Old Acquaintances and New Beginnings

As the car crunched on the gravel carpark, I felt the first signs of nervousness begin to develop. My stomach tightened slightly as I pulled the handbrake of the car up and switched off the engine. I had ten minutes. I took the small piece of card I had been given at the entrance and placed it on the dashboard like a parking ticket. Checking myself in the mirror, I adjusted my tie before stepping out of the car.

I was parked at the site of an old boarding school, just outside a small village in the rural county of North Yorkshire. The site was just forty-five minutes from Leeds, the city I now worked and lived in. It no longer operated as a school, instead it was visited as a tourist attraction by members of the public and hired out for events. Today, it had been hired externally and thus was only open for organisers and attendees. 

I was twenty-eight years old, and after a few too many beers one night, had signed up to a ‘Finishing School for Wayward Twenty-Somethings.’ It was one Saturday a month for six months and was free. Looking down the list of attendees on the fetish website I often frequented, I was quite impressed with the talent. Spanking had always been one of my kinks, and something I was keen to explore more. So, I signed up! 

Eight days later…I was here. Closing the car door with a bang, I pulled down my shorts which had ridden up my leg during the journey and headed for the entrance. I entered through the thick open doors and was met by a rather fierce looking woman.

“Your name, boy,” she said, holding a clipboard.

“J-j-Jamie Matthews” I stammered.

“Matthews. Yes, here you are. Your first visit here?” she said, and I nodded. “Very well. Have you left your phone and other possessions in the car? Your car key please, Matthews,” she said holding out her hand. 

Once I’d given her my car key, I was told to walk down the corridor on the left and queue up silently outside the classroom. I did as I was told. I joined a queue of around ten people who were lined up on one side. They were all dressed similarly to me, in grey school uniform. The boys were asked to wear a dark grey blazer, white shirt and school tie, grey shorts and long grey socks. The girls wore the same blazer, shirt and tie but swapped the shorts for a pleated school shirt that was knee-length. They also wore grey socks. 

After a few minutes of nervous hush, we were shown into the classroom by the same woman who I met at the door. There were around thirty of us, and we all headed single file into the room. We were told to stand behind our desks which were laid out in six rows of five desks. When everyone was in position, we turned to face the front.

“Good morning. I am the Mrs Taylor, the headmistress of this school. You will always address me as Mrs Taylor or Miss. You are here to learn and be taught. Over the next eight hours, you will receive several lessons from myself and my colleagues. No doubt some of you will misbehave and will be punished. Let me be clear that myself and my fellow teachers will punish you in whatever way we feel fit. We expect you to take any punishment we give you with a minimum of fuss. Is that clear?” she said. We all nodded.

As she finished speaking, three more teachers entered the room and stood in a line near the blackboard. When I caught sight of the final one, I felt a shiver run down my back. I knew the man. He was an old teacher of mine, someone who had taught me during my time at secondary school. His name was Mr. Wherity, and he had taught me geography for five years. We didn’t have the best of relationships in school, and he was the one of the teachers I was very glad to see the back of.

The other two teachers were female. One was a similar age to Mrs Taylor, but much skinnier and pale looking. She introduced herself as Miss Phillips. The final one was Miss Small, who looked no older than 25. Despite her name suggesting otherwise, she was probably 6ft, with an hourglass body and sweeping blonde hair. As I looked at her, I could feel my excitement beginning to grow. 

“When you open your desks, you will find lined paper and a pen. You will write two sides on your life so far, what you expect from today, and how you would like to improve yourself. You have one hour to do this, and I expect this to be carried out in silence. Any questions?” she asked. The room stayed deathly silent. “Well get started then.” Said Mrs Taylor, taking our silence as understanding. 

Lifting open the old-fashioned desk, I found a selection of items stored beneath. There was a pad of lined paper, two pens, a pencil, a rubber, and a thirty cm wooden ruler. I lifted out the paper and pen and began to write. I say I began to write, but I spent the first few minutes just thinking about how an earth I’d come to be in the same room as my old geography teacher. 

