The Headmaster's Office Ch. 01

"Which one, front or back?" asked the headmaster.

An eternity seemed to pass on by as Sarah thought about the question inside her head. If she chose her front, then she would only receive a single stroke between her legs. If she chose her back however, she would have to receive two instead. Normally, that was still the better option, but with the ginger root inside her now, she didn't even want to think of how it would feel to be punished back there.

"M... my front," said Sarah.

The headmaster nodded, and with trembling hands, Sarah reached down to spread apart the lips of her most intimate place, opening herself up so that the entirety of her folds was on display. Between the pink contours of her flesh, the entrance of her hole could be seen, along with the virginal barrier of her hymen inside. It was here that the headmaster placed the tip of the leather crop, and she winced as he tapped down against her sensitive folds a few times.

"Your hole, or your..." he started to say, but she interrupted him before he could finish.

"Please, my hole!" she cried, "Not the other place!"

The headmaster smiled a little, amused by her sudden desperation, and her heart skipped a few beats as he moved the leather crop up to hover over the hidden nub at the top of her spread open lips.

"Are you sure you don't want it here instead?" he asked.

"Please, punish my hole," begged Sarah.

"Even if it means two strokes instead of one?" said the headmaster.

Sarah trembled as she watched him rub the tip of the leather crop against the covering of her hood, slowly peeling away the flap of skin that protected the sensitive nub underneath. Two strokes, could she take two full strokes between her legs? But looking down as the headmaster drew back her hood, there was just no way she could take the punishment, even if it was only a single one, up there.

She swallowed hard, her voice shaking as she forced herself to answer.

"Please, I beg you, punish my hole," she said.

"Very well then," said the headmaster, "And why are we punishing your hole?"

Her legs shook with the effort of keeping herself spread open for so long.

"B... because I tried to masturbate," she whispered.

Here she was, lying naked on her back with her legs spread open and a knob of ginger shoved up her backdoor. Between her thighs, her privates glistened with the fluids of her own arousal despite the pain from the earlier strokes of the cane. Even now, she struggled to push aside the feeling of emptiness and frustration that her body sought so desperately to fulfill.

The leather crop came up, and she watched in slow motion as it came down, landing right between her legs and on top of her aching virginal hole.

"AAAIIIIEEEE!"

Her voice cut off halfway through the scream as she gasped for air, her breath no longer existing in her body. Her legs twitched as her toes curled down, shaking and trembling like a leaf caught up in a storm. Through some miracle, however, her fingers remained where they were, keeping her most intimate place spread open for the headmaster to see, even as molten fire flowed through her veins. Had she let go, then the stroke wouldn't have counted.

"Did that feel good?" asked the headmaster.

"No!" cried Sarah.

The headmaster tapped the end of the crop against the pinkness of her abused flesh.

"Are you going to keep sticking your fingers down here where they don't belong?" he asked.

"No!" cried Sarah.

"And are you going to play with your bottom, or the little nub that you begged me not to punish?" he said.

"Please Sir, no more!" cried Sarah.

The crop rose up one more time, and she watched in horror, her hands frozen in place as it came down again between her legs. It landed with a sharp smack, and her vision turned white as every muscle in her body clenched down all at once, the pain shooting through her amplified further by the burning in her rear. Between the spread lips of her privates, she felt the frustration rising as the blow threw her towards the edge of the abyss. Scrambling desperately to keep from falling over, she clung to the knife's edge, desperately praying that she would be able to keep herself from spending.

Then, it was over, and she sobbed as her legs gave out, lying back against the surface of the desk with her head turned away. Gently, ever so gently, she felt the headmaster reach out to take hold of the ginger root, and she hissed as he drew it out of her backdoor. Setting it aside, he reached out with a tissue to wipe away the tears running down her face.

"Hush, now," he said, "It's over at last."

Sarah tried to close her legs only to fail miserably as the muscles in her thighs refused to obey. Laying there with the wetness of her own fluids still seeping out of her now thoroughly punished privates, she sniffed as the headmaster held her hair out of the way. Slowly, after a good minute of crying, she was finally able to climb back to her feet. Stumbling a little, she wiped her eyes one last time and reached for her clothes.

"One last thing," said the headmaster.

Slowly, Sarah turned around, her mind already anticipating what the headmaster was about to say. As expected, a moment later, he reached into a drawer to pull out the familiar metal bands of a chastity belt. She winced as he slid it up around her waist and locked it in place. Then, he bent her over again to push a medium sized plug into her bottom. Held in place by the belt, every time she needed it to be removed, she would have to ask to borrow the key.

"Two weeks," said the headmaster, "One week for each time you've been punished. After that, you may come to have it removed. Please do your best to ensure we won't have to go for three weeks the next time, however, Ms. Whitney."

He smiled, and striking a match, he bent over his pipe to light it again, and taking in a careful draw, he blew a ring of smoke up over her head. Despite the soreness she felt, and the plug stuck up her rear, Sarah couldn't help but smile a little in turn. Even if it was only because she was glad the punishment was over, it still felt nice to do so.

Pulling her skirt and her school uniform back into place, she opened the door of the office and left. She would have to return again in two weeks of course, but for now, with her worries behind her, she was finally free.