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Stories From Boarding School Part 1

"Pain and pleasure"

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You'll have heard many tales of the goings-on at English boarding schools. I'm here to tell you there's a lot of truth to those tales. I went to an all-male boarding school many years ago. It was okay most of the time, but life got a lot more interesting when I turned sixteen, and moved up to the Senior House, a separate boarding house for the older three years of school life, where 100 hormone-drenched teenagers lived in a world of locker rooms, communal showers, and dormitories. As well as the dormitories, there were four single 'study bedrooms' in the attic, once servants' rooms, for this was an old house. These rooms were occupied by school prefects, older boys in their last year of school who were supposed to impose some sort of order on the rest of us.

The possibilities for erotic discovery were endless, and I thought you might like to hear my own 'growing up' story.

This is part one, and I might have called it The Awakening; you'll see why. This all happened not long after my sixteenth birthday and my move to the world of the Senior House, and a few weeks before the end of the summer term.

By way of background, the school has a simple system of discipline. If anything happened that shouldn't have, the oldest boy present took the punishment. In my case one afternoon I happened on a couple of boys fighting and making a mess, knocking over a chair and breaking a lamp. I stopped to pick up the chair, and at that moment the Housemaster came into view. It took moments to discover I was the oldest of the three (by two weeks!). The other boys got sent to do the washing up, I was told to expect to hear from the headmaster for my punishment as since I was the oldest in the room it fell to me to be disciplined.

Well, that was that and I was beginning to think maybe nothing would come of it when...

I was in the shower one evening, idly admiring the way bubbles of soapy water were cascading over the taut buttocks of my sixteen-year-old companions when I heard my name called. It was one of the prefects, a good-looking eighteen-year-old who would be leaving school in a few weeks. If I had to have someone looking for me, I was happy it was him. He'd always been friendly which is more than I can say for some! I never knew him by any other name than his surname, Roberts.

He told me to dry off and get in my pyjamas as he'd been sent to take me to the headmaster's study. I asked him if I shouldn't get properly dressed, he said that wasn't necessary, and he had an odd expression on his face for a moment.

As we walked along the corridor, me now in pyjamas and dressing gown, he said, quietly, "A word of advice. Admit whatever it is, and don't argue. If you protest at all he'll just make it twice as hard."

When we got there, he knocked on the door and we went in I was surprised Roberts came into the room, it seemed he was there to witness what came next.

I was told to hand my dressing gown to Roberts, to loosen the drawstring on my pyjama pants, and stand facing a plain chair. As I stood there my pyjamas dropped to the floor leaving my ass barely covered by my pyjama jacket. I was told I was guilty (!) of damaging school property and did I have anything to say? Taking Robert's advice, I apologized for my errors, "I'm very sorry sir."

I was told to bend over the chair, holding onto the seat - of course, my jacket fell about my shoulders, and I was naked from ankles to armpits.

I could hear movement behind me, a long pause, a sharp intake of breath and a swish of the cane. Fuck! A searing burning pain flared over my butt cheeks, a pain that roared and penetrated, pain beyond anything I'd ever felt. I gasped, clamped my mouth to hold it in, gripped the chair tight - Crack! Oh Fuck, this hurt, and the bastard was waiting a good while between strokes to give me the full impact.

Again and again, the cane slashed into my bare flesh, sending a firestorm of pain through my ass. After five strokes he paused, then came a bigger grunt of effort and the final shocking impact, that had me gasping, barely containing myself, the last stroke low down on my buttocks and perilously close to my exposed balls, making me writhe and moan with the pain.

I managed to stand, pulling my pants up and flinching as the fabric rubbed over my ravaged butt. Roberts silently handed me my dressing gown and I just about made it outside the room and staggered to a stop.

Roberts, of course, as a prefect was one of the privileged with one of the study-bedrooms on the top floor, and after he waited a few minutes for me to catch my breath and get some control over myself he suggested we go there while I recover. He said he had some lotion that would help if I'd like to try it. I sure wasn't ready to go back to the dorm, and all the questions I'd get so I was happy to go along with the idea.

