I was eighteen at the time my adventure began with Jean. Jean who originally came from the US was the wife of an older and prominent businessman in our town and was quite a character. I had known her since I could remember.

One evening at a party given at home by my parents she said, “Peter, would you like to see something nice?” I turned around and she flashed her tits at me!

Mama was horrified but I of course thought it was wonderful. Jean was in her late forties with sharp looks, a lovely figure, and perfect skin. At another social gathering that summer she looked ravishing and I got an erection looking at her and she noticed; I think she was impressed!

Not long after that, I met her in town during the school holidays and she took me off to a coffee bar. Over coffee, she told me she was doing a lot of work in their garden and she needed some help and was happy to pay.

I thought at the time there was nothing else to it and immediately accepted Jean's request. She lived within an easy bicycle ride and I guessed she would be good fun to work for. I didn’t know how much fun right then though!

So the next day I cycled over to her place and began work, clearing up rubbish and cutting stuff up small enough to be bagged as rubbish or cut for firewood. We would do two or three hours of work and stop for a coffee on her veranda. The first day passed off normally. But on the second day, in the afternoon, she got around to some direct chat.

She wanted to know about discipline at my all-boys school and asked about caning. She asked if I had ever been caned and very embarrassed, I admitted I had been caned a few times, blushing furiously.

Jean asked why I was embarrassed. I wondered what to say but I think I stammered something about the whole thing being embarrassing because everyone else knew what had happened to you, it was humiliating, etc.

I wasn’t going to let on that a couple of hours later I always had a raging erection and I fantasised about caning a girl as a result!

But Jean knew plenty and gently laughed at me. She said that it was only humiliating because the others knew and if it had been done in secret it would not be humiliating. I think I must have turned bright red from top to toe and of course, she was well aware of that.

Jean said, “You know that your headmaster would not cane you if it wasn’t good for you and now you are going to university it will stop, but you probably still need it.”

I stared at her. I had been thinking a similar thing in that I was in a way going to miss it because it wouldn’t happen at University and I had no idea what to do about it.

“Peter,” she said, “I know that stimulation to the buttocks is a huge turn-on despite the pain. How would you like me to cane you?" I was speechless! She reached out and touched my arm.

“Don’t worry,” Jean went on, “Not today, you don’t have to answer me now. Think about it overnight and tell me tomorrow. I know all about it because I was caned a few times in the past."

I looked at her and generally not being one to hesitate, I took the plunge! I replied, “No, it’s OK, but how do we make sure your husband won’t find out?”

Jean smiled. “Tomorrow he will be off early to a big meeting sixty miles away, he won’t be back until later in the evening, we have all day. Let’s work in the morning and if you like it, I will cane you in the afternoon.”

I rode home on my bicycle in a daze, wondering what the next day would bring.

The next day dawned bright and clear, which I took to be a good omen. I rode back over to her house thinking I might be sore on the way back. We put in a good morning's work in her garden and Jean made sandwiches for lunch. That morning there was no mention of the previous day’s conversation, as if by mutual consent.

By this time I had gotten over my embarrassment because this was quite unlike the experience at school – we were alone, no one else knew, it would be erotic and Jean was a beautiful, sophisticated woman.

After lunch, Jean took my hand and in silence, lead me to a downstairs room. I guessed they used it as a guest room with its own en-suite. It was at the back of the house and had one small window which was double-glazed and looked out over part of the secluded garden.

Jean opened a cupboard and got out two canes. Both were about thirty inches long and one was fairly thin and the other was thicker and looked very like the item used on us at school. I got an instant erection which I know she noticed. This was going to be something else.

“Peter,” she said, “Before we start, I need to discuss matters with you. I hope you will be able to cane me later. I won’t let any man cane me until I have caned him first so I can judge his reaction to a caning.

"If he feels the pain and finds it at least a bit hard to deal with, I am happy because it means he may have empathy with me when I receive his caning.

"But it’s not only that; the man must not be at all aggressive and I need to know about his background which is easy in your case. So if all goes well with your caning, please will you cane me afterwards?”

I was speechless. I had not realised this was coming although I had understood what happened to Jean in her past.

