Sky had never been in a position like this, cuffed, and strapped to a bench, completely immobile, her bare arse on display. An arse that had just been pounded like she had never had before, she felt like she had been ripped in two. The pain was subsiding to discomfort now, and she could not believe that she missed that big fat cock in her. The fact that it was her sister's boyfriend and that he was blackmailing her into this should have made this the worst experience of her life, and to be fair she would have pretty much given anything to not have gone through it, but it had made her pussy wet, she wanted to cum, and she really wanted the spanking that was about to be delivered.
Rob un-cuffed her right hand, and she flexed her fingers trying to get blood moving. She moved it up to get to her clit, as she was being allowed to rub while taking her spanking. It was only 10 today, she had tried hard to keep it low, she had not expected to take the arse fuck as well as she had and really did not want to add to the pain too much, even if she normally enjoyed a spanking.
Her hand was a little squashed and she could not rub effectively, so she took a deep breath, and said to Rob, 'Please sir, will you release the waist strap a little, I can't rub.'
Rob said nothing, but released the strap, not a little, he completely removed it.
'Now young lady, how many was it, 20?' Rob enquired.
'I believe it was only 10, sir,' Sky replied.
From the clothes that he made her wear, Sky was convinced he wanted her to be the naughty school girl that was meek and compliant when caught and punished. Of all of this situation, she found this the easiest, she had role played that several times, and it actually excited her.
'I can't believe I was so lenient,' said Rob, 'but I am a man of my word.'
'Thank you, sir,' Sky replied, she could see his dick was growing again, it had gone soft after pumping its load into her arse only 2 or 3 minutes ago, but this exchange was clearly reversing that.
'Now I was thinking back to basics today, that you needed that personal touch, so it is my hand,' Rob instructed her.
'Thank you sir, I will enjoy that,' Sky said, and it was true, a week ago she never would have believed it would be true, but it was, and she never believed the next thing to come out of her mouth ever would either, but she continued, 'and if I did not completely satisfy sir, with by arse, then please use me however you want to ensure you are........ Satisfied.'
This stopped Rob in whatever it was he was doing, there was a pause, then he appeared in front of her again, and when he spoke he was very Rob, not this head teacher character that he was playing.
'You serious?' he asked.
She replied as confidently as she could, 'I do not want to be here doing any of this with you, although I think I might want to borrow some of this stuff with a boyfriend, but as I have no choice, you are forcing me to experience it, I might as well get the enjoyable part too.'
'The enjoyable part?' Rob looked genuinely confused.
Sky thought that she had just taken some of the enjoyment out of this for him, and a moment of panic crept into her mind.
'Look, the anal, I hated, I really never want that again, the tears were real, although it was not as bad as I had expected. But I like getting spanked and you are good at it, and yesterday I walked up stairs dying for a cock in me, and wanked loads before I came down again,' Sky blurted all of this, and paused before she continued.
'I actually missed the butt plug yesterday, it creates pressure when I push a dildo in and helps. What I am saying is, I will willingly submit to all of this, if you make it the full experience.'
Rob stood up, and spoke, back in the full head master, 'Young lady, I find your proposal acceptable, however, there are a couple of things, and firstly for not enjoying my big fat cock in your arse I am adding 5 to your count. Second, I will be replacing the butt plug when we are done, and the same rules apply, your bottom needs more training, it will be taking my cock again. Lastly, do not expect to enjoy every experience, I will withhold the part you enjoy as punishment sometimes. Is this all acceptable?'
'Yes, sir, I would prefer you didn't put it in my tight little bottom again though,' Sky didn't think that would work, but she was trying.
'Oh, No, young lady, it is most defiantly going in again, but I will reserve it for when you have been extra naughty, it will not pay your rent again,' with that Rob disappeared around behind her.
All through that exchange Sky had continued to rub herself, she meant what she said, she did not want any of this to be happening, and if anybody asked she was an unwilling participant, but while it was happening she would try to make it as pleasurable for herself as she could. Her thoughts were interrupted by Rob's hand stroking across her bottom, something close to a sensual massage.
Whack, his hand rose and came back down onto her right buttock hard. She had not even registered that he had moved his hand when the slap arrived, and she squeaked.
'I think you should count,' Rob said.
'One,' Sky said, in a voice that betrayed the shock of that first spank.