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When we got to his room he was careful to check no one was around; we slipped inside and I heard a bolt slide home. I guess this would have felt weird, but I was so focused on my ravished ass that all I cared about was being somewhere quiet for a bit.

He reached out and I again shrugged out of my dressing gown, which he hung on a hook. "Let's see how bad it is," he said, in a calming voice that I was happy to trust. I leaned over his desk and yet again slipped my pants to the floor. There was a mirror opposite, and a glance over my shoulder shocked me - six bright red raised wheals, evenly spaced from the top of my crack almost to my balls. I sighed, closed my eyes and tried to relax and let the pain subside.

Being naked with other guys was nothing new at school - it was routine, but there was an unusual tension in the air, especially when he knelt down and gently lifted my right leg out of my pyjama pants. "You'll be more comfortable with your legs further apart," was all he said.

He came up behind me with a bottle of some sort of lotion, and the next I knew he was gently spreading it over my welts. It did seem to help and feeling his firm hands on my ass certainly was a distraction from the throbbing pain. He smoothed the lotion gently over my swollen butt cheeks, and without a change of pace or pressure slid his hands down to my thighs, massaging and squeezing, his hands roaming from mid-thigh to lower butt and up to my hips.

By some instinct I found myself bending over, spreading my legs and giving him open access to my inner thighs. His hands slid upwards and brushed my balls, just a light touch as his thumbs smoothly stroked upwards into my crack. From nowhere I felt my cock start to stiffen and the same instinct had me spread even wider, offering him my ass while I found myself moaning with pleasure until I realised moments later that my cock was rock hard, my balls tight and aching. I stammered an apology but he just kept stroking my thighs and teasing my ass crack and talking softly about how he enjoyed my body and hated to see it abused.

What he did next drove all thought out of my mind, and almost made me forget my throbbing ass. He leaned forward, reached around me with his lotion-slick hand and took hold of my cock, and at the same moment with his other hand circled my anus, almost forcing his thumb inside. I gasped, driven almost instantly to the edge of orgasm, while he stroked my swollen cock and assaulted my hole. I could feel the hot shaft of his erection pressed against my thigh through his pants. His breath was ragged in my ear, his hands hot on my body, and I slipped into oblivion.

The whole focus of my mind was on my ass, as he ran his wet thumb round and over my tight bud it felt like I was melting, the sensations so powerful and so new. I'd been masturbating for ages, but the pleasures of that were nothing compared to what I felt that night. I just wanted it to last forever, but inevitably I felt my balls suddenly tighten and I lost my mind, my body convulsed and stream after stream of cum sprayed from my cock, and the room suddenly filled with the sharp smell of my semen.

I leant over his desk, panting, feeling ashamed but elated, embarrassed by my wanton display, afraid of what Roberts would say. But he wasn't quite done with me. He calmly fetched a towel, dropped to his knees and lay it over the white pool on the floor. He reached again for my still engorged cock and astonished me again by slipping it into the wet cave of his mouth, gently sucking the last drops of cum from the tip.

He stood then and told me he hoped I'd enjoyed some relief from the beating. I almost said 'what beating', so much had happened since my session in the headmaster's study.

"I wondered," he said seemingly from nowhere, "how your Algebra was going?"

"Badly," I managed after a moment.

"Hmmm," he murmured, "I think I could fit in some tuition here in my room, say Sundays after lunch. You'll need some fresh ointment on your ass anyway."

And so it was I spent an hour in his room every Sunday until the end of term, during which I learnt many things, but no algebra.

I learnt the feeling of ropes of hot cum sprayed on my back and ass.

I learnt to stroke and lick a guy's erect cock and suck his balls.

I learnt the pleasure of two lubed fingers deep in my butt, and the intensity of an orgasm at the same time.

I learnt how having my nipples sucked sent a spasm of pleasure to my balls.

And then it was the end of term, we all scattered to our homes, and I never met Roberts again.

Six long weeks before I would be back enjoying a communal shower and eyeing up the naked young bodies around me.

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Written by Fox1725
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