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The Headmistress, the Teacher and the Dirty Schoolgirl

Headmistress Miss Pemberton invites me to help schoolgirl Ashley live out her sex fantasies

As one of the few male teachers in St Matilda’s Academy for Young Ladies I considered myself fortunate to have a position in such a prestigious school at the age of thirty. I teach a final year class of eighteen to nearly nineteen-year-old girls. They all seemed to want to outdo each other in showing off their wares in the shortest skirts and the tightest, thinnest blouses school regulations would let them get away with. I certainly considered myself lucky to be working in such a voyeur’s paradise!

One afternoon I was unexpectedly summoned to the office of the headmistress, Miss Pemberton, a blonde beauty probably in her early forties. She was sitting in her black leather swivel chair behind her big oak desk displaying her excellent figure in a blouse, a charcoal grey pencil skirt just on the knee, black nylons and black high heels. Even the sexy rhythmic click-clack of Miss Pemberton’s high heels as she walked down the school corridors always started my erection rising. I never minded a meeting with Miss Pemberton!

There too, seated on an upright chair, was one of my brightest pupils, Ashley. She was a pretty little thing, nearly nineteen, with shoulder length straightish dark hair and glasses which give her an innocent look. She was in her school uniform of a white blouse with necktie and a grey pleated knee length skirt, with bare legs and sensible shoes. Her blouse made it obvious she was a big girl for her age, and from what I could see of her below her skirt she had a decent pair of legs. I was single and, needless to say, Ashley had been the subject of many of my night time masturbation fantasies, as had Miss Pemberton and indeed most of the girls in my class.     

“Sit down Mr. Thompson,” said Miss Pemberton, her friendly smile putting me at ease. I sat myself on the other upright chair opposite Ashley, wondering what this was all about. Then Miss Pemberton dropped her bombshell. “Ashley here tells me you can’t keep your eyes off her breasts and you’re constantly trying to look up her skirt in class.”

I felt as if an electric shock had hit me. This sort of accusation could destroy my career as a teacher. I’d certainly watched Ashley strip and I’d peeled off her sexy underwear. She’d posed nude for me in every erotic pose I could imagine and I’d run my hands over every inch of her naked body. She’d sucked my cock off and I’d jerked my hungry penis into her in every sex position I could think of, like I’d done with most of the girls in my class. But that had only been in my fantasies in my lonely bed at night. Regretfully there it had only been my frantically stroking hand tight around my straining penis, not Ashley’s sweet lips or young vagina. In class my eyes had certainly wandered over the mini-skirted little beauties around me, but I’d always kept my lustful thoughts and my hands to myself. 

“Miss Pemberton … I …” I began to splutter, feeling my blood run cold and my face turn red.

Then, in an instant, everything changed. With a mischievous grin on her face, Ashley spoke.

“I really like the way you look at me in class Mr. Thompson. I feel as if you’re taking all my clothes off and I’m doing something naughty for you. Oooooh! I get so excited. Is this what you want to see?”

Ashley turned on her chair to face me, then swung her legs wide and pulled her skirt high up her bare thighs. My eyes almost involuntarily went down to the triangle of white cotton between her spread legs bulging over her mound. Her knickers were school regulation “white cotton, modest and opaque”. There was a dimpled “cameltoe” and a slight yellow stain along the line of her vagina slit, and her knickers were’t quite opaque enough to hide the shadow of a full dark bush of her young cunt underneath. 

In class Ashley was a quiet, well behaved girl and she’d never behaved overtly sexually provocatively, unlike some of the micro skirted little tarts in my class. I wondered what had been building up inside her all the time, turning her into a sex mad minx. I was shocked, but I certainly wasn’t complaining! 

Ashley stood, fumbled with the clasp of her wraparound skirt, let her skirt drop and kicked it aside. She did a slow twirl to show off her white cotton schoolgirl knickers to the full. They were deliciously tight over the curves of her cheeky young bottom, with embroidered hems crossing her well rounded buttocks, and much briefer than I’d guessed school regulations allowed. Her long lightly tanned legs were everything I’d dreamed of! But Ashley had more to show me than her knickers!

“Do you like seeing my knickers Mr. Thompson? You were interested in my bra too. Would you like to look at it more closely?”

