Young Winston Ch. 10-11

CHAPTER TEN

ELEMENTAL

How can one but regard a society with derision that lacks the courage and maturity to face up to the sexuality of its most virile citizens. These young adults placed in my charge should have been out fornicating at every opportunity day and night, but instead they were subjected to ceaseless, commercialized, sniggering titillation on the one hand, and knuckle-dragging, ignorant, puritanical repression on the other, and then expected to sit still and memorize the Gettysburg Address. What utter nonsense.

Now, I am the last person to advocate that they be allowed to run riot in an orgy of free love and erotic indulgence, after all, our biological ancestors had to... earn... their opportunities to fornicate. But rather than deny their basic evolutionary demands, I intended to harness their vitality and use it to control and motivate them to become decent, hardworking citizens. The potential here was enormous, so it was with considerable excitement that I observed young Winston when he arrived promptly at seven A.M. Saturday morning. His mother was being difficult; claiming that because of a change in her plans she could not allow him to be away from home that evening. It was annoying to say the least, but I had determined that I would simply step up the tempo of the experiment.

For simplicity's sake I intended to concentrate on the most difficult population, the eighteen and nineteen year olds. My concept was not rocket science, in fact it was so... elemental... so natural that even my low wattage secretary could understand it.

Is there any chance that my theories will be accepted? In some distant future perhaps, when I will be seen in retrospect as a courageous pioneer, but in America, in ...this... century, most certainly not. Frankly I don't care; my lifelong, selfless dedication to teaching, has led me to a position where I finally have the opportunity to put my long-held theories to the test. I will record my findings for posterity certainly, but I do this primarily for my own... intellectual satisfaction. Should I also achieve some sexual gratification as well, and I believe I might, that will be purely incidental to the main purpose of the experiment.

The task before me was difficult but relatively straight forward. I had to ascertain how many orgasms these young beasts required every day to bring them to a state of sexual satiation and docility. Then I had to determine the best possible method for achieving these orgasms without wasting precious teaching time or getting anybody pregnant. I also acknowledged that it would have to be sufficiently pleasurable to everyone involved that they would be motivated to keep it all a secret. A tall order, but I was never one to shrink from a challenge.

I knew that there would be individual variations, of course, but I suspected that the number of orgasms required would be between three and six. To get to the hard truth we would have to engage in diligent and persistent experimentation and observation, starting with young Winston and a suitable female subject as soon as one could be obtained. After that we could slowly increase the pool of test subject until we had gathered a representative population.

Miss Stella Daily, who rents a room from me, complained that it was too early in the day to be sexy, but on the contrary, I told her to leave herself just as she was when she rolled out of bed that morning. With her sleepy eyes, her cloud of red hair in unruly disarray, and her natural blowsy, boudoir look about her, I knew that she would be perfect for the task at hand. Naked under a short, thin, nightgown that glided over her wonderful pale skin I knew that she would be as distracting to a boy like Winston as a class room full of tight skirted teenage girls.

None the less I understood that she might require assistance, and I was willing to get my hands dirty, so to speak, in the interests of science. To that end, I was up early as usual, but dressed in a thoroughly inappropriate manner. I am not unfamiliar with the display and use of feminine charms, although I had never had to put mine to the test before. I squeezed into a very proper knee length skirt that I had outgrown in every direction, and pulled it over top of black nylon stockings. On top I wore a crisp, far too tight, white blouse that stretched across my ample bosom over top of a so called "push-up" brassiere. I wore four inch heels purchased specially for this occasion. It had been a long time since I had worn such shoes, but the feeling of power they gave me was unchanged.

I didn't want to situate the estimate, but there was no need, and in fact no time, to approach the problem with robotic thoroughness. My thesis was that the maximum number of orgasms would be six, and that the maximum acceptable time to achieve them would be twenty minutes apiece. Therefore we would endeavor to make the boy "come" as they say, as often and as quickly as possible. After each orgasm we would then subject him to the appropriate degree of sexual stimulation required to return him to a restless, inattentive, condition.

The boy was prompt, well-scrubbed and eager as he stood before me in my large library den.

