Verity and The Headmistress

This is another very old story, maybe early 2000s. Please check out my newer stories written as Robert_Anthony.

All characters are over 18.

*****

Verity was shaking. She hadn't really wanted to get involved in the 'prank' the other girls had planned, but they had embarrassed her into going along with it. And, of course, she was the one who had been caught, while they all got away. So here she was, outside the head's office, awaiting her fate...

It was getting late and the halls were empty, save for Mr Harwell the caretaker and his stupid floor polishing machine. She looked up at the clock, it was past 4:30 - she was going to be late for her paper round... more trouble!

She took a sharp intake of breath as the head's door opened.

"Verity Marshall?"

The girl nodded.

"Right, in you come."

Verity slunk across the hallway and into the head's office. It was warm in there, it struck her right away.

She stood in front of the desk, while the headmaster sat down behind it.

"Well, I haven't seen you before, is there a good reason why I'm seeing you now?"

Verity looked at the floor.

"Are you going to tell me their names?"

Verity shook her head.

"Speak up girl."

"No Miss."

"No, I didn't think so..."

Miss Page exhaled deeply.

"Still, you'll just have to take the punishment for everyone, won't you?"

She looked into Verity's eyes and registered the obvious fear there.

"I suppose you're right... snitches don't get an easy time of it do they. Easier to take some short term pain, should make you more popular with your so called 'friends' at least. Although I don't understand how a smart girl like you got involved in the first place."

"I don't know Miss."

"Hmm, and how old are you?"

"Eighteen Miss."

"I see, and you've been at the college how long?"

"About four months Miss."

"Hmm."

"I am sorry Miss," muttered the girl.

Elizabeth Page moved her hand down between her legs under the desk. She pushed her fingers between her legs and found that her knickers were already damp. As she spoke to the girl she rubbed herself with slow, deliberate movements.

"Well, that's all very well, but the point is you are here to be punished, and punish you I shall."

As she said this her fingers pushed harder against her cloth-covered pussy and she squeezed her legs together.

"Mr Lewis told me he thought there were four girls involved, but only you got caught. Is that right?"

"No Miss," Verity blurted out.

"No?"

"No Miss, there were five altogether."

"I see," she said, smiling. "So now we're looking for four accomplices instead of just three... interesting. Well, you might regret telling me that, seeing as you will be taking the punishment for 'all' of them, but still, never mind!"

Elizabeth stood up and walked around the desk. The girl was visibly shaking - and this only made her want her more.

"Take your blazer off," she ordered.

Verity slipped the blazer off her shoulders and the head reached out her hand and took it off her. She folded it and placed it on the desk. When she turned back to the girl she noticed that she could see her bra through her thin white shirt.

"I'm afraid to say that, as, by your own admission, there were five of you, that means I'm going to have to give you thirty strokes of the cane."

Verity's mouth fell open and her eyes welled up with tears.

"Six each, you see... unless you want to give me their names of course?"

Verity sucked her lip, she wanted to tell her their names, but she knew that if she did they would never forgive her. She hadn't found it easy making friends at the school and this would put her right back to square one, worse even, as she would have a reputation for being a snitch.

"I can't Miss."

"I see. Tell me Verity, have you ever had the cane before?"

"No Miss."

"I didn't think so. I'm sorry to have to tell you, but it's very, very painful. Still, I guess I can go easy on you for the first few, after all... I'll need to save my arm, I don't think I've ever given thirty strokes in one go before."

"Thank you Miss," mumbled the girl, nervously.

Elizabeth walked to the door of her office and from the hook on the back of the door she pulled down her trusty cane. She flexed it and then swished it around a few times, getting a feel for the instrument before walking back over to the trembling girl.

The head circled her prey, she loved to look at them like this, nervously awaiting their punishment, it made her wet.

Verity's long blond hair fell over her shoulders and down her back, while her pleated grey skirt was cut just below the knee, leaving only a short expanse of bare leg before her white socks and highly polished black shoes.

'At least the girl presents herself well,' she thought.

"So, Verity... as keen as I am to get started, I have to say, I don't actually think you're a bad sort. Your uniform is spotless and your hair is beautifully combed, I actually think you're a good girl who got into an unfortunate situation. Still, I can't not punish you, but... I can let you into a little secret, being as it's your first time."