I’d already noticed a button at the front of Ashley’ blouse was open showing her white bra. As she stood there she took off her necktie, slowly unbuttoned her blouse and slipped it off her shoulders behind her. She arched her back to thrust her breasts forward. I’d always thought she was a big girl for her age, and I saw I’d been right. Her skimpy white bra matched her knickers and the cups were barely big enough to sling her big firm young breasts and cover her nipples.

“Naughty girl!” I heard Miss Pemberton say, and I glanced at her. 

Watching Ashley’s striptease I’d almost forgotten about Miss Pemberton. She was still sitting in her black leather chair with a smile even more mischievous than Ashley’s on her face. As my eyes lingered on her she slowly crossed and uncrossed her black nylon clad legs and I saw a glimpse of bare thigh above stocking tops. I was getting the message fast.

“Ashley,” Miss Pemberton began, “you know the school rules about girls’ underwear. Nothing too brief or provocative. That bra is far too revealing for a girl with breasts as big as yours.”

“Sorry Miss Pemberton. I’m a very naughty girl.”

Ashley could barely conceal the smirk on her face. She reached behind her back, unclipped her bra took it off and tossed it to me. I caught it.

“There, Mr. Thompson. Do you like my bra?”

Right then I was much more interested in what her skimpy white bra, still warm in my hands from her breasts, had contained. Finally confirming my suspicions that she certainly was a big girl, Ashley stood there just in her knickers and sensible shoes with her back slightly arched to thrust out her big round breasts. They were young, firm and shapely with little pink nipples surround by quite large areoles, and were rhythmically rising and falling with her excited breathing. 

“Do you like my tits Mr. Thompson? Oooooh! I’ve never shown them to a man before!”

As Ashley was showing off a pair of boobs that were certainly well worth ogling, Miss Pemberton spoke.

“Ashley, you’ve been so naughty wearing a bra so revealing, persistently leaving your blouse undone and wearing such brief knickers, all in violation of school regulations. I can even see your pubic hair through your knickers, you dirty girl! I’m hardly surprised Mr Thompson might have been tempted to look lustfully at you. You must be punished. Bend over, girl, to have your bottom smacked.”  

With a big grin on her face Ashley turned and bent over the chair so her white cotton clad bottom was toward me and her big breasts swung deliciously. Miss Pemberton rose from her chair and strolled round to my side of her desk.

“Mr. Thompson,” continued Miss Pemberton, “I think you should administer the punishment because you’ve been wrongly accused. And I think you should pull this naughty girl’s knickers down. We don’t want to soften the blow do we?”
Ashley wiggled her bottom at me and rubbed the insides of her bare thighs together. She looked at me over her shoulder with that same big grin.    

“Oooohh Mr. Thompson! Be gentle with me!” Ashley cried in mock terror. “I’ve never had my bottom smacked by a man.”

I’d guessed by then what was expected of me. Ashley was getting her sexual thrills with Miss Pemberton acting as chaperone to make sure my cock didn’t stray into places it shouldn’t go, and obviously getting her own kinky voyeur thrill too. I reached down and Ashley purred and gasped with pleasure as I fondled her bottom through her thin cotton knickers. I ran my fingertips along the hemlines crossing her buttocks and along the thin gusset strip under her between her slightly spread legs. I brushed my exploring hand against the inner tops of her thighs, a place I knew gets girls wild.

A memory flashed back of that glorious summer afternoon when I was Ashley’s age. In the bushes in the park on my walk home from school one of my classroom colleagues had lifted what little there was of her mini skirt just for me! There, for the first ever time, my so excited hand had explored a girl’s bare thighs and her bottom through thin white cotton knickers just like Ashley’s. I’d slipped them down her thighs for my first sight of a girl’s naked cunt and feel of her pubic hair. Then I’d watched incredulously as her hand wrapped round my penis, as hard and upright as only a teen’s can get, and she treated me to my first ever hand job from a girl, sending my semen splashing over the bushes. 

I slipped Ashley’s knickers down and she she let them fall round her feet. She kicked them aside too, spread her legs wide and shoved her sweet young bare bottom up toward me. I couldn’t resist running my fingers over Ashley’s spread thighs, down her bum crack and under her to play with her juice soaked vagina lips and ruffle her soft pubic hair. Ashley gasped, moaned and squirmed with sex pleasure and spread her legs even wider. Then I set her soft buttocks quivering with half a dozen not very hard slaps on her bottom, more gentle pats really.