"Take off your clothes," I commanded.

"Yes ma'am," he replied and started stripping at once.

"I want to be able to observe your cock at all times," I added. I had decided to use current slang when referring to anatomy and sexual activities as it was commonly regarded as more sexually stimulating than clinical language.

"Yes ma'am," he replied again, and by that time he was completely naked and standing at attention. I could see that we would be able to commence with the experiment immediately as his large member was standing out fully engorged.

I was perched on the edge of my desk, purposely posed with one leg raised so that I could swing my foot from which a shoe dangled seductively. My skirt was hiked up higher than was necessary in order to display the tops of my stockings, and all but one of the buttons on my blouse was undone. I had given considerable thought to my appearance and pose, whereas Stella required no forethought or coaching. She sat crosswise in an armchair a little to the side of my desk with her legs up on the arm so that her gown had fallen back into her lap revealing her fiery thatch of pubic hair. She regarded Winston with frank interest and licked her pouting lips with the tip of her tongue.

"Masturbate," I said.

"Ma'am?"

"Masturbate," I repeated firmly.

"Jerk off," Stella called out from her chair.

"Yes... jerk off Winston," I said.

"Right here?"

"Yes, I want to watch you and time you."

"Just like this, right here, standing up?"

"Yes," I replied and hitched my skirt up a bit higher so that he could see the crotch of my expensive, black silk panties. Stella shifted her position a little and pointed her "pussy" right at him.

"Is that going to be a problem?" I demanded sternly.

"Ah, no, ma'am, if that's what you want."

"Well get on with it boy, and be quick about it, as quick as you can."

I had never done this sort of punishment, or treatment if you will, before. Through my years as a teacher and headmistress, almost entirely in private schools, I had witnessed a great many sudden ejaculations as a by-product of a good spanking, especially if I had a boy across my knees. Also, I had caught a great many boys in the act of self-abuse, as we used to call it, in many different places, always to have them stop and shrivel up in fear and embarrassment. This was entirely different, and surprisingly pleasant to watch.

Winston was, as I had suspected, quite shameless. He had an excellent body in all respects and the confidence that goes with it. He stood boldly, legs well apart and began stroking his cock with his fist, pointing it straight at me. He obviously understood the intent of our appearance and looked us over with his clear, blue eyes, smiling with appreciation.

The room was air conditioned, but I quickly began to feel very hot prompting me to completely undo my blouse and fan it to cool the droplets of sweat gathering on my breasts. My pussy became quite restless, but I managed to keep my hands off of it. Stella on the other hand, had cocked one leg up and was idly, seemingly thoughtlessly, toying with hers.

"Ummmm," she said staring at Winston's cock, "very nice," in her sleepy voice which immediately caused him to speed up.

I made a mental note of that, aural stimulation seemed to be very effective. I shifted uneasily as I watched him grab his balls in one hand while vigorously working his shaft with the other, drawing lubrication from the beautifully swollen head. I had to stand up to keep him from seeing that my panties were now wet from my own lubrication. A natural, sympathetic reaction, I assumed.

"Come on, Winston," Stella purred. "Come on, baby." She began to finger herself quite openly without taking her eyes off of the boy. I had explained the experiment to her, and once she understood what it would entail, and how important it was to me, she had been an enthusiastic supporter. She clearly knew what was expected of her. What she lacked in education she more than made up in loyalty and earthy sexuality. "Ummmm, you're making me all wet," she added in a breathless tone.

That seemed obvious enough, went without saying really, but it had a positive effect on Winston. Well I was "all wet" too, but I wasn't about to announce it. I removed my blouse and tossed it wantonly aside.

Winston groaned, stiffened, and began to ejaculate. It was so forceful a stream that it landed just short of my new shoes. I exhaled and tried to moisten my dry mouth, and then remembered to look at my watch.

"Eight minutes," I croaked. "Very good."

CHAPTER ELEVEN

REMARKABLE

This was turning out to be a great day. I was getting a free peep show, and I was allowed to jerk off while I was watching it. She wanted me to jerk off! Principal Harden wasn't trying to stop my body from functioning, she was encouraging it, and enjoying watching it too, which made it all the more fun.

