School is Hard for Headteacher

Emma and I had met nearly a year ago. I'm in my mid 40s and was in a bar finishing a beer after my work colleagues, all teachers, had left. Emma walked in with a couple of girlfriends and I could see she wasn't entirely sober. As she went to sit down she caught me looking at her and instead of glancing away I held her gaze, expecting her to look away dismissively. She was after all anywhere, between 18 and 25 and half my age. Though I new I really shouldn't be looking at a girl that could have been the age of my daughter, I couldn't help it as the beers had dulled my sense of propriety.

She was so incredibly beautiful and sexy. She was slim, Asian - possibly Chinese - with short bobbed black hair, medium sized breasts and long legs. Her eyes were bluey green. She turned away and I finished my beer and went to the toilets. As I was coming along the corridor back from the toilets the girl was walking towards me, I smiled at her and before I knew what was really happening she had planted a kiss square on my lips.

I won't go through the subsequent period after that first meeting, other than to say Emma, who turned out to be 22, entered into what can only be described as a totally wild, filthy, sexual relationship with me. I'm not married, but as a Headteacher of a local private girls school I had to conduct the relationship, with this much younger girl than me, with some secrecy to avoid opprobrium from the parents and staff; let alone the pupils.

Emma was completely uninhibited, seemed to have no fear of embarrassment and had the most inventive mind regarding sex. We enjoyed sex in every way and in nearly any situation: In bed; on the kitchen table; in cars; fields; theatre seats; restaurant toilets and friends bedrooms and gardens. She loved anal, rimming both ways, toys and mild BDSM. She could be dominate or sub. I spent an inordinate amount time thinking about what I wanted to do to her and she seemed to spend all of her time suggesting or doing filthy things with me. We particularly liked to indulge in role-play: boss/secretary; me and her best friend, etc.

I was in my office one day after lunch and some of the upper-sixth (grade 12 in US) were playing rounders outside in the playing field. God some of them were gorgeous and I'd spent some time thinking how nice it would be to get one or two of them bent over my desk for a bit of corporal punishment and mutual pleasure. I absolutely new this was a quick way to end my career and had never been really tempted to act on these thoughts.

An idea - a crazy, dangerous idea - entered my head.

I knew Emma was at home and rang her. " I'm feeling ridiculously horny and want to do a role-play! Would you still be able to fit into your old school uniform? I want you to be an 18 year old schoolgirl that becomes more and more suggestive with her teacher, me, and seduces him into the most depraved acts possible."

Emma replies, "Oh my god yes a student teacher role-play. I think that's is probably the naughtiest thing you have ever suggested, and was wondering when you would get round to it. I actually do still have my old school uniform tucked away in the back of the wardrobe, I'll be wearing it when you come home"

"No. I want you here now, wearing it!" I urged.

"What, me walking into your office with my pleated skirt way too short and my white blouse unbuttoned just enough to be dangerous"? She laughs. "You are fucking mad".

"Yes I do! But make sure you are wearing a long coat when you get to the school reception, so as to not raise any eyebrows or awkward questions!"

"God the thought of being one of your naughty schoolgirls is really making me quite excited. I'll get changed and come to your office right now!"

Twenty minutes later... a knock on the door. Emma enters and immediately takes off her coat throws it on the sofa.

"Excuse me Sir. I am so sorry to enter you office without making an appointment, but I was having such a hard time focusing on my homework last night. I think I might need some private tutoring to really understand the material. Is this a bad time?"

Emma radiates a sort of sexual energy anyway, but now there was something irresistible about her. She stood in front of me in a typical school uniform of tartan skirt, white blouse, short socks and sensible shoes, not dissimilar to the uniform the pupils wore at my school. God what a dream (or nightmare!). She could almost be one of my own students, as she still looked so young. I could see she was not wearing a bra and her nipples were clearly visible under the thin polyester. I try and maintain composure and play along.

"No, No its fine. Come in and tell me what's troubling you".

She sits in the chair on the other side of my desk with her legs slightly apart. The chair is a couple of feet from the desk and her skirt is too short. I can just see a glimpse of white panties.

"Well Sir it's not really the homework, it's that I know you have been stealing surreptitious looks at me over the last few days and to be honest I hope you fancy me, because I fancy you a lot Sir".