“Oooh! Ahh!” Ashley cried pretending I was hurting her.

“Thank you Mr. Thompson,” said Miss Pemberton. “I think our naughty little girl has been punished enough.”

Ashley stood and turned, treating me to a full frontal view of her completely naked body. She had a full but neat dark bush of fresh cunt hair between her legs. As if suddenly conscious that I was ogling her naked body Ashley put her hands behind her back, spread her legs slightly and rocked sensuously on her feet.

“Is this how you were imagining seeing me when you’re looking at me in class Mr. Thompson?” she asked, giving me another of her mischievous little smiles. Then she gasped “Go on… touch my cunt and tits!” 

A moment later she gasped and shuddered with sexual pleasure as I cupped my hand over her dark furred mound and stroked her slit with my fingertip. She gave a little whimper of excitement when I ran my hands up her front and over each of her soft warm breasts. 

“I think he’s imagining you posing rather more provocatively Ashley.”

“Do you mean like those girls in the pictures you showed us, Miss Pemberton? Like those pictures of that girl in an office posing in a chair just like yours?” 

It suddenly dawned on me that there was more to the kind of education girls were getting at St. Matilda’s than I knew about! 

Without waiting for Miss Pemberton’s answer, Ashley went to Miss Pemberton’s big black leather executive chair. She stepped her foot up onto it, getting her legs wide and thrusting her breasts and pussy forward. She knelt in it with her bottom toward me and her knees spread so her pussy peeped out below her bum cheeks just right for me to have fucked her from behind. She sprawled over it in breast thrusting, spread legged poses, and ended up sitting in it with her legs spread and hooked over the arms. Spreading her legs that wide pulled Ashley’s vagina open so her juice glistening labia were peeping through her dark bush. She tossed her dark hair back over her shoulders and arched her back so her breasts swung up and forward. 

“Oooohh! It's so exciting being seen by a man like this!” Ashley reached down and fingered her vagina. “Miss Pemberton, Mr. Thompson’s trousers are bulging.” I was suddenly very aware of how stiff my penis was, and at Ashley’s innocent young voice, it became a couple of notches stiffer. “Does that mean he’s having an erection and wants to fuck me?”

I felt a moment’s panic. I could see where this was heading. I’d always told myself I’d gladly take a hand job or blow job from one of my little beauties, certainly no one under eighteen, and I’d never take their virginity. Even a dirty minded bastard like me has some principles! Miss Pemberton came to the rescue.

“I think he’d like to masturbate over you Ashley. Men like to do that when they look at those filthy pictures of naked girls. Like those boys did in that video I showed you and the other girls last week.”   

A grin appeared in Ashley’s face. Still gently fingering her vagina, she looked at me with her big innocent brown eyes, fluttered her eyelashes and smiled sweetly.

“Mr. Thompson…. Would you like to masturbate over me? I’ve never seen a man’s  thing for real.”

I headed for Ashley, unzipping my trousers on the way. As a teacher I’m only too pleased to help a young lady with any aspect of her education! As I stood right in front of Ashley sitting wide legged in the black leather chair my penis was at just the same height as her breasts. I dropped my trousers down round my thighs. My erection was pushing my dark blue cotton briefs far out from my body in a huge cone, and there was already a wet patch over the bulge of my penis head. Ashley took off my necktie and unbuttoned my shirt to get it out of the way. Ashley ran her soft fingers over the straining ridge of my erection through the cloth. I nearly jerked my load into my briefs, but I managed to hold back, though the wet patch got bigger! Ashley herself pulled my briefs down round my thighs. My erect penis sprang out, bending up full length from my hairy balls and quivering stiffly. 

“Oh wow!” Ashley gasped. “It’s huge! It’s even bigger than that man’s in those pictures you showed us last week Miss Pemberton!” 

My sex kit’s nothing to be ashamed of! Ashley felt my balls and shaft and ran her fingers through my thick pubic hair. She reached right under me to stroke me between my legs, and leaned forward to kiss me and lick me right on the big soft head of my penis.

“Was that nice? Go on, masturbate over me... over my breasts!” 

Ashley moved forward so my penis was aimed into her cleavage. Miss Pemberton spoke.

“Mr. Thompson, aren’t you concerned about splashing semen on your clothes? Ashley’s had the good sense to take all her clothes off.”

