tagGroup SexThe Headmaster's Office 05: Wedding Cake Island

The Headmaster's Office 05: Wedding Cake Island


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.

Earlier Today...

This is a continuation of my previous stories: Ingenious Toys, and Dirty Talk. Briefly, this is what has happened so far:

I was bikini shopping with Rupali before a trip to Bondi beach when we met Spike, a cute surfer and shop assistant at the surf shop. One unwitting orgasm later and Spike offered to drive us to Coogee instead. Planning a day of fun with him, we agreed readily and before the afternoon was half way gone, Spike had made Rupali come when a session of rubbing in suntan lotion got a bit out of hand, and then I took Spike into the surf for some "hand relief" but then improbably ended up slipping him into my pussy without him noticing.

There is a small, rocky island just off Coogee beach called Wedding Cake Island. Tonight at low tide, Spike said a full moon would rise over the Pacific Ocean, and would Rupali and I like to come out to the secluded and romantic Wedding Cake Island to watch.

What do you reckon?


Wedding Cake Island

Spike went for a walk at about 4:30pm and came back half an hour later with a waterproof dilly-bag over his shoulder and a surfboard under each arm. One of the boards looked pretty normal but the other looked more like a ten foot long banana. It was huge, yellow, three times thicker than the other board and looked like it could float a small family to New Zealand.

"Gnarly board, dude," I teased. "Gonna do some carvin'?"

"Very funny," he said. "This is the thanks I get for thinking of you. I'm not loaning you one of my boards because your tiny little body will get carried off to Tasmania in the current. I borrowed this from a mate at the Surf Life Saving Club; it's a rescue board. You're riding tandem with me."

"Oh, how thoughtful," I chirped apologetically. "What's in the bag?" It looked heavy.

"Wax," he said straight faced. Obviously not all was forgiven. I guess I would find out in good time.

"When do we go?" I asked.

"Now, if you two are ready," he said. "It might take half an hour to get out there, depending on how Rupali paddles."

"Do you have wetsuits for us?" I asked.

"Nope. Overnight low of 27 degrees Celsius," he said. "It'll still be over 30 by the time we come back in."

He'd thought of everything. "Amateur meteorologist?" I asked with a grin.

"Weather bureau," he smiled. "Home page of surfers the world over."

Rupali took her board. "Is this one special?"

"Not so much. I use it on rocks and reefs," Spike said.

"Oh," Rupali looked deflated, realising she'd been handed the surfboard equivalent of a 1973 Datsun 180B.

"Oh, I almost forgot ..," she quickly turned and dashed back to her beach bag, rooted around in the bottom and brought out a black velvet pouch concealing a large, ominous shape that could have been a socket wrench ... or a maybe an Xbox controller ... but probably wasn't either. "Pop this in your bag for me will you Spike?"

"What is it?" we asked in unison, Spike with curiosity, me with incredulity; if I knew Rupali then it had to be some kind of sex toy, but I didn't recognise it -- obviously a new purchase and one that she hadn't let me in on.

"Lipstick," she smiled.

"Touché," muttered Spike as he knelt down to pack away Rupali's mystery prize and attach the surfboard's strap to her ankle. Tease that she is, she stepped forward with the other foot, legs apart and vagina a few inches from Spike's nose. He finished with the strap and then reached between her legs and goosed her on the bottom. She squawked and jumped back, a little more contrite. This was not the same gentlemanly, shy boy we met this morning; if we played games with him, he was going to play them right back.

He picked up the board, popped it under Rupali's arm and then stood back to take in the view: long brown limbs, black hair cascading over one shoulder, hot pink bikini clinging to her curves and a surfboard under her arm. "Now that looks hot," he said.

"What did I look like before?" she laughed.

"Well ... hot," he stammered, back on uncertain ground. "But all girls look hotter with a board. It's a proven fact. Ask anyone."

I tried to pick up the rescue board, failing miserably. I managed to get one end of it to waist height with knees wobbling and back bent awkwardly. He watched me with a smile. "And there's the exception that proves the rule," he laughed. "Let me carry it, Belinda. You can just walk in front and look hot without a board." I already knew he fancied me, but I still felt a little tingle every time he reminded me.

We walked all the way to the south end of the beach so that we wouldn't have so far to paddle. Spike watched Rupali get on the board and called after her: "Get a bit further back, otherwise you'll nose dive into the first swell." He watched her wriggle back; "Better," he called out. "Get past the break and then paddle in between the island and the shore. Don't get into the surf and rocks around the front of the island or you'll be tomorrow's crab-shit."

