The Headmaster's Office 02: Fantasy Night

He started laughing, his cock pulling deliciously against me with the effort. "Is that really your fantasy, Belinda? What you've just described is the fantasy of every boy in the world old enough to masturbate to internet porn. I wish I found you 20 years ago."

"No, it's not my fantasy. I was just curious; it seemed a bit ... scary. What about older guys, why don't they get off on that?"

"Oh, we do," he said. "We just recognise the paradox."

"What do you mean?"

"Well, it's impossible, right. If she doesn't want it, it's rape, and that's not sexy. So you would have to know she wants it, and then it couldn't be a surprise. Paradox!"

Stretched and lubricated now, he started stroking into me with an increasing rhythm – just the first 6 inches – while massaging my breasts and pinching my nipples. I stopped talking and just enjoyed the ride – that wonderful feeling of friction and fullness. He came before me but – at usual – the extra pressure created by his cum spurting deep inside me triggered my own imminent climax.

As we lay together afterwards I asked "What if there was no paradox? Couldn't someone in the middle set it up without either person's knowledge?"

"Now THAT, Belinda," his hand under my dress, stroking me back to readiness, "THAT is the ultimate fantasy. Sign me up when you work out the kinks."

That's a promise, I thought.

With all the pieces now in place, it was just down to execution. If this went right, I could fulfil the sexual fantasies of two people in a single stroke. Maybe three, I wasn't sure yet. But if it went wrong, I could ruin lives. The stakes were high, but the risks were low; I was confident of my players in this production, they just needed to play their part. (Spoiler: they did).

Saturday night was the night. It was usually pretty quiet on Saturday; all of the day-boarders go home for the weekend and only the full-semester girls remain. Legendary things don't usually happen on Saturday because it's no fun without everyone to share the experience.

After dinner, I was in my room listening to music – I don't know where Rupali was – probably at the gym. I sent a text to Trish (she was probably just down the hall, but mobile phones are a curse of our generation, right?)

"Playing 'What's up Doc'. My place 11:30pm. Bring your roomie. Rupali's in."

Then one to Rupali:

"New game. Our room 11:30pm. Trish is in."

And another to Mr Gallows:

"Fantasy night. Teachers' lounge 11:45pm. Wait for me. Wear a hoodie."

And I waited. That was the hard part.

Rupali came in at 8:30pm wearing just a crop top and bike shorts. The tight lycra clung to every curve and she was glowing with perspiration. Been for a run, obviously. "Hey babe," she greeted me. She was still catching her breath as she sat on the floor stretching down. Long, beautiful, legs spread wide and flat on the floor she reached for one foot, her full breasts parting against one knee and hair spilling over the top of her head, hiding her face. I stared openly, not tingling any more, just wanting.

"What's the game?" she asked, not looking up.

"Huh?" she startled me out of my study of her gorgeous body.

"Your text. What's the game?"

"Oh. 'What's up Doc'. We haven't played since last year, but you're not the only newbie, Trish is bringing Mandy." I explained the rules: 'What's Up Doc' is a guessing game. One girl picks an item from the dorm and slides it into the pussies of the other girls – who are blindfolded of course – until one guesses right or all pass. The girl who guesses correctly gets to go next. It works best with small groups – it's faster moving and easier to keep a lid on the peeking.

"Sounds fun. Trish is coming?" Seems like she was hoping for a repeat of Thursday night. I was hoping for something better.

"Yep; and Mandy. Just the four of us. We'll play in here."

"Cool." She was in. She stripped off her crop top and shorts ready for the shower. I was trying to play it cool but I couldn't help watching. Her large brown nipples were fully erect from her exertions and she rubbed them with her fingertips to get them to sit down again. I imagined putting one in my mouth when her long eyelashes flicked in my direction. I was sprung.

She was standing naked in front of me – watching me watching her – but I couldn't look away. With a swish of long black hair she pivoted on one foot and turned away. Facing the door now – very slowly and keeping her legs straight – she reached down to the floor to pick up her sweaty clothes, holding the pose for a few wonderful seconds. I let my gaze run all the way up those long, long, legs; lingering at the top to study her shaved brown pussy lips bracketed between perfect buttocks and thighs.

"Jump shot!" she sang, suddenly leaping up, full breasts bouncing, and tossed her clothes towards the hamper. She looked at me, winked, then grabbed her robe from the door and left. You know, I was beginning to think that show was for me.

