Sexuality at St. Matilda's
by cruiser_2015

A raunchy sex lesson at a posh girls' school.

I'm one of the few male teachers at St Matilda's Academy for Young Ladies, an expensive English private school for girls. I teach a class of eighteen to nearly nineteen year olds. I'm single, in my early thirties and needless to say most of the girls in my class perform regularly in my masturbation fantasies.

Another regular performer in my fantasies is the Headmistress Miss Fiona Pemberton. She's early forties, a blonde sophisticated beauty. Her good figure is usually displayed in a well-filled blouse, a charcoal grey skirt tight over her pert bottom and ending just on the knee, black nylons and black high heels that go clickety-clack as she walks along the school corridors.

One afternoon late in the summer term I was in a corridor when from behind me I heard that familiar clickety-clack. A moment later there beside me was Miss Pemberton.

"Have you got a moment, Mr Thompson" she began. I always have a moment for Miss Pemberton. "Some of our oldest girls will soon be leaving St. Matilda's" she continued. "It's time for the preparation for student life seminar that we give our girls who're about to leave home for university. You helped with it last year if you remember." Miss Pemberton gave me a mischievous smile. It was not a seminar one would easily forget. "Are you up for helping with it again?"

"They're all eighteen or over I assume?" I asked

"Of course. This year's girls are Abbie, Cathy, Jayne, Lucy, Natalie and Ruth."

I was happy with that. The youngest, Abbie was just two months short of nineteen and the oldest, Ruth would be nineteen just after term ended in a couple of weeks. I told Miss Pemberton I'd be happy to help.

"Thank you. Next Friday after school in my flat. We'll tell their parents the usual, that they're on a preparation for university life seminar."

Then with my eyes locked on the backs of her sheer black nylon clad legs and her bottom through her tight skirt Miss Pemberton clickety-clacked away down the corridor.

As she departed thoughts of one of the girls in particular filled my mind. Ruth was a penis-straining brunette combination of an innocent young face, a smouldering "want you" look in her eyes, the best filled blouse in my class and usually the shortest skirt. I knew Ruth had a "crush" on me. In class she was constantly "accidentally" brushing her bulging blouse against me and giving me glimpses up her skirt. I'd spurted plenty of semen in my lonely bed thinking of Ruth.

So after class that next Friday I went to Miss Pemberton's flat. The girls were already there in the spacious lounge wearing their school uniforms of white blouses with school neckties, grey pleated wraparound skirts and sheer black tights. They were sitting gathered round a big TV screen that was showing a video that seemed to consist entirely of naked men masturbating.

"Now we're all here let's start" Miss Pemberton began.

The girls turned away dutifully but reluctantly from the screen to face Miss Pemberton.

"Now girls. At St. Matilda's we like to prepare our girls for all aspects of life. One aspect I know you are all becoming very aware of is your sexuality."

As Miss Pemberton paused Ruth's eyes met mine. The look in them left me in no doubt that she was very aware of her sexuality, and mine.

"At university you will be free from parental restraints and you will meet similarly unrestrained boys." The grins on Abbie's and Lucy's faces showed what they thought of that. "So the purpose of this seminar is to acquaint you with the challenges of sexuality. Mr Thompson has kindly agreed to help us from the male angle. The first thing to get used to is being nude in the presence of the opposite sex. So lets all play a little game."

The game involved getting into pairs, taking a garment off each other then going to someone else to form another pair and doing the same. Appropriate, I thought as the first thing any boy would do with these beauties is get their clothes off. Accompanied with giggling and excited squeals from the girls Miss Pemberton, six girls and I systematically undressed each other.

Soon six pairs of firm young naked breasts were bouncing and swinging, six nicely rounded young bottoms were gleaming smoothly under the lights, and six young pussies ranging from Jayne's smooth shaven mound to blonde Natalie's unkempt bush of brown cunt fur were on display.

