The Headmaster's Room Ch. 03byMag58©
My story jumps forward 20 years to May of this year. In the intervening years I've been married twice, lived with two other guys and never had any children. My career, as it is, has consisted of a succession of dead-end shop and restaurant work; moving from town to town across the UK and a Summer in Ibiza.
"Well, well, well...some people never change. Do they Miss Simpson? It is Miss Simpson?" My legs nearly buckled as I recognised 'that voice' from my teenage years in the middle of an argument with the Chef of the smart restaurant that I was working in.
"Get back in there," I hissed at the young man in kitchen whites, "and get it fucking right this time!"
My face was like a beetroot as I turned to face my tormenter.
"It is you...isn't it...Lisa?" The grey haired man in an expensive tweed suit asked me.
"Jesus Christ!" I virtually whistled, "Mr. Skinner; fancy seeing you here." I was grinning like the Cheshire Cat as I held my hand out to greet him.
The old man's green eyes twinkled as he took my hand, stood up and kissed me on both cheeks.
"Lisa Simpson!" he gasped and smiled, "you could always get into an argument in an empty room!"
I was still blushing as he introduced me to his dining partner; Mr. Millhouse a small, squat Jewish man, who was a Physics teacher at the local Private school where Skinner was the Headmaster.
As the restaurant wasn't very busy I stood chatting for a few minutes; quickly telling him of my recent past and admitting to being currently single.
As the night wore on Skinner smiled and winked at me every time our eyes met; making my pussy very wet as memories of being caned filled my mind and I'm sure his too.
At one stage Skinner overheard me calling one of the young waiters a 'dozy cunt' when I discovered that he had tried to over charge a customer.
As I handed him his bill, Mr Skinner took hold of my wrist and whispered, "People who use language like that should be punished...don't you think... Miss Simpson?"
Both men were smiling as I nodded and agreed, "I suppose so."
He paid the large bill and slipped a ten pound tip into my hand.
"Come to see me on Thursday at 3.45 and I'll see what I can arrange." Skinner then kissed me on the cheek and whispered, "Wear something business like...smart...I like smart and don't be late...because you know that I can't stand people being late."
I'd had a couple of glasses of red wine for courage, when the taxi picked me up from a local wine bar at 3.30 to make the short journey to the school.
By the time that I was finally sitting outside Skinner's office I was gasping for a cigarette and my palms were becoming increasingly sweaty.
"The Headmaster will be another few minutes," his pretty young blonde secretary told me as she handed me a large mug of coffee that I hadn't asked for. I nervously drank it as I kept asking myself what I was doing there. This was madness; I was now 37 years old and had done most sexual things a red-blooded woman can do over the years; including oral, anal and a couple of threesomes but nothing ever took me to the heights that my masturbation had done after each of Mr Skinner's canings!
It was 4.20 when the secretary finally answered the phone and smirked, "The Headmaster will see you now."
'Did she know why I was here?' I thought, 'perhaps he caned her too; she looked as if she would enjoy that sort of thing. Quite tall, big tits and aloof', I thought as I stood up straightened my black dress and brushed away some invisible fluff from my cream leather jacket as I knocked on his door.
I nodded and smiled to her as I walked past the meticulously tidy work station. She responded with a thin smile.
"Come!" he barked; as I knocked on thick wooden door like a naughty schoolgirl. Twenty years on his voice still had 'that effect' on me. My stomach was in knots as I entered his study. The age old smell of floor wax and old books took me back to my schooldays.
"Lisa...welcome," Skinner greeted me. "Marge," he pressed the intercom, "can you bring us coffee for three please?"
"No, I've just had a cup thanks." I waved my hands in a negative manner. "Well I'm ready for a cup and I'm sure Mr. Millhouse will be ready for one too".
We chatted about our lives, in particular his move to this area and, when my eyes spotted the box of canes in the corner, Skinner sighed and told me of his disappointment that corporal punishment had been made illegal in British schools and he only kept them on show for sentimental reasons. Then his eyes twinkled as he told me that I was the only girl that he'd 'ever had the pleasure' of caning. I was still squirming in my seat when Mr Millhouse and the secretary came in with a tray of coffee and biscuits. "Goodnight Marge," Mr Skinner waved to the young woman as she left the room, "I'll see you in the morning".