Verity looked up, curiously.

"Did you know that the cane will hurt a little less if your bottom is warmed up before hand?"

"No Miss."

"I mean, don't get me wrong, it will still sting... but it will take the edge of it a little bit. Would you like me to do that for you?" Elizabeth's breathing was becoming shallow as she spoke.

"I... yes, please Miss."

Elizabeth exhaled sharply as she felt her pussy growing wetter by the second.

"Good girl, lean over the desk then."

She pressed her hand into the girl's back to encourage her and Verity put her arms forward and slowly lowered herself onto the desk in front of her.

"That's it," Elizabeth purred.

Verity felt her skirt being lifted up and placed neatly on her back, then the head's palm being placed on her behind and moving in a swirling motion over her entire rump. Strangely Verity found this quite pleasant and relaxing. After a few moments though she felt the hand lift away and then slap down, softly at first, but quickly increasing in both speed and velocity. The slapping continued until it was anything but relaxing, the sound of the spanking echoing off the walls of the office.

As the heat in her skin increased, Verity became more aroused. It was as though the heat in her ass was spreading to her young pussy. And for her part, Miss Page couldn't help but notice the small but obvious wet patch beginning to form on the cloth between the girl's legs. She smiled to herself as she hammered down a few more ringing slaps and then stood back to admire the girl's glowing cheeks.

She waited a few seconds, just long enough for Verity to think it was over and then stepped forward again, now she really let her have it with both barrels and soon Verity was squirming on the desk.

"Keep still girl," the head barked. "If you think this hurts, just wait until you feel the cane!"

Verity tried her best to keep still, but Elizabeth's skilled palm was slowly turning the girl's cheeks a nice reddy-pink, at least the parts that weren't covered by her panties.

"There, that will do..." said Elizabeth, signing off with a brutal slap to the girl's right cheek.

She plucked the cane from the desk and stood behind the girl, admiring her tight cheeks and long slender legs. She pointed the tip of the cane between the girl's legs and tapped it from side to side against her inner thighs.

"Move your legs apart," she ordered.

Verity shuffled her feet sideways until there was a good six inches between her thighs, allowing the head a good view of her panty-clad pussy. The damp patch was getting bigger now and as she moved the cane up the inside of the girl's legs she heard a faint murmur escape the girl's lips.

"I think we need to get these panties out of the way," said Elizabeth.

No sooner had she spoken than Verity felt her knickers tugged down and the air circling around her warm ass and exposed pussy. This only made her wetter and she turned her head to the desk, ashamed and praying that the head wouldn't notice.

"Now Verity, I think you should count each stroke for me. You wouldn't want me to forget my place and have to start again, would you?"

"No Miss," breathed the terrified girl.

"Very good, then we shall begin."

Verity tensed up, waiting for the first stroke to land, but Miss Page waited, and waited, until she saw the girl's muscles relax, then she brought the cane down hard. Verity screeched loudly as the first burning, red stripe appeared on her ass cheeks. Tears filled her eyes as she tensed her buttocks again as she waited for the next stroke, could she really stand thirty of these without cracking?

"I don't hear you counting," spat Elizabeth. "Never mind, we'll start again."

"No, please!" Begged Verity.

"What? We've barely started girl, don't be so pathetic."

Again the cane swished through the air and cracked against the young girl's ass.

"One!" The count came, strained through gritted teeth.

"That's better, but a little louder if you please."

Again the cane came down.

"TWO!"

"That's it. Good girl."

Miss Page continued to lay six precisely placed stripes across the girl's backside, almost perfectly parallel and equally spaced. Elizabeth was slightly annoyed that one of the stripes was slightly lighter than the others, but overall it was a textbook display.

After six strokes Verity was struggling to keep her legs from buckling, she had never known pain like it, her skin felt like it was on fire and she couldn't begin to imagine taking twenty four more like that, and Miss Page said she would start off easy on her!

Mercifully, the older woman paused at this point and placed the cane on the desk in front of the girl. Then she went around the desk and opened a drawer, pulling out a pot she returned to the girl's rear and pressed a slathering of cold cream against her burning skin.

"This will help," she said, as she rubbed the cooling substance all over the girl's tight rump.

