The Anals of Academia

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Ex-student teaches her teacher the joys of anal love.
3.6k words
4.22
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Part 1 of the 2 part series

Updated 10/31/2022
Created 06/21/2001
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kneeonsigh
kneeonsigh
44 Followers

Dedicated to my collaborator, the Sylken One

things are not always what the appear to be,
even as they are appearing

* * * * *

"I believe you boys have much better things to do than litter the halls with your presence during class time." George Ballard's booming, authoritative voice echoed in the hall. As Vice Principal of Market Street High, had found his prey on one of his daily hunting trips through those hallowed, but now peeling walls.

"What a pompous ass he is," muttered one of the letterman jacketed "prey".

:What a pompous ass I am: thought George, smiling to himself in his secret reverie of duplicity. :If they only knew:, he thought, as he squeezed his pompous ass's cheeks, to send tingles of pleasure throughout his body as he enjoyed the "gift" his mistress/slave/lover had given him this morning.

As the boys scurried in all directions to the classes they were supposed to be attending, George walked, in his straight backed, militaristic march-like gait, down the hall, his hard heeled shoes sending echoes of his steps bouncing off the hall's walls. "God, I love this job", he said under his breath, reveling in his "power".

As he turned the corner, he came to the fading, well-worn doors of the library, and pushed them with a flourish, to make his entrance. Still in his upright manner, "Have those books I asked you to order come in yet Ms. Swenson?" he said, knowing his voice was way too loud for a "library" voice, but loving the fact that he gets away with this transgression.

"Yes, Mr. Ballard, they are in the back room, I haven't yet had the time to enter them into our system, to get them cataloged and placed in the shelves," was the mousey, assistant librarian's answer. Mr. Ballard had hired Ms. Lila Swenson this year, and no one could figure out why. Oh, she was a wonderful librarian, but her dress was so plain, and she seemed to be afraid of her own shadow's shadow, as she slumped around in her shy, quiet world. Any verbal intrusion by someone trying to enter her world, was responded to with a voice so faint, one had to lean their head further down than hers to hear it.

She was nothing like the women he had hired before. It was widely thought that Mr. Ballard considered himself quite the ladies man, and had always hired what the male students called "Babes". Lila, with her blonde hair tied back in the tightest of buns, her reader glasses resting awkwardly on her little upturned nose's tip, and plain, baggy dresses that left everything to only the most vivid imagination, would never even be considered into babedom by the boys.

"I should think you've had more than sufficient time to get these small tasks finished, Ms. Swenson."

:God, what a pompous ass: thought Ms. Yun, the pretty Korean librarian. She was so tired of the way Mr. Ballard picked on her new assistant. Ok, so she was beyond shy, but she was a wonderful, intelligent, and very conscientious assistant, the best she had ever had. There was no need for him to pick on her so, but of course, Ms. Yun, for fear of his wrath, said nothing.

"Show me the books," he commanded.

"Yes, Mr. Ballard, sir, they are back this way, in the storage room." Ms. Swenson turned and led him. Even her walk was shy, as if she was afraid to make much noise. With her flat, soft-soled shoes, this was impossible, for she walked as if she wore tap dancing shoes, and was embarrassed by the noise they created. Mr. Ballard, of course walked in his regal manner, gloating in his power over this "subject".

Once inside the storage room, with the door closed, Lila turned to face George. Her face no longer held down in shyness, but held straight, to look into, and almost control George's gaze. Her hand shot out with athletic precision, grabbed his ass, right at the crack, and pushed hard, feeling the tip of the butt plug she had inserted earlier that morning. She pushed hard, smiling as he winced in both pain and pleasure. She reached over and bit his ear lobe, roughly, loving his whimper. She then let go with her teeth, but with her hot breath attacking his ear, she hissed, "Hmmm, George, you turn me on so with your moans."

Lila licked her lips, and kissed his warm lips quickly, and fully, aware of the possibility of someone entering at anytime. It was so erotic, the relationship they shared. Switching back, and forth between Master and slave, and lovers all the while, especially sharing the love of anal play. Lila fingered his anus, all warm with the butt plug spreading him there. She slid her finger in gently beside the plug, as George pulled her close to him, and lifted her skirt, spreading her own ass cheeks apart, fingering her puckered entrance and inserting a plug in her ass. Lila moaned against his neck, muffling the sound, as she pressed her body against his, feeling his hard cock throbbing against her, as his arms pulled her close, and his lips and tongue found hers.

