This Fictional Story is written by Mat, and contains explicit sexual material and situations involving consenting Adults. No reference to u******e persons is intended or implied. No reference to real Persons dead or alive is intended or implied.
This is a fantasy I have about spankingjenny. Enjoy.
It had been about a year and a half since the small all-boys private school that I was headmaster that merged with a similar sized all-girls private school. Due to some initial turmoil and friction at the time of the merger, I found myself as Headmaster of the new combined school. Here is one of my stories about the difficulties of managing that job and disciplining students.
It was a sunny afternoon near the end of term, when the Computer Studies teacher, Miss Jenkins brought one of our Senior girls and two of our senior boys to my office. I must admit, I was a bit surprised that three of our best, most senior students would be brought to my office on a disciplinary matter, but I was not sorry to see the busty redheaded Miss Jenkins enter my office.
“Dr. McGuffy” she began, “Masters Johnson and Bates here have informed me that Miss Jennifer Jones has been using one of the school computers to access a pornographic website, and post stories of a sexual nature”.
“This is a very serious allegation” I said, looking at the two young men directly. “Is this true, Miss Jenkins? Miss Jones?” Miss Jenkins confirmed that she had viewed the website that Jenny Jones had been frequenting, and Jenny agreed that the allegation was correct.
“Well”, I said, still somewhat amazed. “You have broken a very serious code of conduct, Miss Jones. Perhaps the school’s most serious code, given that you were made aware at the beginning of the year that this would not be tolerated.” I then turned to a filing cabinet behind my desk, and pulled out Miss Jones’ personal file. The file was very thin, and included no previous disciplinary slips. I then returned to the file to look at the files of the two senior boys. Their’s were a bit thicker, including several references to instances where they had taken school disciplinary matters into their own hands, or had brought false disciplinary charges against fellow students. I also noted in each of the three files that all three students had recently turned 18.
“I find your files quite interesting. Jenny, yours interests me because up until this point, you have been a model student with absolutely no black marks on your record. Master Johnson and Master Bates, you seem to make a habit out of bringing disciplinary issues to the fore, some of which have been completely fabricated”. At this point, I leaned across my desk to emphasize my next point to the boys, “no one likes a snitch!”.
“The disciplinary code of this school is quite simple. If you have been found to be in contravention of school code, you must face whatever discipline the Headmaster feels is appropriate. As you are now all adults, the special clause of the school’s disciplinary protocol is in f***e, and by the school’s disciplinary contract that you signed at the beginning of the year, you may elect to face school discipline, or dismissal from this institution and forfeiture of your grades for this school year”. As this final point sank in, I could see on Jenny’s face that she was beginning to realize that she would have to either take whatever punishment was to be handed out, or risk and ‘F’ for every course in her senior year, which would most likely scuttle any plans for admission to university.
“I’ll take the punishment” she mumbled.
“I thought you would” and with this a wry smile came across Miss Jenkin’s face. “but you will not be the only one punished here today. I don’t think that students should be purposefully going around snitching on their fellow students. Master Johnson and Master Bates, your punishment will be to watch your fellow student Jenny’s punishment, and you will do so standing at attention. If either of you moves as much as an eyebrow, you will get the same punishment”.
At this point, I turned to Miss Jenkins and asked: “What do you think an appropriate punishment would be?”
“Well” begin Miss Jenkins, “the one of the websites that Jenny was visiting was about bondage and spanking. Why don’t we start there?”
“Yes, an excellent idea!” I agreed. I then instructed Jenny to come around my desk, and lay across my lap. Her breasts rested on my left thigh, and her crotch straddled my right thigh. I had to be careful not to allow the growing bulge in my pants rise and sweep her belly. I began to smack her ass with my bare hand, and it made a dull thud as it hit the thick tartan wool skirt of her school uniform. It seemed to me that the skirt was getting in the way of an effective strike. Meanwhile, Miss Jenkins was making sure that the two lads stood at attention in stark witness of this punishment.
“Jenny” I said, after a few smacks on the ass, “This is not having the desired disciplinary effect, and I am either going to have to ask you to remove your skirt, or I am going to have to use something harder on you, like a riding crop, a cane or my belt. Which would you prefer?” At this point, Jenny stood up, swiveled her skirt around on her hips to unclip it, and allowed it to fall to the floor before stepping out of it. Her hips and ass were amazing and her legs were accented with white stockings held aloft by a lacy white garter belt. But this lingerie and the black patent leather pumps with four inch stiletto heels were not part of the standard school uniform. I informed her that there would be extra discipline for these breaches of the school dress code. Despite the length of the tails of her crisp white oxford cloth shirt, I could tell that she was not wearing panties that she had shaved her pubic hair completely. At this point, the boys eyes grew as big as saucers. Clearly they could not believe that this was happening.
Jenny then resumed her position on my lap, and I proceeded to administer hard smacks with an open palm to each of her gorgeous ass cheeks in turn. As my hand came down on each cheek, it would rest a while and almost massage the firm young flesh. At this point, I started to worry less about the bulge in my pants, and managed to shoot a glance at the two young men. They were frozen like statues. Jenny, on the other hand, was starting to writhe around on my lap, grinding her pussy into my thigh.
