I had been a sailing club member since I was thirteen, and I was now seventeen and doing my A-level studies at a local technical college. Joan was the Commodore of the sailing club following the last committee meeting.

Joan had divorced and owned an old traditional keelboat racing yacht with a varnished hull above the waterline and wooden decks. There was an enormous amount of work required to maintain these boats every winter. I had a fourteen-foot fibreglass racing dinghy which needed minimal maintenance.

Joan ran the club strictly, had stopped underage drinking and insisted on excellent behaviour in and around the club. Woe betides anyone who broke the club rules. But she was a senior police officer. I thought Joan was a real hard-arse, and it didn’t bother me. In fact, I approved.

One day she asked me, “I know you can use a blow lamp because you used to burn the paint off your old wooden dinghy every winter. Could you please spare me three to four hours on a Saturday afternoon in helping to carry out the surface preparation of my boat above the waterline before I give it coats of varnish? I would be most grateful.”

Of course, I agreed, and we worked on the boat in a big, dry shed and started it on the next Saturday afternoon early in November. The work made steady progress, and by late February, the hull was almost ready for its first coat of varnish at the next warm spell, which usually happened during March. Joan had brought an electric kettle to the shed and there was a small workshop where we often had a welcome coffee and a chat halfway through the afternoon in the unheated shed.

My mock A level exam loomed. The work preparing for it mentally drained me and Joan must have seen my drawn look. Unless you were one of life’s geniuses, you had to work for your grades. Sixty years ago there was no grade inflation, and the best universities ensured fierce competition for their places in terms of grades from us countless baby boomers.

Joan said, “Peter, do you have to get back for tea today, or can we spend more time?”

I assumed Joan meant time working on the boat. My parents were away at my father’s regimental reunion. It was going to be a big event, as a member of our royalty would be present. They were staying overnight. I’m sure this was because my dad did not want to have to drive back after a skinful with his old comrades in arms. I did not need to be back by a certain time.

“Peter, you are not yourself. You are working well, but I can see the drawn look on your face. What’s wrong?”

“It’s the awful pressure of getting ready for the mock A level exam. We have another six weeks to run in this term because of the late Easter and the mocks are at the end of term. It is almost like a death sentence, and I think this misery will never end. It will end, of course, but it seems such a long way off. If it wasn’t for coming here and working on your boat, I think I would go nuts.”

The exam pressure had driven me way off mental balance, but in those days, you would man up and get on with it. Joan checked the locks on the two large doors at the far end of the shed, and we were alone. She was my height and quite attractive in a butch sort of way. Joan closed the workshop doors and locked them. For the first time, she took me in her arms. I thought at that moment it was just an act of tenderness.

“Peter, this examination pressure is tough on young people because so much of your lives depend on it, but I understand, and I can offer you relief. You need some stimulation. Would you like me to cane you, please? It will have a wonderful effect on you, I assure you.”

At first, I was speechless! “What? We can’t do that!”

Joan turned my head to make me look into her eyes.

“Why not? At about your age, I was in a similar situation and my uncle offered me, and I accepted a stimulus caning. It hurt, of course, but it gave me a changed perspective and that was what I needed. It will hurt you, which is an important part of it, but the stimulus to your system and the sensations a few hours later will be beyond belief.”

“We can do it in comfort at my house. Amanda is away abroad on an exchange visit with her language class at the college, and I am alone there. A sore bottom will take you out of yourself and reset your outlook. All you have to do is to accept it and keep your mouth shut.”

The idea of being caned, possibly bare bottom, by the older and mature Joan was attractive. I had been embarrassed that when I saw her in public a few weeks before, I got an erection and she had noticed. Joan was sophisticated, and would know exactly how to deal with me and would do it erotically. I had never had a fantasy like it, and I could feel my penis stiffening. I could visualise receiving a caning from her.

The thought of the attractive, strict, and authoritative Joan standing over me, brandishing a cane, almost gave me an orgasm on the spot. My earlier erection just looking at her was proof of her attraction to me, so why not take the plunge? No one else would know.

“OK, I agree, and thank you. We need to do more work today, because the hull is not quite ready.”

