This was like my wildest dream as I had had such a crush on Miss Mason at sixth form college. She was my biology teacher and seemed to enjoy the blushes most of us had when she gave us a few sex lessons.

I hadn’t appreciated the age difference, though, at the time. I was sixteen years old and didn’t connect that she was a trainee teacher as she seemed so authoritative when teaching in class, but today I discovered that she was only three years older than me.

It was an all-boys sixth-form college and most teachers were men so Miss Mason, Hannah, stood out. She was slim with shortish dark hair and normally had her arms covered and wore dark stockings, even in the summer. One time, though, she wore a short-sleeved light blue blouse and had bare legs, and I was smitten.

Now, though, I had finished college and was nineteen years old and met Hannah again quite by chance as we were walking in the same direction close to the shops. We recognised each other immediately, and although I was hesitant, when Hannah smiled at me I suddenly had the courage to approach her and said, as though introducing myself, “Mark Johnson, Miss.”

“Hi, Mark,” she said smiling, and added kindly, “Call me Hannah.”

We got chatting as we walked and she put me at ease, and soon we were chatting about my days at college. Mind you, as we chatted, I could not help but glance at her and saw her dark hair in a bob around her beautiful face, her smile and flashing sexy eyes, her bare shoulders and arms as she was wearing a red vest top and white shorts and had bare legs, which was all so different to the sedate clothes she wore when at college.

Mind you, I noticed that Hannah was also eyeing me and wondered if she thought the same as I did as I was in a dark blue t-shirt and jeans.

I was relaxed very quickly and we spoke about the days at college. I even told her about the time she caught me in the bike shed kissing Emma, from my class, and she gave us both a double detention. I knew that if you got a double detention then partway through you would be called to the headmistress’s study and given four strokes of the cane. Well, neither I nor Emma had ever been caned and that was why we were both concerned.

I went on to explain, “Emma and I were so worried when we got to college on detention day but knew we would be caned. Then you took us both to one side and told us you didn’t give us the detentions and we were so relieved.”

Hannah smiled and obviously remembered the incident. “Mark, I didn’t put your names down on the detention sheet because Emma was one of my best students and I didn’t think she deserved to be caned, but I couldn’t just put your name down, so I let you both off.”

I smiled back at Hannah and said in a surprised tone, “Wow, I didn’t know that. Well, I know Emma didn’t ever want to be caned, but I suppose I was all keyed up to take it and it was even a bit of a let-down when I wasn’t caned.” My voice trailed off.

Hannah smirked and asked, “So, did you want to be caned, Mark?”

I blushed even though I tried not to but just couldn’t prevent myself, because ever since that fateful day when I expected to be caned, I suppose I felt I had missed out on an experience. I had seen others after they had been caned and they had reddened tear-filled eyes and were rubbing their bottoms, but after just a short while they were saying it wasn’t all that bad and were even laughing.

I did tell Hannah about one time when one of the boys in my class, James, had been caned and was starting to boast that it wasn’t that bad. The headmistress came by and heard the gloating sound of his voice and asked in a very stern tone, “Are you telling everyone that being caned is easy, because we can go back to my study and discuss that, boy.”

The look on James’s face turned from smiling to fear in just a split second so we all suspected being caned hurt from his wet eyes but those of us, the vast majority, who had never been caned, tended to be in awe of him when he started to gloat. Now, though, we knew for sure that it hurt.

However, for me the wonderment continued and over the following weeks I found myself masturbating as I imagined being caned. Slightly differently, I imagined being caned by Miss Mason and not the headmistress, but then I had a crush on her so fantasising about the two things together seemed just right.

Hannah listened intently as I explained my fantasies out loud for the first time ever, and, smiling wickedly asked, “Well, Mark, if you still want to be caned, I have a cane at my house which is actually just round the corner.”

I was wide-eyed at the suggestions and wanted to say yes, yes, yes, but held back. I dropped my eyes and knew I was blushing and supposed I wanted Hannah to tell me to come with her.

Hannah must have read my mind because she tapped my hand and said in the same authoritative school mistress’s voice I remembered and loved, “Actually, my lad, I am not asking but telling. I now realise that I should have put just you down for the double detention.”

I looked at Hannah’s stern face as she told me what I had wanted her to, and, whilst I bit my lip as she spoke, once she had finished I just said a submissive, “Yes, Miss.”

Hannah looked surprised, and supposed that she was just play-acting and assumed I would say, ‘No way,’ but when I just agreed she smiled and said, “Okay, then, let’s go to my house now.”

