Losing the Bet: Pizza and Promises

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“Zoe can come for pizza instead,” I said. “As long as she’s wearing trousers.”

Elena looked at me for a full three seconds. Then she threw back her head and laughed, and typed it word for word.

Zoe replied with a single gif of a pizza on fire.

Twenty minutes later I was sitting on the sofa in my jeans and an old jumper, having been permitted to dress, eating a slice of pepperoni while Zoe told us about the guy she’d been seeing who owned a ferret. Elena was beside me with her legs across my lap. Every time I reached for another slice, her hand slid higher up my thigh. Zoe noticed. Zoe noticed everything.

“You two are filthy,” she said, around a mouthful of crust.

“We’re having a quiet night in,” said Elena.

“You’ve got him wired like a bomb.” Zoe finished her wine and winked at me. “Next weekend. I’m free. Just saying. I’ll bring the prosecco and my own safeword.”

“It’s marmalade,” I said.

“I’m going to need a better one.”

When the door finally shut behind her, Elena was off the sofa and in front of me before I could draw breath. She pushed me back against the cushions, unbuttoned my jeans and sank down onto me in one slow, wet slide, her forehead against mine.

“Good boy,” she murmured. “Pizza and promises.”

I came with her mouth on mine, and the pizza box going cold on the floor.

Ending 16 of 16: Pizza and Promises. Go back and try a different choice for the full happy ending.

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Losing the Bet: Gold Star

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“What would you like me to do?” I asked.

“Everything.” She stood and pulled me up by my hands. “Get me a glass of water, then come and find me in the bedroom, and bring the lamp.”

I did exactly that. She was lying on the bed in nothing at all, hair spilling over the pillows, and she crooked a finger. “Kneel. Mouth. Take your time.”

I settled between her thighs and took my time. I kissed her slowly, from her knees up, through the soft dark curls to the place she’d been waiting for. I licked the flat of my tongue against her again and again until her hand found my hair and she began to rock against my face. She came with a long, deep moan and told me I was perfect.

“Up here,” she said. “I want to look at you.”

She wrapped her legs round my hips. I slid into her slowly, face to face, her hands cradling my jaw, her eyes locked on mine. The pace was gentle. The whole thing was gentle, and filthy, and enormously tender at once. She kissed me and whispered the things she’d wanted to say all night. How proud she was. How much she loved me. How much she’d wanted this.

“Now,” she said, and I came inside her with a long, shuddering gasp, and she held me through the whole thing.

Later, in the dark, I felt her press something small and sticky onto my chest.

“Gold star,” she whispered. “For saying no. You’ve earned it.”

I wore it to bed.

Ending 15 of 16: Gold Star. Go back and try a different choice for the full happy ending.

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Losing the Bet: Front Row

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“Watch,” I said. “Just watch. Please. I’m not sure I could cope with more.”

Zoe grinned and sat back in the armchair, tucking her bare feet under her. “A front row seat. Brilliant.”

Elena had me on the bed in minutes, face down, hips lifted. The cuffs, the pillow, the lube. Zoe pulled her chair up to the end of the mattress with her prosecco, her dress hitched up round her waist, and I realised she wasn’t wearing any knickers and was touching herself, slowly, with two fingers.

“Talk him through it,” Zoe said. “I want the commentary.”

“He’s very tight.” Elena’s voice was calm, businesslike, and utterly filthy. “I’m going to put two fingers in. See how he opens up? He’s so good at this. Aren’t you, Mark? Tell Zoe.”

“I’m good,” I said, into the pillow.

“Louder.”

She slid the strap-on into me slowly, and I moaned. The two of them looked down at the long, hard line of my body taking it. Zoe’s breathing was loud. Elena drove in deeper, her hand on my back, and said, “Now, Mark, you’re going to hold it for the audience.”

I tried. I really tried. But I could hear Zoe’s wet fingers, and feel Elena’s eyes, and the tightness hit me all at once like a train.

I came untouched in forty seconds, with a yelp.

There was a silence. Then Zoe began, solemnly, to clap.

“Forty seconds,” Elena said, withdrawing, with an air of enormous disappointment. “Is that a record?”

“I think it’s a personal best,” said Zoe.

I hid my face.

Ending 14 of 16: Front Row. Go back and try a different choice for the full happy ending.

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Losing the Bet: Two Mistresses

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“Touch me,” I said. “Both of you.”

Zoe’s smile turned wicked. She slid off the chair onto her knees on the rug, put her hands on my chest and kissed me, a soft, curious, wine-sweet kiss that had Elena watching us with her lip caught in her teeth. Elena stood and fetched the cuffs.

