Detention with the Headmaster Ch. 02

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She is forced to strip naked and endure a spanking.
1.7k words
4.37
186.2k
60

Part 2 of the 3 part series

Updated 10/07/2022
Created 01/24/2011
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It was one week after the first detention Bree had with the headmaster. It was the class leading up to lunchtime and she was finding it very hard to concentrate, feeling extremely nervous. She wondered what he was going to do to her, whether he would go easy on her or if he would spank her again. She was worried that he might punish her more severely if he had heard about what she'd done after school on the day of that detention. She knew the next day the footy guys had been sniggering about something whenever they looked at her, but hoped the rumour had gone no further.

As class ended she felt her heart rate speeding up, barely noticing her friends making smart comments about her having to do detention again. She left quickly, not wanting to aggravate the headmaster by arriving late.

As soon as she walked in, she could see by his cold appraisal of her that he had found about what she had done after the last detention. "Close the door," he snapped as she faltered under his glare. She jumped and did as he asked, dropping her bag and standing stiffly in front of the desk, breathing fast. "Well, Bree, I see you did not learn your lesson from last week. I thought a bare spanking would make enough of an impression on you, but obviously not."

"I'm really sorry, sir, I didn't mean to, I mean-"

"Enough! You have acted like a little slut again and it is obvious that you need a punishment more severe than last week's. Take off all your clothes."

"Wh- what-"

"Do you want to be expelled, especially so close to graduating?"

"I-" Bree stammered.

"Then strip yourself NOW!"

Feeling as though she had no choice, Bree slowly began to unbutton her school shirt as the headmaster watched. She began to turn away, not wanting him to watch, but he snapped, "Stay where you are. You were quite happy for all of your boyfriend's mates to see your tits!" Bree flushed and kept going, slowly sliding the shirt off her shoulders and dropping it onto the floor by her bag. She felt slightly embarrassed by the headmaster seeing her plain white bra, but desperately wished this was as far as the exposure would go as she slid her tartan school skirt off her hips. There she paused, standing in her white cotton underwear and bra, looking pleadingly at her headmaster. "Keep going, I didn't say you could stop!" he ordered. She looked away and, wanting to get it over with, quickly unhooked her bra and tossed it to the floor, then slid her underwear off. "Keep your arms at your sides," the headmaster snapped as her hands moved self consciously to cover her breasts and pussy. She stood stiffly in front of him, feeling her nipples hardening slightly in the cool air conditioned room as the headmaster deliberately looked her up and down.

"Well," he said, "I hope being completely naked in front of me will make a more lasting impression on you for this punishment. Now bend over the desk with your feet apart like last week."

Bree obeyed, feeling extremely exposed being completely naked. Her breasts pressed against the cold hard wood of the table and she felt the air conditioned air cool between her legs as the headmaster got up and moved around behind her. He simply ogled her for a moment, enjoying the sight of her completely naked and bent over with her arse pointing up and her pussy visible between her legs.

Suddenly he spanked her arse, making her jump as he watched her arse cheeks wobble from the hit. "Now Bree, I want you to tell me why I'm spanking you naked like this. Tell me exactly what happened last week after the detention, and make sure you tell the truth as you don't know how much I know." He spanked her again, fingers curling into her arse cheek for a moment as she began to talk.

"Well, er, after school I went and found my boyfriend and, um, told him I wanted-" smack "I wanted to have sex."

Smack . "Feeling horny were you?"

"Um, yes." Smack. "He wasn't too interested at first as he had footy practice really soon. But I, er, kind of begged him for it so-"

Smack. "You were desperate for his cock, were you? Like a wanton little slut?"

"Well, yes." She jumped as the headmaster spanked her slightly harder. "So then he kind of pushed me up against the wall and, um, fingered me-"

"Your boyfriend pushed his fingers into your pussy inside a school building?"

Bree blushed at the headmaster's words. "I didn't ask for it! He just- ahh!" she cried as he spanked her even harder.

"Keep going."

"So then he told me he'd only have sex with me before his footy practice if we did it out on the field, close by you see-" she winced as she felt the sting of another spank of the headmaster's hand on her arse- "and also if, um, he came on my face."

"I see. And when he gave you those terms, did you refuse them like any sensible girl of this school would?"

"Er, no." SMACK. "Ahh!"

"So you were so desperate for some cock inside your pussy that you agreed to something very similar to what got you into trouble in the first place?"

"Y-yes." She shifted uncomfortably, feeling her arse stinging slightly from all the spanking. The headmaster slapped her arse again, enjoying his power over her.