My pals thought I suffered from a gross excess of focus and had told me so a few times. Whilst I had enormous focus, I had an equally enormous imagination. They recognised my dark moods, but were probably not aware of the breadth of my imagination. My dark mood had lifted already in anticipation of the erotic caning.

“That’s my boy. The idea of it has lifted you already. I can see from your face. You don’t have long to wait for your sore bottom.”

After a little over an hour, we stopped work, turned off the blow lamps and left them on a heat-resistant surface to cool. We swept the floor and bagged the debris into bin liners, pouring some water into each bag to make sure it could not catch fire. After waiting for ten minutes to check everything was ok, we locked up and left. On my bicycle, I made the five-minute ride to her house. She unlocked the rear garden gate and put my bike in the back so no one would see it from the road. We went in through the kitchen door.

“Peter, I will cane you in the back bedroom, which is unoccupied.”

She took me upstairs and showed me the bathroom.

“Get naked, relieve yourself, and wash your bottom and your penis. With a bath towel around you, when ready, go to the back bedroom and wait for me. Take your time.”

I did as I was told. The realisation that I was about to be taken on an unusual journey was sinking in. Joan prepared herself in her en-suite bathroom and came to me wearing a dressing gown, holding two canes.

“Peter, I don’t think you have received a caning before, have you?”

“No, I didn’t get into enough trouble at school and my parents don’t do it. There is nothing like that at the technical college.”

“I want to see how well you receive the cane and the effect it has on you. It’s best to cane the bare bottom, so I can check my aim. An excellent position is for you to stand by the corner of the bed and bend over to get your head and shoulders down as close as possible to the bed. This position tightens the skin of your bottom. Remove the bath towel, drape it over the bed where you are standing, get the rest of it on the floor and stand on it. If you become aroused and ‘drip,’ it will fall on the towel, not the bed or carpet.”

I shyly removed the towel and could no longer hide my erection. I blushed all over.

Joan smiled. “Don’t worry. You are a normal boy. I would be worried if you didn’t have an erection.”

She got hold of my buttocks with both hands and squeezed them hard.

“These are going to be so sore in a few minutes, but another part of you will be as stiff as a caber. Bend over, please, keep your legs straight and try to curve your back downwards to emphasise your bottom.”

I did as I was told. I felt the cane rubbing backwards and forwards across my bare bottom.

“Are you ready, please?”

“Yes.”

Tap-tap ‘crack,’ and I received my first ever cane stroke. There was an instant of numbness and then a line of fire erupted across my bottom. I gasped, but stayed in place.

My penis was throbbing. I looked around and saw that Jean had dropped her dressing gown and was naked. This was the first time I had seen a naked, ravishing lady, and it fulfilled my earlier fantasy as she stood there, brandishing the cane with a smile on her face. She had an impressive figure, but I did not realise how alluring she would look naked. Joan was a natural blonde and her breasts were in excellent shape.

“Well done. You took it well. Ready again?”

“Yes.”

Tap-tap ‘crack,’ and stroke number two struck home. I yelped in pain.

“Well done again.”

Tap-tap ‘crack,’ stroke number three. My bottom was on fire and I was going ‘ow, ow.’ When I looked around, Joan had a hand down at her crotch and was touching something with her fingers. It was then that I understood caning me was a turn-on for her and would lead to sex. I was close to orgasm, despite the pain, which drove everything else out of my mind. I could feel fluid at the end of my penis and I had taken a pee before we started. Joan had been correct in thinking that I might ‘drip.’

“Halfway to six strokes, my brave boy.”

It carried on like this until I had received six strokes. I was so stimulated and I would have had an orgasm had not the pain of each cane stroke temporarily reduced the feeling. I was so turned on by her presence that didn’t feel humiliated or afraid. It was our secret, and I was ‘living a fantasy.’ I stood up, and rubbing my bottom, I could feel the six hot welts as the pain of the impact of the cane decreased. Joan took my head in her hands and kissed me. Then she reached down and took hold of my rigid penis.

The wonderful feeling of sexual arousal enveloped me, mostly because of the expertise and seductiveness of my ‘torturer’. Joan took hold of my penis and massaged my balls, and I almost exploded. My pains were decreasing and the sensation in my bum was so erotic.