After I came the first time, she sat me down in a normal, one-piece school desk in front of her large, dark wood paneled one. I'm sure I looked ridiculously out of place in her deep carpeted, book lined study. I felt that way at first too, and the wood of the seat was hard on my ass, but I wasn't going to complain. Anyway, I had a sheet of math problems, my worst subject, in front of me and I had to pay attention. That was hard because Principal Harden was always moving around, sometimes perched on her desk in front of me, sometimes pacing behind me so that I could smell her sweat and perfume, and hear the swish of her nylons. She had taken off her blouse, and she just left it off which was so cool, because it was so out of place in this school-like setting.

It was all like a wet dream. The principal pacing about the room, very straight and upright as usual, only better because the heels she was wearing pushed out her ass and made the muscles on her calves stand out. She had on a black bra with long straps that cupped her tits low and gave them miles of cleavage. Her hair was all prim and proper, and she wore her pointy, cat's eye glasses with the chain that went around the back. She kept her chin up and kept looking down her nose at me, trying to look very dignified, like there was nothing unusual going on.

I didn't know if Miss Daily had come when I did, she had sure sounded like she was getting ready too, before I closed my eyes and let fly. As soon as I was done spurting she jumped up, got down on her knees and cleaned up my spunk from the carpet with a cloth, showing me her round, white ass as she did it. This was so great, I didn't even have to clean up after myself! Then she went away.

I finished my questions in the time I was allotted, and when I stood up to give it to the principal, the sight of her made me start to swell up again, let's just say I was swinging lead as I approached her desk. She looked at it with interest, and sat down behind her desk.

"You get one stroke for every wrong answer," she said, pulling a big black strap out of her drawer. "There are no silly school rules here."

"Shit," I said, if I had known that I would have been more careful.

She looked up at me, and raised an eyebrow. "That will be three more," she said.

While I was waiting, Miss Daily came back into the room, she was all made up now like I usually saw her at school, but only more so. Her red blondish hair, redder, but not fake looking at all, was piled high on her head and then came down the sides of her face to just about level with the bottom of her cute little nose. It was thick at the top but light and feathery at the sides and the bangs. Her eyes were a light, misty blue, and she had this innocent look about her even though she had on thick eyeliner and very light powder-blue eyeshadow. I figured that it was her eyes, and her plump lips, that were always a little parted, that made her look kinda helpless and confused all the time, but like helpless and confused because she was so horny and didn't know why. Really horny and needed someone to help her out with that, you know.

"Hmmm, seven wrong - that makes ten strokes," Principal Harden announced as she stood up.

"Poor Winston," Miss Daily said with a little pout and ran her nails across my shoulders.

"Lean forward and support yourself on the desk, arms stiff, that's it, bum out further," she commanded and I obeyed.

I didn't want any trouble; these past few years the woman most like a mother to me was not Gloria, but Miss Lee the local librarian who was in charge of this fantastic library and had almost no patrons because Cocoa Beach people didn't read that much. I ended up spending every free minute I had there. She taught me a lot of things, she appreciated my mind and expanded it. The last thing I wanted was for her to get into trouble on my account, in fact the less said about her the better.

The first smack made me shout in surprise. It had been a long time since I'd been hit that hard, and with such an effective tool, never by Gloria, in fact not since back at the orphanage. I guess I had gone a bit soft.

Miss Daily looked shocked, she had jumped almost as much as I did at the loud slapping sound. She bit her lower lip and looked past me at the principal with a worried expression. I had straightened up a little from the blow, but I grimly returned to the proper position. I heard Principal Harden chuckle, and then, in the silence of the room, I even heard her panting a little, and I imagined that she was building herself up for another stroke, so I jumped again when instead of the broad strap, I felt her cool fingers lightly brushing my bum.

"Now, now, Winston, you really must get hold of yourself," she admonished me and I could hear great satisfaction in her voice. "I expected better from you."

Her fingers continued to play over the hot area where the strap had struck, and then they wandered a bit more. I tried hard not to tense up.

