The Headmaster’s Office 03: Ingenious Toys


Author’s Note

All characters appearing in this work are over the age of 18 and are fictitious. Any resemblance to real persons, living or dead, is purely coincidental.


If you haven’t already read The Headmaster’s Office and Fantasy Night, now might be a good time to do so. It provides the back story for Belinda, Mr Gallows and Rupali; much of which is assumed in this story.


Last week was the final hot week of an Indian summer that stretched all the way into April. The still, humid air made the school week hell, especially in the un-air-conditioned classrooms of the old wing. You go to a posh private boarding school and you’d think the expensive fees would stretch at least as far as air conditioning, but Mr Gallows (headmaster and … secret boyfriend?) has been trying to get the Trustees to fund a refurbishment of the old wing for years.

By the time the weekend came, Rupali (roommate and … secret girlfriend?) and I had had enough. We got day passes from the Boarding House Mistress for Saturday and planned to head to Bondi to cool down and let off some steam. But first we needed to go shopping; I hadn’t been to the beach all summer and my only bikini pre-dates the miraculous and belated maturing of my breasts over the Christmas break. The old 6AA bikini top would now barely cover my nipples and my generous new 8C rack would spill out the sides. I suppose it would probably fit right in at Bondi, but it’s just not my look.

The shopping trip was a perfect opportunity to test-drive Ike and Mike: an invention of Mr Gallows. Before I can describe Ike and Mike, I need to rewind and explain Earnest and my discovery of Mr Gallows ingenious mad-inventor streak.


If you read my earlier stories, you will remember that I masterminded the fulfilment of Mr Gallows’ and Rupali’s sexual fantasies. Rupali still doesn’t know the owner of the nine inch cock that brought her to her first orgasm with a man … and I’m going to keep it that way! Those two are way too compatible and I want to keep them both to myself.

On the same occasion I discovered – and fulfilled – my own desire for Rupali and we have been lovers and roommates ever since. Strangely, I don’t think of our relationship as lesbian or bi-sexual. We use tongues and strap-on dildos to do to each other the same things men would do, only better in many ways because we know what girls like. In almost every way it seems to me that sex with Rupali is completely hetero-sexual.

The night after that adventure I was alone in our room with a vibrator that I had liberated from the dorm toy box and was disgusted to find that the batteries had died and hadn’t been replaced. There’s a code of honour covering batteries: ‘She who dries em, buys em’. I didn’t have spares and was about to march back out to the toy box to pilfer replacements when a text came through from Mr Gallows:

“Owe you a gift for last night. Any requests? In teachers’ lounge if you are free.”

Super! Who needs a vibrator when there’s nine inches of real cock downstairs? Not missing an opportunity for a gift, I rifled through the toy box and pulled out 3 more dead vibrators; Mr Grateful could buy me batteries! Not even bothering to put panties on, I ran downstairs in my nightie and burst into the teachers’ lounge. He was standing, so I vaulted from the coffee table into his arms, my own arms and legs locking around his slim, powerful body and planted a long, hungry kiss on his lips while I ground my naked pussy into his six-pack stomach. He was a bit surprised to see me so ready; if his text had come 10 minutes earlier or later then I might have been a little less desperate. He returned my kiss and then prised me loose, lowering my feet gently to the floor.

“What’s in your hand?” he asked, looking at the vibes. “Mine not enough for you anymore?”

“Yours is plenty … when it’s around,” I pouted. “When it’s not I have these, but I need batteries. That can be your payment for fantasies fulfilled.”

“Well, I was kind of hoping to pay in services rendered. But if you want batteries more than this,” he said with a touch of sarcasm, rubbing a growing bulge in his trousers, “then I am your humble servant.”

“Don’t be a dick. I want your dick and I want your batteries,” I shot back, smiling. “Unless you think a balls-deep sex-with-a-stranger fantasy three-way isn’t worth it?”

“Touché,” he conceded. “What do we have there?”

I handed over the four dead vibes. Three of them took normal AAA batteries so no problem there. The last one was Earnest, which I grabbed on a whim. Earnest is an ancient gold vibrator that we give to new girls – mostly virgins – who have never used a toy. He is only as thick as a lipstick and takes three little watch batteries. Mr Gallows put the others aside, seemingly uninterested, but was studying Earnest with a curious expression.

“Where did you get this one?” he asked.