As soon as the door closed Skinner stood up from behind his desk and poured the coffees. I began to loosen up as we chatted about my life and some of the things that Skinner and Millhouse had done in their jobs until we eventually finished our coffee. Skinner didn't look as old as I'd expected. He must have been about 60 now, his thick grey hair still combed in severe, almost military style. He was still the most unfashionable man in the world; his suit and shirt both slightly too big and beginning to fray at the edges.
As I was placing the cups back onto the tray in the corner of the room I turned to see Mr Millhouse moving the chairs behind the Headmaster's desk.
I must have looked puzzled because Skinner suddenly took hold of my arm and gently kissed my ear and whispered; "Now that we are all suitably relaxed I think that we can get down to the business that you came to conclude."
"Oh my God!" I thought as my chest tightened and heaved at the thought of what was going to happen next.
"Can I go to the ladies room first?" I naively asked. The men looked at each other and chuckled; "No!" Skinner shook his head, "Of course not!"
My face went crimson and my nipples throbbed as I realised that he had already told Millhouse that he had made me piss my pants 20 years previously.
I automatically 'stood to attention' as Skinner slowly walked around me admiring my curvaceous womanly body; occasionally running a bony finger across my heaving breasts or along my ample backside making me shiver with anticipation.
The short, be-speckled Physics teacher stood grinning next to the window like a mischievous schoolboy; although he must have been in his mid-forties.
"We can forgo any pretence or the need to play games; don't you think Mr Millhouse?" The Headmaster turned to his friend, "As we all know why we are really here."
"That would be correct Headmaster," The small man replied; obviously excited at the prospect of watching me get caned.
My legs were like jelly and my bladder felt like a balloon as Mr Skinner ordered me to take my dress off.
I was in a trance as I reached behind to pull the full length zip down on my dress. With a deep breath, I closed my eyes and dropped the straps off my shoulders; letting the dress drop to my ankles. There was a palpable silence as both men stared at me standing in my underwear and heels.
Presuming and hoping that something like this was going to happen I'd dressed accordingly: a black lacy half-cup bra that hardly covered my 34c tits; a matching see-thru thong, suspender belt and 8 denier black stockings.
"Mr Millhouse," the Headmaster motioned to his friend, "can you pick Miss Simpson's dress up please? I wouldn't want it to get soiled...if there was to be...an accident."
I could feel the giggling man's breath on my legs as I stepped out my dress and he picked it up off the floor.
"You've grown into a beautiful young woman, Lisa," Skinner murmured, "and I'm going to cane you exactly the same way that you...enjoyed as a young girl. That's what you've come here for...isn't it?"
I replied by smiling.
"Only this time I'll let you choose the cane that is going to tear into the lovely soft flesh of your gorgeous arse."
"Off you go then." I nearly swooned as he gently tapped my buttocks to send me on my way.
The only sounds that could be heard as I slowly crossed the long room were the rustle of my stocking clad legs and the click of my heels on the heavily waxed floorboards. When I reached the same box of bamboo and willow rods that had in his room in 1985 I meticulously bent over letting the two perverts feast their eyes on the tiny piece of black lace that cut into my crack and looked like it had split my ample arse in two. My heart pounded as I spent a minute or two pretending to select a suitable cane, eventually choosing a very thin one; remembering that was the type that stung the most.
I turned and walked towards him making sure that my tits bounced as much as possible. As I handed my method of punishment to the Headmaster he told me to turn around and bend over.
I complied by running my hands down the nylon on my thighs then grasped my knees as the need to piss was making it very uncomfortable for me to bend over any further and my head was now becoming dizzy. "Are you ready...Miss Simpson?" Skinner barked. Before I could answer the thin cane whipped through the air and hit my plump arse making me yelp.
Both men laughed out loud as I wriggled with pain. "I don't think that there is any need for silence tonight," he sniggered, "as everyone has gone home." SWISH – CRACK. "Aaaaaggghhh," I squealed as the cane hit me a second time making me rock forward and one of my tits fell out of the small cup.
"Mr Millhouse can you make Miss Simpson a little more comfortable," Skinner motioned to the sniggering man. Millhouse reached beneath my chest and plucked my other tit out of my bra leaving them both swinging for the mens' amusement.
SWISH – CRACK. "ShhhhIIITT!" I yelped again as I felt the cane break the skin on my left cheek. Both men were laughing at my embarrassment and pain as I desperately struggled to keep my pee in as my backside burned deliciously.
"Grip the desk if it would make you feel better," Skinner advised me. Grateful for small mercies I shuffled forward trying to keep my legs together and grabbed the front of the oak desk.