He put the rescue board in the water and placed the bag about in the middle. "You sit forward of the bag and hold on. I'll paddle and steer from the back. It looked pretty stable so I climbed on my knees, sitting back on my heels. Spike also knelt a bit behind the bag and pushed us off, leaning down and paddling with both hands at once. The nose of the board cut through the first wave we came to and bucked in the air, nearly throwing me off. "Don't forget to hold on," Spike said. "It's a lot less stable up there."

He got us through the break and then turned south, catching up to Rupali. I tried paddling like Spike, balancing on my knees and digging both hands through the water at once. After a dozen strokes my back was killing me. How does he do it? I looked over my shoulder and caught Spike staring straight at the narrow strip of white bikini covering my pussy. With my bottom in the air and head down low paddling, I had been putting on a show without knowing it. I was pleased to finally catch him perving. "See anything you like?" I asked, smiling.

"Hey, it's not my fault," he grinned. "All girls look hotter with a board. It's a scientific fact. They did a study."

"Oh, really?" I said, scepticism and maybe a little sarcasm in my voice. Concentrating on not falling off, I flipped over onto my side and propped on one elbow. This brought my breasts into profile, but hid my vagina behind curled legs. "How about now? Still hot?"

"Smoking," he replied.

I giggled, still a little bit flattered by his attention. I stayed in this reclined position; the board was amazingly stable as it rose and fell over the swells and looking backwards I could watch the muscles on Spike's chest and shoulders bulge as he paddled. I was beginning to think there was something to this science -- guys look hot on surfboards, too.

We caught up to Rupali and paddled alongside her until we reached Wedding Cake Island. It only took about ten minutes, so Rupali obviously did better than Spike thought she would. It was nearly low tide and the top of the island was high and dry, although we could hear waves crashing into the rocks on the other side.

Spike helped us both onto the rocks and carried the bag and boards up to the top of the island. It was a picturesque spot; waves crashing on the rocks below us and an uninterrupted, panoramic view of the Pacific Ocean. He arranged the big yellow rescue board on a couple of rocks to form a makeshift bench, and then opened his bag to reveal a six pack of beer, a selection of sushi rolls, sashimi, a plastic container of soy sauce and three sets of disposable chopsticks.

"Ladies, your table awaits," he said with a bow and a big flourish of his hands.

"Oh, wow!" Rupali cooed. "I like being spoilt."

We sat down on the big surfboard either side of him, watching the waves, drinking beer, eating sushi and making small talk as the sun went down behind us. As the sky darkened we could see a glow on the eastern horizon from the moon, which was soon to rise. Spike was right: this was romantic. But what now? Our Etiquette elective at school taught us the correct protocol in most social situations, but I don't recall anything about initiating a ménage-a-trois; maybe I was sick that day. I didn't know how to ask and I was too shy to just reach out and grab his cock. Help Rupali! All I could do was let both of them know I was ready and then see what happened.

I put down my beer -- I was only three quarters through my first one and already felt a little light headed; cheap date, huh -- and lay down on the makeshift bench with my head in Spike's lap, facing out and watching the waves, heart hammering in my chest. I felt Spike's hands on my head, stroking my hair, and I felt a twitch of movement beneath my ear. Well, it was something, but it was going to take more.

Suddenly a face appeared in front of me. Rupali lay down of the other side of the board, her face an inch away from mine in Spike's lap.

"Hello sweetie," she said in a stage whisper that Spike could hear.

"Hi gorgeous," I said in the same whisper.

She tilted her head back and kissed me on the tip of the nose. I returned the gesture. We kept going in the same loud whispers. "Watcha thinkin'?" I asked.

"I'm thinkin' you look hot," she said.

"You're sweet," I said, tilting my head back for another kiss. Rupali leaned back as well and our mouths met, tentatively, just nibbling at each other's lips.

"Mmmm, nice," she said. "I want another."

We kissed again, more passionately this time, her tongue darting into my mouth, trying to draw mine out. She didn't have to try hard; our tongues locked together, twining, teasing, and tasting, all right under Spike's gaze. His cock stirred beneath my ear again; I felt it harden a little and press back against me.

Rupali broke off the kiss. "Can I tell you a secret?" she asked, still in the stage whisper for Spike's benefit.