The girls' underwear was school regulation "white, modest and opaque." But Miss Pemberton's blouse and skirt came off to display black satin panties barely big enough to cover her neatly trimmed brown bush, a matching black bra only just big enough to sling her large breasts, and sheer black nylon stockings with a garter belt. Her naked body was everything I'd dreamed of, with big full mature breasts, a neat snatch of brown cunt fur and legs that looked as exciting nude as in her nylons.

My eyes were constantly on Ruth. Her young breasts were every bit as big and round as her well-filled blouses suggested, and the neat strip of almost black hair lining her vagina slit was just as penis-straining exciting as I'd imagined all the times I'd masturbated thinking of her.

In the melee I forget who's clothes I took off except that I managed to take off Miss Pemberton's bra and one of her stockings. But I certainly remember how Ruth managed it so I got to slip her knickers off and run my hungry fingers through her soft young pubic hair.

Of course all the girls' eyes were locked on me when Cathy, already nude, slipped my light blue briefs down my thighs and my naked penis bounced out and swung, still mostly flaccid.

"Before we continue, girls" Miss Pemberton explained, "you will have noted I was wearing underwear a lot more daring than you were, with stockings. Boys love girls' sexy underwear and they go wild over stockings."

"My daddy looks at pictures of girls in underwear like yours Miss Pemberton. He takes my knickers from my laundry" Cathy called out. "I'd love to know what he does with them."

The girls giggled.

"Cathy! We don't want to hear about your father's perversions. Now. Let's turn to the male anatomy."

I was standing there naked with my naked penis swinging in front of me. Miss Pemberton came up close enough to me that her nipples brushed against my arm and her naked thigh brushed against mine. My penis strained a notch or two stiffer.

"Gather round girls. Let's look at Mr Thompson's genitals."

Miss Pemberton reached down and lightly fingered my balls. I spread my legs for her exploring hand and for my young audience.

"This is Mr Thompson's scrotum. Its very sensitive, so when you touch a boy there be very gentle. Just stroke him lightly, or..." Miss Pemberton paused and grinned. "Kiss him or lick him with your tongue. Boys like that." Her light fingers on my balls and the tone of her voice made obvious that she spoke from experience.

"Boys call them their balls Miss." Natalie replied.

"Bollocks!" someone called out. The girls all giggled.

"Girls! Behave!"

Miss Pemberton's gentle hand went to my penis.

"This is Mr. Thompson's penis. Now watch carefully girls. See what happens as Mr Thompson gets sexually excited. You don't mind us touching each other do you Mr Thompson?"

I certainly didn't. I felt her snuggle a bit closer against me so her bush of pubic hair brushed my thigh. As her fingers played with my penis her touch told me she knew exactly what a man wanted. My hands almost involuntarily found her smooth warm thighs, her big soft breasts, her smooth round bottom and the bush of cunt fur between her thighs. As we ran our fingers over each other my penis stiffened and rose till my seven inches of stiff muscle were bending back with its erection-swollen cock head pointing up vertically.

The girls watched, wide eyed with excitement.

"Wow! Look at his cock!" I heard, followed by another girl's "Its bigger than my daddy's!" and another's "Mmmmmm! I'd like that up me!"

"Girls!" called out Miss Pemberton, bringing order.

The lesson continued.

"You can see, girls, that Mr Thompson's penis has now grown and is standing up hard. That's called an erection. Boys have erections when they are sexually excited by a girl and want sex with her. It makes his penis stiff and ready to enter a girl's vagina."

As she spoke Miss Pemberton's hand stroked my penis as if testing it for stiffness and readiness.

"Its massive!" Natalie gasped. "He'd never get that up me!"

"Natalie! Control yourself!"

I was sure I could, once I'd got Natalie hot and juicy, and with some good hard thrusting on my part.

"A boy's penis is the most sexually sensitive part of a man's body" Miss Pemberton's eyes met mine and the smile she gave me made it clear she knew all the other sexually sensitive parts too. "Especially here, just under where its head meets the shaft."