Miss Page applied more cream and Verity relaxed, enjoying the way the head's fingers moved over her skin. Soon Elizabeth's fingers moved lower onto the tops of her thighs and then inwards, inching closer and closer to their ultimate target.

The head felt the girl shudder as her fingers grazed right at the edge of where her pussy lips met her thigh and then pulled away again. Verity started making tiny movements, willing her tormentor's fingers to brush against her pussy, but Elizabeth was way too clever for her and kept her fingers just out of reach.

"Now Verity, listen to me... I know you're sore, but I have to finish your punishment."

Elizabeth picked up her cane again and pulled it back to strike, the whip through the air causing Verity to clench her cheeks hard in anticipation.

"Unless," paused the head. "There's something else you'd prefer me to do?"

Verity froze. She knew what she wanted, but she couldn't possibly ask for it, she was too embarrassed and confused.

The head dropped her arm and Verity felt the cane sliding up the inside of her leg.

"Maybe you 'want' me to cane you then?" Whispered the head.

"No, I...please."

"Please what?"

"Please don't cane me anymore."

Elizabeth placed her hand on the girl's ass again and gently massaged her skin.

"Is that what you want?" Asked Elizabeth.

"..." Verity couldn't bring herself to speak.

"Do you want me to 'touch' you Verity? Is that what you want?"

Verity nodded slowly, her jaw shaking.

"Ask me then, ask me to touch you."

"Please... touch me, Miss."

"Where do you want me to touch you Verity?"

"..." Again Verity faltered.

"Do you want me to touch you between your legs, is that it?"

"Yes Miss.."

Elizabeth breathed hard and the cane moved a little closer, just brushing the light hairs at the side of Verity's needy cunt.

"That's a very naughty thing to ask me, isn't it Verity?"

"Y-yes Miss," the girl stammered.

"I thought you were a good girl, but it seems I was wrong. In fact, you're a very naughty girl, aren't you?"

Verity's head dropped to the desk.

"Yes Miss."

The head dropped the cane to the floor and knelt down behind the girl; she put one hand on each of the girl's cheeks and pulled them gently apart, exposing her wet slit and her pink little asshole.

"Beautiful," whispered the older woman.

Her head moved closer and she breathed in the girl's scent.

"Oh God," sighed Verity.

Elizabeth used her thumbs to pull Verity's slippery, wet pussy lips apart allowing a few drops of juice to drip out of her and down the insides of her thighs. Elizabeth resisted the overwhelming temptation to lick them up; there would be plenty of time for that later.

"You're very wet Verity. I hope you don't make a habit of this sort of behaviour."

"No Miss." In truth, no one had ever touched her before... she hadn't had so much as had a kiss since she grew too old for kiss-chase.

Silently the door of Miss Page's office opened and in stepped a male figure. Verity didn't hear him enter until the door clicked shut and then she tried to stand, to cover herself up.

"STAY STILL!" Barked the headmistress. "I did not tell you to move... or would you like me to continue with the cane?"

"No Miss," wailed the girl. "I'm sorry."

The head laid one very hard slap to the girl's backside, before resuming her previous position. Then she slowly slid a finger into the girl's hole. She turned to face the man next to her.

"Nice and tight, just like I promised..."

The man smiled back and undid his zip, his cock was quickly pulled free and he stood there stroking it as he watched Miss Page fingering the girl. Meanwhile Verity was squirming on the desk now, more turned on than ever, but also scared of what was coming next.

"Pass me that cream," said the head.

Verity saw the man's hand appear to her right, reach across the desk and grab the tub of cream that the head had applied to her ass previously. His sleeve was brown in colour, just like Mr Harwell. 'He must be well over fifty!' she thought with disgust.

The man passed the tub of cream to Elizabeth, who placed it on the floor and issued a stern warning to the girl about moving, before turning her attention to Mr Harwell's erect prick.

She shuffled over to him and grasped his thick rod in her right hand. He wasn't much to look at, but who would have guessed he was packing such a thick, long cock? She hadn't given him the time of day until she became aware of some staff-room gossip about how 'blessed' he was, after that she made it her business to get to know him and ever since she regularly enjoyed feeling his fat cock stretching her holes over her desk.

