Sky got up soon after Lily left for work, she examined her bottom in the full length mirror in Lily and Rob's room, the welts had all gone down, but it was still red, she popped the butt plug out, and put it on the side, and headed to the bathroom.
Sky showered quickly, she wanted the whole house immaculate today, she would not have time tomorrow with her interview, so she needed to make sure the requirements were minimal. Once she was out the shower she started to clean the bathroom, carefully removing all the water from the shower door, and cleaning the edges where mould would grow. As she moved onto the areas around the toilet and sink, her phone buzzed on the side, she grabbed it, and looked.
She answered the incoming video call from Rob, and said, 'I'm up, what do you want?'
'Show me,' was all he said.
'I can't, I am in the bathroom just got out the shower, and not had chance to put it back in yet,' sky explained.
'Go get it then, I want to watch you put it back in,' Rob said with an evil grin on his face.
Sky put her phone down and went and got the plug, stopping at her room to pick up the lube. She got back to the bathroom and picked up the phone.
'Place the phone somewhere I can see and pop it in then,' Rob sounded enthusiastic.
Sky positioned the phone against the wall facing her and knelt down, she had discovered this was the easiest way to get it in. She picked up the lube and was just dripping it onto her finger when Rob said, 'Stop, without lube.'
'What, no, I can't do that,' Sky protested.
'If you have just got out the shower, then you will be wet and slippery, and it will go up,' Rob sounded very much like he was lecturing.
Sky had got a tiny amount of lube on her finger, and as she moved the butt plug between her legs she managed to transfer this to her hole, it was nowhere near enough, but anything was better than nothing. She positioned the plug and slowly lowered herself down, the tip slipped in easier than she expected, maybe this would be ok.
'That's it, Rob said, eager to see.
Sky pushed and more slip in, but it already hurt, and she had to stop, she could feel skin being pulled in that shouldn't. She moved her hand to hold the base firmly, and moved back up slightly releasing the pressure and the hurting.
'That's it,' Rob said again, 'make it a show.'
'It's not a show,' Sky said angrily, 'it is not easy without lube.'
She could see the evil grin on Rob's face as she moved down again, quite a bit more went in before the skin caught, and the pain started, so much that when it did, it was a surprise to her, and she squeaked in pain. She saw in Rob's face that he loved that, the bustard. Sky waited a moment, composed herself, and then moved down again, it was almost all in millimetres from the base when it caught again, Sky closed her eyes, gritted her teeth and pushed in popped in, but her arse felt as bad as when Rob's cock had gone in.
Her breathe out and sigh of relieve was much more audible than she would have wanted, and Rob laughed.
'It's not fucking funny,' Sky said with heat.
'No it is exactly what I wanted it to be,' Rob said and hung up
Sky grabbed the coconut oil, and massaged a little into her arse moving the plug to get it to the sore skin. Once she was happy she was as comfortable as she was going to get, she dried off some more, and went and grabbed some clean knickers, before she finished cleaning the bathroom.
Sky carried on cleaning, getting dressed when she got to her room, she made the beds and picked up Lily and Rob's clothes from the floor, they had both got in the habit in the middle of last week of not clearing up after themselves, and after last night Sky understood why, and her sister was a bitch.
About 11 as she hoovered the dining room, her phone buzzed again, and again it was a video call from Rob.
'What now?' she grumpily asked as she answered.
'Don't you take that tone with me young lady,' said Rob, 'Show me.'
'What again?' She complained
'I need to know that the reason you didn't have it in really was the shower,' he said very matter of fact, like it was obvious.
Sky undid her jeans, and pushed them down with her panties, she shoved the phone under her, and held it there for about 3 or 4 seconds then brought it back to her face.
'Happy?' she said.
'No I am very angry, but you will hear about that later, however yes, it is where it should be,' Rob concluded and hung up.
That did Sky in a right foal mood, not that she had been that happy before. She carried on with the cleaning, after pulling up her jeans and knickers.
By 1:45 the house was spotless, there was not a mark or dust anywhere, the washing was all on, with a load in the machine and one in the dryer. The washing up was done and the dishwasher was on. There was not a single thing for him to pick up on. So Sky grabbed some lunch and sat and watched TV. At 2:30 she went upstairs removed all the clothes she had on, except her white lace panties. She tidied them away, and took out stockings and suspender belt that matched her panties, putting them on. She stood and looked at herself in the mirror, she looked good naked, and the minimal clothes made her look hot. Hopefully this with perfect house would plicate Rob from whenever bug was up his arse.
Sky was still thinking about that when she heard Rob's car pull up. She rushed downstairs and stood to attention by the front door.
As Rob came in she said, 'Welcome home master, I hope everything meets with your satisfaction.'
Rob looked her up and down, and she could see he was devouring her with his eyes, then he said, 'In the living room, assume the position.'
Sky complied and followed him to the living room, and while he looked around assumed her position leaning over the coffee table hands on it, legs apart. She listened as he walked around the house, checking everything, then she heard some fumbling about in his room, before he returned. He was carrying a cane, and strap on dildo, why the fuck would he need a strap on.
'The house is perfect, and the way you look is very pleasing, you have set a standard,' Rob said, before continuing, 'I will reduce your lashes today as a result. However, over the weekend, you spilt tea on your way upstairs, you left a teacup in the sink not the dishwasher, and biggest of all, you fucking told Lily.'