“Who knows? It’s been in the boarding house longer than I’ve been Ankara escort alive. It was probably bequeathed by one of those tight old bitches on your Board of Trustees when she was a boarder,” I joked.

He smiled briefly and then shuddered at a mental image that I’m glad is in his head and not mine.

“It’s just … very strange …,” he trailed off. He rummaged through a drawer and pulled out a small screw-driver. Removing the screw at the base of the battery compartment, he slid the innards out of the barrel and started mentally cataloguing the parts. “There’s no motor in here,” he said – hopefully to himself because I have no idea about mechanical gizmos. “But this thing looks like a tiny … Van de Graaff generator? Are you sure this is a vibrator?”

“Search me. It’s a dildo as far as I’m concerned. It’s never worked because we’ve never had batteries. That’s where you come in,” I hinted.

“May I take it for a few days?” he asked. “I want to do some more research.”

“Sure, knock yourself out.” I was getting impatient and sat on the coffee table to unbuckle his trousers. He was still staring at it and turning it over in his hands when I took him into my mouth; but I got his attention soon enough.


We met again after lights-out the following week and he presented me with Earnest 2.0. Now there was a thin black wire plugged into the base with a little vinyl and velcro loop at the other end, and Mr Gallows was wearing a big goofy grin as he held it out to me.

“You’ve given it a … carry-handle?” I asked, feeling and sounding a bit underwhelmed.

“It’s not a carry-handle,” he sounded hurt. “It’s a pressure-sensitive remote control.”

“Huh? Translation?” I asked, one eyebrow raised.

“It’s the cuff from an infant sphygmomanometer and …,” he started. My eyebrow hadn’t moved. He got the message and started dumbing it down. “It’s the cuff from a blood-pressure machine for babies. It’s sensitive to pressure and it can be used to send signals down the wire … like a remote control.”

“Soooo,” I began slowly, thinking it through, “if I had a baby I could get it to remotely control my vibrator?”

“The cuff doesn’t go on a baby’s arm, it goes on me.”

“But it’s too little for you … Ohhhhh!” I brightened, suddenly catching up. “It doesn’t go on your arm!”

“Very astute,” he mocked gently.

“But I still don’t get it. If the cuff goes on you … and you go in me … where does Earnest go?”

He didn’t answer, but looked at me waiting to see if I would work it out. Then the light-bulb went on in my head and I turned on him with feral light in my eyes. “Not on your life! My puckered little back door is strictly one way, buddy.” I sounded angry, but there was that little tingle of curiosity as well. A cock deep in my pussy and a vibrator buzzing in my asshole … what would that feel like? I didn’t think I could feel fuller than when his long, hard shaft was buried deep in my vagina, but with a vibrator next door … it had possibilities. He kept silent, probably watching a bunch of different emotions wash across my face.

“But why a remote control,” I said finally. “Wouldn’t you just leave it running to vibrate while you fuck?”

“It’s not a vibrator,” he said cryptically.

“Then what the fuck is it? A stick-blender?”

“Do you want to keep asking questions, or do you want to try it out?” he asked. He reckoned he had me hooked and the big goofy grin was back.

“Will I like it?” I asked.

“Yes,” he said unequivocally. I was a bit worried; but now I was lot interested.

I was in. I came over to him and started running my hands over the muscles of his chest. “OK Edison, so what do we do?”

“Well, I need to be hard first …,” he offered.

I slid my hands down over his pecs, his hard stomach, and then on to the growing bulge in his pants. I followed its length through his trousers back to the root and massaged it there with my fingertips. It pulsed and throbbed under my touch; already wood and forging quickly towards iron.

I was wearing my short satin nightie without panties or bra and he put Earnest on the coffee table so that he could explore my body through the slippery, sheer fabric. He stroked the undersides of my breasts, gently applying pressure and feeling their weight; his fingertips moving in circles and working their way up to my nipples.

I loosened his trousers and dropped them around his ankles. His cock was at its full nine inches and tucked down the tight leg of his lycra trunks. I closed my hand around the shaft through the fabric and as I gave him a firm squeeze, his cock strained back against my grip, bulging and resisting the pressure just like it does inside me. I could feel my heart speed up with excitement and anticipation. I always got nervous and fluttery when I felt his cock; he was so big and I could feel my pussy clenching with anticipation as if it knew it was too small to tame this throbbing tool. I reached into is trunks, grabbed Ankara escort bayan a handful at the base and stroked back towards me, his skin flowing like quicksilver over the hard flesh underneath. Wanking his giant shaft up and down with one hand, I dropped his trunks with the other and he kicked them away along with his pants.

