To say that Mr. Lavender and I didn’t hit it off would be something of an understatement. In this strict all-male environment us boys were referred to by surname and teachers as “Sir”; we stood when they entered the room and sat when we were given permission. Having just turned sixteen I’d frankly had enough and while I still attended classes a paid no heed to the maths lesson or the homework; I had better things to do which mainly revolved around music, idly doodling and sexual fantasies. The thing that annoyed him most was that he knew I was capable but showed no interest in his beloved equations.

I glanced at my watch, three fifteen – thirty more minutes of mind-numbing boredom. A silence gradually permeated into my consciousness; the sound of his voice, the chalk on the board had ceased. I slowly raised my eyes and was met by his icy stare.

“The answer, Jenkins?” The thin metallic sarcasm in his voice cut through the silence.

“I… I um….I don’t know, Sir…”

“No, you don’t know do you because you’ve got more important things to do than pay attention don’t you Jenkins?”

This small cold man was relishing the ritual humiliation and all I could do was stand in silence as my cheeks burned. After another thirty seconds of unblinking silence he sneered:
“Go and explain yourself to the headmaster.”

I stood and walked to the door without a word. It was a relief to be out of that room but a sense of foreboding immediately descended as I went down the three floors of stairs. The walk along the corridor seemed to go on and on as my mind fell into a strange numbness – it felt as if I wasn’t really there and was just observing the scene as it unfolded. I saw my hand rising and then knocking on the panelled door. It opened and then I was inside standing in front of the Headmaster’s desk. Finally, he looked up.

“Name?” he said with an air of indifference.

“Jenkins Sir.”

“And why are you here Jenkins? Spit it out I haven’t got all afternoon.”

“Mr, er… Mr Lavender sent me Sir…”

“Well clearly somebody sent you boy, but why – on what purpose?”

“I…. um…I wasn’t paying attention Sir…” My voice trailed off into silence and I felt like my head was spinning.  The Headmaster looked at me for a while in contemplation but remained silent. Finally, he let out a sigh and then said in a surprisingly quiet voice:

“Take down your trousers…”

I fumbled with the belt then undid the button and pulled down the zip. I pushed them down to my knees and stood there waiting.

“Take them all the way down…”

I obediently did as I was told.

“Now your shorts.”

I hesitated. His voice seemed to be getting quieter and sounded less threatening with each command.

“You shorts,” he repeated softly.

Sliding my thumbs into the elastic I lowered them over my hips and bent forward pulling them all the way down. I stood, my shirt tails the only thing covering my genitals. The air around my balls felt good but I was willing myself not to get lost in the sensation and dreading what would come next.

“Well, it’s hardly a caning offence is it?” he said quietly.

I looked at him, confused.

“And did you do anything to provoke Mr Lavender?” he asked.

“No Sir, I don’t… um, I don’t think so….”

“Lift up your shirt Jenkins – that’s it – all the way up to your chest.”

As I raised it exposing myself to his gaze I saw a faint smile forming on his lips.

“Well, you look like a fit young lad to me, there’s sometimes more to life than maths lessons and exams. Do you like to masturbate Jenkins? Most boys your age do.”

My mind was already numb and couldn’t really process what was happening; all I could do was nod in silence.

“Why don’t you slip that blazer off and unbutton your shirt – it will feel much more comfortable…”

His words were no longer commands but seemed to be encouraging prompts. My penis was already starting to respond to the feeling of being exposed and the familiar tingly sensation was stirring in my balls. I took the blazer off and stood there holding it not knowing what to do. To my utmost surprise, the Headmaster reached forward, took it from my hand, folded it, and then placed it on his desk.

“There’s no need for your tie or any uniform at the moment Jenkins…” he said now sounding almost kind. I undid the school tie and handed it to him, watching again as he neatly folded it and placed it on top of my blazer.

“Keep going…” was all he said this time.

Button by button I undid the white shirt knowing that when the last one was gone I would be standing completely naked in front of him. My cock twitched and I could feel it starting to swell. When I slipped the shirt off my shoulders and handed it to him he had a pleasant smile on his lips and the feeling of being totally naked in front of him was intoxicating sending the blood rushing to my groin making me light-headed. I loved being naked; in my bedroom, out in the woods, other secret places I had found – anywhere I could enjoy myself without the fear of getting caught with my sixteen-year-old erection in my hand – but being naked now in front of an older man, my Headmaster was really strange.

“You’re a fine young lad.” His words filtered through into my heightened consciousness and growing arousal.

“You may as well take your shoes and socks off – there’s no point in keeping your ankles all bound up is there?”