Her thumb and forefinger closed round my penis and stroked just across the base ridge of my penis head, catching my frenulum. In the burst of sexual pleasure I involuntarily grunted and thrust my hips forward. Mercifully she only gave my cock a couple of strokes before she let me go.

"Thank you Mr Thompson" Miss Pemberton gave my backside an affectionate pat as she stepped back from me.

"Now girls. I'm sure Mr Thompson will be happy for you to examine his genitalia for yourselves."

A moment later I was standing there wide legged with my hips thrust forward as six naked nearly-nineteen year old girls snuggled around me. Their hands were all over me feeling my backside, ruffling my pubic hair, stroking and tickling my balls, feeling the length and stiffness of my straining penis shaft and its head and stroking that sensitive spot Miss Pemberton had pointed out.

They got close enough to me that their naked young bodies brushed against mine, and of course my hands explored them. Ruth snuggled against me for a good long feel of my naked body and for me to nuzzle my cock and balls into her exploring hand.

"I want you in my vagina!" Ruth whispered in my ear.

The girls were getting excited in this feeding frenzy of man flesh. Squealing with excitement Natalie squatted down in front of me and took my cock head into her mouth. She sucked my cock head, massaged it with her lips and rolled her tongue over it fingering my balls as she did. Somehow I managed to resist the urge to ram my cock as far down her throat as I could. Natalie's lips slipped off my penis leaving it feeling stiff enough to snap and with its saliva-glistening head almost glowing purple.

"Was that nice, Mr Thompson?" Natalie asked, looking up at me with her big brown eyes. "I saw girls doing that for boys in the dirty pictures my big brother looks at."

"Natalie! Control yourself!" Miss Pemberton called out, bringing order back to the lesson. "Now lets learn a bit more about male sexuality."

After the girls' attention, especially Natalie's I was desperate to jerk a load. Mercifully relief was soon to come.

"What's 'jerking off' Miss Pemberton?" Jayne interrupted. "My boyfriend keeps asking me to jerk him off."

"All boys do it" Cathy added. "They play with their cocks imagining they're fucking you till they shoot their cum."

"Jayne! Cathy! Not so fast. We're just coming to that. Don't use that dirty word again Cathy. Now. We all play with our pussies and we know about orgasms don't we girls?"

With a mischievous smile on her face Miss Pemberton looked round the girls. Some faces went red, some girls grinned or suppressed giggles, others looked sheepish. Yes they all knew about masturbation and orgasms. Ruth smiled at me and briefly fingered her pussy. Ruth wanted me to know she pleasured her pussy too.

"It's called masturbation. Boys do the same" Miss Pemberton explained. "It's usually a boy's first sexual act."

"Boys call it wanking don't they Miss Pemberton?" One of the girls asked.

Some of the girls giggled.

"My big brother does it" Natalie called out excitedly. "I spied on him doing it. He was calling out my name all the time he was stroking his cock. He squirted his stuff all over himself."

"I've never watched a boy wank" one of the girls said sadly. I heard a murmur of empathy from some of the other girls.

"Do you wank Mr Thompson?" Lucy asked, all innocent. All the girls looked at me. Miss Pemberton took control.

"Well Mr Thompson. As part of our lesson and to satisfy Lucy's curiosity and that of some of the others would you like to give us a practical demonstration of male masturbation?"

As Miss Pemberton spoke she got next to me again squeezing her breasts against my arm and brushing her hairy pussy and naked thigh against my thigh. She fondled my backside as if to encourage me. I hardly needed any encouragement. Even before she touched me my straining hard cock felt ready to explode. The girls gathered round me to watch.

I spread my legs and thrust my hips forward. I braced myself for pleasure and wrapped my hand round my penis. I reached my spare hand round Miss Pemberton's waist and slid it down her back to her smooth round bottom. I began to tug and stroke full length from my pubic hair round my balls brushing my hand at one end to my hand sliding right up over my cock head.

"That's just how my brother does it!" Natalie called out excitedly.

I made sure put on a good meaty show of my technique for the girls. I took my time, I held back, I thrust my cock forward and grunted loudly. The girls watched enthralled.