He had been pinching and rubbing my nipples to hardness and had them firing off little sparks of pleasure through my breasts, but then he relented for a moment to remove his shirt. He was now completely naked (if you don’t count my hand stroking his throbbing cock) and I was still in my nightie; he hadn’t tried to remove it yet because I think he likes the mystery of reaching underneath to feel my wetness with his fingers before he can see it with his eyes. I never let him down either; holding and feeling his massive length gets me soaking wet and steaming hot, anticipating the spasms and contractions as I stretch my tiny pussy around his girth.

I also think he likes to cheat himself, stealing peeks at my pussy under the nightie, trying to see whether my inner folds have opened up yet. Usually I stay wet but closed and then open up like a flower at his first touch. If I’m watching his cock I always see it pulse when he watches my pussy open, knowing that it was his touch that made it happen. But if he peeks under my dress and sees my glistening lips wide open and inviting him in, his cock leaps and bucks like a wild animal, as if it knows it’s been wasting time when it should have been inside my tight, wet embrace.

Giving him a show, I stood up on the sofa and – holding the back for balance – I spread my legs and slowly bent over, back arched so that my bottom stuck out further, until the hem of my nightie was right at the level of my pussy. I was looking over my shoulder to watch him; he wasn’t peeking, he was openly staring at the tips of my outer labia visible under the hem of the nightie. He couldn’t yet see how ready I was – and I was! My pussy was gaping wide open and casting out heat like an open furnace door. Watching him closely, I bent lower, raising my bottom just a bit higher. As my steaming entrance moved into his field of view, his cock throbbed and the knob turned an angry purple and doubled in size. I’ve seen it before, but it always surprises me and I think he is going to cum even though he never does; not until he is deep inside me, at least.

He moved towards me and I hoped he would slide that beautiful shaft into my steaming canal; but instead he knelt down and bought his lips to my entrance. He kissed my labia with an open mouth, using the lightest contact to transfer moisture to his lips where he could taste me without using his tongue directly. I wanted him to go fast and hard but he kept titillating me with his lips, slowly increasing the intensity and sucking my inner folds into his mouth. Still he hadn’t used his tongue or touched my clitoris and I was dying for him to do both, moaning with desire and frustration and pushing back against his face.

With a final deep, searching kiss of my pussy he broke contact; but before I could complain he slithered between my legs and sat on the couch with me standing over him. He pulled my nightie over my head and dropped it on the floor. Now I was completely naked, standing over his giant erection, breasts heaving with excitement and bobbing just a few inches from his face. For a moment I thought he was going to shift focus to them and I briefly flirted with the idea of unlocking my knees and impaling myself on his shaft before he had the chance to stop me. Instead he closed his giant hands around my hips and buttocks and lifted me off my feet. I let out a little shriek of fright, thinking I was going to topple over, but he held me so powerfully and firmly that I only needed to keep my hands on the back of the couch to balance my upper body.

He brought me to his mouth with both hands like he was drinking from a sacred chalice. I opened my thighs to him and extended my legs over his shoulders, now holding his head for balance and leaning back to open up my centre to his lips and tongue. He kissed and sucked at my labia like before, this time drawing my clitoris into his mouth and applying deep suction. He released the suction and brought his tongue to the bottom-most point of my vagina right near the anus. He tickled the sensitive skin there, making me squirm; I wanted to push harder into his face but held in the air as I was, I had nothing to brace against. Then with one long lick he ran his tongue up my slit, pressing deeper as he reached my entrance before continuing up to my clit, circling it a few times then sucking it between his lips and flicking it hard with the tip of his tongue.

Moving his tongue back to my entrance he pushed it deep inside my vagina, flicking and licking, tasting and teasing, all the while rubbing my clitoris with the tip of his nose. I crossed my ankles behind his head and dragged him deeper, crushing his face into my pussy, my moans of pleasure Escort Ankara joining to a single, extended ululation. He must have run out of breath because he withdrew his tongue and pushed me firmly away from his mouth. Would it be unfair to ask him to get a tracheotomy so he could breathe through a hole in his neck while I came on his face? I don’t think that’s too much to ask.