I bent down. Untied the laces, struggled to get them off almost losing my balance; finally slid my trousers and underpants over my ankles and then quickly pulled off my socks.

I stood slowly fully aware of my complete nakedness, my cock now semi-erect pointing forwards towards him. I watched as if the whole scenario was happening in slow-motion. He stood up from his chair. My eyes went from his white-haired, no-longer stern face down over his immaculate dark suit and tie that were cloaked in a long black gown and saw an eight-inch firm erection standing out through his open flies. He'd either been aroused before I entered his office or had been taking secret pleasure in transforming my predicament into his own particular wishes.

Neither of us spoke as we looked at each other, both obviously in a state of arousal.

“It’s perfectly natural for boys like you to play with themselves and masturbate…” he said gently breaking the silence. “And sometimes it’s even nicer if you do it together, providing of course you like and trust one another.”

He walked slowly around the large desk until he was standing very close to me and made no move to cover his enormous erection. I’d seen my classmates in the shower after sports every week for years but I’d never seen an older man or a cock like this. I’m about seven inches but he was at least an inch and half more and so much thicker than anything I’d seen or even knew about. He placed his hands gently on my shoulders and turned me with my back to the desk before guiding me down so I was perched naked on the edge. As I sat his hand drifted down over my chest, across my belly and then lower until he gently wrapped his fingers around my shaft. His hand stayed still as I settled into a comfy position but then began to move very slowly up and down my engorged cock. He raised a finger to his lips in a “Shh” gesture telling me to keep quiet and allow the feeling of what was happening to take control.

I stared down at my erection gently encased in his fingers and watched as he expertly began to massage my arousal. Each slow stroke pulled my foreskin slightly further back, gradually revealing my shiny purple helmet. After several minutes of this, I was moaning deeply, my breathing coming in irregular gasps but he was very skilled and had no intention of bringing me to climax anytime soon. When he finally got my foreskin all the way back leaving my glans completely free he stopped for a moment and looked at it admiringly.

“You have a very nice penis, Jenkins. Close your eyes and I will show you some other ways to enjoy this.”

I obeyed.

I felt his hand release from around my shaft in the darkness behind my eyelids. There was no touch or sensation, just a faint ruffling as he moved. I had no idea what was happening. He made me wait. He knew that the anticipation and suspense would only heighten my sensuality. He was about to initiate me into the deliciously seductive world of sensual abandon.

I felt the varnished wood of the old desk pressing against my buttocks, my hands gripped the edge tightly for support, I was trembling all over, my erect cock standing rigid with it’s swollen purple head now adorned by a clear drop of my pre-ejacular fluid. I waited, trying to take deep breaths.

Then it started. At first the most delicate, light slide of his warm, wet tongue across the very tip, gently licking the single drop of clear viscous fluid into his mouth.

Silence.

“You taste sweet, young man,” he said very quietly.

I didn’t move, I was hardly breathing. My eyes were tightly shut. Waiting. Wondering. Trembling. And so fucking turned on I would have done anything he told me to.

But he remained silent. He made me wait. I don’t know how long passed.

Then it happened. There was no warning, no gentle lead in. One moment I was a trembling naked boy waiting for I didn’t know what but then…

A warm silky wetness engulfed me taking first the head and then most of the shaft inside. It felt exquisite. I let out an uncontrollable guttural moan as he started moving up and down using his tongue to flick and lick each inch of me. As I grew used to the intensity of the sensations I bucked my hips forward pleading for him wordlessly. He happily obliged taking my erection deeper inside with each movement until my entire length was buried in the luxurious warmth of his mouth and throat. I felt his hand close gently around my scrotum and after remaining still for a while the fingers began to slowly manipulate my testicles in time with his lips and tongue. At some point I think I let out a primordial groan of ecstasy and opened my eyes drinking in the sight of my engorged erection hidden inside his mouth.

He knew that I was on the edge of the precipice and would ejaculate very soon and after a few more sucks he raised his head and looked up at me.

“You seem to be enjoying this so let’s make it last a little longer,” and with that he got to his feet. Taking my hand he led me back around the desk, sat in his chair and pulled me down so that I was sitting on his lap, my naked back against his chest. His huge erection was visible below mine. He reached out and pressed a button on the intercom.

“Miss Williams, I have a rather adept pupil with me at the moment – would you mind coming in and giving some assistance…” He didn’t wait for a reply but sat back and whispered in my ear.

“Here’s a little treat for you.”

There was a knock on the door to the adjoining room which he acknowledged with a simple, “Come.”

