Diary – Chapter VI – The Gym Mistress

The cane bit into her rump for the sixth time with a loud swish-crack. The young woman took it mostly without crying out; jerking her shoulders a little and gasping, and suffering only one additional stroke. But otherwise taking it bravely, as she had taken the whole beating. The Headmistress said, “You may stand up now,” and the young woman straightened, turning to face her tormentor.

My eyes were on stalks. The young woman was completely naked, and the Head, my Headmistress and fiancé, had stripped to the waist before starting the caning. I knew she had done this to please me, knowing how I loved watching the movement of her breasts as she whipped her torso from right to left as each stroke was unleashed. Joan held out her arms to the young woman and drew her close. I watched their bodies touch, breasts flattening as they pulled themselves together. I had never seen two women kiss before, and this stirred me as no erotic vision had affected me before.

I felt Annette sidle up to me from behind. Her hand covered my crotch and she said, “My, but aren’t we a naughty boy then! Perhaps it should be YOU getting the cane, my lad.” She unbuckled my belt and slid fidgety hands inside my trousers. In no time at all I had covered her busy fingers with a gallon of something warm and sticky.

Annette laughed happily. “You wait till I tell the Headmistress!”

I was in the Head’s study. We were finalising our plans for the following day, when the Head’s secretary, Annette, came in with letters for signature.

Joan signed them busily, and as Annette was gathering the papers together she said, “I’ve been having a long talk with Carol. You know, the young teacher who runs the gym.”

“Oh yes,” replied Joan. “I know her very well. How’s she getting on?”

“Very happy in her work, Joan,” said Annette. “We talked mostly about caning, though. She seems quite obsessed by it. You know, I think she’s just like us. Wants to be caned from time to time.”

There was silence while Joan took this in, until she said, “Well that’s not a problem, is it. Who does she want to be caned by? John, here? Or do you want to do it yourself, Annette?”

“Actually. . . well. . . certainly not me. I’m not into caning others; I just get the urge once in a while to be on the receiving end. . . No, actually she wants you to cane her. She’s got a real crush on you. Admiring from afar, and all that. She thinks you are very beautiful, that you carry your headship very well, authority and everything. . . She just thinks you’re magnificent.”

“I think you’d better get her to come and see me, hadn’t you? Perhaps tomorrow evening after school?”

And so it was arranged.

I wasn’t present at the meeting, nor was Annette. But Joan and I had a long talk about it afterwards. First I asked what Annette had meant by ‘having a crush’ on Joan.

“Ah, well, its usually very innocent, you know. All girls ‘have a crush’ on someone, sometimes a teacher, sometimes older girls. It doesn’t mean they are fully-fledged lesbians, you know. Although sometimes. . .”

I was agog. “What do you mean? I’ve never known a lesbian, but the idea of a girl making love to another girl is very erotic. Come on, you can’t leave me in the air. . . ”

Joan was silent for a while, evidently recalling memories of her own schooldays. “Well, I did have some wonderful experiences myself. One of my friends had a boyfriend from the village, and wanted him to come to the school at night for a tryst. She had no idea where they could meet, and was very nervous about the whole thing. So I suggested they meet in the hockey pavilion. I managed to get hold of the key and have it copied. That gave me some power, as I wanted to be in on the scheme. (We hardly got sight of a boy from start of term to the end). We recruited a third girl, Angela, who was the idol of the school. Captain of hockey and netball, due to be the next head girl, brilliant at everything. The entire school had a crush on her, including me.

“So it was arranged for the Saturday night. We got out of the building by a back window. I had the copy key for the pavilion, and we met the boy there. He was a bit shocked to find three of us waiting for him, but it didn’t stop him getting physical with our friend.

“That left the two of us, very excited, hanging on in the dark like idiots, listening to the two of them making love, noisily. It wasn’t long before we were holding each other. One thing led to another, and, well, we learned as we went on, but we started to make love. It was the first time for both of us, and I must say we enjoyed it.”

I listened to all this dry-mouthed.

Joan went on. “The following week we insisted on taking our turn with the boy. He was very crude and clumsy. No idea at all of how to please a girl. A quick grope, and before you could say Jack Robinson it was all over. While those of us lucky enough to be making Sapphic love had a whale of a time. One night Angela got so annoyed with the boy she turned him over and gave him a good spanking. This only made him worse, because he was so turned on he actually came without anyone touching his prick. We turned him over, and there he was, spouting away like a whale.