Ruth stood right in front of me with her legs slightly spread. My eyes enjoyed her naked body, roaming between her legs, pussy and her breasts as I masturbated. I held back as long as I could, edging on the almost agonisingly exquisite brink of orgasm. In the final moments before I came Ruth's eyes met mine.

"Want you!" Ruth silently mouthed.

"He's coming!" I heard an excited girl cry out.

Finally I shot my load, grunting and ramming my hips forward as my semen spurted and arched out in front of me. The girls squealed with excitement.

"Is that cum Miss Pemberton?" asked Cathy. I've found stuff like that on my knickers when my daddy's had them."

Miss Pemberton still didn't want to hear about Cathy's father's kinks and ignored her. Then with the aid of some extremely explicit video clips and diagrams on the TV which set the girls giggling she explained the basic mechanics and biology of sexual intercourse. She told them a bit about pregnancy and some ways to avoid it short of celibacy. She showed a penis-straining video of well-hung men and busty women methodically and passionately fucking each other in every position I could think of and some I'd never even imagined. As we watched the on-screen action Ruth's hungry eyes kept meeting mine.

With Miss Pemberton and six girls nude around me, watching hot explicit action on the screen and Ruth's eyes telling me what she was thinking my erection was soon swinging up again. In fact I soon guessed Miss Pemberton was watching for my erection to rise before the really interesting part of the lesson began.

"Now girls, some practical work. We've just learned about sexual intercourse. Now we'll think about some of the sex positions we've seen. Let's start with the most common. It's called missionary position."

With that Miss Pemberton lay on her back on the big soft rug in the middle of the floor with her legs spread wide. She folded her legs so her knees were near her shoulders. With her legs as wide as that her gaping pink vagina lips peeped through her dark pubic hair hungrily inviting my iron-hard penis.

"Look how wide open it gets my vagina, girls, ready for a penis to enter me." As she spoke she looked up at me, fingering her pussy at the same time. "Mount me Mr Thompson like you would for sexual intercourse with me but don't enter me." She grinned at me. "At least not this time!"

I got on top of Miss Pemberton between her folded-up thighs so my belly was against hers. My hungry penis head poked the soft entrance of her vagina. I felt her cunt hair tickling my cock head. Everything within me screamed 'Get your cock in her and fuck her' but somehow I resisted. I was in a cold sweat of blazing lust. Her hands wrapped over my back to pull my chest down against her breasts. Her legs wrapped over my thighs and her heels patted against my bum cheeks.

I thrust gently, sliding my penis up along the smooth lips of her juice-moistened vagina and through her bush. She responded with an excited gasp, her arms pulling me more tightly and an upward thrust of her hips against mine. I knew instantly she wanted me. I thrust so far my cock slid up her front and her cunt hair tickled my balls.

"Thank you Mr Thompson" said Miss Pemberton and her arms and legs let me go.

"Now girls. Try that position and see how it feels."

A moment later six nude young beauties were on their backs with their legs wide poised ready for me to mount. Miss Pemberton inspected them, with comments like:

"Legs wider Abbie... Thrust your hips up a bit more Lucy... You must trim your pubic hair Natalie."

But I only had eyes for Ruth. Her young firm breasts didn't flop but quivered and her vagina lips peeping through the dark hair between her straining wide legs were already glistening with juice. The lesson moved on.

"Here's another position boys like." Miss Pemberton stood and bent over a chair. She spread her legs so her pubic hair peeped out just below her cheeks. Her breasts swung pendulously as she wiggled her bottom. "Its called doggy, for obvious reasons."

Abbie giggled and set the other girls off. Miss Pemberton continued.

"The man slides his penis into the woman's vagina from behind. Mr Thompson. Again without entering me."

