The Headmaster's Office 06: Twisting on the Gallows Pole

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.

Prologue

It's possible I'm not Mr Gallows' favourite person at the moment. It's equally possible that I am in fact his number one favourite person ... OK, top five, whatever. It very much depends on what is happening right now in the gym.

My two minute biography -- in case you need catching up -- is this: I'm in my final year at a posh boarding school in Sydney. At the beginning of the school year, I accidentally seduced the headmaster (that's Mr Gallows -- very tall, cute, little bit nerdy, wonderful lover) and we have been seeing each other secretly ever since. Not long after, I was seduced (that's my story, and I'm sticking to it) by my roommate (that's Rupali -- very tall, sexy, little bit funny, wonderful lover) and we have also been seeing each other ever since.

Now here's the tricky bit, so pay attention: Rupali and Mr Gallows had complimentary sexual fantasies. I took it as my solemn duty to put them together and as a result Mr Gallows knows about me and Rupali, but Rupali only knew that I was sleeping with a mystery man. She thought it was one of the boy boarders and I was protecting his identity; she had no idea it was a faculty member, let alone the headmaster. This was a good thing because if news gets out then he's out of a job: forever probably.

The reason I might not be so popular with Mr Gallows is because Rupali found out. From me, no less! But it wasn't my fault. The reason why I might be very popular is because Rupali wants to share him with me ... and she can be pretty persuasive. And it's all happening right now.

Anyway, that's a story for another day. For now, here's the first part of the story of how she found out about us. Enjoy.

Love,

Belinda.

P.S. One more thing you need to know in case you missed my earlier stories: Mr Gallows invents and modifies sex toys as a hobby. I told you he's a bit nerdy. Love, B.

~~~

I may only be 18 (well 19 next month) but I know how the world works. If you need a favour, a big favour, then you're wise to catch your target when they're grateful for your company -- or in a moment of weakness -- but ideally both. I needed a favour from Mr Gallows; I needed him to make me a sex toy.

Rupali recently bought me a gift: a strapless strap-on dildo. Our relationship is not especially lesbian -- or even bi-sexual -- we're just curious girls and we have sex the way we would with guys. It's more convenient this way because we don't get many opportunities to go out with guys in the senior girls' dorm, so tongues and strap-ons make a lot of sense.

The dildo was a gift for me -- not for her -- because of its size; I mean I could wear it to make love to her (yes, I've tried), but it's too small to make her come. She can climax with my tongue or my fingers, but the only other times have been using nine inches of Silver (the famous Senior Girls' Dorm double-ended dildo) and with Mr Gallows (also nine inches). Try as I might (and yes, again, I've tried), I can't find a nine inch strapless strap-on online.

Why strapless? Nobody who had tried both a strapless and a strappy (is that even a word?) dildo would ask. There is no comparison. Spike -- that's our name for the strapless dildo - is ready to go in seconds; no mucking about with straps and buckles and tightening and blah, blah, blah; just slip it in and get to work. But that's not the main thing: a girl with a strappy looks ... well ... a little ridiculous. I'm not sure why; she just does. Even a beautiful girl like Rupali -- it just detracts. But a strapless looks like it belongs; I wouldn't exactly say it looks real -- unless you get the light just right -- but it looks right ... purposeful ... sexy.

Mr Gallows has made us some stunningly impressive sex toys and I promised Rupali that I would ask my mystery man for a nine inch strapless. After I agreed to ask, then she dropped the bomb: she wanted the dildo modelled on his cock. I tried to imagine his cock -- with all of its familiar curves and contours -- on my body while I made love to Rupali. Weird? Maybe a little. Sexy? Oh my goodness, yes! Would I ask him? Oh, please!

~~~

I was going to have to pull out all stops for this favour; he was going to need some serious softening up. I love an erotic game and the people I involve usually approve; Mr Gallows is no exception. I figured that a new game -- one tailored especially for him -- was a sure bet to curry favour.

All this happened last month. Mr Gallows and I always time our meetings so that we can come and go undetected, but that makes it difficult when I share a room with Rupali; more so these days when we share a single bed. As a result, it had been a fortnight since we had last met and our texts to each other were getting a little desperate.

I considered that the best approach was to come clean with Rupali and let her know what I was planning; otherwise I would never get the chance to pull it off.

"Sweetie," I began, choosing a vulnerable moment when we were changing out of our uniforms after school. "Would it be OK if I snuck out tonight after lights-out? On my own?"