"Sure," I said.

"I want Spike to fuck me," she said.

"I want Spike to fuck me," I replied.

"Yeah, that's what I said," she sounded confused.

"I know. I heard you. I mean, I want him to fuck me too," I clarified. More stirrings beneath my ear.

"Well he can't fuck both of us!" she retorted.

"Why not?" I asked.

"Because we'll never agree on who gets to go first," she explained. "He might not be able to cum twice."

I still hadn't told her about "accidentally" fucking Spike in the surf earlier that day.

"Three times," I corrected her.

"Three times?" Rupali asked.

"He's already come once," I explained.

Her eyes widened. "Ewwww! You're not lying in it are you?" she laughed.

I snorted -- very unladylike. "Ewwww! No!" I retorted, laughing. "It was before, after he made you come."

"Shhh," she hissed. "He doesn't know I know."

A voice from above: "Is this a private conversation?"

Both of us together: "Yes!"

Then stage whispering again: "How do we decide?" Rupali asked.

"We could play for it?" I said.

"Play what?"

"Russian Roulette," I smiled.

"But we don't have a gun," she said. She didn't know where I was going with this, but she was playing along.

"We've got this," I said, lifting my head. I reached underneath with my hand and gave his hardening erection a squeeze through his shorts; it pulsed back against my grip. Rupali reached a hand under my head and gently gripped Spike's cock, giving it a tentative squeeze. Her eyes widened as it kicked back in her hand.

"I don't get it," she said. "It's nice, but it doesn't have a trigger. How does Russian Roulette work?"

"We take it in turns to suck it, thirty seconds each," I said. "Whosever mouth he cums in gets to fuck him first."

Rupali's eyes lit up. She's only been in the boarding house a few months and still marvels that I can surprise her with new sex games. This is not one we play in the dorm, of course, because we don't have any real cocks, but we giggle and dream about far more mischief than we ever get up to.

"But then he'll have to cum three times," she argued.

"Four times," I corrected her.

"Spike sweetie?" she said -- louder, as if he couldn't hear us before.

"Uh huh?" he coughed.

"If you cum in my mouth, will you still be able to cum in my pussy later?" she asked sweetly.

"Ummmm. Yeah, I reckon," he sounded confident.

"And will you still be able to cum in Belinda's pussy?" she asked suspiciously, as if checking the fine print.

"I've cum six times in a row before," he reassured her. "And that was just one girl. I reckon it'd be easier with two." We stared at each other, boggle eyed. Six times! Holy crap! My pussy would melt!

Rupali leaned in very close, her lips to my ear, whispering so that Spike really couldn't hear this time. "I've never sucked a boy before. What if I do it wrong?"

I put my lips to her ear. "I'll show you how. And I'll give you extra time."

Rupali looked back at me. "Challenge accepted," she smiled.

"Hey," she said, concern crossing her face. "What if he doesn't want to fuck us?"

"We'll force him," I grinned. "I'll distract him, you get his shorts off."

We sat up together. I took hold of Spike's shoulders and pulled him down on my side of the surfboard; at the same time Rupali lifted his legs onto her side so that he was lying supine. I knelt on the board behind his head and leaned over so that we were upside-down face-to-face.

"Spike, I need your help again with my bikini," I said in a fair-maiden-in-trouble voice. "Could you please unhook it for me?"

He nodded agreement, pretty willingly I thought. I propped up on all-fours and moved forwards to bring my right breast to his lips. I craned my neck down so that I didn't smother him with my boobs and kissed his hard stomach, which fluttered nervously under my lips. "Clasp's in the back," I said, running my tongue around the contours of his abdominals. As he reached behind me I looked at Rupali: "Right, I think he's distracted."

Rupali hooked her fingers into Spike's waistband and dragged them down over his hips. He was still fiddling with the clasp on my bikini, trying to figure it out by touch. He lifted his hips for Rupali and she pulled his shorts down slowly, dragging his cock with them so that we were rewarded with an inch-by-inch reveal of his erection. The waistband slid over his knob and his cock flicked back hard, slapping into his stomach, startling both of us with the force.