"Well I hardly would have believed that you were so lacking in common sense. Go on."

"So then we went out onto the field, and, well, you know what happened..."

"Tell me exactly what happened. That's what I asked of you!" Smack.

"Ok, well, he told me to get on all fours- so I did- he pushed inside me and had sex with me like that."

"And how did him fucking your pussy from behind out in the bushes, treating you like a whore, make you feel?" She bit her lip and said nothing, then cried out as he spanked her arse hard. "Answer me!"

"It turned me on," she whimpered.

"Did it turn you on so much that you had an orgasm?"

"Well, no, I got really close but he pulled out before I could-" she cut herself off, shocked that she had just admitted it.

"So that must have been frustrating for you, getting so close but with no release?"

"Um, yes."

"So you didn't enjoy being left wanting?"

"No," she answered as he continued to spank her, wondering if it was a trick question.

"I see. I wonder if perhaps sexual frustration might be a good punishment for you?" With that his hand slipped down between her legs and lightly touched her pussy.

Bree jumped about a foot in the air. "Sir! What are you doing-"

"I'm punishing you," he said menacingly, as his finger found her clit and lightly rubbed it. She gasped and squirmed, heat rising from the unexpected touch. "What's this? You're dripping wet, you're such a slut aren't you..." He spanked her arse with his other hand as he continued to rub her clit. He had her panting and gasping, unable to believe how much the headmaster's touch was turning her on, then just as she felt like she was about to explode, he suddenly took his fingers away. "Oh..." she whimpered.

"What's that? You were so turned on at being spanked naked by your headmaster that you were about to cum?" Bree felt even more humiliated at his words, then gasped again as his fingers slowly rubbed her clit. Again, he touched her until she was on the brink of orgasm, wriggling around on the desk, then took his fingers away. Bree bit her lip, determined not to let him know he was getting to her, but when he did it a third and then a fourth time she let out a frustrated, "Please..."

"Please what?"

"You're driving me insane, please just keep going..?"

"You want me to make you cum? You want your headmaster to make you cum like a slut as you're bent over my desk completely naked with your arse red from being spanked?"

His words humiliated Bree but she was almost beyond caring as she quietly said, "Yes..."

"Well Bree unfortunately the reason you are here is for you to be punished, so I'm not going to let you cum. I hope that this punishment will make a lasting impression on you, I'm sure you wouldn't want to be sexually frustrated over and over like this again..." His fingers found her clit and ever so slowly stroked it, making Bree clench the desk hard with her hands and fight to not completely writhe around too much in the unrelenting torturous pleasure of it.

The headmaster himself was extremely turned on and entertained the idea of sliding his cock into her dripping wet pussy... but he held back, wanting to make sure that he had enough of a hold over her by the time these detentions lost all illusion of being a legitimate punishment. Besides, he was enjoying sexually frustrating her...

Just as Bree thought she was going to scream from the extreme frustration, the headmaster took his fingers away, slapped her arse one last time and pulled her up by her hair, pulling her back against his front. Her heart pounded as she felt the hard bulge of his erection pressing against her arse.

He bent his head to speak right into her hear, quietly saying, "Now, I hope you've learnt your lesson... no more exposing these-" he cupped her breasts, gently squeezing them- "or giving into this-" he slid two fingers over her clit and inside her pussy, slowly pumping them in and out a few times- "when it only gets you into trouble." He breathed into her ear for a moment while groping her breasts with one hand and ever so slowly pushing his fingers in and out of her hot tight pussy with the other, hearing her breathe fast, hard knowing she was so turned on he could do anything to her right then.

He withdrew his fingers, stepped back and said, "Get your clothes back on and get out. I'll see you next week. Remember what I said."

Bree was red faced and breathless as she quickly threw her clothes back on under his eyes almost burning into her skin, and left at top speed.

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AnonymousAnonymous4 months ago

Fantástica!!!!!

AnonymousAnonymousalmost 12 years ago
wow

Even better than the first one. My cock is so hard. I think I am going to have to stroke it. Mmm that feels nice. Thinking of Brea bent over naked. Rubbing my cock a little harder. Thinking of how wet her pussy got. Now my cock is oozing precum. Massaging balls with one hand as I slide my other hand up and down my throbbing cock. Imagining myself fingering her clit. Rubbing my precum over the head of my cock. Picturing myself dropping my pants and sliding my cock deep into her pussy. I wouldn't be able to resist like the headmaster. Rubbing my cock so fast as I imagine it slamming in and out of her pussy. Cumming hard as I imagine.myself cumming deep inside her.

Just d from od

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