What’s Up Doc?

by

I feel like the spy who saved the world. The monumental improbability of the scheme that I pulled off this week might never be recognised, except by the two people closest to me in the venture. But in many ways, not even they know the entire story. To be sure, it’s not as though I have gone completely unrewarded. Indeed, as I write, I can feel a tingle of excitement spreading through my loins at the memory of what I did … and what was done to me.

* * * *

The plan began with my roommate Rupali; we were in bed in the senior girls’ dorm of our boarding school. I thought my life was complicated enough trying to keep secret my affair with Mr Gallows, our headmaster, and then Rupali comes along and casually calls me out as a latent bi-sexual. How do you respond to that?

It would be easier to deny—I freely admit—if I hadn’t let her seduce me. So now I have two secret lovers. I can’t tell Rupali about Mr Gallows; that’s like Top Secret with one of those big red stamps on it. The reverse is not true though. There’s no reason why I can’t tell Mr Gallows about Rupali, but the question is: how?

Oh, hey, G-man. You know I’m fucking my roommate, right? … What? A girl? Of course she’s a girl. You got a problem with that?

At least that’s how it went in my head, and the problem dominated my thoughts even as I lay curled in Rupali’s arms, still basking in the afterglow of our first strapon lovemaking.

“Earth to Ashley.”

“Sorry. What?” I’d been drifting into a lovely dream involving both her and Mr Gallows.

“Do you want me to challenge you next week?” Rupali whispered. In our spooned position, her lips were right next to my ear. “We could put on an even better show if we planned it properly.”

She was talking about her epic Double Dildo Tug o’ War against Trish earlier that night. Wednesday is Games Night in the senior girls’ dorm, and as that week’s challenger, Rupali got to pick her target for next Wednesday.

“Only if we play a different game,” I said. The idea of battling Rupali to the middle of the dorm’s double-ended dildo held a strong allure, but my problem was more physical than motivational. Unless you’re a beanpole like Trish or Rupali, half of an eighteen-inch dildo simply won’t fit.

“Didn’t it hurt?” I asked. “At the end, I mean, with all that …?” —cock inside you. I squeezed my thighs, unconsciously wincing at the thought of nine-inches of rubber Latex impaling me. I’ve been on the receiving end of Mr Gallows’ huge dick, and I came out of the experience walking like a penguin for a couple of days.

“Hurt? Not really. There was stretching, but it felt amazing. It filled me in a way that a man never will.”

Never say never, sweetie, I thought to myself. From personal experience, you just never know when you’ll be kneeling splay-legged before a man with his hand up your school dress stroking you to orgasm, then inviting you back after school for a night of cataclysmic fucking. Just saying, you know?

I fell silent in my own thoughts for a while and then, changing subject: “Rupali, you’re Indian, right?”

“My parents are. I’m Australian, I guess.”

“Aren’t you supposed to be a virgin?” I asked candidly. “You know, for your wedding night?”

Her musical laughter lifted me up and made me smile in the darkness. “They’re not very traditional. If you met them, you would laugh too. My parents have embraced what they call ‘The Australian Way’, and they will tell you so at every opportunity.” She paused a moment, and when she continued, it was with some sadness in her voice. “I will choose my own husband, I suppose.”

“Isn’t that a good thing?” I couldn’t imagine why anyone would want their partner chosen for them.

“Maybe.” She snuggled me closer into her body. “But there’s something indescribably sexy about the idea of going to bed with a man you have never met.” After a thoughtful pause, she continued with cautious enthusiasm. “Don’t you fantasise about a stranger? You’ve never seen his face, never felt his touch, and then his cock—one that you’ve never had, so you can’t know how big it is—slides inside you, but slowly. You don’t know anything about it—he’s behind you, so you can’t see—and every inch that goes in might be the last, but maybe it’s not, maybe he fills you up and there’s still more.”

Wow! My nipples went hard. “That doesn’t sound like an arranged marriage to me. At the very least you’d have seen your husband at the wedding.”

“True,” she sighed. “But it doesn’t hurt to fantasise.”

We fell quiet again, and after a while I heard her breathing deepen as she neared sleep.

“Rupali?”

“What?” she replied sleepily.

“What if I could make it happen? You know, what you were talking about before.”

“Ashley,” she said in a dreamy voice, “you make that happen and I will stick my tongue so far up your tiny, tight snatch, you’ll come out my ears.” Then she fell asleep.

Oh. My. God.

It would be a long time before I got to sleep that night.

