As far as I can remember, I had a very ordinary time at school until that is, I went to College. My Dad had said, "Now you are eighteen, you’ve become a man. Now you’re off to College and away from home for the first time."

Then he decided it was the appropriate moment to give me a lecture on the birds and the bees and girls and boys and sowing my ‘wild oats’ and taking precautions and all that. Trouble is, I had never actually had a ‘proper’ girlfriend and I was still a virgin. Almost unique in my year!

So off I went, to a tiny room in the halls of residence, which became my new home. There were parties and girls everywhere but somehow I wasn’t part of the right scene, so it was all happening around me in a parallel universe. There was another ‘loner’ in my hall nicknamed, ‘Dopey’ Derek, for no apparent reason except he kept himself to himself and didn’t bother anyone else, so I dreaded to think what they called me!

Things weren’t all bad at college; there was Lauren, Miss Gregg, one of our teachers! She was just fabulous, word had it she was twenty nine but who was counting? She was perfectly formed, long blonde hair and short flared skirts, showing off her shapely legs, beautifully toned by high spiked heels. Every boy in the class ogled her every move, looking for a glimpse up her skirt when she sat down, stood up or stooped to pick something up. All of us, with the possible exception of Dopey, had wanked ourselves silly over this vision of loveliness.

Incidentally, the first time I can remember getting myself off was after watching John Wayne spank Maureen O’Hara in McLintock! Ever since then I have fantasised about spanking women, older women in particular; and Miss Gregg was my latest fixation! She had been over my knee more times than I could remember! I had spanked her over her skirts, the seat of her panties and across her pert little bare bottom, until she squealed with pleasure, all in my dreams of course! Still, I had my bi-monthly spanking mags to satisfy my cravings, but one day, hopefully, I would get to spank a pretty little bum for real.

I almost missed it and even now I can’t believe what I saw that day. My lovely Miss Gregg drives a metallic purple convertible, very distinctive, perfectly emphasising her pretty personality and there it was pulled up at the side of the road, in a discreet side street, near the College. It wasn’t that which was unbelievable, it was the sight of Dopey Derek climbing into the passenger seat! Maybe she was just giving him a lift somewhere; completely innocent perhaps, but there was something odd about it. They sped off, leaving me completely bewildered at this turn of events. I had found a little known footpath through a disused quarry so off I went for a long walk, not expecting to see them again.

There it was, parked in a small clearing on the edge of the quarry when I stumbled upon them by accident. They hadn’t seen me, even though I was only yards away; they were far too busy for that. I had a terrific vantage point from halfway up the heavily wooded hillside, looking down into the convertible. My dream woman was still sitting in the driving seat with Derek next to her, only now she was bending over into his lap, unbelievably giving him a blowjob, her blonde head bobbing up and down on his shaft.

I just couldn’t believe it, let alone fathom why a gorgeous woman would be granting that sort of favour to an eighteen year-old student, especially him! Within seconds, she had stopped and was hand massaging his cock, before getting out of the car and walking round to his side and opening the windowless door. Derek got out and incredibly, she bent herself over her car door and lifted her skirt up at the back, spreading her legs wide.

The ‘loner’ was fingering her womanhood, before pulling her panties aside and slipping himself deep inside her, ‘dogging’ her as she bent over with her rear end perched high on top of her magnificent legs, themselves supported by strappy stiletto shoes. The spotty teenager’s hands held her hips as he shagged her to an orgasm and I watched in awe, as he jerked his load. No ‘home alone’ handjob for him; I was green with envy. I had craned forward so far for a better look when I lost my balance and slid down the slope, trying to cling to something to stabilise me but it was no use.

It was hard to tell which one of us was the most surprised, as I slithered to a stop, almost at the side of the car.

“What the Hell are you doing here?” gasped Miss Gregg, as she pulled down her little skirt, then turning to Derek. “Did you put him up to this?”

Neither of us said anything, I was dumbstruck and Derek gave his usual non-committal shrug.

Almost immediately, Miss Gregg gave him a kiss and jumped back into her car, leaving Derek standing there in the clearing with his cock still sticking out and me with my tongue hanging out. He adjusted himself and set off towards his Hall of Residence, leaving me open mouthed and mystified by what I had witnessed. I tried to discuss the event with Derek as we made our way through the quarry but as usual he was of few words and the conversation quickly dried up.

I replayed what I had seen, over and over again in my mind and shot my load twice, in quick succession, still seeing with full clarity the lovely Lauren sucking on his cock.

It took two days before I was instructed to stay behind after class; Miss Gregg sat behind her desk as I waited for her to speak, feeling both excited by what she might say and a little worried she would accuse me of being a 'peeping Tom'.

"I suppose you want the same treatment?" she asked nonchalantly.

