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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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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