After about a dozen or so smacks, I asked Jenny to get up. “I think we are going to have to consider a more severe form of punishment. The spanking was ok, for a warm up”. At this point, Jenny was rubbing her ass with a slight tear forming in her eyes, and starting to look concerned about what might come next. Miss Jenkins, I noticed, had unbuttoned one of the top buttons in her blouse and was simultaneously rubbing both her thigh and her left tit. I could see clearly that her breasts were encased in a lovely teal green push up bra, and it as obvious why she had developed a reputation for teasing the younger boys in the school to the point where they creamed themselves in class.
I then instructed Jenny to remove her blouse, which left her standing in front of me in just the stockings, garter belt and a light frilly white bra that encased her budding b-cup breasts. Reaching up, I slid the bra up off her chest and over her head, her tits bounced lightly as they became released from their bondage. I thought that the two boys were going to shit their pants to see their schoolmate almost nude in the headmaster’s office.
Taking Jenny by the hand, I led her around my desk and bent her over the large oak surface of the desk. With her high heels on, her ass was pushed out proudly and deliciously towards her schoolmates. I ran a finger down her back, and through the crack in her ass, stopping for a moment to determine whether the punishment so far was having the desired effect. To my delight, her bald snatch was both engorged with excitement and wet with desire. I reached for a small cane from the top shelf next to my desk and proceeded to bring it down violently across her ass. She yelped in pain. I then proceeded to remove my tie, and loosen my shirt before bringing the cane down again. Again she yelped in pain, and began whimpering. I removed my shirt and began to unbutton my pants. A third whack, and she could not contain her discomfort, and began to weep quietly. I dropped my pants, and stood in the room wearing only my shoes, socks and boxers before administering the next blow.
By this time, Miss Jenkins had removed her top and skirt, and was sitting in my chair furiously fingering her pussy. Unlike Jenny, Miss Jenkins only trimmed a bit of her glorious red haired bush. She had undone her hair clips, and allowed her hair to fall down across her breasts. One of the things I admired about Melanie Jenkins was that she was a sexual dynamo who was game for just about any sexual situation.
The two lads, Master Johnson and Master Bates looked as though they were going to pass out from standing and watching this unbelievable show.
Finally, I broke the silence, by saying “Jenny, you have taken a good spanking for your transgressions with the school computer, but breaking the school dress code on top of this requires that I administer the ultimate punishment.” At this point, I turned Jenny over so that she was lying with her back on my desk, her knees in the air and her heels hooked on the edge of my desk. I proceed to remove my shorts, revealing a semi-rigid 10 inch cock. “Jenny, for your blatant disregard of the school code of conduct, you are required to satisfy the Headmaster”.
A look of fear came across Jenny’s face. “Oh, no” she said, “Please no. And please not without a condom! I’ll do anything for you! I’ll suck you off, I’ll suck you off and I’ll suck Miss Jenkins off. I don’t have any protection! Please, please I beg you. It is my time of the month, and I don’t want to get pregnant”.
Her pleas fell on deaf ears, as I eased the raging purple head of my cock towards her tight opening.
“Oh God, No!!” she cried, but as my cock entered her pussy, the cries shifted to just “Oh God, Oh God”.
As I pounded her pussy with my rigid cock, I could see Miss Jenkins working up a froth in her pussy, and I could see Jenny’s two school mates getting redder in the face and sweating, trying to remain still while not to cum in their pants. The scene must have been something to behold. Their buxom 30 year old redhead Computer Science teacher madly fingering herself with her tits swinging with abandon, each topped with huge nipples and wide areola. Meanwhile their Headmaster lays the most gorgeous (lingerie model gorgeous) raven-haired beauty in the school on top of his desk.
Finally the moment came. I could not hold back any longer. My eyes locked with Jenny’s, and she knew what was about to happen. The look she gave me was essentially “Ok, I know you are going to do this, so let’s do this and enjoy it”. With that, I unloaded the biggest load of jizz I had ever shot deep into her pussy. She started to orgasm at that moment, breaking each wave of orgasm with wimpering cries about not wanting to get pregnant.
Miss Jenkins watched eagerly as I pulled my still twitching cock out of Jenny’s pussy, and almost immediately she started licking my cum out of Jenny’s slit. At this point, the boys started to crack. Master Johnson erupted in his pants, leaving a dark visible wet stain in his crotch before running from the room in embarrassment and shame. Master Bates came in a similar manner, but only as he began to faint and crumple to the floor. Upon regaining consciousness he started to crawl to the door.
“Hold it right there” I snarled, “I told you from the outset that you were to stand perfectly still or you would receive the same punishment as Jenny. What do you think is the equivalent punishment to being fucked in the pussy? Or do you two have pussies that I can fuck?” At this point true fear came across Master Bates’ face as he realized that I might actually be suggesting something heinous involving his ass. He scrambled to his feet and ran for the door.
The next day, I had two letters on my desk. One from Master Johnson and one from Master Bates explaining that they had decided of their own choice to quit school and join the Army. They did not expect to receive credit for their final year. As I read these two letters, Jenny Jones and Melanie Jenkins were standing behind me in their best lingerie. Melanie comment was simple, “Well, we are glad to be rid of those to turd-rats! Good riddance! I despise a man who can’t hold his cum in the company of a lady” and with that she started to laugh. Jenny rubbed my arm and asked “Headmaster? I like helping to make this school better, and by my calculation that is ten students we have gotten rid of. When can we do this again?”