CHAPTER 1: TWO FIRSTS IN ONE DAY
Introduction: The following chapters are supposedly written by an elderly man, recording his sexual adventures whilst a prep school teacher in the 1950s and 1960a.
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I was a 20-year-old male virgin, fresh from my two years' army service. I had decided not to take up my college place yet, because I was unsettled and unwilling to study. I wanted to some more of life. It was quite easy to get a job in a preparatory school. You just needed to be personable, well-spoken and willing to teach anything.
So, I was teaching several subjects to boys between 7 and 13. For £55 per term, with all found and free laundry. No pay in the holidays, but I could live in and cater for myself. Advantageous when, in my second post, the art mistress also stayed on. More of that later.
My teenage sexual activity had consisted of kissing and above-the-waist fondling, but aside from one, brief, investigation up a tightly-elasticked knicker-leg, pussy was a mystery. It was my headmaster's wife who extended my knowledge. I will call her Madam, because that was how we referred to her in the staffroom.
She was in her late forties, I guessed, and large in all departments, rather pale and with a lot of wiry grey hair. She had, I realised after our first episode, been making signals for some time, but it was not till a fine October day that she had the chance to be explicit.
I was sitting in a secluded part of the grounds, on a slatted bench against a cyprus hedge, enjoying my free afternoon and catching up with some marking. My colleagues and the boys were all at lessons. I think she had been watching where I went, and she appeared round the hedge, startling me for a moment.
'No need to jump,' she said, sitting down close beside me. 'I've been hoping to ask you how you're settling in, and whether there is anything we can do to make life comfier.' She put a hand on my thigh for a moment or two, displacing the exercise books.
I assured her I was comfy and we went on to chat, till she shifted her big bum about on the seat and said, 'If I sit on this much longer I shall have a corrugated bottom' There was an implied response, but I couldn't think of it.
She stood up, rubbed her hands up and down the back of her dress and said, 'A little massage might smooth it out.' This I did understand, and I took over rubbing her rear, which was pretty exciting, since no woman had ever invited me to palpate her behind before.
My efforts were rewarded with her bending forward in front of me and saying, 'Oh yes, that's good. But it might be better under the skirt.'
Nothing loth, I reached up and began to squeeze and stroke those large cheeks through the knickers. And this was really exciting, the more so as I was overstepping so many boundaries. Was I really handling the well-filled underwear of my employer's wife? Yes, I was, and it got even more intoxicating when she said, 'Better still if I took these off.' And she reached up under the dress and pulled down a large pair of pink cotton pants and stepped out of them. 'Try now,' she said, bending forward.
I vividly recall that first feeling of bare buttock under my hand. I got both hands to the task and slid them all over, from the first outward bulge at the top to the deep transverse cleft where cheeks met thighs. She began to pant, which was reassuring, because I was breathing hard myself. 'What about between?' she asked. So I slipped my fingers into the crack and ran them up and down, bringing my first touch on an anus. Oh that deep romantic chasm! She opened her legs wider, panting harder and said, 'Would there be a finger?'
Her posture had brought the rear end of her vulva into play, and my finger slid readily into and along it, extracting a gasp. 'Inside, inside,' she instructed, and into the vagina went that questing digit. How hot and slippery it was! I felt as if my whole self was vested in that digit, so intense was the super-awareness of being inside her. That's the response I've always had since then, whether it is fingers, tongue or tool that is within the woman.
She thrust backwards onto that finger and gurgled with pleasure. Then she said, 'Would there be another finger?' And in it went. The backthrusts speeded up and then she gasped, 'Other hand front, front.' I was ready enough for that and round the hand went, plunging into the abundant fuzz like a ferret into a rabbit-hole. More by luck than judgement a finger found the clitoris and I quickly realised there was the special spot. I had a strange, half-comic idea of myself as playing an instrument, the fingers in the cunt like the bow across the strings and the finger on the clit pressing on the fret.
The right hand was held by those deep, deep buttocks, while its fingers slid in and out and wriggled inside. The left index finger twanged the sex-button quicker and quicker. Suddenly the right hand was gripped in that delicious, cushiony but firm vice, and I pressed the trigger finger into the cleft, and her whole body shook with a massive quake She uttered a strange, high yodelling noise and then sagged from the waist. I felt a great sense of triumph. I had managed to give this mature, experienced woman an orgasm.
I was trembling with lust, my erection straining at my trousers, and I was assuming there would be some relief for me. Perhaps she would let me into that soaking, fevered, vagina, having had her own satisfaction? I could drop my trousers and pants and she could simply move back a pace or two and lower that glorious tunnel onto my aching cock, which would come at once.
But she simply stood, shook out her skirt and glanced round at me. She took in the bulge in my trousers and pointed to the pink knickers. 'You can make use of those, if you like,' she said meaningfully. Then she walked briskly back round the hedge.
I could hardly leave those voluminous pink bloomers where they were, so I crammed them into my pocket. You can imagine I didn't feel like going on with the marking. I felt like seeking my room and tossing off, and the idea of doing that onto the knickers was quite appealing. Meanwhile I breathed in the cunt-scent on my fingers, as if needing the evidence for what had just happened. I also recalled that I had seen nothing. I had felt everything but the dress had concealed all. I had never seen female genitalia and still had not.
Five of the single staff lived communally in a detached house near the school, and by the time I got there, lessons were over and two of my colleagues were making tea in the kitchen and chatting in the common-room. As I passed through, the senior master greeted me cheerily and the French mistress gave me a knowing smile. I went to my room to deposit the marking and hid the knickers under my pillow.
The two women who taught the youngest boys were elsewhere, and after a quick cup of tea the senior master left. He was on duty and had to patrol the premises, So the French mistress and I were alone in the two battered and sagging armchairs, with second cups of tea.
She was a small woman, probably in her thirties, with an air of mystery about her, as was the case with many prep school teachers. They were often fugitives from unhappy marriages, or love affairs, or embarrassments in foreign parts, and either reluctant to tell their stories or all too eager to tell their stories. I will call her Denise.
'Had a good afternoon?' she asked with a smile.
'Not bad,' I said as casually as I could.
'Were they pink?' she asked.