I licked my lips and nodded, thinking how I might just live out my fantasy with the teacher I had had such a crush on, and even thought how, just maybe, we could have sex afterwards, but then as I was still a virgin I supposed that that was just too much to hope for.

As we walked the last little way to her house Hannah chatted happily and reminded me about her biology classes, and in particular the discussions about the female body. I was embarrassed and tended to whisper my responses whilst Hannah seemed happy not to hide the subject that she was discussing from passing ears.

Once we got to her house, she opened the front door and pointed me towards the living room, where I slumped onto the sofa and felt relieved that our conversation would not now be overheard. I started to focus on the caning she was going to give me, though.

Hannah followed me into the living room and sat next to me on the sofa and smiled at me and said, “You seemed uneasy about discussing my body as we were walking.”

I was thrown as I hadn’t realised that she was talking about her body specifically as, after all, I had imagined her naked body so often over the years. “Sorry,” I replied, swallowing uneasily.

Hannah continued, “You need to be more at ease with women, so I think when I cane you, we should both be naked. Do you agree?”

I was again shocked but this time I could feel my penis getting stiff and when I looked down, I saw it was pushing my trousers out.

Clearly Hannah also saw my erection and said, smiling, “I’ll take that as a yes.”

All I could do was nod. I knew Hannah was right that I was easily embarrassed when with girls my own age but always felt more at ease with older women, which was mainly because they were quick to make the decisions, which was what I actually preferred. So, as I thought of Hannah as an older woman rather than my ex-teacher, I started to feel more relaxed. “Okay, Miss,” I replied, still not quite able to ignore she was my teacher just a relatively short time ago.

Hannah smiled again as she stood up and said, “I’ll go first then.”

I was wide-eyed and knew my erection was getting even stiffer, if that was possible, and I could see Hannah glancing at the bulge from time to time. My attention was quickly taken, though, when Hannah pulled her vest top over her head and threw it onto the armchair close by. I was ogle-eyed as I was looking at her light red bra, and as she lowered her arms, I saw her breasts and cleavage. I recalled thinking when at school that Hannah didn’t have large breasts, and I suppose that was confirmed now, but I wasn’t really a boobs kind of guy given my general embarrassment when around girls.

I gasped as Hannah put her arms behind her back and the straps suddenly slid down her arms and she caught them and put the bra on the armchair, so now I saw her bare breasts and I so wanted to kiss her nipples, but dared not move even a muscle.

Next moment Hannah undid her shorts and must have caught her knickers with her thumbs, as I did at home, and suddenly she was stepping out of her knickers and shorts and threw them on top of her other clothes. She then stood in front of me, totally naked, and put her hands on her head in a very sexy pose, and smiled down at me.

“What do you think?” Hannah asked with a smirk.

I only had one word. “Beautiful.”

“That’s good,” Hannah replied, still smiling, and allowed me several seconds looking her up and down.

What a looker, I kept telling myself as I eyed her dark hair mound, and I couldn’t stop ogling, I knew.

Hannah said, as though explaining to a class, “We can’t do this at school, but it would certainly make the biology lessons more interesting, don’t you think?”

I swallowed hard as I took in her beauty, and just nodded my head in agreement.

Hannah continued, still in teaching mode it seemed, “I go to the gym and so have a flat tummy and well-toned arms and legs. Would you fancy me if we met at a party?”

The answer was so obvious to me and I spluttered, “Too right, Miss,” and I again reverted to thinking of Hannah as my teacher and saw her smile at my reaction.

“Your turn,” Hannah then said, sitting back down on the sofa and putting her legs together but not her arms so her breasts remained a focal point of my staring.

I swallowed as I stood up, but reckoned that if Hannah could undress in front of me then I could in front of her, and so I quickly pulled my t-shirt over my head and put it on the other armchair. I didn’t look at Hannah, knowing I hardly had a six-pack, and quickly undid my jeans and pushed them to the floor, remembering my underpants and so yanked them down before stepping out of both items and putting them on the armchair as well. I knew I still had my socks on and so lifted each leg and slipped them off, knowing my penis was wobbling about but didn’t care as Hannah had now parted her legs and was showing off her hair mound and slightly stretched pussy.

My erection stiffened again at the sight of Hannah’s pussy lips, and supposed any man’s would.

Once I was undressed Hannah patted the cushion next to her on the sofa and said, “Sit next to me.”

I swallowed again as I sat down and as I did, Hannah put her arm around my shoulders and edged towards me so that our naked bodies were touching in a way that I had never even come close to before.

Hannah leaned towards me and as she spoke, I smelt her sweet breath as her lips were so close to my face. “Have you ever kissed a woman’s naked breast?” she asked in a very sexy tone.