After a while we dropped the boy, and Angela and I used to go to the pavilion by ourselves at dead of night. We made love once a week for a whole term. And enjoyed every minute of it. We tried everything we could think of. Including spanking, my dear. Which is perhaps where I got the idea that spanking on the bottom is not nearly so unpleasant as being strapped on the hands. In fact we got quite hooked on it. We spanked each other, and made love, and spanked again. We spent hours in that pavilion in the middle of the night. And nobody ever caught us.

“Of course, I’ve grown out of that now. You can’t beat the real thing, with a proper grown-up man. A girl needs that hot hard cock inside her. And pretty often, too. Still, I sometimes recall that happy period of my life, and imagine myself in the arms of my idol, Angela.”

There was a pause while I wrestled with my thoughts. “Well, I find the whole thing absolutely captivating,” I said. “”If you really want to do something like that again, its OK by me. In fact I’d want you to do it. And then come back to me, of course. For the real thing.”

Joan looked at me hard. “Are you sure?” she said.

I assured her that I’d love her to do it.

“That’s very generous of you, John,” she said. “And would you like to be present? Would you like to watch? And perhaps join in if she were that kind of girl?”

I told her it was beyond my wildest dreams. Joan looked thoughtful, and said perhaps my dreams might be realised sooner than I expected.

So it came about.

Joan had another long talk with Carol, the gym mistress. It was arranged that we would all meet at Joan’s house on Saturday night at seven thirty. Annette would pick Carol up in her car.

Joan took charge straight away. We each were given a glass of wine, but it was clear we were expected to drink it pretty quickly. We were all out of small-talk. Then upstairs to the main bedroom, where a selection of canes lay on the bed. Joan picked one of them up; a big one we thought too severe for use at school. She pointed to a place near the foot of the bed, where Carol dutifully stood, hands clasped meekly in front.

She wore a lovely little black frock; very short, revealing stocking-tops whenever she moved. At the neckline it was high, coming right up under her chin. Very modest high up, but by no means conservative at the hem. It was just the sort of thing Joan would have chosen for her, and I wondered if they had gone shopping together one evening.

Carol stood meekly, hands clasped in front of her, while Joan circled. Standing behind Carol, she lifted her skirt and peeked at the lovely bottom awaiting her attention. I glimpsed lacy black knickers, another Joan giveaway, I thought. There were suspenders, and her splendid long legs were shown off by black stockings and shiny shoes with not-very-high heels; all looking as if Joan had chosen them for my especial benefit. “Now, my dear, have you been naughty enough to deserve punishment?” asked Joan.

“No,” replied Carol. “No, I’ve been a perfectly good girl. But I hope you will punish me anyway.”

“Well, I think that can be arranged, my darling. I’ve got one of my favourite little canes here, and its just aching to give you six of the best. Six lovely stingers. Would you like that?” Joan was still holding a hand against Carol’s partially knickered bottom, stroking it and weighing it in her hand; as if testing how it would react to the impact of the cane. “I think this dress is in the way, don’t you,” she continued. “Lets have it off.”

She unzipped the back, drew the frock forward off Carol’s arms, and slid it down her legs so that Carol could step out of it. I gasped when I saw Carol’s body. She wore no bra. The black strapping of the suspenders and the wispy underwear below her waist contrasted with the sun-bronzed upper body. Nearly six feet tall, broad-shouldered, with hockey-players thighs, she had a magnificent physique. As a games-playing woman who kept herself super-fit, Carol had no spare flesh, and even her breasts were modest. I noted, though, two very large nipples. I wondered if their size had something to do with being sexually excited. She made no attempt to hide her breasts, nor did she cover her pubes, so confident did she appear. Not at all like a woman about to bend over for a stiff caning.

“This is the cane I’ve chosen for your first flogging, my dear,” said Joan, holding it against Carol’s face. I knew how creepy this could feel as Joan prolonged the tease. “I’ve got bigger ones, but this can be quite effective, I’m sure you are going to agree. Now! Turn and face the bed, if you please.”

With that, Joan laid down the cane and unbuttoned her own blouse. Slipping it off, she handed it to me. Joan, too, wore no bra. I compared the two women. Joan’s breasts were much fuller, not quite able to carry their own weight. The nipples were smaller and the skin very pale, creamy and silk-smooth except for the aureoles around the nipples. These, by now so familiar to me, were very dark brown. I looked back to Carol, noting that although her skin was rather darker than Joan’s, the aureoles were almost the same colour as the rest of her skin.