When she returned 10 minutes later, we both pretended nothing had happened and went through our bedtime routine, waiting for the dorm to quieten down. We lay in bed gossiping and giggling quietly in the dark when we heard a quiet tap on the door. It was 11:30. Deep breath, Belinda; here goes.

I slipped out of bed and let Mandy and Trish in before turning on the light, both girls were wearing short satin nighties (de rigueur for 'Whats Up Doc') and great big smiles. Mandy is about 5'6," skinny, small breasts and bony hips. She's cute in a geek-chic kind of way: a slight overbite, black framed glasses, white teeth and clear skin.

As I tossed some pillows on the floor, Rupali swung her legs out of bed – three pairs of eyes watched every movement as she folded them gracefully beneath her bottom, sat down, and smoothed her maroon nightie (what little there was of it) over the tops of her thighs.

Trish flashed me a conspiratory glance and suggested Mandy go first since she has not played before. This was also true for Rupali, but she didn't say anything. I knew what Trish was doing, so I agreed.

"OK," I instructed Mandy. "Go out and grab something from the dorm and bring it back; we'll be blindfolded. Only rule is it has to fit in our pussies. Remember, I'm small and I haven't had a turn yet, so keep it sensible."

Mandy slipped out silently with a big goofy grin on her face and Rupali handed silk scarves to me and Trish. She kept a giraffe-print one for herself that I hadn't seen before; it should have looked kitsch but instead it contrasted exotically with her glossy black hair and coffee-and-cream skin. We slipped off our panties and waited for Mandy to return.

There was a quiet knock at the door and Trish grinned at me again as we lifted our blindfolds and raised our bottoms in the air, ready to play. We heard Mandy sneak in behind us. "Ready?" she asked.

"Banana!" Trish and I sung in unison.

"You bitches, you peeked," Mandy sounded betrayed.

"No, we didn't," Trish laughed. We all pulled down our blindfolds and sat up. "New girls always pick a banana; it's like a tradition."

Rupali got the joke and started laughing too. Mandy looked at us again, realised she had been had, and joined in.

"Me next," said Trish, slipping out the door.

I handed a spare scarf to Mandy. She stepped out of her panties and we all turned around: head down and bottom up, ready for Trish. She returned quickly – that meant she had been planning ahead. Bad news.

"Ready B'lin?" It seemed I was to be her target for this prank.

"Sure, you only live once."

I heard a squirting sound from the bottle of lube. "If that thing's thicker than a banana," I threatened, "I'm coming back in here with a leg from the coffee table." Nervous giggles all round.

"Don't get your twat in a tangle," she admonished, then "Here it comes!"

Holy crap! It felt like I was being doggy-fucked by Frosty the Snowman; it was freezing. My tiny pussy clenched in shock. "Loosen up, Blinny," Trish said, "or I'll have to leave it in there all night."

The initial shock had worn off and I realised it really wasn't as cold as I initially thought. Whatever it was had come from the fridge, not the freezer. Blood was flowing back into my veins now, so I relaxed and set to work trying to guess what was in my snatch. I only had an inch or so, so I asked: "A little more, please." Trish slipped another inch inside me. The fresh coldness contrasted with the now warmer part and gave me a pleasant shiver. I thought it felt bumpy. "Twist it please."

"My pleasure," said Trish. "Hang on, no, it's yours you horny slut." More giggles. She twisted the shaft inside me. Definitely bumps, round profile and cold.

"Gherkin," I guessed.

"Loser!" she trilled merrily, whipping it out of my hole. "Next."

I left my blindfold on as Trish moved behind Rupali. I could hear her breathing beside me, maybe a little nervous. Blind, I groped about for her hand, found it and gave it a squeeze, which she returned. Still holding her hand, I shuffled a bit closer and we settled our interlocked elbows back on the floor. Our heads nearly touching, the scent of her shampoo filled my nostrils, coconutty and tropical, making me dizzy.

Her hand jerked in mine. "Oh!," she uttered in surprise, then "Mmmm" as it turned to pleasure. Sounds like Trish had started.

"More please," she said in a husky whisper, right next to my ear. At that moment, totally unbidden, an image so complete and so perfect in detail popped into my head ... it was almost real. I was in this same position, crouched over on knees and elbows with my bottom in the air and holding Rupali's hand, but in my image she was beneath me instead of beside me. Her slim arms were raised behind her head, long black hair fanned out beneath them. Our bodies touching, breasts pressed together, her legs locked around my waist. We weren't eye-to-eye, but cheek-to-cheek, her lips close to my ear as in reality. I rearranged my pillow long-ways so that I was straddling it, pressing it into my stomach, my breasts and my pussy, thus completing the illusion.