I stammered out something about, “Of course, if that’s what you want,” but I was in a daze.

Jean said, “Please take a shower and get ready, it will be a hard caning, so take a pee, we don’t want an accident. When you have finished, wait in here for me just with a towel around you.”

So saying, she went out closing the door. I did as bidden, took a pee and showered, dried myself and went back into the room, sitting on the bed while I waited for her. In a few moments, she came back dressed in a T-shirt and shorts. She locked the door behind her.

Jean gestured for me to stand up and began, “Now don’t be embarrassed if you react to the presence of a female, it’s quite normal and all it shows is that you are healthy! What position does your Headmaster put you in for a caning?” Jean asked.

I replied, “We get told to bend over and hold on to a rung at the bottom of a chair which gives some support. I usually got caned on my trousers although once he took me to the Gym and caned me over a beam on my gym shorts for a more serious offence.”

Jean said, “OK, how would you feel about kneeling on the bed on your knees and elbows, head down and bottom up?”

“Fine,” I replied, “Whatever you like.”

Jean smiled and said, ”Get up on the bed please.”

I did as I was told, knelt on the bed and tried to hang on to the towel, but she pulled it away. She ran a cool hand over the skin of my bottom and said, “Your Headmaster never caned you too hard, there are no permanent marks.”

“How are you such an expert?” I finally asked because she did seem to know so much about it!

Jean replied, “My husband and I don’t do it because he won’t, but every so often I find someone to ‘play’ with because I do love it so much. I think I told you I was caned in the US by my strict girl's school. But despite that, I realised what a turn-on it was.”

This was way before the internet so Jean must have found it very difficult to find people with whom she could have spanking ‘fun’ and whom she could trust.

Jean went on, “I expect you often get ’six of the best,’ don’t you?”

“That’s right,” I replied, “It’s the norm.”

Jean smacked my bare bum. “Well, you will get more than that from me, but it will be very slow. I won’t give you another stroke until you have recovered your composure from the previous stroke. How fast did your headmaster do it, do you think?”

I thought about it for a moment and guessed it was generally one stroke every ten seconds or so and told her that.

“Right,” Jean said, briskly, “It will be six from the thin cane to start with, if it gets too much for you, call out 'Jones' and I will stop.

“Why ‘Jones’?” I asked.

“It was my maiden name!” Jean replied. I made a mental resolution not to ask her to stop, no matter what.

“Get ready!” Jean said.

I had learned from canings at school not to tense up because it makes it hurt much more, it is best to try to relax. I heard her swish the cane in the air a couple of times, then felt her rest it on my bottom for a few moments. It lifted off my bottom then whack and that familiar white hot sting. I breathed in and out quite slowly, trying not to show any other reaction.

My erection had subsided during the conversation and I had got myself under control, but under the stimulus of the cane, things were stirring. I felt Jean massage the mark on my bum and the pain decreased A LOT – we didn’t get that treatment at school.

“Brave lad,” she said, “You take it very well, are you ready for another one?”

“Yes,” I replied, surprising myself with the steadiness of my voice.

‘Whack’, a real stinger, she did it just as hard as my headmaster! Again I managed not to make much noise but I rocked back and forward a bit on my knees. The cool fingers massaged the new mark and the pain faded quickly.

“Ready?” Jean eventually asked,

“Yes,” I replied, “Would you like me to tell you as soon as I am so you don’t need to ask please?”

“Wow, yes that would be great!” she replied happily.

Jean was enjoying herself. I was wondering if she would get to the end of six strokes before I exploded! So tap-tap ‘whack.’

Jean’s process of massaging the marks didn’t let the pain build in the way it had done at school and it was much easier to handle the caning. The dreadful sting can be accommodated if it is ‘alone’ and not adding to a fire already burning in your bottom.

I resolved to say ’ready’ whilst Jean was still massaging the mark to see if she would be thrilled that I was taking it well, so this time I did so and quickly called out ‘ready’. Also, I thought I would take numbers five and six close together and would call out ready within a very few seconds of the stroke.

Despite the massaging, the pain was building a bit and this was having an effect on my erection which was declining as a result! ‘Whack’, Jean was getting used to it and increasing the force; it hurt.

