going anywhere, you need to assume the position,' Rob said far more focused now.

'You can fuck off,' said Sky, making to leave.

'If you walk out this room, you can pack your stuff and leave the house,' Rob said quite forcefully, then added, 'You agreed that while you were not paying rent with cash, that you would be punished when you were naughty, and you have been naughty!'

'But...but...you can't be serious?' Sky sputtered.

Her arse was still a little uncomfortable from last Friday, it was Tuesday, and she had hoped it would only last a day, but it hadn't, the tops of her legs still felt it when she sat down.

'I am deadly serious, you agreed, and I intend to see it through, we will turn your lazy ways around,' Rob sounded more normal now, but the tone of his voice indicated he was completely serious.

Sky thought for a moment, but she agreed on Friday because there was no choice, and there was still no choice. She slowly got into the position that Rob had required on Friday, legs about a meter apart, and straight, bent at the waist to 90 degrees and her hands on the coffee table.

'I will get you back for this one day,' she said, 'this is humiliating, and for the record I am doing this against my will!'

'You are free to leave,' Rob said, 'it is your choice to accept this way forward.'

Rob looked at her for a moment, then said, 'lose the gown, I am just going to grab something.'

He disappeared from the room before she could complain. She stood, and just for a moment considered leaving, but she couldn't, she had nowhere to go. She undid the gown and dropped it back on the sofa, then reassumed the position. Sky felt cold now, not because it was cold, but because she was not sure how this would play out. Her mind went back to that rule on Friday, slapping her pussy so hard she screamed.

Oh my god, she felt a flutter down there when she thought about it. That was not how she felt about it, she hated every moment of it, just as she hated every moment now, why the fuck was her pussy fluttering.

Rob reappeared, carrying something she could not quite see in one hand and a big wooden spoon in the other. He walked over to in front of her and said, 'Do you think you will be paying this week's rent with cash?'

'It's only Tuesday, it is not due until Friday,' Sky blurted.

'Very true, but I want to give you the opportunity to prepare for Friday, and in doing so I will reduce your lashes today,' he said with another smirk.

'What am I getting today,' Sky asked, in quite a meek voice, 'I don't think I have done anything wrong.'

'Let's start with the washing up, it is all still sitting in the sink, 5 lashes. The hoover is in the middle of the dining room, you started the job yesterday and left it half way though, but did not complete it last night or today, 5 lashes,' Rob swished the spoon as he spoke.

'10 Lashes again?' Sky said her stomach churning at the thought, but her pussy fluttering.

'I have not finished yet,' said Rob, 'you are getting another five for the curtains all still being closed in the house when I got home, both today and yesterday. So that is 20, then lastly, you get 3 for calling me a 'fucking pervert', is that OK?'

Sky hung her head and said, 'yes sir,' she really didn't want to add to that total, much as she wanted to complain, she believed doing so would only add to it, and she had already decided to take the punishment, so why make it worse.

'However,' Rob continued, 'On Friday when your rent is due, I intend to let you pay it with that tight little arsehole of yours.'

'What, NO!' Sky almost shouted.

'You know the option,' Rob said very calmly, 'you can leave now, or accept it.

'You know I have to accept, but no you can't do that,' Sky could hear the worry in her own voice, so Rob could, and it probably told him he had already won.

'I can, and will,' he said very confidently, 'now, do you want to reduce your lashes today to 15 by preparing for that outcome on Friday?'

Sky thought for a moment, how the fuck was she going to prepare for that? Her mind whirled for a moment, and just as she was about to ask, Rob placed a good sized Butt Plug on the table in front of her. She felt sick, at its widest point it was bigger than anything that had been in her arse before.

Sky swallowed and said, 'What are the terms? Do you just put it in now, or what?'

'Simple, to get the reduction, I help you put it in now, and you have to keep it in until Thursday when I get home. You can obviously remove it and replace it for the things that require that,' the look on Robs face said he was loving this.

'Oh, and I will ask to see it regularly so you are not temped to take it out,' he concluded.

Sky's mind was racing, something about this excited her, but how humiliating. She stood there for what felt like a day, thinking this through, but what was to think about, she was being blackmailed into this, and if she was honest the consequences were things she could live with. She might not want to, but she could.