“No, Miss,” I replied nervously but truthfully. I knew that most nineteen-year-old men had, but I wasn’t one of them.

“Go on then,” Hannah proffered.

I was shell-shocked but was up for it, and so bent down and encircled her nipple with my lips and kissed.

“Ooohh, so nice,” Hannah cooed. After a few moments Hannah added, “Kiss and lick my breast and caress my other breast with your hand.”

I was in seventh heaven as I cupped her breast in one hand, stroking gently with my palm as I kissed and licked and sucked her other breast.

“Yes, yes, that’s sooo good,” Hannah again cooed. “Now go down and kiss my inner thighs,” she said with a sigh.

I quickly did as she asked and, as she sat back and parted her legs, I knelt between them, keeping one breast cupped in my hand whilst kissing her inner thigh. Quickly realising that it was too awkward I let go of her breast and focussed on her thighs, edging towards her hair mound as I heard Hannah gasping erotically and making such encouraging noises that told me to keep working my way up towards her pussy lips. As I got to her hair mound her erotic sounds intensified and her breathing deepened and I found the smell and taste of her sex juice so wonderful. I don’t know why I did, as I had never done anything like this before with any girl, but I was loving every second.

With my face just a whisker from her vagina, I put my fingers on either side of her pussy lips, spread them apart, and buried my tongue as deep as I could inside her lips and was rewarded with Hannah leaning forward, putting her hands on the back of my head, and pressing my head into her. I kept my tongue licking her and suddenly she exploded in what I knew was her orgasm.

Hannah kept my head pressed against her and so even after she had exploded I kept licking her, and loved every second of it. Well, it was far better than being spanked, I reckoned, and wanted to make her cum again.

Next moment, the door flew open but I couldn’t turn around as Hannah still held my head against her very wet and sweetly aromatic pussy lips. However, I heard a woman’s voice say sternly, “Get up, both of you.”

I felt Hannah release my head and I spun around, standing up just as Hannah did. I forgot I was naked, even when I glanced at Hannah and saw that she was, but my focus was on a woman who looked older than my mum, and a girl who I reckoned was younger than me.

As it turned out, I wasn’t far wrong on the ages. The older woman, Margaret Summers, was forty-eight years old and was Hannah’s girlfriend but also the headmistress at the college they both now taught at. What also became clear was that although I always assumed that Hannah was a strict teacher and would want to control any relationship she was in, it was Margaret who was the one in charge, and even regularly spanked Hannah.

The young girl was Ella Carson, who was seventeen years old and was dressed in the school uniform of a green and white check gingham dress with a white belt, and white ankle socks. Ella was a student at the college, and attended Margaret’s house to be tutored by her for teacher training. It turned out that today’s lesson was due to be on discipline in schools, and the local area was one of the first to reintroduce corporal punishment for offending students at all sixth form colleges.

Hannah saw that Margaret was very annoyed with her and tried to explain, “I saw Mark in a cafe and we started chatting and he told me he wanted to be caned so I brought him back here with the sole intention of caning him. I promise, Margaret, us making out just happened and I am so sorry.”

I wasn’t sure what to say as what Hannah said was true. Mind you, I no longer wanted to be caned but would happily give tongue sex to Margaret or Ella.

Margaret gave what Hannah had said some thought before replying, “Tell me, Hannah, what would you expect me to do as I caught you cheating on me?”

Hannah was thrown by the question but, after grimacing, replied in a doleful voice, “I suppose it would earn me a spanking, Margaret.”

“Exactly,” Margaret replied in an authoritative tone.

Margaret then looked at me and said in a thoughtful tone, “Well, if you want to be caned, young man, then you will be.”

I started to explain that I no longer wanted to be caned but Margaret put her finger to her mouth and I stopped.

Margaret seemed pleased with my reaction and continued, “Miss Carson, here, is learning about discipline and I have given her an insight into caning by using a senior cane on a cushion, and it’s good timing so she will use it on you.” She added sternly, “Whilst under her discipline you will address her as Miss Carson and me as Mrs Summers. Understood, Johnson?”

I swallowed hard but rather liked her stern demeanour and even felt my penis hardening. “Yes, Mrs Summers,” I replied, feeling like I was back at college and had to obey whatever the headmistress said, and even addressing Ella, who was younger than me, with respect was a turn-on.

Margaret was good with my reply and, turning to Ella, said, “Go and get the cane from the cupboard, Miss Carson, if you would, please.”

Ella kept a stern look on her face and replied, “Yes, Mrs Summers.”

Margaret watched Ella leave the room and then glared at Hannah and ordered, “Move two of the dining chairs so they are facing each other.”