I try to look stern and pretend I want to reprimand her for such inappropriate comments. And that she is totally wrong about me looking at her. I think - lets take this role-play in an interesting direction.

"Emma I think you have developed a crush on me as a person with power and authority. A crush that is not reciprocated." I say in what I hope is a neutral tone, though I'm feeling excited by what we are doing.

"You are right, Sir. I am fascinated with you." Emma says in a slightly urgent manner. "I fantasise about what it would be like to make you loose control. Wondering whether I could get you, a disciplined, authoritative figure, to indulge in completely the wrong behaviour with me." She pauses for a second. "To risk everything in the pursuit of pleasure with this slutty little girl, who will do absolutely anything you want in order to please you."

I stare at Emma for a short while, she shifts in her chair slightly as my eyes drop to the hem of her skirt she widens her legs slightly. I can feel my prick hardening in my trousers.

I moisten my lips, my excitement building.

"Emma I could get angry with you for being so inappropriate. However I think I will try and explain what is going on here. You are being influenced by the power imbalance between us. I think you find my obvious power over you erotically stimulating and you wonder whether it could be exploited to satisfy your desires and fantasies that are present, to be fair, in any normal 18 year old girl."

Emma is not interested in my explanation of why she has these thoughts.

"Sir, I think you are talking total bull-shit. I can see the way you are looking at me and the bulge in your trousers, that all you really want to do is bend me over your desk and punish me for my slutty thoughts."

She continues in a lower toned, suggestive voice, "I could be a very good and dedicated student, if you would only demonstrate what you are really thinking."

With that she stands up and turns her back on me. She leans over the chair and pulls her skirt up. I see her panties covering most of her gorgeous little bum. Oh my God, I can see the top of a butt-plug pressing against the thin fabric!

I know that my ability to continue to role-play the 'upright headmaster resisting the horny schoolgirl is over'. I move towards her and place a hand on a buttock. Am I totally insane? I'm a Headmaster, in my study, touching the arse of what, to all intents and purposes, is a schoolgirl in my office wearing a butt-plug. The danger of it sends me into a state of reckless excitement. I pull down Emma's panties to her ankles.

I kneel down, my face an inch from her glorious behind. I place my lips around the butt-plug button and can smell a slight muskiness from her lovey arse. I slowly pull the plug out with my teeth. It is surprisingly big and hesitate a while at the point it is stretching her anus to the maximum.

Emma make a low moan. I pull it all the way out. It leaves a large gape lingering in front of my face. I spit the plug on the floor and insert my tongue deep into the lovely gape. It slowly closes on my tongue in a sensation so erotic it makes the erection, trapped in my trousers, very painful. I stand up and drop my trousers and boxers and kick them away. My prick leaps to full attention.

Emma turns round and smirks at me. "Oh Sir, you have done it now, you have broken the cardinal rule: 'Thou shalt not gape and rim one's students'!. Now that you have completely broken the boundaries of professional behaviour, and have no remaining standards to uphold, I demand you fuck this poor girl into a total, sweaty, whimpering little mess. Please Sir, use and totally exploit me for your pleasure, I beg you."

I can't help myself, I know we are probably making enough noise for the secretaries, down the corridor in a side office to hear us, but I don't care.

"Get on your knees, you little tart, and suck your master's cock!" I command.

Emma obliges. She expertly takes the whole of my throbbing cock into her mouth. She has practised many times suppressing her gag reflex and takes it deep into her throat. I start to rhythmically face fuck her. The sides of her throat and mouth feeling not dissimilar to her lovely cunt.

After a couple of minutes, her eyes gazing up at me with a look of pure lust, I can't control myself any longer. I shout,"I'm coming!"

So as not to choke her I withdraw partially, the tip still in her. A stream of semen pulses out of me filling her mouth. Emma lets some dribble out, while swallowing the rest. God she looked so beautifully filthy.

Just as she is standing up a senior grade student enters my office. The student stops and stares at us, trying to make sense of the scene in front of her.

Finally she manages to stutter out, " I did.. I did knock Sir. I did... I thought I heard you say... Come in".

My mind, and no doubt Emma's starts racing. We say nothing just stand there. in our obvious state of disarray, wondering what she will do; praying that she wont scream or run out. I can see my whole life being destroyed in that one mad instant.