SWISH – CRACK the cane ripped into my arse a fourth time making me throw my head back as I tried not to scream with pain but failed, "Aaaaaayyyyyaaa!"
I was now biting my ruby-red glossy lips and had my eyes tightly closed as I fought back the tears when I felt the end of the willow rod probe between my buttocks eventually sliding across my engorged labia. "You bastard!" I hissed as I desperately tried to stop myself peeing; although I knew that I was eventually going to and wanted to, for them.
"Spread your legs...Miss Simpson," his husky voice got even lower, "and Mr Millhouse; will you do the necessary please?"
I eased my feet apart about 18 inches and gulped for air as my arse glowed and my need to piss became more and more desperate. A second later his perverted friend was beside me and had his fingers in the sides of my g-string. As soon as the Headmaster had finished tormenting me by see-sawing the long cane between my extended pussy-flaps, Millhouse quickly pulled my pants down to my ankles; only stopping to let me step out of them. The silence was broken by their heavy breathing as I straightened my legs and arched my back making my arse jut high in the air and giving them an unobstructed view of my freshly shaved cunt which was absolutely full of boiling urine.
Just as I took a huge deep breath ...SWISH-CRACK, the cane hit both cheeks with so much force I screamed with pain and finally my bladder emptied with a flood. The feeling of release was awesome as the hot urine gushed out of my hot cunt and splashed onto the hard floor.
"Huh, huh, is that what you wanted" I grunted with relief as the golden piss clung to my nylons as it ran down my legs into a large puddle at my feet.
"She's finished," Millhouse sighed as I shook the last few drops out of my throbbing cunt. Swish-crack, swish-crack the Headmaster thrashed my arse with the cane another four times; until he felt my arse felt couldn't take any more. "It's your turn now Mr. Millhouse," Skinner told his friend, as I gasped for air and my heart felt like it was going to explode.
"Thank you Headmaster," the creepy little man wheezed. The next I knew Millhouse was gently stroking my throbbing arse cheeks as if they were porcelain.
"Oh you beauty," he whispered, "ooohhh you beautiful girl." The he began kissing the long red welts that the cane had carved into my soft flesh. My legs were now so weak I had to grip the oak desk to avoid sliding onto the floor and into the puddle of piss. As he kissed and licked my arse Mr. Millhouse's hands were gliding up and down the soft nylon on my legs; alternating between the inside and the outside. I was so worn out from the thrashing I hardly noticed when he pulled my cheeks apart and began slowly licking my sweaty arse crack, until the tip of his tongue touched my anus which made me twitch.
"Oooooohhhhh," I sighed as he forced his warm wet tongue into my tight brown hole. My breathing became more forced as his tongue buried deeper inside me and his hands erotically stroked my stocking clad legs.
My pussy was now burning as brightly as my tanned backside. All I wanted was something – anything to be shoved inside my gaping cunt.
Millhouse alternated tonguing my anus with kissing and licking my stinging arse cheeks which was now driving me crazy with excitement.
"I think that's enough Mr Millhouse," The Headmaster panted. Millhouse planted a big sloppy kiss on my left cheek then left me wide-legged and at their mercy. I moved my arms to push myself back up, but the Headmaster prodded my fleshy arse with the tip of his cane. "I don't think so young lady." He told me as he pushed the thin cane between my legs until it edged between my oozing cunt lips.
"Oh God," I sighed as the cane sawed across my prickling hole.
"You've done a very good job, sir," The Headmaster quietly told his friend, "I think she will be very receptive now."
I turned my head to see that Millhouse was already unbuttoning his trousers. "Turn your head away, young lady." The elder man grunted and flicked the cane until it stung my cunt.
"Aaaaaayyyyyaaa bastard!" I squealed. My head was spinning with pain and passion when I felt someone press against my smouldering arse. Then with no preparation as his cock easily slid into my sloppy cunt. "Ohhhhh yyyyeeeeessssss," I gasped as the rock hard prick filled me up. Millhouse grabbed my hips with his clammy hands and began forcefully fucking me from behind. I was ecstatic as his cock pounded my willing pussy as he banged against my sore backside.
"Yes...yes....yes!" I kept panting as he knocked the wind out of my stomach with his hammering. When I arched my back to try and meet his thrusts his hands quickly moved over my stomach and grabbed my swinging tits; mauling and pinching them.