I got behind her and held her hips. Thrusting forward at first my cock head slid up the smooth warm valley between her cheeks. I took my penis in my hand, held it down against its stiffness, poked it between the tops of her thighs and thrust smoothly till my pubic hair nestled between her cheeks. I felt her cunt hair against my cock head. Miss Pemberton trembled as my hard penis slid between her legs and her inside thigh tops gave my stiff shaft a little squeeze. Miss Pemberton rocked smoothly back and forth a few times. Her thighs round my shaft felt just like a tight warm vagina, lacking only juice. In response I involuntarily thrust so my hips against her bottom pushed her forward.

"Thank you Mr Thompson. I think we'd better leave it at that before we both get too excited."

I stepped back from her. As my stiffly swinging cock bounced out from between her thighs its head smeared pre cum on her cheeks.

"There are variants of this position" Miss Pemberton looked around the girls. "Lucy, kneel on the sofa facing its back and spread your legs."

Big-bottomed and big-breasted Lucy's breasts swung heavily as she moved into position on the sofa. Her legs spread wide and she leaned forward to expose her lightly-furred mound and vagina lips just below her big round bum cheeks. Lucy looked over her shoulder with a grin that said she was enjoying this.

"You see how Lucy's pussy is so perfectly positioned for a boy"

As if to make her point Miss Pemberton reached down and slid her hand across Lucy's bottom and fingered Lucy's vagina lips. Lucy quivered, let out a gasp and strained her legs even wider. With a look Miss Pemberton motioned me to stand behind Lucy. She took my penis in her hand and poked Lucy's vagina lips with my cock head.

"Thank you Lucy." Grinning at me, Lucy climbed off the sofa. "Now here's a position for the girl who likes to be in control."

"Oooh! Yes please!" Laughed Abbie.

"Mr Thompson, would you like to lie on your back." Anticipating what was to come I dutifully obeyed.

Miss Pemberton squatted astride me straddling my hips. She lowered herself so her cunt fur brushed my cock head. She smoothly rocked back and forth so her pubic hair rubbed rhythmically along the underside of my shaft and across my cock head. I bit my lip. Her big breasts swung above me.

"In this position the girl is in control. She has the pleasure of guiding her boy's cock in."

Smiling down at me she briefly caressed my balls then took my stiff cock in her hand, guided it to her vagina lips and rubbed my cock head against her juice wetted labia. Somehow I managed to hold back from ramming my cock into her.

"I'll let you into a secret, girls. You'lI love how this position lets your boy get his hands all over your body."

Miss Pemberton's smile showed she spoke from experience. She moved slowly up my body, running her cunt fur along my shaft till my cock bounced out between the tops of her thighs and its head rested in the valley between her bum cheeks. Her naked thighs were perfectly placed for my exploring hands and her breasts swung just above my chest so her nipples brushed my bare chest. She moved up further so her breasts were swinging just above my face.

"I love it when my boy friend plays with my tits!" I heard a girl say excitedly, but with my face buried between Miss Pemberton's big soft breasts I couldn't tell who it was.

I slid my hand down Miss Pemberton's front and through her cunt bush to cup my hand over her mound and slip my fingers into her vagina slit. I felt her tremble with excitement and she nuzzled her pussy against my hand.

"Later!" she silently mouthed. Her face was down so close to mine none of the girls would have noticed. Then she leaned back above me. I reluctantly removed my hand from between her legs and she climbed off me.

Miss Pemberton then gave a brief talk on safe sex sternly instructing the girls to use condoms every time it looked like a lucky boy was going to get his cock up them. That was followed by another practical lesson as the six girls each slid a condom over my straining hard erection. Abbie squatted in front of me to do it. Not to be outdone Little Ruth made a meal of the task, snuggling against me and spending ages fumbling with my cock and balls before she luxuriously slid the thin condom full length down my shaft.

"Well done girls!" Miss Pemberton said when they'd all completed the task. She tossed them all a pack of condoms each to get them started at university.

"Now some more practical work. The first sex act you are likely to do with a boy is a hand job."

"My boyfriend's always asking me to give him one" Lucy interjected. "How do I do it Miss Pemberton?"