I finally got writing about ten minutes in and was going well until I felt something hit me on the back of my shoulder. I turned around and found a young woman staring at me. She was around my age, with dyed dark red hair, and a fantastic smile. She nodded down to the floor where I found a screwed-up piece of paper on the floor. I bent down, picked it up and unravelled it. 

You’re hot ;) Let’s hang out at break? 

I found my face flush slightly, and I was just about to turn around when the note was snatched from my hand. I looked up and found Mrs. Taylor standing above me.

“Well, what does this say then?” she said, breaking the silence. I said nothing. “You’re hot with a winking face. Let’s hang out at break,” she continued, reading the note. I heard a few sniggers around the room. “Who wrote this?” she asked.

“I did,” I said, not wishing to get mynew friend into trouble.

“And who was this note for?”

“Nobody.” I said, aware that the whole class were staring at me.

“Don’t go shy now. Clearly you think it’s a good use of your time to write notes in my class. Who was it for?” she continued. I paused for a second and then slowly pointed at the girl behind me.

“I see. Isn’t that nice? Well, I hate to burst your bubble but you won’t be hanging out with anyone at break. You’ll be spending your break writing lines for Mr. Wherity. In fact, you can pick up your stuff and go and see Mr. Wherity now. Explain what you’ve been doing and why you’ll be spending your morning break with him. I’m sure he’ll be most pleased,” she said, handing me the note and pointing at the door. 

Red-faced and ashamed, I took my pen and papers and stood up. I walked towards the door and left the classroom. Mrs Taylor followed me out. She told me where his room was before turning back inside and shutting the door. I walked down the corridor to the end, where I found the room was his name fastened to the door. I knocked twice. 

“Enter,” said a deep voice. I did as I was told. I entered the room and closed the door behind me. It was a smaller classroom than I was in before, with just six desks. There was a large oak desk at one end, with a blackboard behind it. Mr. Wherity was sitting behind the desk reading a newspaper. After a few seconds, he lowered the newspaper and looked across at me.

“What is it, boy,” he said, looking a little annoyed to be disturbed.

“Mrs. Matthews sent me to see you. I was passing notes during her lesson,” I said.

“Have you got the note now?” he asked, and I nodded. He held out his hand, and I passed him the note. I watched him read the scrunched piece of paper and a slight smile form across his face. I knew he was loving every minute of this.

“Very well, boy. Just half an hour into the day and you’re already misbehaving. Might have known you’d be a handful today. Go and stand in the corner with your hands on your head. I’ll deal with you shortly,” he replied, pointing at an empty corner in the room.

I didn’t respond, just left my pen and paper on the edge of his desk, and went over to the corner. Placing my hands on top of my head, I stood in the corner and waited. I could feel my body tensing slightly as I stood there. I hated waiting. Whether it was for something I hated like the dentist, or something I liked like a roller-coaster, I still didn’t like it. Just as my arms were beginning to ache, the silence was broken with Mr. Wherity’s deep voice.

“Come here, boy.” I turned and walked across to the nearest desk where he was stood.

“For your misbehaviour this morning, you will be given six strokes of the cane. In this school, all caning is delivered on the bare bottom. Take down your shorts and pants and bend over this desk,” he said, tapping the desk with his knuckles.

Guessing this was coming, I reached down and began to unbutton my shorts. Sliding down the zipper, I placed my hands around my waistband and pulled down the cotton. Once they were round my ankles, I did the same with my tight white briefs. Quick as I could, feeling a little exposed in front of someone I used to know, I bent across the desk and let my hands hang freely over the side.

I felt a cool breeze run across my cheeks as Mr. Wherity lifted the material of my blazer and my shirt and placed it higher up my back. I felt his fingers gently run across the top of my thighs, spreading my legs further apart. Once he was happy with my position, I felt him move away. A few seconds later, I heard the unmistakable noise of a cane being swung through the air.

