William Cyr - The Headmaster

"Ow! Oh, no more! Please! I beg you!" the attractive young woman begged hoarsely. "Ouch, please! It hurts! Please, I'll do anything! Anything!"

Applying his capable palm with even strokes, Frank appreciatively watched the undignified but appealing performance that she was putting on for him. Once again she was reinforcing his opinion that there was really nothing more attractive and erotically appealing than a tearful and obviously distressed young woman wriggling her scarlet bottom and kicking stockinged legs merrily back and forth.

"Stop! Oh, no, please! Pleeeeeeeeeese!" Erica pleaded between sobs.

"Please, I can't take it anymore! I just can't!"

Despite her tears and protests about the mistreatment that her pretty bottom was receiving, it was quite apparent that Erica was finding considerable masochistic pleasure in her torment. Frank was quite aware of the moisture seeping from her pussy over his bare thigh, and could see that her hips were jerking with coital-like movements each time that his hand descended against them. Her buttocks were a bright scarlet and were obviously simply burning up.

"Now I think it's about time for this!" Frank said, reaching back for the belt she had used on him earlier.

"Oh, no! Not that!" Erica screamed when she realized what he planned to do. The miserable young woman turned her tear-stained face back over her shoulder to plead with him with her eyes. "Please! I couldn't stand…"

Frank watched the pretty muscles in her red bottom tightening in fearful anticipation as he doubled up the belt.

Whack!

The belt coiled around her scarlet, cringing buttocks.

"Owwww!" Erica shrieked in a pain-stricken voice, her feet flying upward and her entire body giving a convulsive jerk. "Please, I can't stand it!"

Whack!

Once again the belt descended against her defenseless posterior with a loud smack.

"Ouch!" Erica emitted a soprano shriek, her scarlet buttocks wriggling furiously and her stockinged legs flailing back and forth in a revealing manner.

Despite Erica's shrieks and sobs of anguish, Frank proceeded to give her a thorough working over with the belt. Squirming and wriggling frantically, Erica was in hysterics when he finally stopped. Pausing to catch his breath for a moment, Frank admired the intriguing combination of brightly scarlet feminine bottom and shapely legs attired in black, full fashioned nylons.

"Now, Erica, get into a kneeling position on the bed with your skirt up!" he told the sobbing young woman.

Erica haplessly complied. "Please! Please, you're not going to spank me anymore, are you?" she tearfully pleaded in a distraught tone of voice.

"Please, please, I couldn't stand it! I'm just blistered all over!"

"No, I'm not going to spank you!" the former headmaster told her, standing up with his jutting erection pounding for release. "Spread your legs apart!"

"What are you going to do?" Erica asked in a very small voice as she reluctantly spread her stockinged knees apart. "Oh, no, you wouldn't!!" she gasped with horror when she began to realize what he had in mind.

Without replying, Frank moved into a kneeling position behind the cringing, miserable young woman.

"Oh, NO!" Erica shrieked. "You wouldn't!!! Please, not that! It's too humiliating! Please!" She twisted wretchedly in front of him, looking back haplessly over her shoulder to plead with him. "No, don't! Please!"

"Stay in position!" Frank demanded, ignoring her fervent entreaties.

Sobbing and shaking with fear and humiliation, Erica miserably remained in position on her knees and elbows with her scarlet, blistered bottom sticking up all too vulnerably. Frank caught her by the waist and began maneuvering to complete the anal connection.

"Please! Please! Frank, please!" Erica wept. "It'll hurt too much!

Please, it'll never fit! You're too big! Please put it in my mouth… or anything!"

Frank employed his thumbs to open her scarlet bottom cheeks as much as possible. Erica winced with pain as his masculine fingers brushed against her blistered bottom, and between sobs begged and pleaded to be spared the final indignity.

"Hold still!" Frank ordered.

"Oh, no, please! Please! Please!" Erica buried her face in her hands and sobbed as she made her final appeals. "Oh, please! Please!"

Her feminine body limp with fear, Erica shuddered as she awaited impalement on Frank's thick, lust-maddened masculine organ. Frank moved closer to her, allowing his rigid penis to slide into the crevice of her rotund buttocks. The contact produced violent quakes from Erica, who collapsed into blubbering tears and unintelligible pleas. Slowly, Frank allowed the bulbous head of his prick to explore the entrance to her narrow anal channel.

"Oh, no!" Erica sobbed. "Please, it won't fit! It won't fit! It's too big!"

Holding the squirming, sobbing young woman at the waist, Frank began inserting his thick, hot penis into the small opening.

"OWWWW!" Erica screamed at the top of her lungs as the huge crown began penetrating her anal canal, dilating the small opening in a highly painful manner. "Oh, for heavens sakes, no! Take it out! Take it out!

It's too big!"

As the head of his massive cock disappeared into the tiny pink aperture, Frank paused for a moment and then began thrusting forward to complete the anal penetration. Erica wept bitterly as she found herself impaled on the huge masculine weapon, and her sphincter muscles flexed desperately in an effort to expel the foreign intruder. Her kneeling body was convulsed with sobs, and her feminine spasms provided added thrills for his madly pounding shaft.

"Please, I can't stand it!" Erica begged. "Please, take it out! You're killing me!"

"Now you're really going to get butt-fucked, you little Nazi!" Frank told her.

Frank began thrusting his rock hard, thick penis back and forth inside the warm, incredibly tight canal. Each forward thrust produced a convulsive sob from the distraught young woman. Pumping with firm thrusts, he slipped his hands down between her legs and began to fondle her dripping-wet cunt. Erica's fountain began to gush its warm liquids over his fingers, and her bright red bottom wriggled girlishly as he worked his fingers between her slippery cuntal lips. Probing her hot, sticky pussy with his fingers, he continued thrusting his wildly throbbing penis back and forth inside her little butt.

"Oooooohhhhh! Ouch! Oh! Ouch!" Erica began to reveal in the mixture of pain and pleasure. "Oh! It hurts but it's… Oh! Ouch! Oooh! Oh!

Ooooohhhh!"

As Frank's probing fingers aroused her more and more, Erica began moving heir spank-reddened bottom around with progressively more frantic gyrations. As his pulsating shaft slid back and forth in the tight confines of her little rear, Frank could feel her anal muscles clutching frantically at him. His blood-dilated cock was aching for release and he made no attempt to hold himself back. Sliding his fingers past her lust-crazed clitoris and into her vagina, he began thrusting with almost brutal strokes that sent his rock-hard prick deep into her constricting anal tunnel. Finally, he simply let himself go and blasted his hot semen into her little butt with voluminous spurts.

"Oh! Ooooohhhh! Oooooohhhhh!" Erica wriggled and squirmed frantically and Frank could see that she was deep in the throes of an intensely masochistic orgasm.

Afterwards, Frank quickly picked up the gun that she had placed on the nightstand earlier. "Okay, Erica, I'm afraid the party's over for you for the duration!" he told her.

As he expected, Erica lost no time kneeling before him with her hands folded prayerfully in front of her. "Please! Please!" she begged. "Don't turn me in! I'll do anything you say! I'll be your slave! Please!

Please!"

"I'm afraid not, Erica!" Frank told her. "You're a real temptation, but this time I'm afraid we'll have to put duty ahead of pleasure." As he spoke, he reached for the telephone and Erica collapsed in sobs on the floor.