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.
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 gaziantep escort reklamları 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.
I was shocked and felt myself blushing, and could think of nothing to say.
She laughed and said, ‘About as pink as your face, I would guess.’
I was still speechless and she continued, ‘It’s all right. No-one else knows. But your predecessor was a good friend of mine.’
‘So, he was -‘ I didn’t know how to express it.
‘Oh yes, he was expected to provide other services than geography and history. Which was why he left after a year. He couldn’t stand the frustration.’
‘So she kept wanting him to -‘
‘She certainly did, and if he was unwilling she threatened she’d tell her husband and get him sacked without a reference.’
‘Will she do the same with me, d’you think?’ I asked.
‘Probably. But you’re not like him. He was older and married, though separated.’
I thought about this. ‘She never let him…’
‘No. And he wouldn’t have, anyway. He could bring her off, but because he was still married he couldn’t do it with another woman. So I couldn’t help him completely, either.’
I wondered exactly what she meant. Did she mean she would have had sex with him, if he had felt able? Did she mean she would fetch him off instead? Would she do it fully with me, or toss me off if not? How did I ask her?
‘You’re wondering what I was implying, aren’t you?’ She spoke with a broad smile.
‘Yes.’ I studied her intently, agog for what followed, and for a long moment she said nothing. Then she said, ‘What’s in it for me?’
‘What was in it for you with him?’ I had the wit to ask.
‘Oh, he was pretty skilful.’ She grinned at me.
‘I did all right with Madam,’ I offered, ‘As for as it went.’.
‘She was easy,’ Denise said. ‘But I would want more than that.’
‘I’m ready to learn,’ I told her.
‘Am I ready to teach, though?’ she remarked, with a laugh. Then, ‘Let’s be clear. You are quite a good-looking lad, and I think you’re a kind and thoughtful young man, so I could probably respond. But you have to consider whether you could be intimate with me.’
So far, after a few weeks of knowing her, I had not considered her as a sexual partner. Now she was asking whether I could see her in a different light.
She said, ‘I know very well I’m not immediately attractive. I’m small and slight. My bust is negligible and my behind is meagre. I’ve got a slightly hooked nose, my face is thin and my mouth’s too big.’
‘You’ve got beautiful eyes, though,’ I said.
She laughed. ‘Yes, but you’ve agreed about the rest.’
My life was changed by the inspiration which came to me at this point. ‘But I haven’t seen you naked. The size of your bust and bottom is not as important as the shape.’ I paused to collect the rest of the inspiration, and she nodded. ‘Well, they are neat and tidy.’ I went on, ‘The real point is that I already like and respect you, and I want to get close to you.’
‘Well done!’ she said. ‘Despite the differences of age and experience we might get on, in bed as well as in the school.’
This was so inviting that a wave of emotion went through me and I reached for her, wanting to kiss her. But she drew back. ‘That’s the vital consideration,’ she said, pushing away my hand. ‘We have to be completely secret, because if it became known our professional lives would be finished. You realise that?’
Reluctantly I agreed. If the parents got to know it would mean the sack. They wouldn’t entrust their sons to the guidance of immoral teachers. So how were we to manage?
‘One step at a time,’ she said. ‘We need to find out first if we’re compatible. It’s lucky that Ben [as I will call the senior master] puts himself to sleep with whiskey – you didn’t know that? And Gwen and Tony are Lesbians – you knew they shared a room but hadn’t realised there was more to it than that? That’s their secret, mind, and we must keep it that way. Ben doesn’t know for sure, and wouldn’t care, or say anything, and Madam isn’t interested in anything beyond her own comfort and convenience.’ We both knew our principal was too other-worldly to be aware of sex amongst his employees.
‘Tonight,’ she suggested, ‘I’ll come to your room when I think it’s safe. It’s handy yours is separated from the other bedrooms by this room, and an advantage of being small and light is no-one will hear me. Now you can make me another cup of tea.’
You may find it unbelievable that I began my sexual career with two experiences in one day, just, as it was just before midnight that Denise silently pushed open my door and tiptoed in. ‘Are you still interested?’ She whispered, but was quite able to perceive the state of quivering anticipation I was in, naked in bed and shaking in the glow of my bedside light.
In a voluminous dressing-gown, she sat down on the bed, smiling. ‘What now, then?’ she murmured, and I reached for and parted the lapels of the gown. Beneath it she was in a cotton nightdress through which her breasts were visible. I pulled down the gown. Then I reached for her and drew her into a kiss. Her mouth tasted of toothpaste and something else, which I identified as ‘woman.’ Our tongues quested and caressed each other. The kiss went on and on and my trembling increased.
Eventually we paused to draw breath and I took hold of the top of the nightie. She stood to let me pull it over her head, and there she was, so beautiful. I was on the verge of tears. Yes, her breasts were small, scarcely more than mounds on her ribs, but the nipples stood out, hard and deep rose.
She could see I was moved beyond desire and slowly turned. Her pubic hair came into view. It was light brown and fluffy, truly pussy-fur. Then her bottom. ‘Meagre’ it might be in comparison with Madam’s arse, but it was tight, swelling from the small of her back into those rounded, rounded cheeks, suddenly tucking under into the top of her thighs. In that slow gyration I learned never again to judge a woman’s body until it’s nude.
‘May I?’ I asked, starting to stroke that sweet, sweet bum. ‘That is the most beautiful thing I have ever seen,’ I told her. ‘And your breasts are perfect.’