I handled it OK but I still thought I would let her massage this one but try to take strokes five and six close together by calling out 'ready' as soon as I could bear it after receiving number five.

So I let Jean massage the mark; she was making noises about this brave lad and talking about the red welts swelling on my bum! So as soon as I felt comfortable I called out ‘ready’ and ‘whack,’ another stinger landed low on my rump.

I counted up to six then forced myself to call out ‘ready’ again. I heard her gasp in surprise because she had hardly started to massage me! ‘Whack’ number six. I remained in position and Jean massaged me again. The pain steadily decreased.

Jean rubbed a hand against my cheek and said, “Brave lad; get up and look at your bum in the mirror in the bathroom.”

I got up, stark naked, not caring what she saw and went into the bathroom. Over my shoulder I could see the red welts which were turning purple, Jean was an expert! I touched them and they were hot and swelling up a lot! I was going to be sore for a few days!

I grabbed another towel and went back into the bedroom. Jean said, “Now that you have had six with the thin cane, do you think you could take six more hard ones with this thicker cane?”

I guessed the thicker cane would not sting as badly as the thin one but would produce a deeper, longer-lasting ache. I was a bit apprehensive but I could hardly refuse and got back on the bed. This was going to be bad I thought.

“Jean,” I said, “How about three strokes quickly then massage me before you give me the final three of the set?”

“Alright,” she said, “Remember about ’Jones’!”

I heard the rattle of the thicker cane as she picked it up from the top of the drawer.

Tap-tap ‘whack’. My bum felt as if it had exploded and I gasped quite loudly but stayed in position. The pain was awful, just like it had been at school. No massaging this time! Tap-tap ‘whack’; why did I ever decide on this? My erection had shrivelled under this assault; tap-tap ‘whack’; now I would be massaged!

Jean used both hands on my flaming rump and I appreciated quick relief from the worst of the pain; this massaging worked well! I decided to make sure I was sufficiently composed before I let Jean loose on me again!

Eventually, I called out ‘ready’ and resolved to take it as well as I could. ‘Whack’; I tried not to wriggle about too much and soon 'whack' and the final 'whack'. Finally, it was over, I thought I was cut in half and the pain was pretty bad.

Jean massaged my severely throbbing bum again then she said, “It’s good for you to understand how turned-on I am by giving you a caning.” So saying, Jean took off her T-shirt and shorts and stood there stark naked.

I had never at that time seen a naked, ravishing woman in the flesh and I think I gasped in awe!

“Peter," she said, “Come here and feel the effect it has had on me.”

Jean grabbed my wrist and said, “Stick out your middle finger.”

Jean guided my finger into her vagina which was very wet.

“Feel how wet I am,” Jean said, “That’s evidence of how turned-on I am, it’s good for you to know that.”

Jean went on, “It’s my turn now and you need to cane me. I will show you how to go about it.”

Jean got up on the bed on her knees with her bum up in the air. She said, “Stand to one side of me, whichever side allows you to hold the cane against my bum."

Being right-handed I went to the left side of the bed.

“Which cane should I use?” I asked.

Jean said, “We will start with the thin one and unless I ask, you don’t have to massage the marks between strokes. I only did that for you because it’s such a turn-on for me.”

Jean instructed, “Hold the cane just touching across the middle of my bum. The tip should be just past the crack of my bum and the cane touching both cheeks. If you are too far forward or back it will only touch one cheek. It’s better to stand a bit too far forward.”

I did as I was bidden.

Jean said, “Using your forearm and wrist, swing the cane slowly back and mainly with the wrist, give me a stroke across the middle of my bum where you were aiming. Don’t try too hard yet and DO NOT hit me high up near my tailbone or lower back.”

My heart rate was enormous.

I hesitated. “Jean,” I said, “What if it leaves a mark and your husband sees it”?

Jean looked around and smiled, “He won’t see it, we never do anything these days, it's secret but he is not well enough; please keep that to yourself.”

So now I understood. I was standing in for her husband in more ways than one.

