My Online Kink Match Part 6

[ve****]

The door swung open and there he was, dressed in a suit. This is the first time I had seen him in other than his khaki shorts or slacks and collared knit shirt. The suit looked expensive too. Who was this guy? I noted this room was much superior to the two we had been in previously. Of course it was a nice hotel.
“Come in my ward. I am sure you have an idea of why you are here. I heard from the college on your latest grades and some other goings on that I disapprove of. You are letting your friends influence you way to much. You are flunking out and I have reports that you were whoring around during spring break in Florida when you should have studying. Now don't try to deny it, I have pictures of you from that wild site Girls Gone Wild flashing your breasts and some others from my private idea where you are with boys and providing them oral sex. We will get to all of that in the moment. As you are aware, your inheritance has a codicil in it that makes you ineligible to inherit your trust if I believe you are acting immorally or if you do not graduate from college. Both are unlikely events at this point. You were through this at those private schools when you were bad. So find your spot and stand at attention.”

I didn't know if I was allowed to speak back to him at this point so I just entered the room and looked around. I saw that he laid out some a paddle, a strap, a switch, and a cane on the bed. I figured it was a good bet that my spot would be someone on that side of the bed and sure enough, my duct tape marked rectangle was there. As I passed the dresser I saw he had the ice chest with water for me and the beers for him out on it. I went to the rectangle, spread my feet to the outside and put my hands behind my head feeling ridiculous in my school girl uniform. I was facing the bed and like most hotel rooms there was full length mirror on the wall so I could see myself. I also saw the tripod for my phone set up directly opposite of me. He grabbed the phone from my hand and took a few pictures of me standing in the uniform.

“Now then girl, I am extremely angry but I am not going to allow you to fail. You and I are going to work this out tonight and then we will review routinely until you are schooled up properly and get your grades up. As for your whoring around, perhaps we have to do something about that as well. When I was younger, my father caught me smoking and he cured me of it by making me smoke an entire box of cigars underneath a blanket. It made me sick as hell but I never smoked again. Perhaps by the end of the night you will discover the same thing about pre-marital sex. So what do you have to say about all of that.” I guessed that was my cue to start my role.

“Please sir. I am so sorry. I can make up the grade and I promise that I will mend my ways. I just need another chance. Please don't punish me.”

“Don't be impertinent. All of this needs correction and I intend to make sure we do. Now just stand there for a few minutes and be quiet. You get nothing to say unless asked.” With that he picked up the cane and ran it over my lower legs slowly up between my legs behind me and when he got to the skirt he raised it ever so slowly until he could see my thighs and ass.
“I see that at least one of your teachers understands the importance of discipline. Obviously he was almost as disappointed in you as I am. Tonight I intend to chastise you until you are ready to make good on that promise you just so rashly made a few moments ago.” While making this s***ch he ran the cane between my legs along my slit causing me to squirm a little as I started to get excited and started kind of like this role playing idea.

“Please sir, I ….”
He cut me off roughly y saying “Enough Girl. No more talking. Lean over the bed and put your hands on the bed and present you butt to me as a target. This will be some of what you can expect tonight.” When I got into position he went over and put the camera on the tripod, framed his shot and started the video feature.
“Get your shameful head up, girl and look directly in front of you.” I knew that meant to look into the camera as he punished me.

I heard him swish the cane through the air and then felt the cane strike me hard through the skirt and panties. “Count Girl”
I panted out “One Sir!”
He hit me again as soon as I was done.
“Two Sir”
And again.
“Three Sir”
“Now that is just a taste of what is going to come. It will get worse.”
He reached over and pulled my skirt up over my panties and put it on my back.
He gave me another stroke over my already bruised butt.
“Four Sir!”
Then another at full strength. The previous ones had been moderate. This one took my breath away and I stomped my Saddle Shoes on the floor.
“Five Sir!”
Another at full *** and again I was dancing and singing out for a full 20 seconds or so.
“Six Sir!”
“Ok then, that half dozen will give you an idea of what you are in for on that bruised bottom of yours.”
He took a break to get the camera and brought it over to take a few pictures of the new welts on top of my already bruised ass.
“Now widen that stance and I moved my feet a little further apart.”
Again he set up the phone and started the video on it. When he came back he pulled the panties down to my knees and had me step out of them. He threw them on the bed in front of my face and said “If you get too loud, those panties will be in your mouth so keep the cries down. Have some discipline while being punished.”
“Yes Sir!”
I was already wet and I knew it because I could see the moisture on the crotch of the panties in front of me. I really did not want those panties in my mouth and I vowed to keep my cries down to a minimum.