'Good,' said Rob, 'That sounds like you are remembering who is in charge here.'
'Yes sir,' Sky said, her mind more on the warmth rising in her pussy, and the tingles in her clit.
Bam, the left cheek this time, same as the right.
'Two,' Sky said more confident this time, this was more like the spanking that she wanted.
Rob's hand stayed put, this time it stroked around her warm bottom, gently rubbing across the areas he had just struck, there was no way he could see from looking, her arse was still red from yesterday's spanking. His hand moved across her pussy, the wet greasing his hand, and there was the slightest contact between her rubbing hand and his.
'See I knew you enjoyed this,' Rob said, but Sky was focused, her mind was elsewhere as the rub was bringing the climax ever closer.
The hand rose and smacked back down, then again on the other cheek before Sky had time to say anything. She moaned, a sexual moan as the fourth landed, there was a sting across her cheeks from it, and at that moment her mind had been in the right place for it to be perfect.
There was a firmer feel to Rob's rub this time, which she was sure was because of the delay, and she cleared her throat.
'Three and Four, sir,' Sky said, in more of a sexual moan than a clear voice.
Rob's fingers grazed her pussy again, but this time two fingers slipped in. The pressure of them pushing up was too much and Sky spilled over the edge and climaxed. Not a hard and mind numbing climax but it worked.
'Yes, that's good,' said Rob, clearly enjoying it.
In a quick motion the fingers withdrew, and Spanks landed across her cheeks, they prolonged the climax and the moan became deeper and the pleasure was starting to show in the moan.
'Five, Six, Seven, Eight,' said sky, 'thank you, sir that made it so much better.'
'Good girl, you are doing well, the next set are coming quickly and you do not need to count,' said Rob.
Strokes nine, to 14 landed, alternating between cheeks, and it must of lasted no more than 3 or 4 seconds, these were very hard, punishment strokes, they stung a lot, but she loved the pain, and it stopped her from completely calming from the first orgasm.
Stroke 15, as she had come to expect fell across the length of her pussy, the fire it created made her move her hand back and start rubbing.
Rob's fingers slipped into her arse, very easily, and he said, 'well that does not need anything more.'
He disappeared away for a moment, and when he returned Sky felt the cold of a metal butt plug push into her arse, the discomfort that she had got used to returned, but this did feel different, and Rob pushed hard to get the last bit in before it settled. Sky yelped at that last bit, it felt worse than his cock. But it also excited her the rubbing had her back to almost cumming again.
'That is a size bigger than the one you had yesterday,' Rob said, 'same rules apply.'
'Yes, sir,' Sky said, more on instinct that anything as she was about to cum again. Moments later, as Rob pushed his fat cock into her pussy she did. The pressure of the butt plug and the width of that cock caused her to push over the top and climax, she kept rubbing and Rob kept pushing in, the orgasm extended and she felt a shudder that rocked through her body, only her body moved because her legs were so tightly tied down.
Rob paused once his cock was all the way in, it had slid in easily, the position she was tied in made her pussy perfectly placed for a deep doggy style stroke. He held in that position until her orgasm was over and her breathing calmed, then he withdrew slowly, and pushed back in again fast, the way he had inside her arse. The push in felt close to painful, with the butt plug, there was no room for his fat cock, but it pushed in anyway, and Sky knew there would be at least one more orgasm.
Rob continued the slow rhythmic pounding and she started to rub again, she closed her eyes and slowly lost herself in the moment, feeling the shove from behind, the inability to move against the bench, she faded into a trance like state, the way people exercising do where their body just continues with the exercise even though they have zero attention on it. She was like that grunting as Rob pushed in every time, but lost in her own world. She barely noticed when Rob changed his stroke, in her world is was not Rob, it was somebody else, and she was so close to cumming again.
Then it was there again, she felt her body tighten, with warmth wash over her, and then the calm relax, flowing through her, and her rubbing hand went limp, that was it, she was done. Just before she thought that, she felt the spasm as Rob shot his load. She just lay there, not that she had any choice, and she felt Rob withdraw.
The next thing she knew Rob was asking if she was going to move, and was her alright. She was fine and said so, daze like. She did move, and realised she was free, she stood up, shaky but made it to her feet. She stood there for a moment, then shook her head, the fog cleared and she was fully back from wherever the hell she had gone.
