Losing the Bet: Overstimulated

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I couldn’t help it. I reached under myself and wrapped my fist round my cock, and the moment I touched it I knew exactly how stupid I’d been.

“Mark.” The slap on my arse rang like a gunshot. “Did I say you could?”

“Sorry. Sorry, I couldn’t, it was too much.”

“I know. That’s what the rule was for.” Her voice went dark and delighted. “So here’s your penalty. You’re going to come. Right now. And I am not going to stop.”

“What?”

She pulled my hand away and drove deep. I came almost at once, shouting into the pillow, a hot, pulsing release that went on and on. And Elena kept fucking me. Slow, steady, relentless. My cock was tender and swollen, and every thrust pressed that spot inside me, and the pleasure turned sharp and prickly and almost unbearable, and I started to laugh and swear all at once.

“Oh my God. Oh my God. Elena, no, yes, no, oh my God.”

“Is that a safeword?”

“No!”

“Then you’ll keep taking it.” She grabbed my hips and ground into me, and I came a second time, dry, shuddering, a strangled yell, my legs completely gone. Then she slowed, eased out and rolled me on my back, where I lay gasping like a landed fish.

“Mercy,” I managed.

“That’s not the safeword either.” But she was grinning. She lay down beside me and kissed my wrecked mouth. “Next time, hands off.”

I could not feel my toes.

Ending 6 of 16: Overstimulated. Go back and try a different choice for the full happy ending.

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Losing the Bet: Earned

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“Please,” I said. “Make me earn it. Please, Elena. I want to earn it.”

She went very still behind me. When she spoke again her voice was warm and rough, a voice I’d only ever heard in my head.

“Oh, you perfect, filthy thing. All right. Earn it.”

She fucked me deep and slow, hips snapping, one hand gripping my shoulder, the other still wrapped loosely round my cock. “Count for me. Every time I push in, you say thank you. And I want to hear it.”

“Thank you.” Push. “Thank you.” Push. “Thank you, Elena.”

I lost count at thirty. She edged me with her fingers every time my voice cracked, and I knew I’d never been so full, so open, or so utterly helpless. My cock was leaking onto the sheets. I was sweating, shaking, sobbing little noises into the pillow. When she changed the angle and the head of the strap-on pressed hard against my prostate, I felt a light go on inside me and thought, this is it. This is what everyone’s been talking about.

“You’ve been so good,” she panted. “So brave. Do you want to come?”

“Yes. God. Please.”

“Then come, Mark. Right now.”

She stroked me three times, hard and fast, and I came with a roar, hot ropes across the duvet, my whole body convulsing around her while she held me through it. She slid out and gathered me up, trembling and soaked, against her chest.

“Same time next Friday,” she whispered into my hair, “and I think you should let me pick the category.”

She was already planning a second list.

Ending 5 of 16: Earned. You found the full happy ending.

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Losing the Bet: Too Late

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“I’m sorry,” I said. “Elena, I’m sorry. I didn’t mean it. Please.”

“Oh, Mark.” She turned off the vibrator. The silence in the room was awful. “That is the first thing you’ve said tonight that you meant, and I’m afraid it’s too late.”

“Too late?”

“You smirked. I gave you a chance. You made your choice.” She unbuckled the cuffs, one after the other, with a gentleness that was somehow worse than anger. Then she sat on the edge of the bed, naked and glorious, and picked up the pink vibrator, and I understood.

She used it on herself while I lay beside her. She didn’t touch me. She didn’t let me touch her. She stroked her breasts with her free hand, pressed the toy against her clit and rolled her head back against the pillow. I watched her fall apart, shuddering and gasping, thighs squeezed tight, saying my name, my actual name, in a voice that made my balls ache.

When it was over she kissed my forehead, switched off the lamp and rolled over.

“Night, Mark. No orgasm for naughty boys. Ask me nicely in the morning.”

I lay awake until three, hard as stone, listening to her breathe. At seven I woke to the smell of coffee. She put a mug on my bedside table and said, without looking up from her phone:

“You may begin asking.”