Between them they got me onto the bed, wrists clipped, ankles loose. Zoe pulled her dress over her head. She was lush and freckled and wore nothing under it. Elena stripped too, slowly, and the two of them knelt on either side of me and kissed over my face, a long, hungry kiss with a lot of tongue.

“Who goes first?” Zoe asked.

“You.” Elena’s voice was husky. “Sit on his face. Mark, use your mouth.”

Zoe straddled me, her thighs warm against my ears, and I licked her. She was salty and sweet and so wet she dripped down my chin. She rode my tongue and gasped and swore, while Elena crawled between my legs and took my cock into her throat. I groaned into Zoe, and she shuddered and came with a cry, her fingers twisted in Elena’s hair.

They switched. Elena sank down onto me, and Zoe kissed her, then bent to suck my fingers, my nipples, my neck. They were laughing and moaning and giving orders, and I was just a pair of hands and a mouth and a cock.

“Come,” Elena said, finally. “Come for us.”

I did. Gloriously. Loudly. Twice as long as I’d ever managed.

“We’ll do that again,” said Zoe, lying across my stomach.

“Next weekend,” said Elena.

Ending 13 of 16: Two Mistresses. Go back and try a different choice for the full happy ending.

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Losing the Bet: Ambush

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I didn’t think. I lunged.

I’d like to say it was a clever tactical decision. It was more like a man who had been told to be patient for far too long. I grabbed her wrist, spun her round and shoved her gently backwards onto the sofa, and she let out a shriek that was half outrage, half joy.

“Mark! You absolute”

Unfortunately my foot caught the coffee table.

The bottle of red went over in a long, slow, beautiful arc and emptied itself onto the cream rug. We both froze. Elena stared at the stain spreading through the weave. Then she looked up at me with her mouth open, her hoody half off, and I watched her decide between fury and hysterics.

She chose hysterics. She laughed so hard she cried. I laughed too, until I was clutching my stomach on the floor.

“Salt,” she gasped. “Get the salt. Naked, if you please. I like the view.”

I scrubbed a rug at midnight in my boxers while a woman in my hoody supervised from the sofa with her feet in my lap. She directed me with a wooden spoon. She tapped my arse with it when I missed a spot, and I felt myself harden through the whole ridiculous thing.

Afterwards she took pity. Under a tea towel, on the sofa, with enormous patience, she gave me a slow handjob while telling me exactly what she planned to do to me next week.

“The ten minutes are void,” she said. “You broke the rug.”

It was worth it.

Ending 12 of 16: Ambush. Go back and try a different choice for the full happy ending.

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Losing the Bet: Compound Interest

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“How much interest?” I asked, which was the wrong question, and also the right one.

“Let’s find out.” She slipped the blindfold over my eyes, buckled the cuffs round my wrists, and I felt my hands pulled gently above my head. “Twenty minutes, remember. But I like to round up.”

She rounded up to an hour.

I lost all sense of time. There was only the dark, the sound of her breathing, and her hands. Warm oil spread across my chest and belly and thighs, long, slow strokes that made me shiver. Her mouth on the inside of my wrist. Her teeth on my hip. A feather-light touch along my cock, there and gone, over and over. When I pleaded, she shushed me. When I swore, she laughed. Twice she brought me right to the edge and sat very still, her fingers circling my balls, until the urge faded and I whimpered with relief and despair.

Finally I felt her weight settle over me. She slid down on my cock, hot and slick and impossibly tight, and I made a sound that I think was her name.

“This is the balance,” she whispered. “Everything you owe me, with interest. Every minute you saved.”

She rode me, slow, deep, tight little circles, one hand on my chest, until her breath broke and she clenched around me, and I heard her say, “Now. Good boy. Now.”

I came like I was falling off a cliff.

She took off the blindfold. Her eyes were wet and shining.

“Balance carried forward,” she said, and kissed me.

Ending 11 of 16: Compound Interest. Go back and try a different choice for the full happy ending.

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Losing the Bet: Turned Tables

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I stood up, stepped into the harness, pulled the straps tight and heard myself say, in a voice I didn’t recognise, “On your back, Elena. Knees up.”

She stared at me. At the silicone jutting out in front of me, shiny with lube. At my face. For the first time in the six years I’d known her, Elena was lost for words.

“I’ve never,” she began.

“Do you want to?”

She looked at it again. Her thighs shifted. “Seven minutes,” she whispered, which I decided was a yes.

I eased her down and pushed in slowly, one inch at a time. She was so wet that the toy slid in almost easily, and she gasped and gripped my forearms, and her eyes widened and then fluttered closed.

“Oh God. Oh, you bastard. That’s, oh, that’s good.”