I was stunned and once again found myself completely dumbfounded.

I looked down at her, sitting crossed legged with her hands clasped in her lap. She was wearing a lilac jacket and matching short flared skirt, which had ridden up her thighs showing a good portion of her long shapely legs. They were finished off with a pair of delicate high heels made up mostly of slender strips of leather holding them to her small feet, displaying matching nail polished toes. Her words had caused a huge bulge in the front of my trousers impossible to hide.

She looked at my crotch and added, "I thought so. I like young men," her voice was drooling with excitement. "I am a teacher, and I'll teach you a thing or two," she whispered huskily.

She told me to meet her in twenty minutes at the same spot she had picked up Derek. I freshened up quickly and probably overdid the aftershave and made sure I was early!

As we sped away from the pick up point, I marvelled at her figure, her long blonde hair streaking behind her in the slipstream with the car roof down, dark glasses adding to her sexy look and her little skirt right up her legs. My cock was rock hard and bursting to get out of my trousers, when she reached her slim hand across and stroked it for me. Watching her long slender fingers caressing the outline of my manhood through my trousers was almost too much and luckily she needed both hands on the wheel to guide us into the quarry.

The engine had hardly stopped when she was unzipping me and sliding her hand inside to fish me out, her head leaning into my lap. Her lips slowly enveloped the end of my shaft, before swallowing me almost whole; I was blown away by this new experience and not able to fully appreciate her efforts. It was the first time a woman had touched me there and getting a blowjob from the most gorgeous teacher I had ever had, was awesome. I stared down at the back of her blonde head as she bobbed up and down in my lap, then my attention was drawn to her bottom, sticking up on her seat as she was almost in a kneeling position.

Her cute lilac skirt barely covered her fabulous assets and my cock hardened inside her mouth. Cool air surrounded my shaft as she released me and got out of the car coming around to my side, just as she had done for Derek. I got out and waited for her to take up her position bending over the low door of her car. This time her skirt couldn't hide her beautiful twin peaks but to make sure, Lauren's manicured hands appeared behind her and hoisted the little skirt way up over her back fully exposing a pair of crisp, pure white panties with a tiny frilled edge up each side of the vee, tightly stretched across her gorgeous bottom. Before I knew it my hand was smoothing across those panties and instinctively I gave her a good spank across her right cheek.

Her bum was firm but warm and slightly bouncy beneath my palm and I couldn't believe what I just did. I had dreamt about it for years and now I had finally spanked my hand across a girl's bottom. Lauren gave me a backward glance that had a mixed expression of surprise, pain and, dare I even think it, anticipation! She turned back with her head down so I gave her another whack on the other cheek bringing her up onto the tips of her toes and raising her fabulous rear end towards me.

"Spank me harder," she husked.

'SLAPP! … SLAPP!' My hand swatted the seat of her panties in exactly the same place and Lauren let out a low moan.

'SLAPP! … SLAPP!' Her moan became louder and suddenly her hands appeared, rubbing both cheeks lightly. I thought that would be it, but she hooked her fingers into the elastic waistband and tugged her panties down to just below her rounded cheeks. My eyes were on stalks as I ogled her derriere, now a pinkish-red from my hand, the entrance to her 'secret' pouting from the top of her long legs, still snug against the crotch of her inside-out panties.

'SPATT! … SPATT!' The staccato sound of my hand against her bare bottom was everything I had imagined it to be, the feel of her firm but quivering cheeks against my hand sexier than I could ever have hoped for.

'SPATT! … SPATT!' She turned again and her sultry look told me she was actually enjoying it. Her pretty orbs wiggled from side to side slightly. She was willing me on!

I set about her with renewed confidence and raised her to a husky squeal after each spank.

My cock was at bursting as she danced beneath the flat of my hand and I knew what I had to do next. It was as if she sensed it, her hand reaching from behind her to guide my rod into her moist opening. This was my first time fucking a woman and it felt out of this world. My virgin cock slid deep into her and I felt her pussy muscles tighten around it but didn't last long enough and I pumped my load deep into her in three or four trembling jerks.

She stood up and turned to face me, she was only shoulder height on me. "A bit quick, young man," she rebuked. "Was that your first time?"

I gave an embarrassed nod.

"That was a first for me too," she husked. I looked at her quizzically. "The first time I have been spanked by a pupil," she clarified.

Again I felt embarrassed, "Sorry," was all I could muster.

"Don't be," she whispered. "I might let you do that again, if you are a good boy!"

Words still failed me.

"Would you like to spank me again?" she queried.

"Yes… Yes please," I corrected.

"Do you think you can handle me?" She asked. Her hand encircled my spent shaft as she spoke bringing me back to full attention.

"Can you handle me as well as I can handle you?" She asked again.