"Can I have a volunteer?" six eager hands went up in response to Miss Pemberton and twelve young breasts bounced as the girls bobbed with excitement. "Thank you. Ruth, would you like to help us learn how to give a boy a hand job? Go on, stand next to Mr Thompson."

It was as if Miss Pemberton knew I fancied Ruth and that she had a crush on me. With the biggest most mischievous smile I've ever seen on a girl's face and her big breasts gently bouncing Ruth strode purposefully toward me. She snuggled the naked body I'd dreamt of so often as I'd masturbated against me with her breasts squeezed against my bare arm and her naked thighs and furry pussy brushing my bare thigh. My hands almost involuntarily found her soft smooth round bottom and thighs, her firm young breasts and of course her pussy.

"Now Ruth, fondle Mr Thompson's penis and scrotum until his penis is really stiff." Miss Pemberton laughed. "I don't think you'll have to try very hard. That looks quite stiff enough."

My erection already felt stiff enough to snap as my hands savoured the girl I'd wanted for so long. Ruth ran her young fingers along the straining length of my shaft, caressed its big soft so sensitive head, gently tickled my balls and reached right under me between my legs. Her other hand ran over my backside and up and down my bum crack.

"Now Ruth, wrap your hand round Mr Thompson's penis shaft."

Ruth's petite hand wrapped loosely round my straining shaft.

"It's too big for me to get my whole hand round Miss Pemberton."

"I don't think Mr Thompson will mind."

Ruth could only just get her fingers and thumb round my shaft, but I certainly didn't mind!

"Now Ruth. Stroke his penis smoothly and rhythmically up and down full length. Slide your hand up over its head and pull that loose skin up and down."

I spread my legs and thrust my hips forward bracing myself for exquisite sexual pleasure. Ruth was a fast learner. After a couple of strokes she got the action just right pulling my foreskin and with her thumb and forefinger catching my frenulum as it slid up over my cock head just the way I like. As Ruth wanked me he spare hand gripped my backside and my roaming hands enjoyed her naked body.

"You're doing very well Ruth. Just carry on. But ease off when his penis suddenly goes really hard in your hand. That means he's about to climax."

A few exquisite minutes later my orgasm pleasure started to rise. I gripped Ruth's bottom hard to pull her against me.

"Ease off Ruth... Good girl, that's right."

As my penis tightened in its rising orgasm Ruth eased off just as she'd been told, stroking my cock just across the base ridge of my cock head. Moments later my hips rammed involuntarily forward and in my explosion of orgasm pleasure my cock pulsed in Ruth's hand. The watching girls squealed excitedly as spurt after spurt of my semen fountained from my penis.

"Well done! You can stop stroking him now Ruth."

Ruth let go of my penis and stepped back from me smiling.

"Was that nice Mr Thompson? Did I do it right?"

I stood there panting with my swinging still half erect penis dripping a long strand of semen onto Miss Pemberton's rug.

"You were perfect, Ruth!" I gasped. I'd remember that hand job for months in my lonely bed.

"Now girls. One thing you've seen is how messy boys can be when they get aroused. Make sure you don't get any of their semen on your clothes, except your knickers of course."

"I'll make sure I always take all my clothes off Miss Pemberton." Abbie said with a grin.

To emphasise her point Miss Pemberton picked up a pair of girl's white knickers from the floor and used them to wipe off the semen dangling from my cock and where it had trickled down my thigh.

"Whose knickers?" Miss Pemberton asked, waving the semen-wetted knickers.

They were Cathy's. Miss Pemberton tossed them to her.

The lesson finished soon after that with just time for the girls, Miss Pemberton and me to find our clothes scattered over the floor, to dress and for the girls to collect their "How to survive university" packs, full of useful information about everything other than sex, before their grateful parents arrived to take them home.

When the door closed behind the last girl to leave Miss Pemberton smiled at me.

"Well done again Mr. Thompson. There are all those unused condoms the girls left. It would be a pity not to use them, don't you agree?"

I agreed wholeheartedly. Later that Friday evening and through to Saturday morning those condoms were very well used. But that might be another story.