I fucked her slow and deep, long strokes that made her toes curl. I leaned over to kiss her, and she kissed back like a woman starving, her legs wrapped round my waist, heels digging in. When she climbed on top to ride it, I held her hips and watched her take it, her head thrown back, the swallow on her hip tilting with every roll. She came with a cry, shaking and swearing, and collapsed forward onto my chest.

“If you ever tell anyone,” she said, still panting, “I will kill you.”

Then she slid down my body and took my cock in her mouth, and I came in under a minute.

The timer beeped. She wiped her mouth.

“Back in the bag,” she said. “Next weekend, you’re on your knees.”

Ending 10 of 16: Turned Tables. Go back and try a different choice for the full happy ending.

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Losing the Bet: Time’s Up

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I put the strap-on back in the bag, to her visible disappointment, and went back to work with my mouth.

She tasted incredible. I sucked her clit gently between my lips and flicked it with my tongue while sliding two fingers inside her, curling them upward. She let out a long, shaky moan and fell back on the bed, her knees dropping open, one hand pressed to her mouth.

“Five minutes,” she gasped. “Mark. Oh, Mark. Don’t stop. Don’t you dare stop.”

I did not dare. I licked and sucked and stroked until her thighs clamped round my head, and she came with a wail that she bit off in her fist. I kept going. A second one rolled through her almost at once, harder, her back arching off the sheets. By the time she pushed my head away she was pink to the collarbone, dazed and boneless.

“That’s,” she said, and swallowed. “That’s not ten minutes.”

The phone began to beep.

She looked at it. She looked at me. Then she rolled me onto my back so fast I didn’t see it coming, snapped a cuff round my left wrist, clipped it to the headboard and straddled my hips.

“Time’s up,” she said. “The bet resumes. With interest.”

“You’re not even dressed.”

“Neither are you.” She took my cock in her hand, slick and unhurried. “I’m going to ride you until you’ve paid it all back.”

It took a very long time. Nobody was counting.

Ending 9 of 16: Time’s Up. Go back and try a different choice for the full happy ending.

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Losing the Bet: Softer

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“Can we try again?” I asked, an hour later, after the tea and the toast and the slow, wordless cuddle that had put me back together. “But softer. Smaller. On my terms.”

Elena propped herself on one elbow. “Are you sure? Not because you think you owe me?”

“I want to. Properly. I just want to go at my pace.”

“Then that’s exactly what we’ll do.” She slipped out of bed and came back with a different toy, slim and curved and a gentle shade of blue. “I bought this one first. I’ve been saving it for a rainy day. This is the rainy day.”

She had me on my side, her chest against my back, my knee drawn up, one arm wrapped round me so I could feel her heartbeat. She used plenty of lube. She stopped every minute to ask me how I was doing. The first slide of the toy was a slow, warm stretch, nothing like the panic of before, and my body opened for it with a long groan of relief.

“Good?” she whispered.

“So good. Don’t stop.”

She rocked it in a tiny, patient rhythm, and her hand slid down my belly and took my cock, slow and slick. The pressure built from deep inside, warm and rolling, and when I came it was gentle, trembling and long, my face wet against her arm.

“Next weekend,” she murmured, “we can try the big one. If you want. And only if you want.”

I pressed back against her and said, “Rain check.”

She laughed into my hair.

Ending 8 of 16: Softer. Go back and try a different choice for the full happy ending.

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Losing the Bet: Marmalade on Toast

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“Just hold me,” I said. “Is that all right? I don’t need anything else. I just need you.”

“That’s more than all right.” She tugged the duvet higher and pulled me back against her until we were spooned, her breasts soft against my shoulder blades. “That’s the whole point.”

We lay like that for a long time. Her breath on my neck. Her thumb tracing slow circles on my hip. I told her what had gone through my head, the sudden panic, the stupid fear of disappointing her, and she told me it was never stupid, and that she’d been secretly terrified I’d say no to all of it. We both laughed at that, a bit wetly.

“Are you hungry?” she said, around midnight.

“Starving.”

She went out in my hoody and came back with a plate of buttered toast and a jar of marmalade, which she set solemnly between us on the duvet.

“I’ve ruined it forever,” I said. “I’ll never eat this again without flinching.”

“Or you’ll eat it and think of how brave you were tonight.” She fed me a corner. “Eat.”

Afterwards, in the dark, my cock stirred against her thigh, sleepy and shameless. I asked, and she said yes, and she took me in her hand, slow and unhurried, until I came quietly with my face in her hair.

“There,” she said. “Aftercare complete.”

I was asleep in two minutes.

Ending 7 of 16: Marmalade on Toast. Go back and try a different choice for the full happy ending.

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