Having already had him in my hand in the water -- and OK, if we're honest, my pussy too, not that I'm telling Rupali about that -- I knew what to expect in terms of length and girth, but I still couldn't take my eyes off it. I didn't have that much experience; are all cocks this beautiful? It was about seven inches and a nice handful around the middle becoming very thick towards the base; it wasn't the perfect training cock for Rupali's virgin mouth but it would have to do. It had a slight upward curve - which would make it hard to swallow except in a 69 position -- and the main cum-carrying vessel running up the underside bulged out, promising a fast and powerful jet of cum that I had already experienced in my pussy and was now trying to imagine it running down my throat.

Having fucked Spike earlier, I had already decided to lose the Russian roulette game. Mr Gallows had trained me very thoroughly in cocksucking and I felt pretty confident that if Rupali couldn't get him there then I could bring him to the edge of orgasm just in time for us to swap over. As absorbed as we were in his pulsing cock, I hadn't noticed that he had freed my breasts until I felt my nipple sucked into his mouth and his tongue flick over the sensitive surface. I yelped with surprise and sat up; he would need a lesson in taking it slow later on, but since he was about to get a double blow-job I forgave him his enthusiasm.

I looked into Rupali's eyes; they looked a bit apprehensive. "You go first," she whispered.

I crawled forwards until I was straddling Spike, my face over his cock and my bikini-covered pussy right in front of his mouth. I looked down the tunnel between my swaying breasts and saw him looking back at me. "That's there for your viewing pleasure," I warned him. "No touching. Got it?"

"Got it," he agreed.

"We need a timer," Rupali said. We didn't really because I was going to help her win, but I didn't want to let her in on my plans. Spike handed his sports watch forward; it had a second hand we could use to time ourselves.

I gave it to Rupali. "Thirty seconds. Count me down when you get to ten."

I held his shaft gently between two fingertips, not wanting to give him too much contact too soon, and held it up to my lips, foreskin pulled back. There was a drop of pre-cum on the tip, which I licked off without thinking. Yum! Spike's shaft jerked with the contact as Rupali glared at me accusingly for starting early. I gave her an innocent look that said I can't help it, I like the taste.

Finally Rupali said Go. I took the tip between my lips and kissed, moistening it without sucking, slowly getting him used to idea of having his cock in my mouth. I took in a few inches, just touching with my lips, not my tongue, getting him lubricated so that I could slide him in and out. I kept mouth-fucking him like this until Rupali called out 10 seconds, in and out with minimal contact, desensitising his erection so that he wouldn't come too soon.

With a few seconds to go, I swirled my tongue around the tip and gave a gentle suck, pushing him into the roof of my mouth with my tongue and feeling his knob throb back against the contact. I pulled him in and out against harder suction until Rupali called time and then handed him over.

"Watch those nails," I whispered, taking the timer from her. "Nothing hard or sharp on his cock. That goes for teeth, too."

She tentatively took hold of him between her fingertips and looked at me, hoping for some more instructions. I leaned forwards and put my lips next to her ear. "Just hold about half of it in your mouth," I breathed. She opened wide and took a mouthful of cock, making worried noises at the foreign feel of this solid bar of flesh between her yawning jaws. "Hold it there, taste it with your tongue and get a feel for the size of it."

I gave her a few seconds to do that. "Try sucking it. Close it between your tongue and the roof of your mouth and suck. You can do it as hard as you like, just don't touch him with your teeth." I heard Spike gasp behind me; obviously she took me seriously and tried to suck him inside out. Atta girl.

"Try massaging him with your tongue and then stroke him in and out of your mouth. Mix it up, but don't try to do it all at once, though. A hard suck, swirl your tongue, then in and out." I watched her as she followed these instructions, cheeks working and head bobbing on his hard shaft.

"You can hold his balls if you want," I whispered. "Tickle them with those nails or give them a very gentle squeeze. Don't use your hand on his cock, though; that's cheating." She played with his balls, but then lost coordination and forgot to suck. I touched her cheek to remind her. It's like patting your head and rubbing your tummy at the same time: an acquired skill.

She was well past thirty seconds and closing on a minute, so I gave her a ten second warning, counted her down and then took over. I sucked him half way in, tickling his shaft up and down with the tip of my tongue as I squeezed his balls in my palm. When Rupali called ten seconds again, I sucked hard and took in another inch or two, bringing him to the back of my throat. I pulled him all the way out and then sucked five inches back in, tonguing his shaft near my lips so that he could feel how deep I had him. With a couple of seconds to go I sucked as hard as I could and drew him out slowly, his dick throbbing hard against my tongue.

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