Jean said, “OK give me six strokes and try not to land on the cane in the same spot if possible. If you slip up, don’t worry, I can handle the very intense sting of a doubled-up stroke. Do it about the same way I did it with about ten seconds between strokes.”

I aimed carefully, thinking of what I had seen Jean do out of the corner of my eye. I didn’t lift the cane much but swung it across and flicked it a bit with my wrist. It was hard enough to make a faint noise in the air and landed on her bum with an audible crack.

Jean didn’t flinch or move at all. I counted silently and slowly up to ten then tapped her bum lightly three times to make an aiming point. I gave Jean the second stroke, a bit harder this time but still no reaction.

The first stroke had left a thin faint red line across both cheeks of her bum and after a few seconds, the second stroke produced a thin stripe slightly deeper shade of red; slightly longer with two tram-line marks and it lay an inch or so higher. I waited a bit longer then gave her the third stroke with about the same force as the second one.

A few seconds later Jean said, “Peter, you don’t have to be such a gentleman; I’m a naughty girl and need a hard caning, now please see to it. Do it quite a lot harder please.”

You get some surprises in this life and Jean had just surpassed all of them, including my shock when she had started talking about such personal matters the day before.

However, basic human instincts usually win and my erection was simply raging to the point where it was almost hurting.

I carried on with her caning, giving her the fourth stroke quite a lot harder. Jean gave a little gasp and wriggled about a bit but stayed in place. Somehow I remembered that the fifth and sixth strokes Jean had given me were the harder of the first set of six and resolved to repeat this method.

I waited until Jean had regained her composure and swung the firth stroke across her bum with quite a lot more force. There was a very satisfactory 'crack' as the cane landed and Jean jerked forwards and rather more than wriggled about, saying “Ouch, ouch,” a few times.

She quickly settled and in warning, I tapped her bum a couple of times then landed a real stinger a bit lower down.

Jean collapsed on the bed rubbing her bum. “God that’s wonderful,” she said, “You are going to be a real expert, those who have been caned are always better at giving it than those who have not.”

I reached down and touched her cheek. “I asked, “Jean are you all right, do you want me to rub the marks?”

Jean replied, “Yes please, use two stiff fingers and press a bit hard on them moving slowly along each mark, one at a time.”

The marks were quite warm and the last four were turning into hard ridges. She winced a little when I pressed harder on these; a good example of pain and pleasure.

After a few minutes, Jean said, “Now it’s my turn for six strokes from the thicker cane. I did it to you; I must take it from you. If you can’t take it, don’t give it; that’s one of my rules and I think it’s a good one.”

Jena handed me the thicker cane and lifted herself on her knees with her head and shoulders down exactly as she had been before.

She said, “Now give me six strokes but give all of them quite hard. Allow thirty seconds at least between strokes or until I settle down after reacting each time.”

I did as requested. This thicker cane was roughly the same length as the thin one and I took care to position it correctly before giving Jean the first stroke. I could feel that the cane was heavier but I tried to swing it at about the same speed as I had done with the thin one. The first stroke was rewarded with a gasp from Jean who this time seemed to go stiff, jerking her head up and controlling her breathing.

I gave her what could have been a minute to regain composure. I could see that the mark left by this stroke was thicker and more vivid than the marks left earlier; it was already turning a deep red.

I carried on steadily and after stroke number three Jean said, “Allow me a minute to handle the pain then give me the final three in quick time please.”

I said, “Jean are you all right, it’s not too much for you?” She replied in a slightly shaky voice, “I will be fine; I need a caning like this once in a while to satisfy me, I’m a naughty girl and need to pay for it somehow.”

I carried on, giving her the final three strokes of this set of six with about five seconds between strokes. Being aware of the effect it was having on Jean, I eased off a bit as I thought she was close to her limit. In the end, Jean collapsed on the bed, rubbing frantically at her bum and trying what I thought was an attempt to pull off the caned area.

Jean recovered quickly and sat up. She said, “You bad lad, I haven’t been caned like that for ages. I will be sore for a week. Never mind, canings always make me very aroused.”

Jean got up off the bed. I noticed that the inside of her thighs appeared to be a bit wet.

“Peter,” she said, “Lie down on the bed. It’s time to let you have something very nice. Roll over onto your back and lie down.”