“I think we’ll have everything else off, too,” said Joan. “Will you give me a hand, please, Annette?” They crouched either side of Carol, and deftly each unclipped a stocking and rolled it down to the ankles. Carol lifted first one foot then the other to allow the shoes and stockings to be removed. Joan slid the lacy panties down, too, and unhooked the suspender belt. I thought she did this rather more slowly than necessary, perhaps relishing the feel of the skin on the way.

Joan picked up the cane and took up her position on Carol’s left. Although it was a large room, Annette and I hurriedly moved to Carol’s other side to give Joan plenty of room to swing the cane. I knew she always swung the cane through a wide arc, starting with the cane well behind her back. Carol had been standing patiently, hands covering her bottom cheeks as though anticipating the ordeal to come.

“Bend over, my darling,” said Joan quietly. “I’m going to give you six of my very, very best. I shall not hold back. Are you ready?”

To my amazement, Carol was in a mood to give us a show. First she reached high in the air with both arms, fingers stretched almost to the ceiling. Feet together, her body was ramrod straight. She held that pose for a moment. Slowly she swung both arms forward, bending at the waist, showing splendid suppleness, until her stretched-out fingers touched the tips of her toes. Touching the toes was clearly no problem for her. She held that pose, stock still, waiting for the caning to start.

But this did not satisfy Joan. “No, my dear. This won’t do. Stand up again, and we’ll start all over again.” Carol straightened up, looking puzzled. “No, I want your feet apart, please, Carol. Feet apart now, and clasp your hands behind your neck for now.”

I think Joan was a little taken aback by Carol’s insolent approach, and was going to make her suffer for it. She walked round the gym mistress, admiring her athletic body. She used the cane, touching Carol lightly at the back of the neck and running it gently down the spine. Carol shivered suddenly. The cane moved over her bottom, stroking and teasing, the intention being to make them ultra sensitive. I realised Joan had indeed been disturbed by Carol’s demonstration when she placed the cane vertically against the crease between Carol’s buttocks, pressing it in so that it stayed in place. It would stay there unless she might for some reason relax her muscles.

Walking in front of Carol, Joan put her fingers on the pair of nipples. I knew from experience that if you are made to stand with hands clasped behind the neck your nipples feel horribly exposed. Joan took hold of both nipples very gently with fingernails. Suddenly she nipped hard and savagely twisted both nipples. I heard a sudden intake of breath, but Carol managed not to cry out. However, the cane dropped out of her buttock-crease, bouncing across the bedroom carpet. Joan was staring hard into the young woman’s eyes at the time, no doubt looking for some indication the pain had got through to her.

It was like a tennis match. Fifteen-all, I thought.

I darted forward and picked up the cane for Joan. “I’m ready, my darling,” she whispered in Carol’s ear. “Shall we have another try? Feet apart, first.”

When she was satisfied, she continued, ”I like your style, my darling, so we’ll have your fingers high in the air, shall we!” She kept Carol waiting. There was tension between the two of them; a sense that a competition was taking place. Annette and I stood motionless, hardly daring to breathe. You could have heard a pin drop.

“Now you may touch the toes if you wish, my dear, or you may hold onto your ankles. But either way, you must stay in place until the caning is over and I say you may stand up. So if you opt to just be touching your toes, I’ll be watching to see that you keep contact at all times. One little upward jerk, and it will be extra strokes. Is that clear?”

“Crystal clear, darling Joan,” said Carol in an insolent tone. She’s just asking for it, I thought.

All this time Carol had been stretching towards the ceiling. “Bend over!” came the command, and Carol swung elegantly forward and touched her toes. So that was it! She was determined not to be intimidated by Joan, and had accepted the challenge. I was sure Joan was angrier than she appeared, and that she would not hold back out of some sort of womanly sympathy.

Barely had the fingers touched when Joan unleashed the first stroke. It undoubtedly took Carol by surprise, but although her body jerked upwards slightly, she managed to keep contact with her toes. There was a short pause, and the next stroke was absorbed by Carol without fuss. I was surprised, because I thought Joan was using almost maximum effort. I’d seen her in a fury attacking the man in the forest, but this was nearly as severe.