"You'll mark him," Miss Daily blurted.

There was another silence, although her fingers didn't stop. "Ummmm, I suppose you're right, and that won't do, will it," she said.

"No, someone'll see," she replied.

"Very well, the flat of my hand it will have to be."

She went back to the desk and regretfully returned the strap to her drawer. She looked at me with a smile. "You really should get a haircut," she said as she fooled with the tight waistband of her skirt. She came around the desk and started in on me with her hand, and I was back in familiar territory. She was more likely to hurt her hand than my hard ass. She delivered the blows slowly, deliberately, making me count them out, which was something that Gloria never did. She allowed her fingers to trail around all over my cheeks, but she didn't grab them the way Gloria liked to do. By the time she was finished my boner was back.

"Oh, excellent," she said. "Stand back from my desk and...jerk yourself off again."

"Yes ma'am," I replied, and I stepped back and looked hopefully over at Miss Daily.

She smiled an encouraging smile, "Come on, Winston, let's see what you've got, show us that you're a real man," she said, as she stood there toying with the only button that held her straining blouse together. With the bra she had on her big tits stuck straight out, and below that she had a very tight orange skirt that came just to her knees, with nude stockings.

I nodded and started stroking harder, casting a look over at Principal Harden who was coming close to my other side her breasts jiggling in her stiff bra as she made long, deliberate strides in her high heels. Miss Daily popped the button with a little giggle, and her blouse snapped back to either side of her white, bullet bra. It had heavy-duty under wiring, and the cups covered most of her big boobs, but they were totally sheer except for a single line that ran from top to bottom and side to side of each one, just like the cross hairs of a sight aimed right at her nipples. Her tits filled the cups right up and pushed inward to form deep cleavage, the shoulder straps were hitched almost to her shoulders pulling everything up high on her narrow chest. I leered openly at her and continued to stroke.

Principal Harden moved in front of me and perched on the edge of her desk again. I stared and stared at the dark triangle at the hem of her skirt above her stocking tops but I couldn't see any panties. Would she do something as nasty as walk around without panties on, I wondered.

I coughed, "I'm a little dry," I said.

The principal didn't seem to know what to say to that, she just shifted a little so that I could just make out a few black pubes.

"Let me help you out, poor boy," Miss Daily said and she came up beside me, took my head in both her hands and gave me a very wet kiss with her soft, fat lips that tasted real fresh and like raspberry's. It was the first time I'd ever had a kiss that didn't taste like booze. The kiss went on for a while, she was giving me lots of wet tongue, and I heard Principal Harden make some impatient, annoyed sounds. I swiveled my eyes over to her, even as Miss Daily held my mouth against hers. She stood up, turned around, and unzipped the side of her skirt. Then she wiggled and stepped out of it, bending over a bit and showing me her completely naked ass framed by her black stockings and suspenders. I groaned, breaking the kiss.

"Oh my," Miss Daily said with genuine surprise. "You are a lucky boy," she added.

I spit some of the saliva she had given me onto my hand and picked up the tempo of my strokes, right hand on my shaft, left hand squeezing my balls. I was very horny, but I was trying to hold back, even though I knew Principal Harden didn't want me to. I was enjoying the show and I was wondering, "Man, if I hold out, how far they will go?"

Principal Harden returned to perch on her desk, now just in bra, suspenders and stockings. She still had her heels on and she dangled one from her toes again which was so sexy that it drew my eyes away from her full wiry bush.

"Well, hurry up," she said, "We're waiting." She looked at her watch, "ten minutes," she said.

"I'm still a bit dry," I said. It was true, I was really whipping my dick, but even with the spit from Miss Daily, and what I could still catch leaking out the head, I really was dry and even to starting to chafe.

The principal looked thoughtful. "Good point," she said. "We will get some lubricant for next time, but you must finish this one now."

"Ahhh, I'm trying, but..."

"More visual stimulation perhaps?" she asked and before I could answer she said, "Miss Daily, remove you skirt and let Winston look at your ...cunt."

I groaned to hear her talk that way, it was so unexpected and nasty.