"I'll try, Miss," I said hoarsely. My cock was as hard as iron again.

"You will do better than that," she said massaging me firmly. "Next time I want you to CANE ME. Hard! Understand?"

"Yes, Miss," I whispered, delivering another load of sticky cream into her hand.

It had been almost a week since that encounter and she just behaved as normal, not even the slightest acknowledgement of that glorious session in the quarry. As the class filed out of the room she suddenly beckoned me to her desk and gave me a slip of paper. "That is where I live; I will expect you at eight. Understood?"

I nodded, smiled, almost shrieked with delight then nearly came in my pants!

It was a little before eight when I arrived. My mind was in overdrive, imagining every possible scenario, hands trembling at the thought of my teacher allowing me to master her. Even so, I wasn't prepared for the sight that met me as she answered the door!

Lauren was in full school uniform and looking every inch like a real schoolgirl. This woman had become fourteen again wearing a maroon blazer with white blouse outside her short grey pleated skirt and loosely knotted school tie. Her legs were bare, except for white knee high socks and black buckled shoes; her long blonde hair had been done in bunches topped off with a straw boater with a maroon ribbon around it.

"Hello, Sir," she greeted. I was both bemused and aroused at her addressing me as 'Sir' in a very little girl voice.

"Hello…" I coughed to deepen my voice, "Hello Lauren," I said getting into the spirit of the role-play.

"I fetched your cane, Sir," she squeaked. "I put it on the table in there." She led the way into a large room. The long thin rattan lay on the dining table.

My cock throbbed with excitement and I was eager to get into the part. "Right young lady, you know what's going to happen?"

"Yes Sir." She answered. "You're going to give me eighteen strokes across my bottom for being naughty with boys." She smiled ruefully, cleverly giving me my orders whilst maintaining the act.

I picked up the cane and swished it through the air. I couldn't believe she wanted me to stroke her eighteen times with it. Surely she wouldn't be able to stand it, would she? How hard do I give it to her? I was unsure of my situation.

She must have read my mind. "You said you would cane me hard, Sir. I know I deserve it," she added, giving her hips a slight swing with her hands contritely behind her back, her little skirt swayed from side to side.

She was so sexy. “You won’t be sitting down tonight my girl,” I warned, “Now bend over and touch your toes,” I ordered. “I'll warm you across your skirt first.”

She obeyed instantly, bending over and stretching her arms out in front of her, reaching for the toes of her buckled shoes. Her school skirt rode up a little at the back but it was much longer than the ones she wore normally and still covered her panties. Her legs were straight and her head bowed low, surprisingly the boater stayed on the top of her head even though the bunches in her hair conformed to gravity and hung limply towards the carpet. I laid the cane across the seat of her skirt and measured my stroke.

'SWISH .. SWATT!' The thin stick whistled through the air and cut a furrow across the pleats in her skirt. "Ooooowww!" she supplied in response.

'SWISH .. SWATT!' Again the thin grey material creased along the line of the cane. "Ooooowww!" she squealed again.

'SWISH .. SWATT!' She remained bending but her bottom wriggled from side to side.

'SWISH .. SWATT!' "Aaaaahhh!" she said softly. 'My God' I thought, she really is enjoying this.

'SWISH .. SWATT!' I was getting in my stride now and that was a good stroke, connecting with both her cheeks at the same instant. "Aaaahh aaaarrrhhh!" she responded as the air was sucked from her lungs.

'SWISH .. SWATT!' That one arrived before she had time to recover and she leapt to her feet, both hands rubbing at the rear of her skirt, hopping from one foot to the other.

My cock was at full attention and I was really living my fantasy, "Touch your toes, my girl. That's only six, you have twelve more to go."

She flashed me the look of a woman who had relinquished all control over her fate and was now merely a girl at the mercy of her master. With renewed confidence, I placed the cane in the middle of her back and forced her to bend over. She surprised me again by bending and lifting the rear hem of her skirt right up to expose a pair of crisp white school knickers. She secured her skirt in the waistband and reached back to her toes.

'SWISH .. SWATTT!' the cane announced on reaching the seat of her knickers.

"Ooooowww!" she responded huskily.

'SWISH .. SWATTT!' A red line from the first one appeared from beneath each side of her knickers where it had connected with bare bottom. The first six strokes had left a red background, with most of the sting having been absorbed by her skirt.

"Ooooowww!" she said again.

'SWISH .. SWATTT!' Her bottom wavered beneath my cane.

"Aaarrrrrhhh … ooowww!" Lauren was beginning to get the message.

'SWISH .. SWATTT!'

"Yeeeooowwwcccch!" She squealed, jumping to her feet, with both hands clamped to her well striped behind.