"Deeper," she commanded in real life. The imaginary me was now wearing a strap-on dildo, the tip poised just inside her pussy. The real me moved her hips in time with the imaginary me – although the distinction was now starting to blur – and half of the long didlo slid into her soft, warm centre.

"Now all of it," she breathed. I felt the muscles in my thighs start to contract and warmth spread out from my stomach – the first harbingers of an imminent climax.

Suddenly I was snapped back into reality as Trish laughed "But you don't know how much there is."

"I'll take my chances," Rupali quipped back, with a smile in her voice. A few moments later: "Is that all of it?"

"Give you a tip, Sweetie," Trish giggled, "don't ever say that to a boy. And yes, it's all in. Any more and you'd be giving me a manicure."

"Now all the way out and back in half way, please." What was going on? Out-sourced masturbation? Then I got it: Rupali was feeling the texture and measuring its length by touch. Clever. "Lift the end straight up please .... Now down ...Thank you." Genius! She was checking the flex. Oh, she's good.

"I can't be sure, but I think it is Purple Pat," Rupali guessed. Purple Pat the Pimply Peter was a purple, latex dildo with raised nodules.

"Not bad, for a beginner," Trish said with typical Australian understatement. We all took off our blindfolds and turned around to see Trish smiling and waggling Pat back and forth.

"You sneaky bitch," I laughed. "You had that in the fridge!"

"Anything goes, remember," she said. "Your turn's coming."

So it was. But now it was Rupali's turn. I had to step my game up if I wanted a chance to execute my plan.

Rupali stepped out and we got into position. She was back in within seconds – not enough time to get to the toybox or the kitchen. What could she have? It must be something from this room. - that narrowed it down.

"Now Belinda hasn't won yet, so I'm doing her first," she said. I felt a warm flutter when I heard those last four words.

Rupali was behind me now, probably looking straight up my pussy and seeing me wide open and soaking wet from my little daydream earlier. What is she thinking? Then I felt a gentle touch near my anus, sliding down through my labia, brushing and then gently pinching my clitoris. Oh my God! That's her fingers! My mind was spinning and my heart was racing; I was as-good-as getting finger-fucked by my roommate.

Still attending to my clitoris with her fingers, she pressed something hard and cool against my entrance. Thank God, I wasn't going to have to guess 'fingers' in front of the others. It was too hard for latex and not cold enough to be metal. Wood? Plastic? She pushed the tip in a bit deeper. "Hold it there a sec," I croaked, trying to control my breathing as I adjusted to the thickness. She wasn't helping me either; increasing the pressure and rhythm on my clitoris with her fingers. "OK, more," I requested.

Whatever it was, more of it slid into my steaming hole. Apart from hard and cool, it was also perfectly smooth and a bit thinner than all of our dildos. And curved! As she pushed deeper it pressed uncomfortably against the side walls of my vagina. "Umbrella!" I blurted, suddenly sorry that I spoke up because it would bring the delicious clitoris-rubbing to an end.

"Careful," said Trish ironically. "Don't press the button."

"Well done, Belinda," congratulated Rupali. We all turned around, smiling and giggling. "I thought maybe you would take longer." She sounded disappointed. I smiled at her a bit sheepishly, hopefully letting her know that I let my excitement get the best of me.

"Off you go, B'lin," said Trish. "Me first when you get back; I'm hornier than a dog with two dicks.

The rest of us in unison: "Eeeeeewww! Trish!."

Uh oh. Speedbump. My master plan was for Rupali; I hadn't reckoned on getting past Trish and Mandy first. I needed inspiration ... quickly. I slipped out the door, heart pounding with anticipation and now with a low panic as well. What could I get that Trish and Mandy would never guess? Think, Belinda! My fantasy of fucking Rupali with a strap-on kept interrupting my thoughts, making it hard to concentrate. And then ... perfect clarity; the extra piece of the puzzle that even I didn't know about slotted in to place and the plan was perfect ... no – beyond perfect – uber-perfect!

I silently padded through the common room to the toybox hidden in the sofa recess. I rummaged right to the bottom, tossing vibrators and dildos out onto the sofa. Found it: Rawhide, (you know, slip it in, strap it on, ride em out, Rawhide!), a thick but plain latex strap-on dildo. Concealed inside the rubber cup that secures the base is a much smaller dildo facing inwards. Working as quickly as I could, I slid the inner dildo into my now very lubricated, very hot pussy. I fumbled with the straps a few times, finally getting them cinched tight around my waist and legs.