"Why?" she asked, turning around to smile at me in her bra and panties. "Got a special delivery coming from your mystery man?"

"Kind of, yeah," I said tentatively, looking down at my feet. "It's been a while."

"What's in it for me?" she asked, grinning.

"Well its funny you ask," I answered brightly. "Because tonight I'm going to ask him for that favour: the new toy."

"Ooooh goody!" she laughed, eyes flashing with excitement. "And he'll model it on himself, right? I only ask because you won't let me have the real thing again."

"I'm sorry Sweetie," I apologised sincerely. "I can't tell you why, but you have to trust me: it's not because I don't want to; I just can't."

"No I'm sorry," she sighed, coming over for a hug. I felt a now familiar tingle as her firm breasts pressed into my cheek (she is thirteen inches taller than me, so that's as high as I reach). "I shouldn't give you a hard time about it. But it's really hard not to feel just a little jealous. In some ways I almost wish you didn't orchestrate that Fantasy Night; then I wouldn't know what I was missing."

I felt bad about that too. Mr Gallows and I aren't exclusive and I would love nothing more than to share him with Rupali -- preferably at the same time -- but he was immovable on the subject. The risks we took on that one night were bad enough and he reckons I was lucky to pull it off without him being discovered. Maybe he's right, but I do hate to keep these two halves of my sex life separate.

So that was Ruplai sorted: I had my leave-pass. The next step was a text to Mr Gallows:

"New game :-D CU 2nite?"

I got a reply back within about thirty seconds; I like that about him: he's not concerned about appearing too keen like boys my age.

"11pm Teachers' Lounge. Can't wait."