And so a plan was born.

* * * *

The plan really made itself; it was just down to execution. I wasn’t Mr Gallows first casualty from the injudicious attention of his giant dick, and I knew for a fact he longed to have sex with complete abandon without having to worry about hurting his partner. So if this went right, I could fulfil the sexual fantasies of two people in a single stroke. Maybe three, if I could watch. If it went wrong though, 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 going to suit my plan better than Wednesday, because all of the day-boarders go home for the weekend, leaving only a handful of us full-semester girls. Legendary things don’t usually happen on Saturday, because it’s no fun without everyone to share the experience. That was about to change.

After dinner, I was in our room listening to music. I didn’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.”

Then I waited. That was the hard part.

Rupali came in at 8:30pm wearing her running gear—a crop top and bike shorts. The tight Lycra clung to every curve, and she was glowing with perspiration. “Hey babe.” She was still catching her breath as she sat to stretch down, her long, beautiful legs spread wide and flat on the floor. She reached for one foot, her full breasts parting against one knee, and her hair spilling over the top of her head, hiding her face. I stared openly, not saying anything, just wanting.

“What’s the game?” she asked, not looking up.

“Huh?”

“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 where one girl picks an item from the dorm and slides it into the pussies of the others (who are blindfolded, of course) until one guesses right or all of them 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 cheating.

“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 make them sit down again. I was imagining putting one in my mouth when her long eyelashes flicked in my direction. Sprung.

She stood naked in front of me—watching me watching her—but I couldn’t look away. She turned her back and then very slowly, keeping her legs straight, she bent 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 pussy lips bracketed between perfect buttocks and thighs.

“Jump shot!” she sang, suddenly leaping up, full breasts bouncing, and tossed her clothes into 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 my benefit.

When she returned ten 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 until 11:30pm, when there came a quiet tap on the door.

Deep breath, Ashley, 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 ‘What’s Up Doc’—and great big smiles. Mandy is middling height and skinny—small breasts over bony hips. She’s cute in a geek-chic kind of way, with a slight overbite, black framed glasses, white teeth, and clear skin.

I tossed some pillows on the floor and Rupali swung her legs out of bed with three pairs of eyes watching intently 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 conspiratorial glance and suggested Mandy go first since she hadn’t played before. This was also true for Rupali, but I knew what Trish was playing at, so I agreed.

“Okay,” 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 that I’m small and I haven’t had a turn yet, so keep it sensible, otherwise I’m coming back with a cricket bat.”

Mandy gave me an amused salute and slipped out silently with a big goofy grin on her face, while Rupali handed silk scarves to Trish and me. She kept a giraffe-print one for herself that I hadn’t seen before—it should have looked kitsch, but it contrasted exotically with her glossy black hair and coffee-and-cream skin, raising my temperature by another degree. We slipped off our panties and waited for Mandy.

There was a quiet knock at the door. 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.

Trish laughed. “No, we didn’t.” We all pulled down our blindfolds and sat up. “New girls always pick a banana. It’s like a rite of passage.”

Rupali got the joke and laughed in spite of herself. The look on her face suggested she would have done the same. 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’d planned ahead. Bad news.

“Ready Ash?” It seemed I was going to be her target for this prank.

“Sure, you only live once.”

I heard the 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,” Trish admonished. And then, in a musical voice, “here it comes!”

Holy crap! It felt like I was being doggy-fucked by Frosty the Snowman; it was freezing! My poor pussy clenched in shock.

“Loosen up, Ash,” Trish giggled. “Or I’ll have to leave it in there all night.”

The initial shock had worn off and I realised it wasn’t as cold as I initially thought. Whatever it was, it had only come from the fridge, not the freezer. Blood began flowing back into my veins; I was able to relax and set about trying to guess what was in my snatch, but I only had an inch or so inside me.

“A little more, please.”

Trish slipped it in further. The fresh coldness contrasted with the now warm part and gave me a pleasant shiver. It felt bumpy. “Twist it a bit.”

“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!”

Rupali was next. 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. I shuffled closer and we linked arms, elbows on the floor. With 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, and then “Mmmm,” as it turned to pleasure. Sounded like Trish had begun.

“More please,” she said in a husky whisper, right next to my ear. Totally unbidden, a complete and perfectly detailed image popped into my head; it was me in this same position, crouched on knees and elbows holding Rupali’s hand and with my bottom in the air, 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 of her lean body beneath mine.