I looked down, my new penis now standing proudly out underneath the hem of my nightie and gave my hips a wiggle, making it jog and bounce. I've never seen Rawhide used; never even heard of it. I could see why: I looked fucking ridiculous. Mandy didn't know about Rawhide so no trouble there. Trish knew, but Rawhide's dildo is the same size and shape as half a dozen others in the toybox, so providing I could conceal the fact it was a strap-on, she wouldn't guess.

Time was running out; the girls will be expecting me back. Silently, I opened the main door and raced down the steps to the Staff Lounge, cock swinging and whacking me on the thighs. How do guys walk with these things? Out of habit, I almost knocked on the door. I poked my head inside – Mr Gallows was there. Phew!

"Come with me if you want to fuck," I said in my best Terminator monotone.

His eyes boggled at the cock standing out under my nightie. "Quick point of clarification: who's fucking whom?" he asked, staying calm and grammatically correct even under duress.

"You can un-pucker your asshole; it's not for you," I said. "It's fantasy night. I worked out the kinks like you asked. Now quickly," I hissed, "pants off; hoodie up; complete silence. Let's go."

"Am I going to lose my job over this?"

"Only if you fuck it up," I glared at him. Then more softly, "I have it under control. Trust me; you will not regret this." I pulled his head down to my level for a kiss.

He looked at me a moment longer: nipples hard under my sheer nightie, latex cock swinging back and forth between my thighs; then: "Fuck it." He stepped out of his track pants and pulled the hoodie up.

"Atta boy. Follow me," I said, disappearing out the door and tip-toeing back up the stairs to the senior girls' dorm.

We stole silently through the dorm, pausing outside my bedroom door, I looked up at him and held a finger to my lips: shhhh! We went in. The girls were in position with blindfolds still on. Thank God.

"What the fuck, B'lin? Did you slip out to catch a movie?" Trish joked, a nervous laugh betraying her outward confidence.

"Sorry, I needed fuel. Now, does anyone know if you need to prime a two-stroke? Stand back while I try to start this thing up." More nervous giggles. I glanced at Mr Gallows to see if he had worked out what was going on. He was standing catatonic, mouth open, staring at the three bottoms raised in the air, pussies peeking out beneath the short nighties. I waved a hand in front of his face to get his attention and directed him to stand behind me.

I knelt behind Trish and massaged some lube onto Rawhide's latex shaft. Being very careful to avoid giving any clues that the dildo was attached to my groin, I placed the tip between Trish's pale pussy lips. "Ready?"

"And waiting. Do it."

Moving my hips forward a little, I gave her about half of Rawhide's 7 inches. He's quite thick, which Trish likes. "Ooooh, big dildo. Thanks Babe."

"Ahhh, but which one, Miss Smarty Puss?" I teased.

"Give me the rest and I'll tell you"

Very carefully now so Trish would think I was holding a dildo in my hand, I planted one foot beside her for balance and leaned forwards, giving her all but the last inch.

"Oh you crafty bitch," she admonished. "Six or seven inch latex dildo, cock shaped, thick, no other features. I can think of five that fit that description."

"Would you like me to fuck you some more while you think about it?" I laughed.

"Just a little; I'm still horny."

Thrusting my hips, I gave her a few slow pumps and then withdrew so that just the tip remained inside.

"Time for a guess, Trish. Mandy is getting wet listening to all your dirty talk."

"Hmmm," she grumbled. "Leroy?" Big, Bad Leroy Brown was one of the half-dozen nearly identical dildo's she had just described.

"Nope! Next victim!" I sung. I took a look behind me at Mr Gallows. He had his cock in his hand – now hard and angry, veins pulsing – and a disbelieving look on his face. He raised his eyebrows at me as if to ask if it was his turn. I shook my head and moved behind Mandy, motioning him to follow so that if he made a noise it would sound like me.

Now for a bit of fun. I lubed Rawhide again and placed the tip inside Mandy. "Ready?" I asked. She made a nervous sound something like agreement, so reaching down with both hands I slipped her nightie up around her waist, grabbed her hips and pulled her onto my thick shaft, startling a gasp out of her.

Then she let out a muted shriek of realisation. "If you're holding my hips then who's holding the dildo?" she babbled.

"I didn't say it was a didlo. Maybe it's a mystery man. Might not even be my hands," I teased. "Anything goes, remember." I looked over at Rupali's bottom, squirming with pleasure as I described her fantasy. Little did she know ...