“Now girl, we are going to warm you up a little before we start the test. You will get swats with the paddle and then you will get twelve with the strap.”I heard the paddle whistle through the air and then it struck me full ***. I could only manage to let out a grunt and then said “One sir!”
Each stroke seemed to be worse then the one before and it seemed ceaseless. He allowed ample time for my bottom to to start the ebb of *** before he delivered the next one. When he covered my ass well with the paddle he moved to my upper thighs. Finally the paddle was done and he was on to the strap. It was a pretty heavy leather s strap well used it seemed and very limber. The first stroke wrapped around onto my loins as he worked from top to bottom laying them halfway down my thighs.

In the meantime I was acutely aware that I was being videoed the entire time and he reminded me to keep my face staring straight ahead. I am sure that was to make sure whatever audience saw this could see my ***. Then it hit me that I had forgot to remove the permissions from the private gallery for everyone else who had requested access. I had a lot of friends on the site who had access since until this morning there had been nothing much else to see except some of the basic glamor shots I had taken and some candid shots of me with nothing showing. Now they had access to all kinds humiliating scenes of me including the two videos. My face flushed a bright red I am sure when I remembered that. I was so humiliated I wanted to cry but you wouldn't have been able to tell since I was already in tears. He finished the strapping and indeed my bottom was really warm.

As usual he was very perceptive since he said “How humiliating it must be for a 24 year old woman having her panties taken down and being strapped and paddled like a young school girl. Well I have news for you, it is about to get more humiliating yet. Stand up and put your hands behind your head.

While I was ding that, he reached into his duffle and rummaged around. Then he turned back to me and said, drop the skirt girl.

I undid the waist band of the skirt and allowed it to drop to the floor. He came over and picked it up, folded it neatly and put it on the bed.
“Now, back into punishment position.
I leaned forward putting my hands on the bed, looking straight at the phone still filming me.

“*** is part of the punishment. Just to make sure that you fee that ***, the butt plug goes in. It will stay in the rest of the punishment session and I will set it on intermittent intervals so you will feel the vibration at unexpected time.”
With that he put some lube in the crack of my ass and allowed it to drip down the crack and cover my asshole. I complied with lubricating the butt plug with my mouth remembering it had been in me last night. He had cleaned it of course but it was humiliating to say the least knowing that.

He pressed the butt plug firmly into me with out all of the niceties he had shown the night before. He set the vibrator to on and it started a random set of interval and settings. I could not know when it would actually go off or on or even what level it was set at. It was disconcerting to say the least.

As he put it in, he ***red between my legs and said “What is this? You seem to be getting wet.” He took up the cane and like a weapon he ran it up and down my slit wetting the end of the cane.
“Now I can see why they called you a wanton whore. You are getting wet from this punishment, aren't you.”
It was true so there was no denying it”
“Yes Sir!” I said sheepishly. “I am wet and excited.”
Great, so that is on video as well. Another *** with me looking directly into the camera. I knew it would not be long until it started to drip out of my slit in a long line that looked like spittle. He used the cane on my backside a few more times and I counted the strokes out loud and clear. Then he ran the cane up and back along the slit to excite me even more as if the butt plug was not doing a good job as it was.
“Are you enjoying this girl?”
What kind of question was that. I was and he knew it but either answer I gave would just make things worse so I chose “No Sir! It hurts!”
Well it is supposed to hurt and you deserve it, don't you!”
“Yes Sir!”
“I wonder if I can make you orgasm with the cane alone? Are you wanton enough for that?”
Another trick question since of course I was and I was showing that to be true but answering yes would do me no good so I denied it. “No Sir!”
“Good, perhaps you are learning not to stray so much. Now, lets get on to your studies.”