I thought I had better do as I was told.

Jean gently took hold of my rigid penis and said, “You are leaking a bit, go and wash it first.”

I tried not to blush because whilst I had not come, clearly I had been very aroused. I washed my penis in the shower then turned round, to find Jean standing there still stark naked.

“Come on,” she said, “time for you to find out what woman is like; help me shower my caned bum and places first!”

She got into the shower and turned it on, legs apart and held the head behind her so it sprayed over her bum.

“Help me wash my arse,” she said, handing me the soap. I gently made some lather on the cheeks of her bum taking care to cover her well-caned area when Jean said, “Don’t be a prude, please wash my arsehole for me.”

What could I do, I did what she asked of course. Eventually, we got out of the shower and dried. She took me in her arms and kissed me, turning it into what I now know to be a French kiss.

“Peter,” she said, “There are other ways to kiss a lady and make her love it.”

She sat on the side of the bed with her feet on the floor with her legs apart.

“Kiss my pussy,” she said.

Her pubic hair (I realise now) was trimmed. This was entirely new to me and my knowledge of female anatomy was almost non-existent

I kissed her pussy but she reached down and grabbed my hair.

“Peter, I’ve got a special place, let me show you.”

She opened her pussy with her fingers and showed me her clitoris. I had vaguely heard about this before but at the time, I didn’t know much. She explained how it is the centre of sexual pleasure in the female and explained that if I licked and kissed it she would experience a huge pleasure.

So of course, I did as asked and I was rewarded with my first experience of being with a woman having an orgasm!

“Now screw me,” she begged, “I can’t get pregnant, I’ve had a hysterectomy.” (All this was well before HIV).

I was rigid and she guided me inside her and I came in under a minute. After we uncoupled we lay on the bed together in each other's arms. I had never known anything like this. Jean had a massive orgasm and dug her nails into my back.

“You bad lad,” Jean said, “You ought to have a couple more hard strokes to pay for your fun. Go on, bend over again.”

“Only with the thin cane,” I begged.

I got back up on the bed and ‘crack’, ‘crack.’ I don’t think she did it quite so hard. Jean did not massage the marks but got me to lie down on the bed. She got hold of my still-hard penis (it arose under the stimulus of the cane as it usually did) and proceeded to masturbate me. What it is to be young. I soon came again and I realised all my feelings of embarrassment had vanished.

Jean sat on the bed as the aftershocks of masturbation died away she said, “Clean yourself up again and you had better go home, I will wash your bum for you and massage the marks one last time.”

I got back into the shower and Jean insisted on washing my penis, the wicked lady! She rinsed down my sore bum and massaged it while it was still wet. It felt better after the massage.

So I went home, rather unsteadily, on my bike. Jean did her best to make a liaison with me every four to five months and it was always the same, a good caning session then sex. She kept this up until I was about twenty-one when she and her husband moved away from the area.

While I was at University, Jean, who knew where I was (she got my details from my parents who at the time did not know what was going on!) wrote to me and said, she would be in my area staying in a hotel alone and would love to see me. We had a session in her hotel room and clandestine meetings like that went on for the whole of my time at the University.

Somehow or other my Dad figured out something was going on and whilst home one weekend took me to a remote pub and had a little talk with me about not getting caught, keeping my mouth shut etc. I never found out how he knew.

Maybe Jean, who liked a drink or two, when in drink had been a little indiscreet because, at our next meeting, she did ask me if there had been any ‘news’ about our relationship floating down from the home area. (Jean loved telling dirty jokes too).

I did reassure her that my Dad seemed to have guessed about us and would keep his mouth shut and that I had never, ever said a word and had burned her letters to me which I received via my mailbox in college.

On the course I was doing I had access to a means of disposing of small flammable items in the laboratory as long as I was discrete about it.

It died down when I went to work as I was abroad a lot. Jean did stay in touch and we had a rendezvous in the US once when we both happened to be over there.

Jean’s husband eventually died and she re-married very quickly afterwards. She wrote to me and told me that she was getting what she needed (in all areas!) from her new man and thanked me for being such a big help to her when she was ‘starving’!

Happy Days!