At the third I heard a bit of a gasp. So she was getting through to Carol after all. I kept an eye on the fingers, and although Carol was jerking as each stroke landed, she managed to keep contact with her toes at all times. It wasn’t until the sixth and last that Carol slipped up. The recovery interval was much shorter, and Carol may have been taken by surprise, because there was a quick intake of breath and her shoulders bobbed for an instant. She recovered rapidly, but it was too late. Joan had spotted that the fingers had left the toes for a moment.

“Oh dear,” said Joan sadly. Except that I didn’t believe she was sad at all. “You may stand up for a moment, darling, but you know you failed to stay in place for that last stroke, don’t you!”

Carol came upright and turned her head to Joan. I was unable to see her face, but I suspect there was little sign of suffering. She was a courageous cookie, alright. It was hard to see that anyone could have kept in place in that situation. I certainly couldn’t.

“Well,” said Joan. “We’ll try to make it easier for you.”

She made Carol kneel on the bed with knees wide apart. Shoulders had to go down onto the bed, forcing her head back awkwardly. What an obscene vision! Carol’s backside thrust high into the air, cheeks forced wide apart so that every detail between her legs was on full view. The six cane stripes were vivid, especially on the right cheek. On the left cheek where the cane had not bitten so deep, the stripes were mostly seen as tramlines. But on the right each stripe occupied a canes-width, the whole area already an angry mass of red, purple and black. The stripes were rising into ridges, and in places close to blistering. Joan had excelled herself.

Joan placed the cane against Carol’s rump and tapped a few times. I watched her body as she unleashed the stroke. I never failed to be thrilled by the sight. Especially the way her breasts thrashed from one side to the other.

The stroke was low, and Carol allowed her guard to drop as she flinched visibly and uttered a squeal that betrayed the extent of the hurt. Joan rarely allowed a stroke to land on the legs; by practising regularly she maintained a superb level of skill. Perhaps it was because Carol’s bottom was higher now she was kneeling on the bed. But I don’t think so.

“You may stand up, now,” said Joan, gently. Carol eased off the bed and straightened to face Joan, who held out her arms to the young woman and drew her close. I watched their bodies touch, breasts flattening as they pulled each other together. I had never seen two women kiss before, and this stirred me as no erotic vision had affected me before.

I felt Annette sidle up to me from behind. Her hand covered my crotch and she said, “My, but aren’t we a naughty boy then! Perhaps it should be YOU getting the cane, my lad.” She unbuckled my belt and slid fidgety hands inside my trousers. In no time at all I had covered her busy fingers with a gallon of something warm and sticky.

Annette laughed happily. “You wait till I tell the Headmistress!”

We watched Carol pulling off Joan’s remaining clothes, and they threw themselves onto the bed and locked their arms round each other. We watched for a while as they made sinuous, writhing sex. But quite soon I became aware that Annette had removed her own clothes and had started on mine. When we were both naked she knelt in front of me and proceeded to clean up the mess she had made. Her mouth was warm and moist, and felt lovely. I was becoming strong again, which was no doubt Annette’s intention.

She removed her mouth from me and looked up. “Spank me, John, please! I haven’t had to bend over for you for weeks, and I really need a spanking.”

What could a gentleman do? I took her to the bed and pushed back at the writhing pair so that I could sit on the edge. They were oblivious. I pulled Annette to me, laid her face down across my lap and spanked.

I went on for ten minutes or more, until my hand was too sore. Annette’s bottom was pink all over, but I was sure the pain was trivial compared with what Carol had just experienced. I made her get up and we went over to the big upholstered armchair, where I sat first, pulling Annette so that she was sitting on my lap, legs over the chair arm on my right. I looked down at the plump body which I found so erotic. She was looking up at me, a happy smile on her face. I slipped a hand between her legs and she closed her eyes, the smile remaining on her face. She was wet and open, and I sought her clit. It was already prominent and she started to spasm almost as soon as I touched it.

Annette had her orgasm in silence, which is not what was happening on the bed. They were noisy and never stopped moving. Judging by the shrieks, both orgasmed time after time. I looked up from time to time. Once I saw Carol on top, head buried in Joan’s crotch, her own thighs either side of Joan’s head. I recognised what Joan had taught me, calling it the sixty nine, and they were loving it. Another time Joan was sitting on Carol’s head, pushing back and forth, and having yet another cum.