Hannah replied obediently, “Yes, Margaret.”

I was so taken by watching the still naked Hannah move the chairs and that was such a turn-on for me as well.

A few moments later Ella came back into the room carrying a hook-handled cane, just as I had always imagined it would look. She swished it in front of me and couldn’t stop a slight smile as she looked at my tummy. I looked downwards and saw that she was, in fact, looking at my stiffened penis, and I could feel it stiffening even more as she swished the cane. It was then that it also struck me that I was as naked as Hannah but all that did was make me even stiffer.

Margaret was still in control, of course, and ignored Hannah and me and discussed with Ella what was going to happen. “I think both these naughty students need a hand spanking first and then six strokes of the cane.”

“That sounds exactly right, Mrs Summers,” Ella agreed.

“Let’s sit down, then,” Margaret said and both she and Ella sat on the chairs looking at each other.

Margaret looked at Hannah and then me and ordered, “Get across our laps. Hannah, you will go across my lap, and you, Johnson, get across Miss Carson’s lap.”

I looked down at Ella’s lap and saw that she had scrunched her dress up and so I would be lying across her bare thighs, which, even with the impending pain, I again found so erotic. I saw Ella tap her thigh and that she glared at me, which told me silently to get a move on, and I thought how dominant she was and that got me moving because I thought she might increase my punishment if I faltered, and so I immediately and obediently eased myself downwards and across her lap, catching my fall with my hands on the floor, and then lowered my full weight on to her soft skin.

Once settled I looked sideways and saw Hannah across Margaret’s lap, and even her side view was so sexy with her breasts pointing down towards the floor, remembering that they were the breasts I was sucking and kissing just a few minutes ago and I longed to kiss and suck them again.

Ella got my attention, though, as she rubbed my bottom in circles and I turned my head back towards the floor and, as I did, I saw Ella’s upside-down legs and suddenly had an urge to kiss them and realised that my attention was being transferred to the young lady who was about to spank me. I glanced upwards and saw the backs of Ella’s thighs and although I could not see it, I knew her pussy lips were now only inches from my tongue and imagined giving her tongue sex.

Well, I thought I was going to just be caned but I supposed that I had fantasised about Hannah, Miss Mason, spanking me over the years and so it wasn’t so bad to be experiencing it now, albeit from a younger woman, but that no longer mattered as Ella had now imposed her authority over me and I knew she was very much in charge.

I heard a loud thwacking sound and glanced sideways to see a pained look on Hannah’s face, and when next moment I felt Ella’s first spank I knew that both spankings had started.

I didn’t think the first spanks were so very hard and even glanced towards Hannah and saw that she was also coping well. However, as the spanks continued on alternate bottom cheeks my bottom started to sting, and again, looking sideways, I could see that Hannah was also starting to struggle.

I looked again at the floor and then at the backs of Ella’s legs and saw how her calf muscles tensed as she spanked and then as the spanks continued, I stopped looking at Ella’s legs or Hannah’s face and concentrated on coping with the increasing pain. That pain only intensified as Ella started to spank me several times on the same bottom cheek before spanking the other bottom cheek several times, and it got worse still when Ella spanked the backs of my legs and I felt tears well up in my eyes. I wondered whether Hannah was going to cry as well, but my vision was now blurred and I couldn’t tell, but I did know that it wasn’t just me gasping out loud and so assumed that Hannah was struggling as much as I was.

The spanks suddenly stopped and I heard Mrs Summers order, “Okay, both of you, get up and put your hands on your head.”

I eased myself up and, once standing and without focussing on the instruction given to me, started to rub my stinging bottom. That is, until I saw a very stern-looking Miss Carson next to me and she snapped, “You were told to place your hands on your head, boy,” as she grabbed my arm and twisted me sideways. I knew not to resist even when I saw her pull her arm back and bring it down hard on my bottom, and as I gasped, so she spanked my bottom three times on each bottom cheek.

Miss Carson let go of my arm and again instructed, “Hands on your head, or else, boy.”

I immediately obeyed, thinking that Miss Carson really was a woman who had to be obeyed, and, as I placed my hands on my head, I remembered that she was actually younger than me, but she was the person in charge and I needed to listen and obey her. As I thought that I glanced towards Hannah and saw she already had her hands on her head and so it was both of us who needed to remember just who was in charge of us.

Mrs Summers had turned both chairs around so Hannah and I would be facing each other when bent over, and sure enough the order came, “Right, then, both of you. Bend over and grab the seat of the chair with your legs apart, tummy dropped and head held up high.”