'Ok,' said sky, cautiously, 'I agree, but you have to be really gentle putting that thing in, I have never had anything that big in there before.'

'My cock is fatter than that,' Rob said with a full on evil smile on his face.

'Yeah, whatever,' she said in a very dismissive manner.

Rob unzipped his fly and his erect cock burst out, he wasn't lying, his cock did not appear to be that long, maybe just a smudge over 6 inches, she was a good judge, but the girth, she did not recall ever seeing such a fat cock. No wonder Lily always said he was hard to handle in bed.

'There is no way that will fit in my arse,' sky blurted out, not being able to take her eyes off it.

'Your sister said the same thing, but we got it in, and she takes it several times a week now. She says it still hurts, but she loves the pain,' Rob said, and Sky could hear the joy in his voice.

'But Lily always was an anal slut, she loved it even as a teenager, I tried it because of how much she loved it, but it wasn't for me, and I have only tried once since then, my butt is not like hers,' Sky was concerned and it leaked into her voice.

'I really hope it isn't, I am expecting the tightest ride I have ever had on Friday,' Robs voice just dripped with anticipation.

Sky took a deep breath as Rob picked up the butt plug and walked behind her.

'I am not doing this,' Rob said, 'You will have to push back onto it, when that time comes.'

Sky felt the cold of lube dripping on to her arsehole. It was not something she was used to, she really didn't do this, and had never had to use it for anything else, and in fact despite everything she could feel that her pussy was wet, and getting wetter.

Rob's finger started to massage the lube, carefully circling it around her hole until a good centimetre out it slipped around effortlessly, then she felt it probe the hole just gently, as he promised, but she could feel it open slightly, and his finger slip in. It could not be more than a nails length, but even that was not comfortable, she felt her bum twitch, and pop his finger back out.

'Now, now,' said Rob, 'I need to get the lube inside too.'

'That was not deliberate,' Sky replied, 'the poor girl is not used to something inside.'

Rob pushed his finger back in, probably not any further than it was before, but now he started to turn it, he slowly worked his finger in more and more, turning, circling, feeling more and more uncomfortable. But it was uncomfortable, not painful. After about 2 minutes of this 'play' she was starting to enjoy it, her mind said, 'what, no, this is not what you want, this is against your will,' but she could not help it, she could feel the fluttering of her pussy, and the warm feeling inside.

Just then Rob slipped a second finger in, this was on the limit of uncomfortable, but she manged to keep silent. Again Rob worked the fingers, and then started to move them apart, she could feel the little stretch to her arsehole, and she let out a tiny squeak of discomfort and pain as it stretched just that little too far.

'That is about 30% of what that plug will manage,' Rob said, in a more caring voice than she had heard all day, 'are you ready?'

Sky did not dare speak, she was sure her voice would betray her, and she really didn't want Rob getting any more satisfaction out of this than he already was, so she nodded.

Rob picked up the plug with the hand that did not have fingers in her arse, and brought the tip in close she could feel it when he took his fingers out, but then he moved it away, and she looked around to see he was lubricating it. She tried to calm her breathing which had started to get quite panicked, without her noticing until then. Rob used the two fingers with lube on pull apart her cheeks, and the cold tip of the plug pushed against her bum. Sky forcibly made herself relax, just as the first push happened. The tip went inside, it felt massive, she was about to scream out when it stopped. She felt it turn back and forth slightly.

'I will just let you get used to that,' Rob said, again kindly, 'it is about a 1/3 in.'

'I can't take it,' Sky said, 'if that is a third it will rip me in two.'

'It will be fine, you are doing great,' Rob said as he pushed again.

Sky felt like her arse was being ripped in two, and let out a couple of suppressed squeaky screams, when it stopped again, it was painful, and there was no other way to describe it.

'Brace yourself, it is just the last little bit, then it is in,' Rob said as his hand stroked her back.

There was another push, which caused her to scream, a full 'arrrggh' sound, before the pain went and it was back to discomfort. Real discomfort, she did not recall being this uncomfortable ever.

'There it is in,' said Rob, as he let go of her cheeks and everything settled.

'I can't wear that for two days,' said Sky, sounding strained.