It's like a car crash where everything seems to slow down. I recognise the girl. It is Susan H, from the upper-sixth (grade 12 in the US) who had just celebrated her 18th birthday the week before. She has often sat at the front when I have taken the occasional class, her legs slightly parted I have found myself wondering whether I can see her knickers or whether she is maybe not wearing any. She always made it just too difficult to see!

What seems like a minute passes. Finally Susan calmly turns around and closes the door, takes a couple of steps towards us and picks up the butt plug lying on the floor. She raises it to nose and sniffs it, puts it in her mouth and sucks on it for a second or two then smiles and hands it to Emma.

"I think you must have dropped this".

Then Susan turns to me and says, "Sir would you mind if I watch? I think I could learn a lot from you both."

My prick hardens, relief and lust growing inside me.

Emma grabs the girls chin with her free hand and says," Fuck watching, the best way to learn is to actually do it!"

She plants her mouth on Susan's and forces her tongue into her. She reaches under Susan's skirt with the hand holding the butt plug and slides it under her panties and into her already wet cunt. She really is an expert in judging what should be done in any sexual situation and Susan gives out a little gasp and forces her own tongue back into Emma's mouth.

All the anxiety over us being caught has disappeared. I go behind Susan and pull her skirt down. She is very thin and I have often masturbated while thinking of her little tities and lovely flat stomach, imagining her ribs in her slim torso being clearly visible and planting kisses on each one in turn. I pull down her panties, Emma forces the plug back into her soaking snatch and I ram my tongue into Susan's lovely little anus.

Susan had obliviously not showered that day and the mildly mucky smell of her arse is stronger than Emma's. The dirtiness of what I'm doing to this lovely girl is making me rampant again. I push a finger into Susan's arse and frig it while Emma is forcing the plug into and out of her cunt. I spit in her crack, insert a second finger and continue fucking her arse with both of them. She is surprisingly loose already and I suspect that has played with anal toys, if not had a prick or two, recently.

I get 3 fingers in and Susan is moaning with what I think is pleasure but could also be a a bit of pain. I'm not in the mood to care. Emma, meanwhile, has undone Susan's blouse and taken off her bra. Susan might only have A cup breasts but has quite large nipples and Emma is enthusiastically sucking and gently biting them in turn.

Even though Susan is quite tall, in order to make it easier to get my prick into her arse I push a cushion from the sofa onto the floor and lift her onto it. She leans over the desk her lovely rear at a perfect height for my prick. Emma is a bit annoyed at having her sex toy taken away from her. To compensate I demand that she licks my arse. Soon her tongue is fervently pushing its way in.

I start to insert my prick into Susan's beautifully lubricated anus, my saliva leaking out as I push in.

Susan lets out a guttural "Yes!" and a low moan as I slide my engorged weapon deep into her. I feel her spasming and keep momentarily still to let the spasms pass. Emma is lapping away at my butt as if she'll run out of time.

"Please, please fuck my arse", Susan requests in almost a whisper.

Needing no more encouragement. I start to move in and out, gently at first, just a couple of inches, not wanting to hurt her too much. Emma is able to keep rhythm behind me with her tongue.

Susan says louder, "Harder".

I increase the pressure and depth of my strokes.

Susan commands again, "Harder!"

I'm now nearly coming all the way out and pushing in nearly to the hilt, faster and faster.

"Susan moans then shouts, "God, yes.!.. God yes!." Fuck me hard! Hurt me! Please I really need it!"

I start pounding hard and deep, my thighs slapping against her little buttocks. I can't believe she can take this mauling, but am totally, almost sadistically, using her as hard as I can. Emma has had to leave off attending to my arse and is just frigging herself while watching in amazement.

Sweat is collecting on my brow, as I thrash my cock in and out of this gorgeous girl's arse for 3 or 4 minutes. Finally I can sense Susan is coming; waves of pulsing muscle gripping my cock.

She lets out a loud, "Yeesss!"

I let my self come, pouring what semen remains in my balls deep into her rectum. I pull out slowly and stand back, exhausted, to admire the lovely gaping arsehole in front of me.

Emma doesn't hesitate, she kneels down and sticks her tongue deep into Susan's gaping anus and tries to lick up what semen she can retrieve. She then stands up pulls Susan's face towards her and pushes the semen into the lovely schoolgirl's mouth. They kiss for over a minute, exchanging my seed between them. God I hope the secretaries didn't hear us.