I saw Hannah immediately do as we were told, and because of her dropped tummy and raised head her bottom was really sticking out but as well her breasts were again hanging down and quivered slightly as she settled down, but was so sexy.

Moments later I had turned and bent over and grabbed the chair and knew that my bottom was also sticking out and ready for the cane from the authoritatively superior Ella.

I suddenly felt the cane being rubbed from side to side across my bottom, but not daring to turn my head, I was unable to look at Ella. I could see Hannah in front of me as the cane was rubbed across her bottom and the tense look on her face and knew then that she had been caned before.

I heard Ella say sternly, “Six strokes, boy. If you let go of the chair then you will earn extras, so be very very sure not to let go.”

“Yes, Miss,” I replied obediently and made sure that I grasped hold of the chair even more firmly.

I knew the cane had stopped being rubbed back and forth across my bottom and next moment felt a sharp pain as the cane bit into my bottom. I cried out with the pain but luckily had kept a firm hold of the chair and whilst the pain was the worst I had ever felt, I still stayed bent over, and was pleased with that, but knew the pain would only get worse.

The second stroke landed and it was indeed worse than the first stroke. What helped was the yelp that Hannah made and as I glanced towards her saw her shaking her head and her hair flew across her face, and I was still watching as the third stroke landed on Hannah’s bottom and her head flew back with her eyes tightly closed and her breasts swirled from side to side.

I didn’t have long to savour the sight as the cane landed on my bottom and it was my turn to yelp out loud, although I again managed to stay bent over but raised one leg and bent the other at the knee in what I knew was an admission that I was struggling.

The fourth stroke landed soon afterwards and I again bent one knee and raised the other leg as I yelped with the pain. If I had known the cane hurt so much, I would never have asked Hannah to cane me, nor would I have held the fantasy for so long, but at least there were only two strokes left, I told myself, at least so long as I held on to the chair.

The fifth stroke had me crying out and then hissing in and out through clenched teeth with my eyes tightly shut. How could Ella hurt me so much? I asked myself. However, at least I was on my last stroke.

The sixth and final stroke landed and whilst it hurt so much, I didn’t think I reacted as badly. Was I getting used to being caned? I wondered. I do know I stamped both feet to try to quell the pain but didn’t bend my leg and thought my reaction was better.

Ella instructed, “Get up, Mark. Your punishment is over.”

I was so relieved as I eased myself up and this time looked at Ella with my hands poised to rub my bottom.

Ella smiled and said in an almost friendly tone, “You can rub now.”

I was so relieved as I rubbed furiously and stepped from foot to foot. I glanced across at Hannah and saw she was also rubbing her bottom and dancing and her breasts bounced and again she looked so sexy.

Mrs Summers interrupted my thoughts as she said to Ella, “I am taking Hannah to our bedroom where she will thank me. You decide how to deal with young Mark.”

I was still rubbing my bottom as Mrs Summers took hold of Hannah’s upper arm and led her out of the room. It was then that I realised Hannah had been sobbing because after she was taken out of the room there was definitely only one sobbing sound, which I realised was me.

Ella came and stood in front of me and ordered, “You need to thank me as well, Mark.”

Ella took me by my arm and led me to the sofa, where she sat down, lifting the hem of her school dress above her waist. Once seated, she edged her thumbs into the elastic of her knickers and pushed them down, and off, placing them on the cushion next to her. She sat back and parted her legs and left me in no doubt that I should kneel on the floor between her legs, and sooner than I had imagined I was once again between a woman’s parted legs, but this time the lovely Ella.

“I know you have done this before,” Ella said with a smile.

I nodded and managed a smile of my own as I leaned down and kissed Ella’s soft inner thighs, edging my way up to her pussy. As I got to within licking distance of her pussy, Ella cupped my head in her two hands, stopping me. She sat forward and with her face just an inch from mine asked, “I need a boyfriend for a party tonight. I want you to be that boyfriend, but I will be in charge and you will obey me as though I was your teacher. Understood?”

I swallowed hard as I was already aroused kissing her thighs and had such a stiff penis and loved her madly already. “Yes, Miss,” I gasped and told myself that I was just so lucky. Hannah was taken by Mrs Summers and so wasn’t available, but Ella was, and she was as authoritative as I had imagined Hannah was. Ella, though, was just the woman I was looking for and felt right with.

Ella smiled broadly as she leant back again, ordering, “Carry on, boy,” in a school teacher-ish stern but haughty tone of voice.

I went back to kissing her inner thighs and almost immediately her wet pussy lips, and as I heard her erotic gasps I was already looking forward to going out with, and always obeying my wondrously dominant Miss Carson.