And yes, I shit you not, he uses grammatically correct apostrophes in his texts.

~~~

Rupali and I went to our own beds that night and when I turned on my torch to get dressed again she opened her eyes to watch me sneak out.

"Why're you wearing that?" she whispered.

"Insurance," I hissed. "Go to sleep, you're making me feel all guilty for leaving you."

"I can't sleep," she said in her best guilt-inducing voice. "Tell me a bedtime story." Then seeing the frustration and urgency on my face: "Please? Just a little one and then I can go to sleep."

"Mmmmm," I grumbled. "OK. Shove over." She knows I'm a sucker for story-telling and she's not above manipulating me to entertain her. I'd be lying if I said I didn't enjoy it. She rolled away from me, facing the wall, and I slipped into bed behind her, reaching around under her armpit to cup one large, full breast. She wriggled back contentedly against my body.

"Who's it about?" she asked.

"This is a story I haven't finished writing yet, so I may need to make bits of it up as I go," I said. "It's about a guy called Bob."

"Is this Bob your Physics lab partner?" she sighed complainingly.

"No-oo!" I said in my most convincing As-If voice.

"Cos you've got such a schoolgirl crush on him," she teased.

"What? Do not!" I defended myself vehemently.

"OK then, what's this Bob like," she said resignedly, giving up the chase.

"Handsome. But in a geeky-cute kind of way. Way shy with girls."

"Oh my God," she giggled. "It is so Bob from Physics. You are so in denial!"

"So it seems you don't want a story ...," I said coolly, belying the blush on my cheeks.

"I apologise Blinny," she said primly, following it with a little snort of laughter. "Please continue."

"OK. So Bob's on a plane. And today he's B.O.B -- that's flight-attendant code for Best On Board -- the cutest guy on the plane ..."

I went on with the story, stroking her breast through the slippy satin of her nightie, lifting my head and whispering hotly in her ear as I got to the sexy bits. I could tell Rupali had a hand under her nightie and was stroking herself to the cadence of my voice and my hand on her breast. As I reached the climax, with a beautiful flight attendant impaled and coming on Bob's hard shaft in the airplane bathroom, Rupali stiffened and reached her own quiet orgasm in my arms.

I quickly closed out the story, leaving an opening for the next instalment in the best tradition of 1001 Arabian Nights, then kissed her and slipped silently out the door, through the dorm and downstairs to the teachers' lounge at the foot of the stairs. Sometimes I meet Mr Gallows in sick-bay so that we can use the recovery cot, but it means I have to sneak all the way out of the building, so I prefer the lounge even without something comfortable to lie on.

Mr Gallows was already there; sitting on the couch drinking a glass of wine. My usual greeting is to run and launch myself into his arms, but with the bag of tricks I was carrying and the awkward possibility of upending his wine glass, I just padded over, left my bag on the coffee table and gently straddled his lap with my knees, leaning my whole body close and kissing him softly on the lips.

"I missed you, Sir," I breathed, kissing him again, a little harder this time.

"Me too," he said through my kisses, adjusting himself inside his pants. "Wine?"

"Are you allowed to offer me alcohol?" I quizzed him. "I thought there was a rule about that."

"Are you serious?" he asked, pulling back and looking at me with his brows knitted together. In fairness, he was deeply conflicted about having sex with a student, but he has long since rationalised it to himself.

"No, I'm fucking with you again," I smiled. "I'll just sip yours; I don't want you getting me drunk and taking advantage of me." I took his glass and did exactly that.

"I think the opposite is a much more distinct possibility," he laughed. "Exactly what do you have in store for me? Oh, and nice dress, by the way, Belinda."

It was tradition for me to wear my old summer school dress when we met privately. I bought it before my boobs grew in and hemmed it to a racy length. It was what I was wearing the first time we made love. It's either borderline obscene or incredibly sexy, depending on your mindset, and Mr Gallows was very firmly in the second camp.

"Well," I began. "You know how you love my games?"

"Hmmmm. Yeeeeees?" he said suspiciously.

"Well I've made one just for you," I chirped.

"How thoughtful," he smiled. "What makes it so special that it's especially for me?"

"OK," I said, getting off his lap and picking up my bag with a smile. "So I Googled the 1980's and according to several impeccable sources you guys practically spent the entire decade playing ....," I paused for dramatic effect, reaching into my bag. "Strip Twister!" I sang, pulling out an ancient Twister game that I rescued from a cupboard in the dorm. I gave him my sunniest smile: "So whaddaya think?"

He laughed, deeply and genuinely; I could see tears standing out in the corners of his eyes. "OK," he said, getting himself under control. "Just a point of interest. No, two points."

"If you know what's good for you then they'd both better be about how good this idea is," I scowled, smiling at the same time.

"That goes without saying," he said. "Your ideas are always wonderful and this one is no exception. But ... ," he paused, then sensing he was out of trouble: "You do realise I was a child in the 1980s; I wasn't playing strip-anything. I'm Generation X; you're thinking about the tail end of the baby-boomers, and even then it was only the ones who were too stoned to realize that free love was over and they missed out."

"Will this history lesson take long, Sir? I'm horny."

"No. But even though Twister was known as Sex in a Box, kids played it too. A lot! But we followed the rules in the box, not the strip version," he went on. "The thing you really ought to know before you get into this is that I ... ," then he stood up to his full 6'4" with his arms spread to a similar span and one eyebrow raised: "... have Go-Go-Gadget arms! I ... am ... a Twister ... Rock Star!"

"What's a Go-Go-Gadget?" I said.

"I thought you said you Googled the '80's," he laughed.

"Well there was some stuff there that wasn't about Twister," I defended myself. "I had to skim it."

"Clearly!"

"Well," I said, circling him and trailing my fingers over his groin as I looked up into his face. "You sound pretty ... cocky, Sir! Are you prepared to defend your Twister title?"