“My bum is on fire, but it’s a sensation, not a pain.”

“Six strokes is for little boys. When are you eighteen?

“Next month. Please, can you give me a few more strokes?” I said this as if in a dream! The experience, whilst severely painful, was so erotic I wanted more!

“OK, can you handle six more strokes, please?”

“Yes, I think so,”

“Get back into position.”

I took up position again. The cane went tap-tap on my bum, and a second set of six strokes began. Joan was doing it harder, and the pain at first grew to a crescendo after each stroke. Towards the end of the six strokes, I was ‘floating,’ and the all-enveloping sexual arousal replaced the pain. I guessed that what Joan possibly perceived as a brave performance on my part was an enormous turn-on for her. My heartbeats roared in my ears. My erection had drooped, but as the pain ebbed and the afterglow started, it returned harder than ever.

As I stood up, Joan took my head in her hands again and kissed me. She eased me back onto the bath towel and took hold of my penis. I was about to lose my virginity to her.

“Get comfortable on the bed, Peter.”

My penis was rigid. Of course, I knew how to bring on an orgasm, but Joan was just holding it and doing nothing else. She let go and got on the bed, her knees on each side of me. She eased my erect penis into her warm, wet vagina.

“Don’t worry. I’ve had a hysterectomy and can’t get pregnant.”

This was before we had heard of HIV. Joan was fit and ‘rode’ me. I climaxed in about fifteen seconds, and she could not have taken more than a minute before she followed me. Despite my climax, I remained hard. My semen was dripping out of her and I wondered how much I had produced. Her vagina was in spasm and maintained the wonderful feeling in my still erect penis. We remained coupled for several minutes. Joan leaned forward and kissed me on the lips.

She smiled and said, “Peter, how do you feel now?”

I could not describe it. My penis was still throbbing slightly, and I was still in a state of high arousal. I believe blondes give off a type of scent unlike any other lady and it is highly erotic.

“I’ve known nothing like it and I’m still feeling so sexy,” was how I put it.

“Let me show you more about the female, and you can help me.”

Joan got up and went to her ensuite, where, sitting on the loo, legs wide apart, she took a pee, letting me see everything.

“Peter, this is how I do it.”

After wiping herself with a tissue, she got up, went into the shower, and directed the shower head to her vagina.

“Peter, please soap it for me.”

I recovered from my amazed silence and helped her soap her vagina. I eased a soapy finger up into it.

“Peter, put your finger in a little further and rub the front side of my vagina.”

I felt her vagina grip my finger and Joan moaned in pleasure.

“You found my G spot at your first attempt. You are a clever boy!”

What is this G spot? I had never heard of it, so I asked the question. Joan explained it may be a collection of nerve endings at the front of the vagina. No one knew for certain what it was, but most females had one and could derive enormous pleasure from it.

“Help me dry, and then I will help you wash your penis and bottom in the shower.”

She rolled back my foreskin and washed around the glans of my penis.

“Your ejaculate and stale pee get caught here. It’s important to wash very well under the foreskin and around the base of the glans.”

Then she washed my bottom and anus.

“Peter, you must always wash your ass very well. There’s more to come, and you will see why I say this.”

Joan waited for me to clean and dry myself and then led me back to the bedroom. She lay on her back, legs apart.

“Peter, let me show you something else. Come and meet my little sister.”

She pulled back a little flap of skin above her vagina and this small pink thing, like a peanut, appeared

“Careful how you touch her. She is very sensitive.”

“What is it?” I asked.

“My little sister here is called a clitoris, and it’s my centre of sexual pleasure.”

I had heard of it but didn’t know what it was.

“My best feeling will come if you lick it, kiss it, or best of all, gently nibble it. That’s why I showered just now to make her clean for you. Go on, please.”

Joan had politely instructed me about what she needed, so I leaned over her and licked at it. She moaned in pleasure.

“Peter, please take it between your lips and gently nibble at it.”

I obeyed and gently rolled it about on the tip of my tongue against my teeth. There were moans and gasps of pleasure.