"Harder...harder," I screamed, "fuck me harder!" Millhouse replied by squeezing and tugging my nipples with his bony fingers making me scream even louder.
"Huh...huh...I'm nearly cumming," he suddenly gulped. "Take it out and push it in her mouth!" The Headmaster shouted at his friend. Millhouse whipped his dick out of my swollen twat and grabbed my hair; twisting me around and down onto my knees.
As I felt the cold piss seep into my nylons my face was directly opposite his throbbing cock.
"Suck it....suck it you dirty cow!" Millhouse screeched. I didn't need telling twice and instantly covered his twitching cock with my ruby red lips. His cock tasted delicious as I sucked my pussy juice off it and until his five inches filled my mouth. Millhouse was trembling with excitement as my head bobbed up and down on his shaft as he continued twisting my hair.
"Biiiittcchhh!" He groaned as my mouth filled with his bitter, hot, lumpy spunk. In his exhilaration the teacher appeared to slip on the piss puddle making him let go of my hair as he steadied himself; making his ejaculating cock spring from my mouth and spray the last of his cum onto my face.
As Millhouse turned and stepped away I flopped forward onto my hands and knees. My senses were now acutely aware of everything around me especially the smells. My nostrils filled up with the stench of his spunk which was dripping from my face and the stale piss that I was kneeling in as well as the normal wax and old books.
I slowly raised my head to see Skinner standing in front of me; naked apart from his long black cape. "Stand up, please Miss Simpson." He told me as he handled his rock hard gnarly uncircumcised cock which was pointing up to the ceiling.
Shattered from my thrashing and Millhouse's fucking it seemed to take an age for me to get to my feet which just made him grin with power.
"Lie on the desk for me please," his voice was still as cold and calculating as ever. I immediately stepped back until I was touching the desk. "No my dear, actually lie on it with your legs as wide open as possible."
As I sat on the edge the coldness of the wood against my red-hot flesh made me gasp. I did as I was commanded lying flat on my back with my knees in the air and spread my legs exposing my shaved cunt to their stare.
Skinner bent forward and began lapping at my dripping pussy making me gasp with delight. "Oh God...yeesssss!" He was an expert with his tongue; licking my slit, my clit my arse hole...every fucking thing beneath my belly button! I was so turned on I wrapped my legs around his head and tried to pull his face inside my cunt when Millhouse moved next to us and began mauling my tits again. Then; when Skinner finally slid two long fat fingers deep inside my hole I howled like a bitch as my orgasm nearly blew my head off.
My legs were limp and my body was trembling as Skinner lifted my ankles onto his shoulders and pressed his fat plum against my gash. "Fuck me...fuck me...HARD!" I spat out as his six inches forced their way into my belly. Skinner lent forward bending me in double as he fucked me rigid. His cock felt wonderful as it pounded my cervix and his balls bounced off my arse. "Fuck me harder...harder you bastard...FUCK ME!" I kept screaming as Skinner hammered his cock deep inside me and Millhouse sucked and twisted my tits and nipples. "Fuck me ...FUCK Maagghhh....uughh!" I spluttered as Millhouse somehow managed to climb onto the desk and shove his stiff cock into my mouth.
I was in Heaven as I got the fucking of my life at both ends by two pillars of the community. Millhouse's circumcised cock was perfect for sucking and filled my mouth without making me gag. "Mmmm....mmm...mmmm." I purred as the men pounded away. Then without any warning Skinner pulled his cock out of my cunt and instantly pressed it against my shithole.
His cock was covered in so much goo from my twat it slid into my arsehole with ease. With a mouthful of cock all I could do was make gurgling noises as Skinner fucked my arse with the same ease as my pussy. It felt magnificent as my arse felt as full as a boil! I don't know how long the three of us had been coupled in sexual ecstasy but I knew that he couldn't possibly hold out much longer and I was right.
"Ugh, ugh, ugh," Skinner suddenly grunted, as he tensed up and spewed his hot cum deep into my bowels.
Millhouse popped his cock out of my mouth and quickly tugged at it sending even more of his spunk across my face and tits.
My body felt strangely empty as both men stepped away from me still lying on the desk.
As I turned around to slide off the desk my arsehole was aching so much from the Headmaster's pounding I suddenly had the urge to fart.
Unable to stop myself I 'let one go', only it wasn't just a fart; and a spunk covered lump of shit curled out of my anus, instantly followed by a longer second one; both splashing into the puddle of piss under the desk.