She was no longer my teacher. I was the teacher and she, merely a schoolgirl dancing on the end of my cane. It was time to be strict with her. "Touch your toes, girl," I barked, my free hand on the back of her neck and forcing her back down. “I won’t tell you again.” She looked at me with a mixture of pleading and pleasure as she resumed her position with her bottom high in the air. I pushed her skirt a little further up and tapped the thin rod against her seat.

'SWISH .. SWATTT!' I had my hand on the small of her back to keep her in position.

"Yeeeooowww! … Ooooooowwwcccch!" she squealed but remained in position, her slender fingers stretching to the tips of her toes.

The cane whistled through the air again before connecting with the tightly stretched thin cotton of her school knickers.

"Yeeeooowwwcccch!" She bounded to her feet, hands up the back of her skirt and hopping from one foot to the other. Lauren turned to face me, her sultry look displaying a multitude of expressions from pain to excitement to surprise to expectation of the final six strokes.

"Wow," she offered, still rubbing furiously. "You certainly do know how to handle that,” eyeing the rattan in my hand. “Are you sure you haven't caned a woman before?"

"First time for me," I answered feeling empowered and suddenly very dominant over this pretty woman. "Now I am your teacher and you are my pupil," I said sternly. "I am going to cane your bare bottom for the final six and you will remain touching your toes throughout, is that understood?"

She nodded meekly; looking incredibly cute with the straw boater still perched on top of her head. I was in control and I could see she loved it!

"If you stand up before I have finished I will spank you over my knee. Now pull down your knickers and bend over," I commanded.

She looked at me, with a mock plea for mercy on her face, before hoisting up her skirt and tugging her knickers down to her knees. I flexed the cane between my hands giving her a demonstration of its suppleness, the massive bulge in my trousers demonstrating my obvious arousal. Lauren noticed it and gave me a knowing smile before bending over in front of me and raising her skirt to display her bright red orbs striped with the parallel lines from the cane on her high spots.

'SWISH … SPATTT!' The cane sang a different tune as it creased Lauren's bare bottom, and so did she. The squeal that left her lips was ear splitting.

'SWISH … SPATTT!' A new deep red line appeared just beneath the previous one and suddenly a pair of hands with long manicured fingers clenched her burning globes. She was careful not to stand up. I gently tapped her fingers with the cane and she quickly resumed contact with her buckled shoes.

'SWISH … SPATTT!' This time she couldn't stay down and reared up with her hands up the back of her cascading skirt.

"Three more and then I'll put you over my knee my girl," I informed her.

She gave me a backward glance and bent over, skirt up and reaching to her toes. My cock was at bursting point, aching to be released and jacked off. I noticed that her knickers had slid to the floor pooling around her ankles.

The next stroke revisited a previous cut and she winced and heaved her little bottom from side to side but she didn’t tell me to stop.

'SWISH … SPATTT!' Now she was sobbing gently between squeals but still bending, willing me to finish her off.

The last stroke brought her back up, hands behind her, fanning the flames on her derriere, her hat now a little off centre, her face flushed and coy, knickers still around her feet.

She shuffled as if in manacles as I led her the short distance to the table, sitting on its corner with one foot to the floor I tilted her across my left knee. She was much shorter than me in her flat shoes and her slim figure didn't weigh very much so she was easy to upend. I lifted back the flap of her blazer and hoisted her skirt way up to reveal the criss-crossed pattern I had put across her and placed my hand on her roasted cheeks. Her little bottom was changing from beetroot red to a sort of red-purple but she needed a spanking and that was what she was going to get.

'SMACK … SMACK … SMACK … SMACK!' My hand swatted each cheek in turn and her legs swung into action behind her, a forlorn moan following each spank.

'SMACK … SMACK … SMACK … SMACK!' I could feel my cock swelling beneath her weight as she wriggled against the inside of my thigh.

'SMACK … SMACK … SMACK … SMACK!' I felt I had spanked her enough and helped her back to her feet; her hat now even more lopsided.

She didn't speak but caressed her rear for a few seconds and then sank to her knees, fishing out my manhood, which lunged desperately towards her. I looked down at this tiny woman dressed perfectly like a school head-girl in her boater and uniform, her head now bouncing back and forth into my groin as she swallowed me deep and sucked me for all she was worth. It wasn't long before I shot my load and I cursed for not saving myself to fuck her but she didn’t seem disappointed and swallowed everything I had given her. I left her to apply plenty of moisturising cream to her blazing bottom!

It was life as usual from the very next day and now almost three weeks later it seemed I had sampled Miss Gregg for the last time. Word had got around that she was leaving the College at the end of this term in a few days time so that would be the end of a fantastic experience.

"My place at eight tonight," she whispered, as I left the classroom. "And bring something leather to use on me," she insisted. I left the room with a hard on like a broom handle.

My encounter with Miss Gregg continues very shortly...