He lowered me back down and I unfolded my legs from behind him so I could kneel on the couch, straddling him with the base of his erection pressing against my aching slit. I pumped my hips, sliding my soaking lips along his cock and lubricating his length with my juices. He reached behind me to collect Earnest the gold not-a-vibrator with its umbilical sphygmomanometer pressure-cuff. This bit looked like fun: I took the little pressure cuff and slipped it over the head of his penis, sliding it all the way to the bottom, not missing the opportunity to stroke and squeeze along the way, feeling it flex and throb involuntarily under my touch. He took over and tightened the velco fastener – tighter than I would have – so that his cock bulged around it, the veins now standing out clearly. It only covered the bottom two inches of his cock, but those two inches don’t fit in my pussy anyway so I guessed I wouldn’t miss them.

He followed the wire to Earnest’s narrow shaft and held it in front of me, silently asking for permission to insert it in my virgin asshole.

Now that the moment of truth had arrived I was having misgivings. I could feel nervous tremors in my thighs and tummy; I didn’t know what was going to happen and I was frightened.

“What does it do?” I had to know.

“Sure you want to know?” he asked.

I nodded. I could feel tears welling in my eyes now and blinked them back.

“What you gave me was an electrical anal stimulator; a zapper,” he said.

“What the fuck?” I blurted. “What kind of perv would zap their asshole?”

“Mostly gay men,” he laughed. “But I modified it. I’ve dropped the voltage and made it release a series of micro shocks rather than one big one.”

“Will it hurt?” Please say no please say no please say no.

“Not really,” he said, “it just makes all of the local muscles contract until the pulse ends. It’s a bit like flexing yourself, but stronger and involuntary.” I still looked confused. “Have you seen those gadgets on late night TV ads,” he tried, “where you attach electrodes to your stomach and then sit back and relax while it flexes your abs until your flab turns into a six-pack?” I nodded. “Same idea, except this one works.”

“What? I stick it up my ass and I get washboard abs?” Now I was even more interested.

“No. It will constrict your muscles, but it won’t give you washboard abs. That takes real work.” He smiled at me, hoping the Q&A was over.

I looked at him menacingly – or at least as menacingly as a 40kg, 4’11” and three-quarter naked schoolgirl can possibly look – and threatened “If this hurts, I’ll ram it up your ass and rip out the cord.”

“Deal,” he said, then held his cock steady. “Hop on.”

It was so long I had to shuffle backwards just to get the tip into my vagina. I seated his knob in my entrance, took a deep breath and then slid forward, impaling myself on the first five inches of his dick. I normally go much slower, but I was so hot and so wet that I couldn’t wait. There was an explosion of exquisite pain as my vagina stretched wide to envelop the unyielding hardness of his erection, my muscles spasming in an impossible effort to eject this massive incursion into my tiny hole. I held my ground until the contractions subsided and then experimentally pumped my hips to make sure my vagina would release him enough to slide in and out of my tunnel. My juices were dribbling down his shaft, lubricating the remainder of his cock so I started pumping deeper, taking in more, bit by bit stretching my pussy until finally I was pressed up against the pressure cuff.

Now fully impaled, I could kneel over him again, so I moved in close and rubbed my breasts against his hard chest. My mouth found his and we kissed deeply, our tongues locked together in mortal combat as our lips ground hungrily against each other.

He broke off first and whispered breathlessly in my ear: “Ready?”

I nodded, not game to speak in case he heard the fear in my voice. He dribbled saliva onto his fingers and coated Earnest’s shaft. Then with the remaining saliva, he reached behind me and lubricated around the edge of my anus. With his giant cock filling my pussy, the feel of fingers exploring at the entrance of my ass was ticklish but really erotic. I was surprised at how much it was turning me on and was clenching with anticipation.

“Try to relax your muscles,” he whispered. Shutting my eyes, I drew a deep breath and let it out slowly, imagining I was blowing out all of the tightness, relaxing my stomach, my vagina, my thighs and finally my anus. His probing fingers felt the change and he pressed more insistently until one fingertip slid tightly into my back door. I clenched down on it involuntarily, but he held it there until I relaxed and then worked it in and out with short movements, lubricating and desensitising me to the foreign touch.

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