"Bring it," he smiled, stopping me and bending down for a kiss. "So tell me, what are the rules of Strip Twister?"

"Simple," I said. "Play like normal, but when you foul you remove a piece of clothing."

"So what constitutes a foul?"

"We'll play by ear," I grinned, laying out the mat. "Don't worry, I'll tell you if you do anything wrong."

"Uh oh. I sense trouble."

"No. You sense fun," I said. "Trust me. How many pieces of clothing are you wearing?"

He had already taken off his tie and shoes. He did a quick tally: "Five."

"Hmmm. I have three," I said, watching his face carefully to make sure I caught the disappointment when he realised I was actually wearing panties, which are not part of our tradition with this school dress. "I'll have to put on some socks," I said reaching back into my bag and bringing out the next part of my master plan to soften him up.

I had them already pre-rolled and ready to go: sheer white stockings with elasticised lacy tops that don't need suspenders. I sat on the couch and rolled them slowly over my feet and up my legs while he watched. They finished about half way up my thighs; just a few inches below the hem of my dress.

I stood up again, smoothing out my dress and looked down at the stockings. "Will these do?"

"Socks?" he said, sensing that I might have more surprises in store.

"These old things? Don't you like them? You could always just take your socks off and we could both start with three," I said innocently. "You know Google says your prudey old 1980's people started with eight or more"

"No," he said, resignedly. "I have no objection to the socks." His eyes hadn't stopped flipping between the sheer white nylon and the strip of bare thigh above. "No objection at all."

"Good," I smiled, standing on my two dots at one end of the game mat, wiggling my hips to make my dress sway enticingly above the stockings. "I'm glad that's settled. Get set Gadget man."

"Who's running the spinner?" he asked.

"Oh, you poor Luddite," I giggled, getting out my phone and opening the voice-activated Twister app. "There's an app for that, Grandad! Spin!" I called.

"Left foot ... yellow," said the phone. His right foot was already on yellow so he quickly moved his other foot over to the adjacent dot. Rather than staying on my end of the mat, I stretched all the way to the next yellow in front of him to trap him at that end. My legs were spread pretty wide, but low-centre-of-gravity is my thing. I wasn't worried.

After a few moves we were both crouched down at his end of the mat and I had him penned. We already had two limbs on yellow and when it came up again I quickly snagged the nearest vacant dot, leaving only the very far end for him. He touched me as he reached behind me with one of those long arms and I bumped him back, knocking him on his ass.

"Foul for sitting," I piped in as soon as he touched down. "And another foul for touching me. Lose the socks, Sir."

He looked at me with a scowl and a smile all in one. "Am I to understand that bumping is permitted, Belinda?"

"Who bumped?" I said innocently. "I was just getting set to reposition my weight when you touched me. You were clearly at fault."

He scowled back, trying not to smile and failing.

"Don't forget those socks ... Sir," I said, deadpan.

He took off the socks and visibly steeled himself to go on without complaint. He was going to get harder to trick after that one.

We played for a few more minutes and between my speed and his reach there were no more fouls. Finally I was blocked, unable to spread my arms to opposite sides of the mat; he called my foul gleefully.

I looked at him with big, innocent, schoolgirl eyes, batting my lashes. "What do you want me take off, Sir?" I asked breathily. "I could start with the stockings ... unless ... you know ... you want me to leave them on? They are part of a matching set ... but, you know, it's your choice."

"Well," he considered. "They do look very nice ... and part of a matching set, you say?"

"Yes, Sir," I said, looking away and smiling, pretending to be shy. "A four piece set. I bought it specially."

"Oh? I see," he mused. "Specially, huh? So really, it would be ungrateful of me not to let you show them all off together."

"Well I didn't say that, Sir," I said. "But sure, that's one way to look at it."

"Oh, I wouldn't like to seem ungrateful," he shook his head. "What else could you take off instead, do you think?"

"There's really only this, Sir," I said softly, looking up at him through my eyelashes as I fingered the collar of my school dress. I deftly popped the top button and then ran a finger slowly down past the remaining buttons. "Do you think you could give me a hand with it?"

With that I stood up in front of him, looking at him crouched in front of me and giving him the whole my-hero and maiden-in-distress routine. He knelt in front of me -- our faces level and eyes locked. Yep, he liked this game. Very slowly, he undid the buttons over my breasts where the fabric stretched a bit too tight; the edges gaped a little but didn't expose anything more than a bit of cleavage. The next button below my breasts exposed the white underwire frame of my bra. I drew a quivering breath, but I wasn't play-acting like before; I was getting seriously aroused now, anxious for him to unbutton me further and discover the special bra and panties I wore just for him.

He continued to the last button at about my navel and then stopped to look at me for a moment: dress unbuttoned and hanging loosely, knowing that with little more that a shrug of my shoulders, it would fall to the floor leaving me standing only in my bra, panties, and those long, sheer stockings.

With very slow, deliberate movements, he moved his fingers under the dress at my shoulders, sliding them slowly up and under the fabric, relishing the touch of my bare skin as he watched the front lift and then open wider as he pushed over my shoulders.

As his hands rounded my shoulders, gravity final took over and the entire dress fell to the floor and pooled around my ankles. His surprise was exactly as I had hoped; he expected a sexy, lacy bra; but not this. It was a quarter-cup; nothing more than strip of lace and underwire separating and lifting my breasts without covering any more than the undersides. It rounded and swelled the tops and sides, leaving the nipples fully exposed; like the stockings and the panties -- which he hadn't noticed yet -- they were part of a set that is designed to be left on for lovemaking.