They kissed passionately, then he smacked her on the butt, and chuckled, " I do have the advantage though," and his hand pulled a small remote from his pocket, which he pressed, looking at Lila intently. The vibrations of the plug deep within her ass caused Lila to jump, and squirm with delight, as she giggled at his new toy.

"Oh, George, how will I manage this 'mousey me' role now?" "I have confidence in you, my dear, but it will be fun to play with you today. Just remember, this remote has a very long range."

George smiled lovingly at Lila, and gave her a quick, parting kiss. "Enjoy your day, my dear." Lila squeezed his hardened cock thru his slacks, and smiled. "I will, darling, you have some clever plans up your sleeve, I know." Just as George filled the doorway to leave, he looked back at Lila, now seated, and moving her ass in her chair, obviously enjoying her plug. She smiled at him, and blew him a kiss, and he pressed his finger on the 'quiver' button on the remote in his pocket. A gentle wave of vibes rippled thru Lila's ass, and she moaned, closing her eyes, feeling her pussy fill. Lila looked up, but George had left, and the vibes had stopped.

At least that is what she thought, until the 'quiver' button on the remote was pushed with George's pocketed hand as he strode forcefully out the library door. He smiled to himself, at the thought of Lila's body reacting to his remote work, and had to continue on his walk with his hands in his pockets, to blouse out his pants, to give his now straining cock some space.

Lila heard Ms. Yun enter the back room; she quickly put her hands to her face, to feign tears, to hide her state of arousal.

"Did that bastard yell at you again Lila?" she asked in deep concern.

"Yes, he really got to me this time," came the reply from behind Lila's (thankfully) face covering hands.

George walked briskly to his office, to keep the blood flowing to less telltale parts of his body. Hearing the damn old door, with the frosted glass, 'Mr. Ballard, Vice Principal' painted in black, block lettering, creak as he opened it, he cursed the old building, regardless of all the past spirits of learning that resided within the aging building.

As he sat down at his desk, he was reminded of his Mistress/slave's handy work, as the plug was pushed even further into his sensitive ass hole. He leaned back into his chair, with his hands behind his head, and gloated. What a find Lila had been. What thrills her anal teachings had brought to him. He wondered for a moment how she had gotten so deeply inside of him (in more ways than one). In this reverie, he drifted off into the reoccurring daydream of the evening he had first interviewed Lila, Ms. Swenson.

School was over for the day, with only a few students and teachers still within the school's confines. He liked to do his interviews after school, so he didn't have to worry about being interrupted. He remembered looking at this mousey, plain woman as she walked in his door, thinking of a way to get rid of this Asst. Librarian hopeful as quickly as possible.

"How do you do, Mr. Ballard, my name is Lila Swenson, so glad for the opportunity to interview for your job opening."

:What the hell is going on here?: he wondered to himself, this plain looking woman grabs my hand to shake, and it feels as if I just put my fingers into a wall socket. Quickly, regaining his composure, and officious, if not compromising manner he says, "Er, yes, Ms. Swenson is it? Please, take a seat." With a magnanimous waving of his arm, he directs her to the chair in front of his desk.

As she sat down, he began walking around his desk, but out of the corner of his eye, he thought he caught a glimpse of something frilly on an alabaster thigh. He turned his head quickly, but her shapeless dress hung in total coverage her body. Disorientated again, he wondered if he had stayed up too late the night before, but pressed on in his role of ultimate power over her employment at his school.

"Now, I have read your resume thoroughly Ms. Swenson, and I have to say, you seem perfect for the job." He heard himself say. :What the? I was going to get rid of her quickly:, he thought angrily.

"Oh, Mr. Ballard, I am so happy! I have so many ideas for your library, I know I will make you very happy indeed you have hired me."

:Well wait a minute,: he thought, :who said anything about hiring you?:

"Here is my home address", she said handing him a note, "bring the necessary papers around tonight." I have to hurry and get some loose ends taken care of, so I can start first thing in the morning!"

"Who said anything about st............ oh, um, sure.... Fine Ms. Swenson, um tonight it is," was his very much less than powerful reply.