'Of course you can,' smiled Rob, 'the hard part is over, and once you have been spanked, the plug will barely notice'

Sky could not deny that her pussy was dripping, much as that was uncomfortable, painful, and so, so, humiliating, it had turned her on.

Rob stood up and picked up the wooden spoon, Sky felt herself brace against the table, but nothing happened for a moment, then Rob's hand was on the plug, there was a bit of movement and a little push. She grunted, but it did not change how it felt, as rob rubbed his hand across her bum, gentle, a stroke that felt good.

'I'm Sorry, 'said Rob, 'the plug just needed to move a little, I don't want to catch it when spanking you, I think that would be quite painful, and it might break the spoon.'

Sky just nodded, still braced and waiting, in her head she was thinking, 'take your punishment like a good girl, it will be over soon.'

Before the thought had finished running through her head the first stroke landed, a wooden whack that made her wince and rock forward slightly.

'That's one, and hold still,' Rob said.

The next landed on the other cheek, then another, in the same place, then immediately a fourth back where the first landed. Sky cried out, god they hurt, and the vibrations they created made the butt plug move, that was very uncomfortable.

'Four, you are doing well,' said Rob as his hand returned to her bottom, it stroked around, feeling the heat that was growing. His hand moved down, and across her pussy, she did not want that, but knew that complaining would just make it worse.

'You are very wet young lady, this is turning you on far too much,' she could hear the tease in Rob's voice, as he stroked, then suddenly a finger went in, and pushed up towards the butt plug, that felt very uncomfortable again.

'Stop, that is not how you agreed to punish me, I am prepared for the spanking but that is not nice,' Sky was surprised how calm and controlled she sounded.

'Very well,' said Rob, 'I didn't say I would tease you.'

Whack, the spoon landed again, Sky could feel the welt, but could also feel the fire starting to rise in her pussy, she wanted to reach back and rub her clit, but that would have given Rob satisfaction that she never wanted to.

As stokes 6 to 8 landed she grunted, half moaned, half screamed, it was a whole mixture and she was not sure what signal it give, but she was very aroused and it would not take a lot to make her cum. 9 and 10 landed, the sting building, but she was distracted by the thought in her head, it was screaming at her, this is assault, you don't want this, he is blackmailing you into this, but it was competing with a desire for the next stroke to land, she wanted the sound, the sting, she pain.

Rob paused again after 10, he stroked again making sure his hands covered the entirety of her exposed bum. It was soft and gentle and she did not want it to stop, but his hand went under and he rubbed her clit. Before she could complain again, she let out a moan, a sensual deep moan, the type that only ever comes on the journey to a climax.

This encouraged Rob, and he put more enthusiasm into it, tweaking her clit. She was close to cumming, but manged to clear her mind for a moment.

'Please Sir, can you finish my punishment first,' Sky sounded every bit the little school girl, but she wanted, desired those last stokes. The fire that was her cheeks probably could not take much more, but strangely she wanted to find out.

Rob, removed his hand and very quickly landed four strokes two on each cheek, the moan that Sky let out was definitely more sexual enjoyment than pain. She was so disappointed in herself, but she actually loved this, even the butt plug was feeling better.

As her mind was absorbing this, and the realisation that while she logically did not want this and it was humiliating, but emotionally, physically, she needed it, loved it.

However, that thought, and every other left her head as she screamed out. The last stroke landed along the length of her pussy again, the head of the spoon smacking with force into her clit. By the time she had got any of here senses back, Rob was already rubbing her clit, and she was most of the way to cumming. It took maybe 5 seconds from there and the warmth and electric feeling flooded through her, she moaned and tensed as this climax washed over her.

It was not until Rob's hand stopped supporting her weigh as he removed it, that she realised that he was, she fell to her knees, shaking.

'Oh my god, that was intense,' she said.

'Glad you liked it,' Rob smiled as he started to head out the room, carrying the lube and the spoon.

'Just because I liked it, does not mean I wanted it,' Sky said, already returning to her sarcastic self. Even if the normal heat was not there, the fire on her arse making it hard to concentrate.

'Whatever,' laughed Rob as he disappeared.

Sky gathered her gown, and started for upstairs she needed to moisturise her bottom, and get dressed. The next three day could be hell!