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What Weapon is Mightiest of Them All
“Whew Wee” Don whistled through his lips as he surveyed the buttocks and thighs of his secretary, bent over at the waist restrained in the pillory before him. “Now that is quite a sight.” Peggy’s entire backside was essentially a single red-purple bruise with tags of torn skin hanging in scattered strips. The whole mass looked more like hamburger than skin. “Well Joan, thank you for cleaning things up,” he said ”I always appreciate it.” Peggy was startled by the entrance of her boss. Nut honestly she was too befuddled by her pain to either think the implications out further or even to be embarrassed by her nakedness, disheveled appearance or bizarre position bound in the pillory. Draper asked her, “Well Peggy have you learned your lesson, not to screw around like a cheap slut?” The pony-tailed head bobbed up and down in concurrence. Joan interjected, “she really has not yet expressed sorrow or begged for mercy.” Don said, “I can fix that” and unzipped his fly. He took his right index finger and inserted it into Peggy’s vagina. “Hmm” he observed as it readily entered all the way, “remarkably moist. Peggy you must have been enjoying yourself.” Only then did Peggy’s fogged brain begin to realize that he was right. She was now aware that her pussy was oozing wetness. She could not remember ever being this moist before. Peggy was startled by being fingered by her boss, who had never expressed any sexual interest in her. Of course considering the range of sexual demands being placed upon him he must be superman. First, he had that beautiful wife Betty to service. Then there was his mistress Midge to keep him busy. Lastly, he was inundating the exotic Rachel Menkin with sufficient charm to melt even that Jewish iceberg. Peggy couldn’t imagine that he would waste his time and energy on a lowly secretary.
Don now inserted two fingers into Peggy’s vagina and began to harvest the juice to lubricate her perineum. She responded by wiggling her ass around and thrusting herself onto his fingers whenever they were inserted. Then he did something that really startled her. He took his index finger and stuck it suddenly and forcefully into her rectum. “Ouch! No! Don’t you do that.” she said as she suddenly broke her silence. Although she had been fingered before my many men, she had never been fingered in that way. She was an anal virgin. Don smiled and began to vigorously lubricate her anal ring with her vaginal secretions while at the same time stroking his penis with his left hand to bring it to full erection. “Oh no, you aren’t going to take me like a boy, you’re not. Oh please no, don’t do that to me, please.” the pony-tailed girl pleaded. Joan also began to smile. She had never thought about it that way. She realized that Don had an insight that she had missed. The slut had a virgin asshole. He was trying to accomplish with his cock what she had failed to do with her whip. And looking back at it, Joan realized that she never had any hang-ups about taking it up the ass. Well different strokes for different folks.
As Don’s fingering of Peggy’s asshole continued, the girl’s protests became louder and more vociferous. “No, No, NNOOOOOH!” she exclaimed as he forced the head of his penis into her anal ring. When he thrust his shaft into her rectum she rent the air with a scream. And as he began moving his penis in and out, she struggled against the bondage of the oaken pillory, albeit to no avail. Peggy became livid from trying so hard to contract her pelvic muscles and keep him out. But Don only smiled at the stimulation that the tight grip on his cock provided. He reached up and unclipped the back of her bra unleashing her surprisingly large tits. He gripped the dangling globes firmly, one in each hand and squeezed as hard as he could when ever he thrust in. When ever the mood struck him he shifted his grip to grasp her nipples between his thumb and forefinger and twisted as hard as he could. Peggy became hysterical and bucked like a wild animal, but to no avail. Don was an experienced rider and she was firmly restrained by the pillory. Finally, he gave one last, deep thrust and shot his woad. Peggy went rather limp and just sobbed quietly. Joan stood by amazed. Don had indeed conquered with his prick wherein she had failed with her strap and cane.