A couple hours later, he found himself knocking on her door, still not exactly sure what was going on. He prepared himself to offer the speech he had been practicing, "Now you see here Ms. Swenson..........." as the door opened. His sentence was cut off before he could really even start, for his eyes feasted on a sight that took both word and breath from him.

Before his hungry eyes, stood a totally different woman from the one who had left his office. Her blonde hair down, loosely around her shoulders, her eyes alive and unfettered with reading glasses, her dress.... Her dress! A shocking, almost neon red, one piece that was either painted on or was part of her lusciously curved body!

"Cum on in Mr. Ballard," said this entrancing vixen.

"Glad to."

It wasn't long before he had regained at least part of his senses, and had this vision of erotic glory in his arms, his mouth virtually attacking any part of her he could. His hands had not missed a beat or any of her curves, as he treated himself to her entirety.

"Not here," she moaned, taking his hand and leading him from the doorway, and towards another room.

"Huh?" he gasped upon entering the room. Once again this woman had totally thrown him for a loop. He expected to be led into the bedroom for some sucking and fucking for all time, but what he saw, had nothing to do with a bedroom. It reminded him somewhat of his schoolboy fantasies, during history of the middle ages, and the Inquisition's torture chambers. Oh he remembered what he was going to do with Mrs. Jenkins when he got her into his chamber.

"Take off your clothes," came the firm command that brought him back into the present. He found himself obeying without thought, anything to fuck this lovely creature. His clothes around him in a heap on the floor, she took his hand roughly and led him to some sort of arched device, like he was facing the back of a letter "C", about 18" wide, with a large hole in the middle, and posts on each top and bottom corners.

"Put that dick through the hole, lean onto my arch, and grab the top posts with your hands." He was starting to have second thoughts here, and hesitated.

"Oh don't worry Mr. Ballard, you are in for pleasure, I assure you." Now, thinking only with the head that has only one eye, he did as he had been commanded. He felt the cuffs being locked over his hands, to the pole before he could do anything. So, unable to move himself, he gave no resistance as his ankles were cuffed to the bottom poles. So there he was, his body forming the "c" shape of this arched device, slightly tilted forward, so his naked ass pointed upwards.

"Just like you always teach your students, 'sometimes, when you can't find the answer, you must look in ways you haven't looked before, open unread books, and open previously locked doors'." Proud of hearing one of his most famous pep talks, he almost forgot.... "Hey! How do you know what I "always teach?"

Lila stepped around so he could see her, as he was locked to the curved apparatus. With one fluid motion, she undid the clasp of her dress, and with exaggerated wiggles, that gave even more hardness to his cock as it peeked through the hole, dropped her dress to the floor. She stood in front of him, in all her glory, and since the only part of him that could move was his eyes, he let them dance upon her nakedness. Her body was one of a gymnast or dancer. Her muscles, though not overly so, were well defined and sculpted. Her breasts were on the smallish side, but so wonderfully round, with that little ski jump tilt to the nipples that drove him nuts. Her stomach was flat, and her hips were a perfectly curved frame to her completely bald pussy. Her legs were strong, shapely, and made his mouth water, as well as his cock tip, although we all know that isn't water.

She threw her head back and laughed, loudly. He enjoyed the way her strong laugh made her breasts jiggle.

"You don't remember me, you don't remember at all." She guffawed.

"What?" He asked, trying to buy time as his normally crisp "find files" feature ran in overdrive in his head.

"You pig, I knew you wouldn't, although I did think there might have been a chance, dressed as I was at the interview."

"Oh, I wanted you to remember me, I tried my hardest to impress you with my work, my intelligence, but all you seemed to care about were those cheerleader titties. You did teach me a lot though, for you showed me, it takes more than just intelligence to get what I really want. Oh, I looked in ways I hadn't looked before, I read unread books, and I opened previously locked doors, Mr. Ballard. In the years after I had you in senior history, your first year here, I learned a lot. And you are about to benefit, as we open one of your locked doors."

With that, she was gone from sight, although he could hear a chest opening and some rustling around behind him. Then he felt her hands, on his ass cheeks. Kneading them roughly, spreading them apart. He felt the cool liquid pouring onto the top of his crack, and even recoiled as it dripped down, touching the puckered hole. Her hands moved, and he felt a finger tip at his anal opening, and then he heard her jeering voice as she thought out loud,

"Hmmmmmmmm, do I enter slowly, to prepare you, or do I just fuck the shit out of your virgin hole?"