‘I shall have to sit on it,’ she said, ‘if we’re going any further.’ She sat and plunged a hand down the bed and took gentle hold of my rigid penis. ‘And it looks like we are.’ She threw back the covers and lay down beside me, half turned towards me, looking down at her left breast. I bent and took the nipple between my lips. She gave a little hum and held my head in place while I sucked. ‘Lick,’ she said, and I ran my tongue round and back and forth across that charming swelling, and she rolled away enough to bring the other one into play.
Meantime she was fondling my cock, stroking my thighs and stomach. ‘Don’t worry if you overflow,’ she said, ‘That often happens the first time. It is the first time, isn’t it?’
My mouth being clamped to her left breast I nodded. Then she took my hand and guided it to her vulva, opening her legs a little. ‘Find the way,’ she said. This I had done with Madam, of course, so I knew what to do. She lifted her pelvis to meet the touch. ‘Use your tongue,’ she said, and I kissed my way down her flat stomach into the soft pelt and into that delicious slippery slit. It tasted of soap, salt, and that something else which is also ‘woman.’
She began to tremble as much as me. Then she opened her legs further and bade me, ‘Put your tongue inside.’ I slid my tongue downwards and pushed as much of it as I could into the waiting vagina and flicked it in and out. ‘That’s it!’ she said. ‘Back to the top,’ she said after a while and the clitoral cunnylingus resumed. She said, ‘Fingers inside,’ and I slid in two and thrust them deep, withdrew them, kept thrusting in and pulling out.
She began to shake more and more violently, so I had trouble keeping my tongue on the target. Then she gasped, ‘It’s coming. I’ll take care of you in a minute. But now I’m going…’ Abruptly she stilled, her whole body rigid, holding her breath for so long I began to be anxious. Then she let it out in a long, gusty exhalation. I took out the fingers and stopped my licking, rested my head on her thigh, giddy with exultation.
She giggled, drew my head back onto her breasts and took my cock in her hand. ‘You may find this a bit odd,’ she said quietly, ‘But even after that I can’t take you inside me just yet. I think it will happen, but, you know, that is the greatest closeness for a woman, and it takes time. I hope you won’t mind?’
I was beginning to fall in love. As soon as that, though I was not, yet, fully aware of it. But I was happy, lying on her breasts with her hand round my cock. I had ceased trembling, somehow satisfied by her giving me the experience of her orgasm. It was almost as though I, too, had climaxed. So different from with Madam.
‘I’m not going to leave you totally frustrated, though,’ she assured me. ‘Especially after what happened with Madam. I’m going to make it happen. Just lie still and you’ll see.’
She joined her luscious mouth to mine in a tender kiss and began to slide the loose skin of the foreskin up and down my shaft. She hummed against my lips and broke the kiss to croon, ‘This won’t take long. I can feel it gathering. You’re ready. Yes, let me see it. I want to see it. You’re getting harder. Here it comes! Oh yes, here it is!’ And I spurted five or six thick jets onto my stomach, her hand, her breasts. She put her mouth back on mine to seal the moment and prevent me crying out with the joy of it.
‘Thank you,’ she said after a long, relaxed kiss. ‘I wanted to do that ever since you came into the staffroom with Madam’s knickers in your pocket. And I wanted to even more after you made love to me. I want to do it again, often. Even if I have you inside me.’
‘That will be wonderful,’ I said, ‘And if you take me inside you that will be wonderful. But I want us to do only what you really want.’
She kissed me again and said, ‘It’s hard to do this, but now I must go back to my room. Otherwise we’ll fall asleep, or we’ll make more love and fall asleep, and oversleep and the secret will be out when I come out of here in the morning.’
She sat up, put her feet to the floor and stood. ‘Please, I said, ‘Just lie down again a minute I would like to see everything.’ She lay and opened her legs, so that I could take in every detail of the first pussy I had could see. My heart turned over when I studied that bright pink channel, with the crinkled lippy margins, the tiny tuck-in where lies the clitoris, and the vaginal opening, like a half-open runway into the mysterious interior. Words failed me and I murmured inarticulate sounds of wonder and delight. How many female genitalia have I seen since then? Dozens, but always with the same wonder and delight.
She said, ‘The first time of seeing? I thought so. Now I must go.’ But I asked her to turn round as before and she slowly revolved. As her bottom came near I leaned over and kissed it on each adorable cheek. Then she slipped the nightdress over her head, shrugged into the dressing gown and eased open the door. A smile and a wave and she was gone.
Had I been dreaming? No, indeed. There was the taste of her pussy in my mouth, the scent of her sweat and bottom in my nostrils, the drying semen on my thigh. I didn’t expect to sleep for thinking of her, but I began to drop off in mid-memory. Then I woke with a start. I hadn’t asked when we could be together again.
Fortunately, our daily business did not throw us together much, and if we coincided it was always in public. Meal times in the dining-hall, break times in the staff-room, where at least one colleague would usually be present. This was partly because although five of us were resident in the building the staff-room was the common room for the non-resident teachers, too. But there was just one moment when we were alone and she said quietly, ‘Tonight.’
This time I sat on my bed, heart pounding. Having no dressing-gown I was naked under my raincoat. She arrived in her gown, but there was no nightdress, so when she took off the gown she was gloriously nude, and I threw off the raincoat. We embraced, kissed, stroked each other, murmured how wonderful it was to be together. I ran a hand down her back, and tucked fingers into her crack, ran them down and under, feeling for her vulva.
‘I’m already ready,’ she said with a little laugh, because she was overflowing down the inside of her thighs. Which was so exciting I gasped. She clenched her buttocks on my hand and said, ‘I’ve been thinking of this all day.’ My cock was jabbing at her belly and when she took hold of it I nearly ejaculated. ‘This is on the edge, too, I think,’ she said.