I did. For a very long time.

Ending 4 of 16: Too Late. Go back and try a different choice for the full happy ending.

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Losing the Bet: Toast Break

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I kept smirking. I regretted it immediately and I did it anyway.

“Is that all? Honestly, Elena, I’ve had better foreplay from a dentist.”

Elena looked at me for a long, long time. Then she switched off the vibrator, put it on the bedside table, pulled on my hoody and walked out of the room.

“Elena?”

I heard the kitchen light click on. The toaster went down. I lay there, spread and tied, harder than I’d ever been in my life, listening to a woman butter bread.

She came back eating a slice, sat on the edge of the bed and did not look at me. I said her name. She chewed. I apologised. She brushed crumbs off her knee. I said please, in six different voices, and she smiled quietly at the wall.

Then she finished the toast, wiped her fingers, pulled the hoody off over her head and knelt over my face.

“Since you’re so good with your mouth,” she said, “let’s find out.”

She tasted of nothing but warm woman. I licked her, deep and hungry and apologetic, and she ground against me, one hand fisted in the headboard, coming with a shuddering gasp on my tongue. Then she slid down, rolled a condom over me and took me in, and rode me hard and fast until I was begging.

“Come,” she said. “I forgive you. Mostly.”

I came so hard the bed rocked.

“You’ll make the toast tomorrow,” she said, and kissed me.

Ending 3 of 16: Toast Break. Go back and try a different choice for the full happy ending.

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Losing the Bet: Ruined

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“Please let me come now,” I said. “Right now. I can’t take any more.”

“Greedy.” But her eyes were gleaming. “All right, Mark. Since you asked so nicely.”

She took my cock in her fist and stroked, quick and firm, with that perfect twisting motion on the upstroke that she knows I can’t resist. The pressure rose in me like a wave. My toes curled. My hips lifted off the bed. I heard myself saying her name, over and over, and I knew it was coming, it was coming.

Elena took her hand away.

She lifted both palms into the air, like a surgeon. I came anyway, helplessly, in long, slow, useless spurts that ran down my cock and over my balls, without a single spark of the proper pleasure, my whole body clenching around nothing. It felt like falling down a flight of stairs in slow motion.

“Oh, that was lovely,” Elena said, deeply satisfied. “Ruined. Look at you.”

“You evil, evil woman.”

“You asked me to let you come. I said all right. I didn’t say how.” She grabbed a tissue and, with great tenderness, wiped me clean, then undid the cuffs and kissed each of my wrists. “Don’t sulk. That’s one of the best things I’ve ever seen.”

I lay there, spent and gutted and strangely grateful, while she curled up next to me and laughed into my shoulder. I did forgive her.

Eventually.

Ending 2 of 16: Ruined. Go back and try a different choice for the full happy ending.

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Losing the Bet: Good Boy

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“Thank you,” I said. “Thank you, Elena. Whatever you want.”

Her smile went soft and dangerous. “That’s the right answer.”

She let the head of my cock slip inside her, a slow, wet inch, and I groaned so loudly she laughed. Then she sank down all the way, tight and scalding, and rested her forehead against mine while I shook underneath her.

“Look at me,” she said. “Don’t you dare close your eyes.”

I looked. She rode me slowly at first, rolling her hips in long, deep circles, her breasts swaying above my face, her breath hot on my mouth. My wrists strained at the cuffs. I wanted to grab her arse, her waist, anything, and couldn’t, and that made it better. She got faster, one hand braced on my chest, the other between her legs, her thighs slapping against mine.

“Not yet,” she panted. “Not until I say. Hold it. You’re doing so well.”

“I can’t. Elena, I can’t.”

“You can. Good boy. Good boy.” She came first, her whole body clenching around me, a cry cracked open in her throat, her head thrown back. I felt every ripple.

She caught her breath, bent down and bit my ear.

“Now,” she whispered. “Come for me.”