“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 one—although the distinction was starting to blur—and half of the long dildo slid into her soft, warm centre.

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

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? Outsourced 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.” Purple Pat the Pimply Peter was a purple, latex dildo with raised nodules from the dorm’s toy box.

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

I laughed. “You sneaky bitch. 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’d have to step my game up if I wanted to execute my plan.

Rupali stepped out and we got into position. She was back in the room within seconds—not long enough to get to the toy box, or to the kitchen. What could she have? It must be something from this room. That narrowed it down.

“Now, Ashley hasn’t won yet, so I’m doing her first,” she said. I felt a warm flutter when I heard those last four words. She was behind me, probably looking straight up my pussy, and seeing me wide open and soaking wet from my little daydream. What is she thinking? 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 spun; I was as-good-as getting finger-fucked by my roommate in front of my friends. 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. “Okay, more.”

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 I had spoken up, thus ending the delicious clitoris rubbing.

“Careful,” said Trish ironically. “Don’t press the button.”

“Well done, Ashley,” Rupali said. We all turned again, smiling and giggling. “I thought maybe you would take longer.” She sounded disappointed. I smiled sheepishly, letting her know that my excitement got the best of me.

“Off you go, Ash,” 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, Ashley! 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, it was beyond perfect. It was uber-perfect!

I silently padded through the common room to the toy box hidden in the sofa recess. I rummaged through, tossing vibrators and dildos out onto the sofa. Found it—Rawhide, the strap-on dildo. 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 stood proudly out underneath the hem of my nightie, and I gave my hips a wiggle, making it jog and bounce. Rupali had used the strap-on on me, but I’d never worn it myself, and now I could see why: I looked fucking ridiculous. Mandy didn’t know about Rawhide, so no trouble there. Trish knew, but the dildo is the same size and shape as half a dozen others in the toy box, so providing I didn’t reveal it was a strap-on, she wouldn’t guess either.

Time was running out; the girls would 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? I almost knocked on the door out of habit, silently admonished myself, then 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. Now quickly,” I hissed. “Pants off, hoodie up, complete silence. Let’s go.”

“Am I going to lose my job over this?”

I glared at him. “Only if you fuck it up.” 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—hard nipples beneath my sheer nightie, latex cock swinging back and forth between my thighs. “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 tiptoeing 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, Ash? 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 maybe half of Rawhide’s seven inches. He’s quite thick, which Trish loves. “Ooooh, big dildo. Thanks Babe.”

“Ahhh, but which one, Miss Smarty Puss?”

“Give me the rest and I’ll tell you.”

Very carefully, 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.”

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

“Just a little. I’m still horny.”

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

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

“Hmmm. Leroy?” Big, Bad Leroy Brown was one of the half-dozen nearly identical dildo’s she’d 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 dildo. 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. Mwah-ha-ha-ha!

“Oh my God!” Trish blurted. “It’s Raw—” She stopped herself just in time. My heart skipped a beat. She almost named Rawhide, ending the game and blowing my plan out of the water. I was getting too cocky (pun intended), letting them know I had a strap-on.

“Guess?” I asked Mandy.

“I’m thinking. Get your mystery man to fuck me some more while I think.” Brassy! You go, girl!

Obliging, I started stroking back and forth, fucking her doggy-style, the inner dildo squirming inside my own pussy every time I changed direction. It was a wonderful, powerful feeling to be fucking like a man. It occurred to me that no matter whether a woman is on top or bottom, she’s still the one getting a fucking, not the one giving it. I was beginning to see the attraction.

I looked back to check on Mr Gallows. He wasn’t even watching; his eyes were locked on Rupali crouched next to Mandy. Listening to the two of us fuck, she had snaked a hand between her thighs and was rubbing her clitoris. With each stroke her labia opened and closed, showing her wet folds to Mr Gallows. He looked down at me, questioning. I nodded silently. Yes, that’s for you. Be patient.

My own excitement mounting, I pushed forward harder, the cup of Rawhide’s base now bumping Mandy on the bottom, deliciously jolting the smaller dildo inside me. I wanted to reach under and rub her clit, but I didn’t dare; I’d already way overstepped the line. Even though she stayed silent, I could feel her body tense with an approaching orgasm.

Bringing out my inner-caveman, I grabbed her hips tight and thrust roughly all the way in. She arched her back as she silently came, tendons standing out in her neck with the effort not to make a sound. Good girl. I slid out and released her hips.

“Time’s up, Mandy,” I said.