Tap. Tap. Tap. THWACK! The cane came down hard across the top of my cheeks. I cried out in pain, not expecting the force of the stroke. I managed to croak out a “One. Thank you, Sir.”

Tap. Tap. THWACK! The second stroke almost as hard as the first came crashing down across the middle of my cheeks. I kept my composure, and it took everything I had not to reach around and grab my burning bottom. He knew how to cane alright!

THWACK! No warning, and the third stroke came down in the same place as the first. I moaned out and could feel the water begin to form around my eyelids. The bastard, I thought, as my arse was on fire. He’s loving every of minute of it, I’m sure.

“Three down, three to go,” he said, walking around to the front of me and taking his time. “This is for your own benefit, boy. You were always a naughty boy, and it doesn’t look like it’s changed over the past eight years,” he continued. Well, that confirms he remembers me then, as I wasn’t 100% sure. Teaching all those boys for so many years it would hard to remember them all, I had realistically considered.

Tap. Tap. Tap. THWACK! The stroke landed across the top of my thighs, and it was the worst one so far.

“F-f-f-four thank you, Sir,” I stammered.

THWACK!

THWACK!

The fifth and sixth stroke landed together, and the element of surprise of this threw me completely. I wailed out as I cheeks burned and stung under the welts.

“Five, thank you, Sir. Six, thank you, Sir.” I said, finally regaining my self-control.

 “Let that be a lesson you won’t forget in a hurry, boy. Stand up and return to the corner. Leave you shorts and pants where they are. Hands on your head and don’t even think about rubbing your bottom,” he said. 

Gingerly, and awkwardly because my shorts were around my ankles, I waddled across to the corner. When I reached it, I took up the same spot as before, hands on my head. This time it felt different, as I felt the tears on my cheeks begin to dry. The nervousness and boredom of waiting was replaced by the humiliation and pain that I was now in. That was my first caning, and it had been harder and more painful than I’d imagined. But I took it, and I was proud of it.

For what felt like an hour, but was more likely to be only fifteen minutes, I stood in that corner and waited. The sting of my bottom had slowly died down and been replaced by a consistent burning. My arms were beginning to ache, and I was desperate to rub my cheeks. The desire would have to wait just that little bit longer I thought. My cock, which had been erect from the start, still jutted out from my body, as excited as ever.

“Pull your pants and shorts up, boy and come over here,” he said, breaking the silence once more. Pleased he saved me the humiliation of facing him half-naked, I pulled them up and walked towards him. He was sitting behind the desk, paper in hand again. He had pulled a chair up to near him and moved his head towards it. I gingerly sat down, wincing as the unforgiving wood contacted my fiery cheeks.

“Have you learned your lesson, boy?” he said, rolling up the paper and placing it on the desk.

“Yes, Sir.” I replied.

“So what won’t you be doing in future?”

“Writing notes in class, Sir.”

“What will you be doing?”

“What I’m told to do, Sir.”

“Let’s hope so.” He replied.

The old school bell rang as he spoke, and I knew that had to be breaktime. At my old school, there was a rule that the teacher dismissed you and not the bell. The lack of movement outside in the corridor suggested it was the same here. We were given a 20-minute break in the morning and afternoon, and were expected to play games in the schoolyard.

“Mrs Taylor has explained to me you won’t be getting a morning break. So instead, I thought we could have a little chat about your form. You stated on it you were bi-curious, boy. Is that correct?” he asked.

“I t-t-think so, Sir,” a little surprised at the question.

“Curiosity in a young man is no bad thing. Although it can get you into a lot of trouble if you’re not careful. What are you curious about?” he asked, sitting back in his chair.

“Men…I guess…Sir,” I replied, almost forgetting my place.

“Do you watch pornographic videos?” he asked.

“Sometimes, Sir.” I replied truthfully.

