The Headmaster’s Room (pt 3)

The Headmaster’s Room (Part 3)


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 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 her 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.