Now began a long hour of instruction and testing from good godfather. He pulled out a long list of questions and took up the switch. I was expected to listen to the question and answer it. If it was wrong I got a stinging flick of the switch on my bottom, between the legs, or on my thighs. The first set of questions was on geography which included the state capitals. He would ask the question, I would answer if wrong, I go switched while he repeated the question and the answer. We went through all the states and started on the capitals in the world. The state capitals were easy for me and I only missed Vermont, but the world capitals was much harder since I have done little traveling outside the the United States. I got a lot of switching. We moved onto American History and went through all the wars, battles, major generals, reasons for the wars. I had to learn the Presidents in order and missed a lot. I was pretty goo don the wars at least. Then it was on to Latin and Roman History which I had never taken. It was almost all switching at this point. Forget science, I only was good at some basic biology and forget the rest. He must have gotten tired from all the switching he gave me. My bottom must have been blushed out. The problem with switches is that they have those little places where the tiny branches had been trimmed off and they tend to freckle your bottom and thighs up well. Finally he gave me a little ret, some water and an orgasm with that the larger vibrator he had used on the first session. The difference was he had an attachment that he switched on and off that was a clitoris stimulator. When he finally gave me permission to cum I was exhausted. I gushed bending over and looking into the camera for the video. I ended up collapsing over the bed as I came and he allowed me to rest. When I was fully cognizant of what was going on, he was rubbing my bottom with a Icy hot salve that further heated my ass up and also slipped a little along my slit that made things worse as well. He fingered me a little as well. I was well worked up as the test continued.In the end he made sure I understood that by my session on Saturday he expected e to know all of the answers to the questions he asked but assured me that he would give me the test and the answers to study from before I left. He had me take off my blouse and bra about half way through the second testing period but did little but play with my tits a little. They were still pretty well bruised up and I think he felt sorry for me.

When he was done with testing me. He told me it was now time for me to satisfy him and I knelt in the rectangle and took him in my mouth again to do the job. When his cock was in my mouth, he asked me if I was a whore. I dutifully looked into his eyes and told with a full mouth “I am a cock sucking whore, sir!”
“Good Girl!”
he finished as usual deep in my throat and making me swallow it all and then clean him up as well as his giving me the semen mustache. Then he had me bend over the bed again, totally naked. He rummaged around and found the little dildo and clitoris stimulator combination and put it inside of me. He set it on intervals like the butt plug and then told me” “I want to see if I can cane you into an orgasm. Do not cum until you have permission!”
Yes Sir!”
With that he proceeded to cane me severely with the light cane. He did not hesitate but just kept on caning and I started to beg him to let me come. He refused to give permission and I counted 24 strokes before I gave out and gushed an orgasm that left me so weak I collapsed again onto the bed. Obviously he was well versed in my massive orgasms and caught me up and laid me on the bed so I could just roll with it. I never lost total conscienceless with this one but it was close and it took some moments for the waves to pass through me. Later he showed me pictures of me with my eyes rolled back in the sockets and that look of anguish and ecstasy on my face.

He made me drink water he held for me when I woke up and applied a soothing balm on my wounds. I found out later he had also gave me a fourth star above my ass while I was half out of it.

When I could get up, I splashed water on my face and tried to clean up. He was already packed and ready to go but waited patiently and asked if I wanted him to walk me to the car but I said no, I would do it myself. I had forgotten I was wearing schoolgirl clothes and must have looked like the wrath of God when I walked through the lobby. No one was there though except the girl at the desk and she just scowled at me. I go to the car, changed my clothes in the garage and made it into the house just at the right time since everyone had just gone to bed. I managed to set the alarm before I collapsed into bed. I didn't even use the bathroom even to brush my teeth. I just went to bed in the clothes I was wearing. I didn't realize I was so exhausted.