“You naughty boy. What you did was so wonderful. You could have hurt me if you had bitten it, but you got it right. Let me pleasure you in another way. Get on your back.”

Joan this time put her knees to each side of me in line with my neck, with her bottom over my face.

She said, “Kiss my vagina and lick my clitoris while I do something lovely to your penis.”

Of course, I did as requested to feel her take my penis in her mouth. With her mouth and one hand, she worked on it while I pleasured her lady’s parts. So that was why my hygiene mattered so much to her and why I had received instruction about her clitoris!

We climaxed and lay there, shaking with the aftershocks. Joan collapsed on top of me, moaning and shaking gently.

After a few minutes, Joan got up, handed me a cane, and bent over the corner of the bed.

“Six strokes, please. Give them good and hard across the fat part of my bottom. Don’t cane me as high as my tailbone or spine and not on my upper thighs. Please keep the strokes on my bottom and try to hit both cheeks.”

A mature woman asking me to cane her was beyond my imagination, and I could almost not move!

“Joan, no, it’s not right.”

“Peter, you have screwed me, fingered my vagina, and nibbled my clitoris. What’s wrong with me receiving a caning from you? Think of what I have done to you!”

These were valid points, but I was still worried about caning a female. It couldn’t be right. My hesitation was clear to Joan. She stood up and pulled me to her and rubbed my sore bottom.

“A few hours ago, you received your first caning, and it was a hard one. You have had full experience of the female sex. These events must be a tremendous shock to you. I feel partly guilty about what I have done, but after you have caned me, I hope we can have sex again and I will explain a few things to you.”

She kissed me on the lips. “Peter, I have done these things for you. I don’t think anyone else is giving you any worthwhile emotional support?”

How did she know? I hadn’t complained. Yet again, I was speechless.

Joan bent over again. “Peter, I’m ready. Take careful aim and beat me.”

I rested the cane on her bottom, tapped twice, then ‘crack,’ a hard stroke struck home. My aim and been good, and it landed on both cheeks of her bottom, roughly in the middle. She gasped and jerked, but stayed in position.

“Harder, please.”

I tapped her again and did my best to crack home a much harder stroke. The ‘crack’ sound was louder, and Joan let out a yelp. Perhaps I got it right.

“That’s better, but try to do it even harder, please.”

I thought, “If that’s the way you want it,” and swung the cane further back and put more effort into it. The impact forced the cane deeper into the flesh of her buttocks, and I saw the shock ripple across them. Joan yelled out loud after this one. I waited for her to stop squirming and calm herself. When ready, I gave her another very hard stroke. My aim wasn’t perfect, and it landed on top of an earlier stroke. She let out a shriek!

If I was trying for accuracy, I could not deliver such hard strokes. I concentrated on accuracy at a minor expense to force and gave Joan the final two strokes.

At the finish, she slowly stood up and rubbed furiously at her thrashed rump. Her welts were a deep purple, and where they crossed at one point, they had turned a dark blue. They must have hurt like all hell. But whose idea was it?

“You wicked boy. That’s one of the hardest canings I have ever had. I will be sore for a week and the marks are at least ‘three weeks’ ones.”

“Three weeks ones? What’s that?”

“It will take at least three weeks before the bruises fade, possibly longer.”

The sight of Joan jumping and down, breasts in motion and her trimmed bush in front of me was electrifying, and I wanted to screw her again!

I took her in my arms for the first time, kissed her, and then put a hand down and fingered her vagina.

“Get on the bed so I can soothe your sore bottom.” Had I said it in my dreams?

“Peter, that’s more like it. So you don’t lack self confidence!”

Joan lay on the bed, legs apart. I felt like a tiger and entered her soaking vagina with my boner of an erection. Her pussy was in motion, squeezing my penis in a tight grip. The memory of my resulting climax will remain with me forever. Joan clung on to me like a limpet. I knew she wanted me to stay hard inside her for as long as possible. She was whimpering in a mixture of pain and pleasure.

“Your caning was close to my limit, but there is nothing like a younger man for endurance.”