I came with a shout that I think the neighbours heard, harder than I’d ever come in my life, my back arching off the mattress, filling her while she rocked through the aftershocks. She unbuckled me, kissed my sore wrists one at a time, and collapsed on top of me, laughing.

“Best bet you ever lost,” she said.

Ending 1 of 16: Good Boy. Go back and try a different choice for the full happy ending.

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Sparring Partners: Tapping Out

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I slapped the mat twice, rolled out from under her and walked out of the sports hall with my head high and my face on fire.

“Running away?” Kat called after me, and half the office laughed.

I made it to the corridor before my legs went. I leaned on the wall by the vending machine and pressed my hands to my cheeks. It wasn’t the humiliation. I’d survived two years of humiliation. It was that the second her knee had pressed between my thighs, my body had said oh, hello, and I hadn’t been able to talk it out of it.

I hated her. I’d hated her for two years. That was the whole point.

I went up to my room, got into my swimsuit, wrapped the hotel robe round myself and went to find somewhere hot to sulk. The spa terrace had three outdoor hot tubs under a string of lights, steam curling into a cold October night. Two were taken by a couple from Marketing. The third was empty, bubbling gently.

From behind me, in the corridor, I heard footsteps. Long, unhurried ones. I knew those footsteps. I’d heard them walking past my desk to every promotion I’d ever wanted.

I had about ten seconds to decide where I wanted to be.

→ I slip out to the hot tub on the terrace

→ I go up to my room and lock the door

Sparring Partners: Count of Two

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“Two!” Gareth bellowed, and I stopped thinking.

I bucked my hips, hooked my heel behind her knee and rolled us both, and for one beautiful second Kat Marlowe’s eyes went wide. Then it was her back on the foam and me on top, my knees either side of her ribs, her wrists in my fists.

“Three! Dani wins!”

The department whooped. Somebody from Finance threw a towel. I barely heard it, because Kat was looking up at me, flushed to the collarbones, ponytail wrecked, and she wasn’t angry. She was grinning, slow and wicked, and she flexed her wrists against my grip just enough for me to feel how strong she was and how much she was letting me hold her.

I should have let go. Instead I felt her ribs rising and falling between my thighs, her stomach hard and slick under my hands, and a heat low in me that had nothing to do with the radiators.

“Get off me, Dani,” she said softly. Then, lower, so only I could hear: “Or don’t.”

I let her up. She stood, tall and sweaty, and leaned in as if to congratulate me.

“Rematch,” she murmured against my ear. “No Gareth. No audience. Hotel gym at ten, if you’ve got the nerve.” Then, loudly, for the room: “Well played, Dani!”

I had a choice. Her turf, a locked-down gym at night. Or somewhere hot and neutral. The sauna downstairs was open until midnight.

→ I tell her I’ll see her in the gym at ten

→ I tell her the sauna at nine, or not at all

Sparring Partners: Room 214

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I went upstairs two at a time, locked myself into Room 214 and chained the door, like she was a burglar. Then I got in the shower and stood there until the water ran lukewarm.

It didn’t help. Every time I shut my eyes I felt her weight again. The knee. The ponytail. The way she’d looked down at me and breathed, “One.”

I towelled off, pulled on an old Calloway Digital charity-run T-shirt and nothing else, and sat on the bed with my phone. I scrolled through a draft email to HR about Kat’s conduct, which I’d been writing in my head for two years. I couldn’t think of a single thing she’d done wrong tonight except being unbearably, unfairly hot.

A knock on the door.

Three slow raps, the kind that sound like a smirk.

“Dani,” said a voice through the wood. Low, a bit rough, minus its usual swagger. “I know you’re in there. I can see your light under the door.”

I didn’t move.

“I brought wine,” Kat said. “And I’m not here to win anything. I wanted to say that was out of order, in front of everyone. And that I’m sorry. And that I’d like to say it to your face rather than your door.”

I looked down at my bare legs. At the chain. At the T-shirt that barely covered my arse.

On the other side of the door, I heard her slide down the wood and sit.

→ I take the chain off and open the door

→ I stay put and talk to her through the door