When Annette’s second cum was over she opened her eyes. “Please kiss me, John,” she said. Her neck was cradled in my left arm and I pulled her head to mine. Her mouth was open and as soon as I touched her she was seeking my tongue with her own. I imagined there were two active snakes in there, rapidly twining around each other, darting quickly from place to place, never still. My hand was still between her legs and I moved it gently through the hot liquid, stroking the engorged walls of her cunt. Before long I could feel her working towards another orgasm, which she performed whimpering, mouth still pressed to mine, tongue active as ever.

Some time later she pulled her mouth away and looked up at me happily. “That’s wonderful, John, but I’m ready for your cock now. I’d love to feel you properly inside me.”

I lifted her onto the floor and as I lay over her she opened her legs. I entered gratefully.

Next morning Annette was up early and away home, no doubt getting there before hubby woke up.

I was having breakfast in the kitchen when Joan and Carol came down. Each wore only a flimsy slip. Carol’s arm was round Joan’s shoulder, and Joan had a hand under Carol’s slip, holding her left buttock.

“Look what we did to Carol’s bum,” said Joan, turning her round and lifting the slip. Carol bent slightly and struck a pose. The stripes were even more livid than the night before. Multi-coloured and shiny they were, and ridged. They were accurately clustered low on the curved part of her cheeks, so close together you couldn’t count them, but I could see the one that had gone astray, a couple of inches down her thighs. I remembered how Carol had reacted to that one and I winced.

Joan stroked the sore area and gave a sudden slap. Carol straightened up and turned to Joan, smiling. I watched with growing excitement as they embraced each other, loving the sight of breasts churning together. Carol’s kissing was still aggressive.

“So would you like your revenge one day, Carol?” I asked.

Carol broke away and faced me. “I’d love to cane Joan, yes. That would be fun. And I’d enjoy punishing you just as much, m’dear. I think you could take a big, big caning.” I could see she meant it, too.

They had a leisurely breakfast, and I drove Carol home. As she was getting out of the car she said, “You know, you two ought to join the Justice Club. You’d both get on like a house-on-fire there.”

I had no idea what she meant, nor had Joan when I told her about the remark.

That evening in bed Joan and I lay in each others arms and discussed the adventures of the night before.

Joan was still worried that I might be jealous when she made love to another woman. I told her yet again that I had loved it, and had no objection to her taking a lesbian lover, provided it didn’t take away her sexual interest in me.

“No danger of that,” she laughed. “How did you get on with Annette?”

“I find her a sexy little thing,” I replied. “She showed me lots of tricks last night that were new to me. And her fleshy little body feels good. But its good to get back to you. This is where I really belong, in your arms.”

She reached down and gave me a squeeze. I was getting hard again.

“I knew from the start I would have to keep you sexually satisfied while I dealt with Carol,” Joan said, “hence my anxiety that you two should get together. I trust you both, and I’m very fond of Annette. She’s so good in the office at school, an absolute treasure, and good company. And she has such an empty married life; I like to bring some her some joy.”

We lay quietly while I digested all this.

“I still worry about how you take it all, though,” she added.

I thought I had the solution. “Suppose every time you make love to Carol, I have to punish you? So the pleasure you had last night has earned you a caning. Twelve strokes! And I shall use the same cane you used on Carol last night.”

I thought some more. “Since it is to be a punishment, not just an erotic part of our lovemaking, it won’t take place in the bedroom. I shall take you to school, one Saturday afternoon, and I shall strap you over the horse in your study.”

“OK,” said Joan slowly. “That would be fair. That way our relationship would be secure. In fact you would welcome me taking Carol occasionally, since you enjoy caning me so much. And if I don’t want to be caned hard any more, I would simply give up Carol. So its all in my control, really. . . Yes, I like it.”

“In that case,” I replied, “you can consider it settled. Next Saturday we meet in your study at three o’clock in the afternoon. The cane we will put in a prominent place in the study first thing on Monday morning, and you can think about it every time you catch sight of it. By Saturday you will be nervous as hell and anxious to get it over with. Its going to seem a long week for you.”

We went silent as we thought about the week ahead. I was already hard just thinking about it, and when I put a hand on Joan’s breast she came suddenly to life, straddling me and guiding my prick deep inside herself.

Just before I came I heard her say, “But there’s the small matter of you and Annette. There’s a price to pay for that little episode. You fucked Annette rigid last night. And a little bird told me you came in her hands; most undisciplined of you! So I’m taking you round to see Madame. I’ll tell her what you’ve done, and she’ll flog your pretty little arse till you bleed.”

My prick exploded inside her and I pumped myself dry.