With me still inside her, Joan said, “Peter, I need to explain a few things. Much of this happened because of things I have learned during my life. I was on a police training course a few years back with other Commonwealth police officers. One of them was a charming senior officer from an Asian country. He told me that on his sixteenth birthday, his mother had sent him to his room where he found clean bed clothes and scented soap, etc.”

“His mother told him to shower using the scented soap and wait in his room. He did so, and a few minutes later, there was a knock on the door. It was his mother with a beautiful girl in a lovely gold-threaded Sari.”

“Ranee is here for you tonight, my son. The girl came in and closed the door, locking it behind her.”

“He told me that later, he had found out his mother thought it was time for him to be aware of his own and female sexuality. He was not required to do anything the next day, so there was all night for the two of them.”

“The officer went into minor detail about what had gone on. This included his initiation into sex and female anatomy, and that his mother had left canes in a cupboard. The girl had shown him the joys of erotic corporal punishment. He said it was the norm for upper-crust people in his culture to do that to their sons and it avoided a lot of problems.”

“I almost had an orgasm listening to this, and I thought one day, I must think of a way of initiating a deserving young man into these matters. This is what I have done for you today. Through a series of coincidences, we have made it work. I hope and believe this will be to your benefit.”

“Peter, please, tell me, how do you feel?”

“How I can say? You have taken me way out of myself and I can’t repay. Whilst you were talking to me in the shed, I had this mental image of bending over as you stood there with a cane. My caning happened so soon after I had the fantasy and it was so close to reality, because you were naked in both.”

“You don’t have to. Repayment will be our next session whenever that is. Peter, there is one risk only in what we have done, but it’s a huge one. You must keep your mouth shut. If this got out, it would finish me. But once you are eighteen, it’s legal. We don’t have long to wait.”

“Don’t worry. The embarrassment will be too much to handle if it gets out and think of what it would do to my parents. It’s wonderful that I have stopped thinking about my mock exams, even for a while, and I feel so refreshed. You gave me the gift of yourself and your experience, and you don’t know how grateful I am.”

“We can do it again if we can take good precautions. There are two key areas, which are your parents and my Amanda. We can do it in security only if they are both unaware of events. At the club, we are in good shape because your help every Saturday is common knowledge, and it’s a perfect cover story.”

“My parents are off on holiday for three weeks during late July and into mid-August. I have a holiday job and look after the house and garden in their absence. Will Amanda be away during that time?”

“Yes, she’s off over the summer break to the Cote d’Azur, working for six weeks to improve her language skills. We can meet at least once a week for three weeks, maybe for longer, if you can get away without arousing suspicion! There is no rush, so don’t worry. I keep myself in shape in all areas.”

Joan winked.

“It’s going to be easier to sneak off once A levels and college are over. The long nights mean I can make excuses about seeing my mates, that sort of thing. You will need to get ready for a sore bottom, too.”

“Peter, I think you get a lot out of your fantasies! Let me give you something to help you with your wet dreams while you wait for our next session. Imagine me standing there with a dressage whip in my hand.”

“What’s a dressage whip?”

Joan laughed and said, “Look in the window of that equestrian shop on the road to Anston. There are some on display. If I use on one for those on you, you will think the cane is a feather duster!”

I knew which shop she meant.

“OK. I will look shortly.”

What would the dressage whip feel like? It was excellent fantasy material.

“Does Amanda ever get a sore bum?” I asked. It was a little forward of me.

“No, she doesn’t need it. She is ‘the cat who walks by herself’ and is emotionally ahead of you and has good mental balance, but girls are often like that at her age. You are fine, but blown slightly off course by the tough nature of your maths and science studies, which are infinitely more of a strain than is the world of the arts in which Amanda is engaged. She pleasures herself, which I can tell and I approve. You couldn’t pleasure yourself when I was a girl. Amanda doesn’t need a caning and I wouldn’t want to do it to her.”

It was time to bid Joan a thankful and respectful goodbye. She was right. I could look the world in the eye for the first time in weeks, and it made me wonder why I had let events weigh down so heavily on me. Joan was the first person who offered sympathy and more than just help. There was none of that at home, which was sad.

I was so happy but a little concerned also about my bottom! I wondered what else Joan would teach me!