But Don was not done yet. He walked around to the front of the pillory and grasped Peggy by the pony tail. As her head came up, the secretary finally understood an aspect of the pillory’s geometry that had early eluded her. When she looked up from her bent over position, her face was almost exactly in the middle of the tall man’s crotch. “Oh no. I don’t do that either.” she exclaimed, anticipating his next move before he even made it. Don once again smiled as he rubbed his now flaccid penis against her nostrils. “Come on Peggy, don’t you like the smell of cum and shit. You’re going to give me a nice cleaning. I need my pecker Hoovered. Open up.” Peggy’s eyes widened as she watched the penis being waved in front of her face. But she kept her lips tightly sealed. Don remarked, “Don’t want to open up, we can fix that.” And taking his left hand he squeezed her nostrils shut cruelly. She wouldn’t open her mouth and now she couldn’t breathe through her nose. Her face started turning redder and redder. Finally the need for oxygen overcame her pride and she opened her mouth just enough to draw a gulp of air. “OOUUCCH – ak” she went as her protest was cut short by the insertion of his cock. Don looked her in the eyes and said softly, “Now Peggy, be a good girl. Because if you bite, that nasty lady Joan over there has a pair of pliers and she will pull out your teeth. Then you will have to suck me off with your bloody gums. And you will have to wear dentures all the rest of your life.” Peggy didn’t know whether or not he was kidding. However she was sure that once Don gave the order to Joan, there was no action, no matter how cruel or outrageous, that the office manager would not do. And Peggy suspected that Joan would enjoy it. So she was stuck with it – a very large cock in her mouth. And so it went, as Don’s cock engorged, he thrust it deeper and deeper into first her mouth and then progressively her throat. There wasn’t much she could do. The smell and taste of shit was overwhelming her and making her nauseous. Don’s fully erect cock was intermittently obstructing her airway. Her nose was full of snot. And the battering of the back of her throat was making her gag. She was gasping for air as he ejaculated into her throat. And just as he pulled out she blew her supper. Don was an old enough hand at this game to have foreseen what was about to happen. He dodged off to the side just missing the spewing forth of a mix of wine and half digested chunks of chuck and potatoes and carrots. “Oh Shit” exclaimed Joan as the mix spewed out over the white rug covering the floor under the pillory. Peggy continued to gag and retch. At one point she willfully pursed her lips together in an attempt to halt the stream but this only forced vomit up into her nose.
At this point Don motioned Joan over to him. “Kneel and make me hard” he commanded, wiggling his limp dick in front of her. Joan knew better than to argue. She knelt and went to work to revive a penis that had already had quite a workout. However, Joan was a master at limp-dickology. The road to office manager had been paved by resurrecting many an elderly executive organ. Soon Don’s tired and weary warrior was ready for battle again. There was one hole in Peggy that he hadn’t properly plugged yet and he went at it doggy style. Totally exhausted, beaten and degraded Peggy just moaned as he fucked her pussy from behind. She didn’t even try and struggle but merely meekly moaned and occasionally retched as he thrust in and out of her vagina. He did what he could to arouse her by squeezing repeatedly her pendulous breasts. This seemed to work. It never ceased to amaze him how really mashing a woman’s jugs got the muscles of their pelvic floor to function. She would have some nasty bruises tomorrow morning but compared to the slaughter inflicted on her backside, his ministrations were gentle. Beside, he was sure that Joan would minister to her later. His third ejaculation in forty five minutes was a relatively weak affair but he was satisfied with his evening’s work. He did make sure, however, that Joan licked him clear before he slipped his pecker back into his pants. “Well folks, see you bright and early Monday morning” he quipped knowing that the women would be in the office at 7 AM sharp while he would saunter in about 9:30. He had given Joan some very specific instructions about that. As he walked out the door he wondered where and how and why was he going to get it up with Betty when he got home -and whether he really cared.
After Joan released Peggy from the pillory she showered herself and the young secretary. She loved toweling off the inflamed body of a secretary made totally submissive by a very thorough beating. She laid Peggy prone on her bed and rubbed a healing ointment into her backside. Joan knew from experience the wonders that Aloe vera worked on the badly beaten backsides of the ladies of Cooper Sterling. Despite the shower, Peggy’s vagina and rectum still held a surprising amount of semen. Joan thought it was delicious. That night the naked girl cried herself to sleep nestled in the arms of the equally nude office manager. Joan appreciated that life was wonderful.
Epilogue
Monday morning there was a spring in Peggy’s step as she entered the lobby of the Sterling Cooper building at 6:45 AM. She was wearing a brand new suit cut to the latest fashion, the skirt of which revealed a great deal more leg than she had ever dared to reveal before. In fact, it might be said to almost be daring even for the summer of 1960. “But what the hell” she thought “I am twenty, single and all of Manhattan is my oyster”. Even more daring than her skirt was the fact that beneath her half slip she was without a girdle. In fact underneath that half slip was nothing more than a garter belt. She had been instructed, No Panties and No Girdle. And Peggy always followed instructions. To be sure, it would have been torture to be wearing a girdle this morning, especially the panty-leg type that she often wore. Anything compressing her tattered and torn backside would be agony. On the subway this morning she was fantasizing that everybody could see up her skirt her naked pussy and battered buttocks and thighs. The thought excited her so much that her vagina started pumping out slime again. Oh but wasn’t it a great day to be alive!
When she got to the 23rd floor Peggy immediately went as instructed to the ladies room. Joan was already there. “Take off your jacket, blouse and bra” the office manager instructed as she pulled a segment of chopped down fiberglass fishing rod out of the cabinet. “Hands clasped behind your back and kneel down” Joan commanded. She continued, “You know the really nice thing about a breast beating is that you can watch the wheals and bruises form right before your eyes. And it is really cute when the blood oozes out of the nipples just like milk. Except it is red.”
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