I got the message. Ashley’s eyes followed my every move as I stripped completely naked in front of her, her excited fingers continuing to play between her spread legs as I did. I positioned myself in front of her and began lightly fingering my straining shaft while running my spare hand over her breasts and down her front to her spread thighs and cunt. I treated myself to a good long feel of her naked body to work my erection up to iron hard readiness. Ashley held her breasts up toward me and I saw her eyes were wide with excitement. I felt my shaft was so tight it was going to snap by the time I spread my legs, shoved my hips forward so my penis head was lightly brushing against Ashley’s breasts and wrapped my thumb and forefinger round my penis.

Miss Pemberton was standing watching, with a smile on her face. I guessed she was savouring voyeur pleasure at seeing her naked male colleague with his big cock up hard, masturbating while he played with her nude young pupil. I was about to masturbate when Miss Pemberton snuggled against me. She was holding her skirt up with her other hand and she’d pulled her own panties down round her thighs below her stocking tops. Her panties were black, and I saw she had a smooth shaven vagina slit. She stroked my naked backside, tickled my buttocks and bum crack, and reached right under me to tickle my balls. 

“Touch me too!” Miss Pemberton said softly, but with an edge of excitement in her voice.

Then with my spare hand roaming over Ashley’s big round breasts and bare shoulders, and over Miss Pemberton’s bottom, the naked tops of her thighs above her stockings, her sex mound and her juice soaked vagina slit I masturbated. My big so sensitive penis head brushed against Ashley’s soft breasts and her arousal tightened nipples. Solitary wanking is every guy’s secret pleasure, and even better with some hot porn. But here I was tugging one off with a sex mad  eighteen year old girl’s nude tits in front of my cock and my hand up another woman’s skirt with her knickers down! It was the mother of all wanks!

I made sure I treated Ashley and Miss Pemberton to a real meaty show, grunting, gasping and poking my penis against Ashley’s naked body. Ashley gasped every time my penis head rubbed over her aroused nipples. She leaned forward to kiss and lick my penis head as I rhythmically tugged and stroked my foreskin with just my thumb and forefinger in a ring, with my whole fist and just with my fingertips. I edged myself agonisingly to the brink till I could hold back no more! I grabbed Ashley’s shoulder to pull her toward me, then stroked my shaft franticly. As my cum pleasure exploded I shoved my penis right between Ashley’s breasts so its purple head was poking out above her cleavage just in time for my fountain of semen to spurt. She squealed as my cumshot hit her face, her hair and splashed over her breasts. Something animal inside me made me grunt:

“Wanna fuck you hard, whore!” as I spurted my load.

I staggered back with my still half erect penis swinging and dribbling a long strand of semen onto Miss Pemberton’s carpet. Ashley stayed sitting in Miss Pemberton’s office chair watching my semen dripping from her nipples and trickling down her cleavage and her front to catch in her belly button and cunt hair. 

“I’ve seen a naked man and he’s wanked his cock off over my tits!” Ashley said excitedly. I guess she felt she was a grown up girl now.

Miss Pemberton stood next to us. She’d pulled her panties up and her skirt was respectably down to her knees again, but she still had that smile on her face.

“Thank you Mr. Thompson. That was a most impressive demonstration, fully up to the high teaching standards of St Matilda’s. I trust you’d be happy to give a similar demonstration to some of our other girls, over eighteen of course?”

“Of course.” I replied, happy to oblige. 

“Well Ashley,” Miss Pemberton continued, “There are some tissues on my desk for you to clean yourself up, then I think you’d better put your clothes on and head back your lessons.”

I watched Ashley’s luscious young body disappear back into her white cotton school girl bra, knickers and skirt, and as she squeezed her breasts into her white blouse. 

“Thank you so much Mr. Thompson for taking the time to give me such an instructive lesson,” Ashley said, beaming a big grin at me.

“Any time.” I said.

She gave me a last little kiss on the cheek and scampered off back to her lessons. I was in my briefs and starting to put on my shirt. 

“Not so fast, Mr. Thompson,” Miss Pemberton said.
She stepped her high heeled foot up onto the upright chair and pulled her skirt up to show me her stocking tops and those black panties. I saw her panties were see through black lace and even briefer than Ashley’s.

“I think we have some staff training to attend to. Don’t you agree?”

I wholeheartedly agreed, but what happened next is another story! 









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