“What sort of videos?”

“Spanking mostly, Sir.”

“Men being spanked by men?” he said.

“A bit…Sir” I said.

“Is it just spanking in those videos?” he said.

“Sometimes more…at the end, Sir.”

“What happens at the end. When the boy has learned his lesson?” Sir asked and I hesitated for a moment. “Why don’t you show me, boy.” He said, tucking his hands behind his head and ever so slightly gesturing with his hips towards me.

I know what he’s asking me to do. I have no doubt at all that’s he also watched gay spanking videos. Was this his plan all along. I wasn’t sure what to do. I was even more nervous that I had been that morning. I watched enough to know what to do but had never thought I’d have to do it. Especially not this weekend. 

“Would you prefer it if we filled your twenty minutes with non-stop caning, boy?” he asked, a little impatiently.

“No, no, Sir.” I said, knowing my bottom couldn’t take anymore.

I stood up from the chair and walked the two paces across. I knelt, my knees making contact with the stone floor. It was a relief to no longer be sitting down. I reached forward and with a slight shake of the hand took hold of his trousers. I unfastened the button and taking hold of the zipper pulled it down. I reached inside, and got a first feel of his member, hardening with the cotton confines of his briefs. He was wearing black briefs beneath his dark blue suit. I found and took hold of his briefs and gently worked the material down, sliding it beneath his cock.

His cock must have been seven or eight inches erect. It was thick, thicker than my own which I had always thought was generous when it came to girth. I could just about wrap my surprisingly small fingers around the shaft. He pushed his body off the chair slightly, allowing me to slide his trousers and briefs down to his ankles. As I did this, he slid his tie from his head and unbuttoned his shirt. I paused, a little unsure what to do next.

“Kiss the tip,” instructed Sir, feeling my breather. I gently bent down and kissed the top.

“Pull down to foreskin and lick the precum,” he continued. I did as I was told, the salty slimy material against my tongue.

“Keep your teeth out the way and give it a suck. Try and take as much of it as you can,” he said, keeping the momentum up.

I slowly began to slide my mouth up and down on his cock, trying to take more and more in each time. It felt alien in my mouth, but as I began to develop a rhythm it became easier. I could probably fit less half his monster in my mouth, but I kept trying. He began to moan, which spurred me on to pleasure him more.

“Go deeper.” He said, taking the rolled-up newspaper and slapping me on the head with it. I tried to go deeper, breathing through my nose, and sliding my mouth further down. It just kept hitting the back of my throat and I felt like I was going to gag. I slid down and felt his fingers slide through the back of my hair. He held there for a few seconds before allowing me to slide back. He repeated these three or four times, before gradually I began to take more. 

“I’m close, boy. I expect you to swallow every drop or you’ll feel the cane again,” he instructed, slapping my head with his paper again.

 I picked up the pace, which he appreciated, as he moaned deeply. I felt his body tense and knew from my own experience of receiving head he was close. I closed my eyes and felt his cock begin to shudder in my mouth. Thicker, saltier, and slimier than his precum, his cum erupted into my mouth. I began to try and swallow the thick substance, but it just kept coming and coming. Eventually, once I’d swallowed every drop, I slid slowly back up his cock. 

“Lick the head clean,” he said, as I let his softening cock from my mouth. I took a long sweep with my tongue and removed his mess. He stood up and pulled up his pants and trousers before sitting back down.

“Not bad, boy. Several mistakes but not bad for a first-timer.” He said, as the bell rang for a second time that morning. “Saved by the bell. You may as well take a seat as your next class is with me. Right at the front so I can keep an eye on you, I think.” He said.

I stood up and carried the chair I’d been sitting in back to behind the desk on the front row. I slowly took a seat, and watched as he moved to the door to let the rest of the class back in. I turned around to look for the red-haired girl but no sign of her. Returning to face the front, I tried to get comfy in my seat, knowing that my next lesson was only just beginning…