She took the head into her mouth and sucked hard on it. She loved the feeling of her mouth being so full, but right now she was only interested in getting him as hard as she possibly could. She reached up and massaged his balls as she blew him, then pulled her mouth off and jerked his meat hard until it was visibly straining.

She let him go and Mr Harwell took over, stroking his cock as he watched the woman picking up the tub and dipping her fingers into it again. Verity felt the coldness as the head's fingers invaded her pussy again, working it into her and making her ready for the caretaker's huge cock.

Miss Page grabbed Mr Harwell's cock and pulled him closer, rubbing the tip against the girl's lips. Verity tensed as the head off his cock parted her cunt and slid ever so slowly inside. Mr Harwell took hold of the girl's hips and eased his meat gently back and forth, working it deeper and deeper inside her tight hole. It was an effort for both of them and it took a while, but eventually Mr Harwell had all but the last couple of inches inside the girl.

Verity felt completely impaled on Mr Harwell's massive dick, and her legs began to shake as he started to gently fuck his cock in and out. She sensed Miss Page to her side and she glanced at her, her face a picture of pain and pleasure as Mr Harwell started to fuck her a little harder.

"You lucky little slut," smiled the head. "You'll never forget this cock as long as you live."

Elizabeth reached under the girl and undid a couple of her shirt buttons, then pushed her hand inside and under her loose fitting bra. She quickly found the girl's left nipple and squeezed it between her fingertips.

"So lucky, and you don't even know it..."

She moved her fingers to the girl's other nipple and pinched that one too.

"Do you like it when I hurt you?" She asked.

"I don't know..." breathed the girl.

"But you like having that thick cock in you, don't you?"

Verity nodded.

"Yeah... feels great doesn't it? Once you get used to it... it took me a few minutes to really appreciate just how good it felt inside me too."

The woman smiled warmly at the youngster, then rose back up to her feet and turned her attention to the caretaker.

"You like fucking that tight little slut don't you Bob?"

He glared at her and reached up, mauling her left breast through her shirt then growling a single word as he put his hand on her shoulder.

"Down!"

Elizabeth sank to her knees as Mr Harwell pulled his dick out of the girl, leaving her feeling empty and exposed and turned towards the older woman. He pushed his stalk into her mouth and then grabbed her head, pulling it down hard as he fucked her mouth. After a few seconds he let go and she pulled back, gasping for breath. He did this a few times and then plunged his length back into the teenage girl in front of him.

Still gasping for air, Elizabeth pulled her skirt up and slammed her fingers into her soaking wet panties as she watched Bob's thick cock fucking into Verity's slick cunt. She watched for a few seconds more and then stood up, pulling her panties down and off over her shoes. She quickly got up on the desk and swung her legs across in front of the young girl, manoeuvring herself until her pussy was right up close in front of Verity's face.

Verity watched as Elizabeth undid her shirt, then stripped it off, exposing her ample breasts, then lifted her skirt to show the girl her dripping wet, perfectly smooth cunt. She used her fingers to part her lips and then slid her middle finger inside the sodden, pink slit. Then she pulled it out and pushed it towards the girl's mouth.

"Taste it," she whispered.

Verity opened her mouth and sucked the older woman's juices from her finger, her tongue curling around it to clean it completely. Elizabeth shuddered with lust, this girl was definitely something special.

She reached forward and grasped Verity's head, then pulled it down between her thighs.

"Lick me," she ordered.

Verity paused, until she felt Miss Page's hand apply more pressure to the back of her head and she felt her lips pressed into the head's steamy cunt. She licked amateurishly, lapping up the older woman's strong tasting juices, while Elizabeth moaned with pleasure when she occasionally flicked her aching clit.

"Yes, right there... That's it! Fuck!"

Elizabeth held the girl's head still with her right hand, while struggling to support herself leaning back on her left.

Mr Harwell was pounding the girl's pussy hard now and Verity was finding it hard to keep still, her tongue kept missing its target and Miss Page became increasingly annoyed. Eventually she let go of the girl's head and found her clit with her own fingers instead.

"Fuck me with your fingers," she barked at the girl.

Verity slid her hand forward and felt her small fingers enter they woman's juicy, slick hole. Elizabeth's fingers blurred on her clit as she started to tense up, while Verity moved her fingers gingerly in and out.

"Yesssssssssssssss," moaned Elizabeth as she hurtled towards her climax.