"Gulp" was all he could muster as he prepared himself for the whatever.

The slow entrance of her one small finger, made him sigh in relief, until he realized he had a finger up his asshole. She turned it, twisted it, and continued pushing it in. Although similar, but very unlike any prostate exam he had ever had, he found to his amazement and to his rigid cock's approval, this was turning him on.

"Kinda nice, getting fucked in the ass, isn't it Mr. Ballard. Well, the nice part is juuuuuust about to end."

With that she pulled out her finger, rapidly, leaving an empty feeling in, not only his newly anointed cavity, but in his very being. He saw her in the corner of his eye, as she walked around in front of him again. But something had changed, this time when he saw her; she had a raging hardon of a strap on dildo attached over her mound. She stroked it in front of his face, as she lubricated it with some greasy substance, which had a very pleasant aroma.

"Does this look nice Mr. Ballard?" She hissed. Before he could formulate a snappy come back, she had walked around behind him.

He could feel her pulling his cheeks apart again, rougher than the first time, and further apart. He then felt the tip of that large dildo, hovering, just barely touching his hole. He could feel himself trying to close himself by moving his legs, to no avail, as the cuffs held him firmly in place. "Get ready you bastard, here is what I have wanted you to do to me for so long. I'm going to fuck that same ass that had those cheerleaders' panties so wet, they wouldn't undress for gym after your class."

With that, he felt the hard lifelike cock enter him. His gasp filled the room, as the searing pain he first felt had him frightened. But then, it was like he learned how to let loose, and just feel. He felt the muscles loosen, and the "cock" moving much easier inside him. All of a sudden, he felt another stopping point and pain. She felt the resistance too, and backed out a bit, but continued to fuck him, in and out up until that 'wall'. He began to feel himself move in her rhythm, matching each thrust into his ass.

"You're beginning to open that door, aren't you Mr. Ballard? Learning something new about yourself, aren't you Mr. Ballard".

Lulled into this now pleasurable little in and out, he was ill prepared for her final, unannounced, violent thrust.

"Oh God!" he screamed, as he was reamed. The dildo's plastic sac slammed into his vulnerable and now aching balls. He felt her pelvis slam into his butt with such a force, he was glad this contraption of hers was sturdy, less the thing topple over, landing him of course on his rock hard (but not hard enough to hold him up) cock.

She moved her arms up his back, as she continued to thrust, even though there was nowhere else to go. Her face now moved onto his shoulder, he could feel and hear her gasping breaths. She plastered her body to his, grinding her groin to him, pushing that deflowering tool into him. He realized her irregular breathing meant all this fantasy turned reality, along with the physical sensations she was creating against her clit with the nubbins on the inside of the strap on harness, were bringing her to climax.

He felt her smooth, but fiery hands move, caressing his sides, and then move around to the front of the arch, to take his hardened penis in one of her hands. She alternately squeezed savagely, and stroked his steel-like cock, whilst her other hand first cupped, then squeezed his balls.

"Yes, Lila, yes!" he screamed, in this new territory of bliss. The compilation of all these new sensations had him quite glad to be held in place by her cuffs. As her moans increased, and her body spasmed to her own pinnacle, he was overcum in his own. Her strong hands working him so, as she filled his virgin ass with her "cock" had him pushing himself hard against the arch as every jet flowed from within him. Her hand had moved, when she had first felt his muscles contract, so she could catch his hot juices.

They both rocked themselves in unison through their orgasms, and soon, as he hung from his restrains, legs completely failing him, he felt her body sag, as she slid down the other side of her orgasm's mountain. As she descended, she reached her hand, full of his cum, around to her mouth, to taste him. "Mmmmmmm, Mr. Ballard, you do taste good! Here, try some." With that, she reached her hand around to his face, and fed his mouth some of his own cum.

At first, he tried (in vain) to move away from this, but since he couldn't, decided to go with it. :After all,: he thought, :this is the day for new discovery:, realizing he was standing there with a plastic cock still impaling his ass. Besides, this woman had just taken him on the most erotic journey of his life, and he was not about to do anything to jeopardize another journey. Something about this woman, his former student, had him knowing she had many more lessons for her ex- teacher. He was going to be a straight A student.

kneeonsigh
kneeonsigh
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