“Well, I’d guess it was a strap-on, but I didn’t know we had one. So I’m going to go with the mystery-man … James Bond.”

“Wrong again. Your turn, Rupali.” I stood up and sucked in my tummy so I could step out of Rawhide without unbuckling.

I looked at Mr Gallows. He was just about shaking with excitement from watching me fuck one girl while another massaged her shaved pussy in front of him. I felt his cock; it was hard as stone, pulsing with his raging heartbeat, and dribbling pre-cum. I put him silently into my mouth, getting an exciting taste of his lubricating seed.

I guided him into position, kneeling behind Rupali, and held up one hand. Stay! Creeping around in front, I gave Mr Gallows a ‘get ready’ signal with two hands, miming a doggy-style grasp.

Understanding, he placed his hands on Rupali’s thighs and ran them slowly up to her hips, pulling up her nightie, moulding her curves and feeling her firm, smooth flesh. With his hands now on her hips where they narrowed into her waist, and that monster nine-inch cock poised just an inch away from her pussy, I leaned back towards Rupali’s ear and breathed, “Fantasy night, Babe. I’ve got a surprise for you. A big one.”

She jumped like she’d been hit with a cattle prod, but stayed silent. She lifted the blindfold from one wide brown, flashing, eye and glared at me in terror. I held her chin so that she couldn’t look around and leaned in close again. “It’s okay,” I breathed. “I trust him. You trust me.” She stared at me a moment longer, then visibly relaxed, nodded, and pulled the blindfold back down.

“I’ll have the James Bond treatment too, please Ashley,” she said in her exotic, musical tones. “I’m looking forward to it.” I nodded at Mr Gallows. All clear. He guided his cock into Rupali’s steaming pussy, and immediately set up a rhythm fucking her with the first half of his massive shaft.

Rupali reached forward, feeling for me. She slid one hand between my thighs and grabbed my bottom, guiding my swollen labia to her mouth. She gave me a few tentative licks, tasting my juices. Had she done this before? Probably not.

I looked up at Mr Gallows. I wanted Rupali’s tongue in my twat, but I absolutely needed to see his weapon in hers. Holding her by the ears, I grudgingly pulled her away from my pussy and then quickly, silently, I slid down backwards beneath her, thighs parted around her head. I slid her nightie up to her shoulders to expose her large breasts, then repeated with my own to feel our erect nipples brushing against each other.

I looked up to check on Mr Gallows, six inches of his iron member now stroking commandingly into Rupali, less than a foot away from my face. She resumed her assault on my pussy, sucking my clit and pushing her tongue deep inside, trying to fulfil her promise to make me come out her ears. She started rocking back and forth onto the headmaster, rubbing her heaving breasts against mine and concentrating her tongue and lips on my burning love-button while the tip of her nose probed my pussy lips.

I was too short to reach her pussy with my mouth, so I reached up both hands, massaging her clit with one thumb, cupping and gently squeezing Mr Gallows’ balls in the other.

All this was done in relative silence, maintaining the charade for the other girls that I was kneeling behind Rupali, feeding a dildo into her pussy.

“I think maybe there’s more, Ashley,” she asked. “I’d like all of it now, please.” Mr Gallows stopped thrusting, keeping six inches in Rupali’s twat. He leaned forward a little, slipping another inch in. “Is that all of it?” she asked.

Trish: “What did I tell you about asking that? Guys don’t dig it, especially not mystery men like James Bond.”

If only she knew.

Mr Gallows pushed another inch in, making Rupali gasp in surprise. Almost there. “Oh my goodness! There was more!” Her voice rose half an octave as I felt a shiver run through her body. When I thought she was ready, I increased my grip on Mr Gallows’ balls and pulled gently. Following my lead, he leaned forward and buried the rest of his cock deep in her hole, pressing hard up against her buttocks. She vocalised a little shriek, then quickly masked it with, “Ah yes, I thought that’s all there was. Move it again please Ashley, as you did before.”

Mr Gallows slowly slid all nine inches out. Rupali’s pink folds tightly gripped his cock as he withdrew, then he plunged strongly back in again, balls-deep. He repeated, thrusting hard, building up the tempo as I tried to stop his swinging sack from slapping against Rupali’s groin—a sound I couldn’t easily explain to the others. She lowered her head back down to my pussy, probing me, grinding her chin into my clit. I felt my orgasm building, and still holding Mr Gallows with one hand, I reached with the other, roughly grabbing Rupali’s head and pushing her tongue deeper into my molten core.