It then hit Sky how much her body ached, she had never been tied up quite like that before, and certainly never to be pounded that much, she looked around at the clock, it was six minutes past four.
'I'm sorry,' Sky said, 'got lost in my own little world there for a minute.'
'No worries,' Replied Rob, 'are you sure you are alright?'
'Yes, fine,' she said, 'going to the shower and I will be 5 by 5 after.'
Sky walked out the room and headed to the shower room, she locked the door behind her, and removed the costume that Rob had her in, she stood there naked, looking at herself in the mirror on the wall. She grabbed towels from the cupboard and turned the shower on, and hopped in. Sky yelped and jumped out, the water was icy cold because she had not given it any time to warm.
'Don't worry, cold shower water is all,' she yelled before Rob could ask if she was ok again.
Sky checked the water had warmed up, and jumped back in the shower, but she stood there letting the water wash over her, as she thought through everything that had just happened. She touched her clit, it felt raw and sore, and she decided not to go there with her hand, so unclipped the shower head and brought it around to fire the water directly on her pussy. As the warm water hit is was like the relief of a drink of water on a hot day, or a cold towel on a burn, she felt herself relax from a tension she had not even known she was holding, and a calm exhale of air that let her slump into reality escaped from her lungs.
Sky washed carefully, including washing the sweat out of her hair, then she came to her bottom, it was sore, and the hot water was uncomfortable on it, she lowered the temperature and gently washed the red areas, they still burned but they were clean. Now for the job she really did not want to do, she gripped the end of the butt plug and pulled, she gritted her teeth, and hissed through them as the plug stretched her arse hole and then popped out. A relieved breath escaped, but how the fuck was she getting that back in?
As Sky relaxed she farted, and a big lump of cum fell to the floor of the shower, the thought of what had put it there made Sky heave. She then did something she had never done before and took the shower head and aimed it right up her arsehole. It actually felt good, she slipped a finger inside and tried to clean, more cum came out. She washed with the water and her finger for a minute or more, until it felt more human down there, and then rinsed off the plug, she positioned it to push back in, it got about 70% of the way in but it would not go that last bit, or more to the point she could not stand the pain of pushing it in further.
Sky finished in the shower, and grabbed a towel for her head and one she wrapped around her. She picked up the plug and unlocked the door, she would use some lube in her room. As she walked out and past Rob's room she saw that everything had been cleared away and it was as if nothing had happened, at the top of the stairs, Rob was on his way back up.
'I hope that plug is going back in very shortly,' he said.
'Yes, sir, I just need a little lube,' Sky replied.
'I will just grab the clothes, they in the bathroom?' Rob continued.
'Yes, was going to grab them once I am dry and this is back in,' Sky said confidence starting to return.
'No worries, I have it covered,' Rob said, 'and I can come back and assist with that, if you want?'
Sky thought for a moment, then said, 'Providing it is just helping me get it in.'
Rob whipped past her and into the bathroom and reappeared with the school girl costume, he smiled and said, 'of course, I have had my fun.'
He disappeared downstairs as Sky walked into her room, and she was almost completely dry when he returned, her hair was wet but that was it. He carried some lube in his hand. Sky turned around and got on all fours on the bed pulling the towel away.
'Actually,' Rob said, 'it is probably easier to get in if you lay on your back with legs up.'
Sky did not even think about it she assumed the suggested position and waited, but in her head she was annoyed at herself for being so compliant.
Rob approached and held her legs with one hand, and with the other dripped lube onto her arsehole, she flinched at the cold, but it actually felt nice, cooling the area of her that was still on fire. Rob proceeded to then rub the lube in, the way he had before, circling and making sure there was no bare skin inside or out. He then picked up the plug and applied a little lube to that too, before she knew it, it was going up, slowly but with constant pressure, that kept the motion going.
The discomfort was intense as the widest part slipped in, but she regulated her breathing and got through it, and the plug settled into place, more uncomfortable than before the shower, but manageable.
'Thank you, sir,' Sky said.
'You are welcome, but I have not quite finished, 'Rob replied.
He grabbed the moisturiser from her side, and applied it to her red areas, the soothing feel of the cream was wonderful, and Sky had to snatch her hand back from going to play. Rob saw this and laughed.
'See you are a naughty girl really,' he said as he got up and left the room. Sky lay there naked on her back, legs up, wondering where the hell that niceness came from.