'She asked me, it was clear she knew,' Sky began to protest.
'Silence,' Rob shouted, then continued more headmaster again, 'We had a bet, Lily and I, that you would not tell her, until at least after you had a job. I lost, and the payment is........unpleasant.'
Rob paused, obviously thinking something, but Sky obviously had no idea what, she just stood in the position feeling more and more nervous.
The he continued,' Todays punishment comes in two parts. For your failings over the weekend you are getting only 6 lashes with the cane, but for your failure to win the bet for me, you are going to experience my discomfort before I do.'
'What do you mean,' Sky said, now starting to feel sick, wishing she had not eaten lunch.
Rob picked up the strap-on, and waved it at Sky, 'Tonight, this is going up my arse,' his tone was not happy at all, 'I really don't want that, but I have no choice. So this afternoon, it is going up yours.'
'What no,' cried Sky, 'you said that my arse......'
Rob cut her off, 'I don't care what I said, you caused me to lose, and this is happening.'
There was a swish and the cane connected with her arse, it was not that hard, but it stung, she had never been hit with a cane before, and this was something new, the actually feeling of the cane on her bottom seemed to last for the slightest of moments, but the sting and the ripple that she felt across her arse seemed to extend out like a burn. She liked that feeling, and her pussy fluttered as she waited for the next one to land, then it did, harder than the first and she let out an 'oowwww' but oh that was exquisite, the rippling sting again.
'Harder daddy,' Sky said, then corrected, 'I mean Master. I deserve the punishment.'
The third landed even harder, and she let out a squeaky scream, as she felt the ripple of pain ran into her pussy, she loved this pain in a way that she had never enjoyed a spanking before.
'When we are alone you can call me daddy,' Rob said, 'Just never let Lily hear it, if you do, I will fuck your arse for a week. Now arch your back more'
Sky complied and gave her back all the arch she could manage, she felt her pussy being pushed out more into the open, and when the fourth landed, her pussy got hit as well as her bottom. The stroke was lower, tops of her legs really, but her pussy exploded in pain. She moved, the first time when Rob had punished her that she had, she squeaky scream, was more scream than squeak, and it really shocked her.
'I can't take many of them,' she said, 'But OMG.'
'Resume the positon and don't move again,' Rob said ignoring her.
The last two lashes arrived in quick succession, both as the fourth, grazing her pussy, as the sixth landed Sky knew if she even touched her clit she would cum.
'Please,' was all she said, and Rob replied, 'OK.'
Sky moved her hand to her clit, and rubbed, it took all of 2 seconds for it to have the effect she wanted, and her knees bent as she felt the climax roll across her.
'You will not be enjoying this next bit,' Rob said as he picked up the strap-on.
Before the climax had finished washing over her, the strap-on was pushing against her pussy lips, it went in easy, but Rob pushed, and it length was in her before she was ready, and the gasp her gave out was loud.
Rob moved the dildo in and out, moving it around, obviously using her own juice as the lube. When he removed it she felt like something was missing. He placed it on the table in front of her, dripping with her juice. It was only about 7 inches long, and by the standards of Rob's fat cock, thin, probably as wide as the butt plug she had in. Rob gripped the plug and pulled, hard, it popped out in one quick motion, she yelped.
'That was not nice,' she said.
Rob ignored her, and dripped lube onto her butt, not a lot, definitely less than she would like, and he quickly, less accurately than before, massaged it around her hole. Nothing went inside though, which caused her concern.
Rob picked the Dildo back up, and pushed it against her arsehole, it slipped in, and he kept pushing, no rest bite, or working its way in, it just kept slowly moving up. Sky let out a wincing cry as it did, the skin that got caught earlier was now on fire, and the juice that was on the dildo was just not enough to fully lubricate it. The cock felt huge in her arse, it obviously went up much further than the plug, and the pressure and pain caused Sky to slip forward, losing her position.
Rob stopped the push, and said, 'resume the position, it is almost in.'
Sky stood for a moment more, before returning to the position, as soon as she did Rob pushed again, but it was a moment before he stopped and Sky could feel the straps of the Strap-on against her legs. The pain was intense, skin that had been pulled to far, she felt her bum twitch, and knew than about an inch of the dildo had pushed out, Rob immediately pushed it back in, luckily it did not hurt as much this time. Sky calmed her mind and relaxed, the actual Strap-on was uncomfortable and not painful that was the skin around it.
'Stand up straight,' Rob commanded.
Sky was not sure she could be but started to straighten up, she made it to standing, but her back hurt.
'I am sorry you lost the bet master,' Sky said.
'I am glad you are sorry,' he replied, 'just stand there and do not push it out.'
Sky stood, trying not to focus on the discomfort. Rob sat down, and relaxed putting the TV onto the channel he wanted.
Sky just stood still, and waited, she start to need to pee, but did not want to risk prolonging this. Rob lent over and pushed the dildo up, Sky did not think it had moved by he seemed happy. After about 10 minutes, Rob reached over grabbed the straps and pulled the Dildo out, that actually hurt, it had become lodged, and Sky whimpered.
'Go clean yourself up, do not replace the plug, and be prepared for punishment later.'
Sky carefully walked out the room, her arse hurt in lots of ways, and she really did not want to have more punishment later. Although she had had a shower earlier, she went to the bathroom and ran a hot bath, she needed some time.