The young secretary entered and closed the door behind her. She took in the scene immediately and without a word discarded her smart jacket and let it drop to the floor. One by one she undid the buttons of her white blouse revealing the black lacy bra that was wrapped tightly around her magnificent breasts. The blouse fell to the floor followed by the bra. Her hands were now behind her back dealing with the short zip at the back of her skirt. This too fell away and was discarded leaving her in just a pair of spectacles and tiny lace panties. She left both of these items on as her hands first cupped and lifted both breasts and then adjusted so that she could hold each nipple between a finger and thumb. She slowly rolled them, twisting and then gently pulling until they stood out firmly. No-one spoke.

One hand moved down over her flat belly and slid inside the tiny piece of lace that covered her. She moved it in slow determined strokes gently rubbing, gradually parting her secret lips. I felt the Headmaster’s fingers closing around my hard cock but he didn’t move them. She was staring directly at us both, her eyes moving from ours down to our erections and then back to meet our gaze. She rubbed her clitoris watching us knowingly.

“Try not to cum yet,” he whispered to me.

Miss Williams was now swaying slowly, moving her hips with two fingers inside herself. They were still covered by the tiny piece of lace which did little to hide her actions. When she was satisfied with her initial arousal she removed her hand and walked towards the desk. She didn’t stop and continued until she was behind it next to us. She offered me her fingers, placing them directly under my nose so that I inhaled her musky scent and then slid them across my lips before pushing them into my mouth. I sucked on them tasting her cunt juice. She raised her foot, stepped over our legs, and sat on the edge of the desk facing us, her legs wide open. She pulled the slip of lace to one side. Her fingers parted her labia and she sat looking at us both, displaying her inner womanhood with a knowing and hungry grin.

“Which one of those is going to fill me first?” she asked in a curious voice.

I felt the Headmaster’s hands move to my shoulders and push me forward. I stood, mesmerised, my erection inches from her open vagina. I felt the Headmaster’s hand on my naked buttocks pushing me forward and then the secretary’s hand guiding my throbbing cock into her. The Headmaster didn’t remove his hand and instead clenched each of my cheeks in his fingers and began to push, then pull me back and forth until my cock was thrusting in and out of the young woman’s cunt. When we got into a steady rhythm he got up from his chair and stood next to us so he had a clear view of my young erection penetrating her. He was slowly rubbing his fat and rigid penis. Somehow the intensity and bizarre nature of events took hold and I didn’t cum instantly. I wasn’t exactly sexually inexperienced but I hadn’t actually fucked my long-term girlfriend at that point or anyone else so getting my cock in this lovely woman, having already had a very much older man playing with me, was something of a very pleasant surprise.

The young secretary was clearly enjoying what I was doing and was moving her hips in time with my thrusts, letting out small grunts which soon became more abandoned. When I glanced at the Headmaster, he was openly masturbating as he watched right next to me. He had a strange smile on his face and nodded his approval and encouragement. He leaned forward without removing the hand from his cock and whispered:

“When you’re ready to cum wait until the last moment and then take your prick out and shoot it all over her – she will like that.”

That was it. That took me to the point of no return and I felt the churning start in my balls. It grew with each thrust which were now full-on forceful movements slamming my hips forward pushing my engorged erection deep into miss Williams’ very wet and willing cunt. My balls were slapping against her nether regions and finally, I knew that they were going to unleash my sperm no matter what happened. With gritted teeth, I managed three more vigorous thrusts and withdrew just in time. Shot after shot of my thick, creamy semen squirted out. The first landed across her nose and forehead, some in her long dark hair. More fell on her beautiful full breasts and began to slowly run down their sides. The final spurts decorated her belly, a small pool forming in her navel.

When I was finally spent I stood there panting, my whole body tingling. Miss Williams looked down across her body and smiled at me with my semen dribbling down her cheeks. I felt the Headmaster’s hand on my shoulder, he rubbed it gently as if to say “well done” and then I watched as his hand moved down and began to rub and massage my sperm into Miss Williams’ body. He scooped up the drops from her belly and added them to those on her breasts then massaged it in thoroughly. He offered her his hand and she licked it, tasting my ejaculation. He bent forward and licked the globs from her nose and cheeks before giving her his tongue and they kissed, sharing my cum.

After a while, he stood and held out his hand to the young secretary. He pulled her up gently and led her round to the front of the desk.

“Turn around and bend over,” he whispered to her. She didn’t need any more encouragement and bent forward until her voluptuous breasts were pressed against the smooth leather writing pad on the large desk. She raised her head slightly looking up at me unable to see but knowing exactly what the Headmaster wanted. As he held his thick cock against her wet lips she turned her hand and curled a finger beckoning me forward until my still hard cock was in her mouth....