Rupali redoubled her efforts, straining tongue flicking and probing inside me. I tipped over the crest of the orgasm and floated weightlessly down the other side, fireworks of ecstasy exploding in my womanhood, my juices mixing with Rupali’s saliva. I wanted to scream but couldn’t, so I just held my breath and hugged Rupali, her breasts crushing mine, until I had control again.

Mr Gallows kept pounding his enormous length into her pussy (where did it all go?), pulling each stroke at the last moment and just touching his pubis to her bottom without making a sound. If it wasn’t happening right in front of my face, I would never have believed that such a monumental fucking could be administered in complete silence.

I guided Rupali up off her elbows so that her swinging breasts would tease mine. Then, still cupping Mr Gallows balls—although I was having trouble keeping up with his powerful thrusts—I moved my free hand back to work on Rupali’s clitoris, rubbing and gently pinching in time with his pumping cock.

Rupali’s body stiffened as her climax approached—her second ever and first with a man. She arched and pushed back, raising her bottom and dropping her head back between my thighs. We were close to the end now. Mr Gallows has few sexual weaknesses, but a coming woman impaled on his cock is one of them. If I come first during lovemaking, then he will follow seconds later. It’s like clockwork. Even in the silence, he would feel Rupali’s building climax, and would be powerless to suppress his own.

Trembling, Rupali wrapped her arms around my raised knees and squeezed them tight around her ears, trying desperately not to scream. On cue, I felt Mr Gallows’ balls draw up ready to unload inside Rupali. He gave one more deep thrust, pumped his balls, and I felt his semen race past my fingers and through his cock on its long, long, journey into the depths of Rupali’s womanhood. He withdrew about half way and then buried himself again, timing each stroke to the pump of his balls, delivering powerful jets of cum to the extreme depths of Rupali’s vagina.

When their spasms abated, Mr Gallows stayed inside and ran his hands over Rupali’s waist and shoulder blades, then down to cup and squeeze her large breasts, silently thanking her for what they had shared. The other girls remained blessedly silent; Mandy presumably allowing Rupali to enjoy Rawhide as she had, and Trish trying to decide whether she wanted a strap-on fucking from her best friend, or just guess Rawhide and end the game. Their patience would soon run out though. I guided Mr Gallows’ long cock all the way out, and wrapped my lips around his softening length, pumping and sucking the last of his semen into my mouth to avoid a clean-up.

Releasing him, I quickly slid out from beneath Rupali, put my lips next to her ear and breathed, “Rawhide” as I pulled her nightie back down over her bottom.

Aloud, I said, “How about a guess Rupali? What’s Up Doc?”

“Well,” she began slowly, “I don’t agree with Mandy’s mystery man idea, because I don’t believe God ever blessed a man with a cock quite like that.” Giggles from the gallery. As she spoke, I backed Mr Gallows to the door. “So that means it was definitely a strap-on. I have looked through the toy box several times and we do have one down at the bottom. I’m sure I heard one of the girls name it. Is it … Rawhide?”

I picked up Rawhide with my foot, jingling the buckles to make some noise as I made a grab for it, and waved Mr Gallows out. For a big man, he could move like a cat. “Ta da!” I sang as the door softly snicked shut. The girls removed their blindfolds and I held Rawhide up for inspection, still wet with Mandy’s juices. It might have been my imagination, but Trish looked a little disappointed. Maybe she wanted a turn. It would have to wait; Rupali was about to start leaking cum all over the carpet so I needed to get the others out.

“That’s one turn each,” I said. “And I need to get to sleep, so I can dream about mystery men sneaking into my dorm to shag me blindfolded.”

“If he does, can you send him to our room when you’re done?” Trish joked. “You got me started with that thing, now I’m going to have to dig Leroy out of the toy box and finish the job.” I opened the door and the girls filed out to the sound of muted giggles.

“If I ask,” said Rupali, eyeing me seriously. “Would you tell?”

“Never ever,” I replied.

Never say never. I should know better.


© 2017 Belinda LaPage. All rights reserved. Content may not be copied or used in whole or part without written permission from the author.

About the Author Belinda LaPage

Belinda LaPage lives and works in Sydney, Australia. Writing is a labour of love for her, but the life of a tortured artist is not, so for now it is simply a part time affair, and a pathway to affording more of the wrong shoes. She enjoys the Sydney beaches, time with friends, and spending lunch time in a café sneakily writing erotica in the midst of strangers.

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