Losing the Bet: Ten Minutes

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“Bedroom,” I said. “Now.”

I’d never given Elena an order in my life. It came out as a squeak. She looked at me with great interest, got up off the sofa and walked ahead of me, the timer ticking on her phone, glancing back over her shoulder.

“Nine minutes forty,” she said.

“Stop talking.” Better. Deeper. “Strip. Slowly. And sit on the edge of the bed.”

She pulled the hoody over her head and let it drop. Then the leggings, with a little wriggle. Underneath was nothing at all, just soft skin and a thin trimmed strip of dark hair and the swallow tattoo on her hip. She sat on the edge of the bed and looked up at me, and I realised with a jolt that she was blushing.

“You’re good at this,” I said, amazed.

“Shut up, Mark. Eight minutes.”

I knelt between her thighs. They were already trembling. I kissed the inside of one knee, then the other, then higher, until she was breathing in little stuttering gasps and her fingers were in my hair. When I put my mouth on her she was hot and slick and tasted like nothing else on earth. I licked her slowly, with the flat of my tongue, then circled her clit with the tip until her hips began to roll.

“Seven minutes,” she said, in a very thin voice. “Oh. Oh, that’s, keep doing that.”

I reached into the open holdall beside the bed, felt something smooth and heavy, and pulled out the purple strap-on.

She saw it. Her eyes went huge.

→ I put it back and keep using my mouth

→ I buckle the harness on myself and ask her to ride

Losing the Bet: Marmalade

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It happened between one breath and the next. Her second finger, a flicker of panic, and my body locking up like a fist. My heart was hammering. My eyes were stinging.

“Marmalade,” I said.

The word had barely left my mouth when she stopped. Not slowed. Stopped. Her hands came off me, the finger withdrew as gently as a whisper, and she was somewhere beside me on the bed, on her side, one palm flat and warm on my back.

“I’ve got you,” Elena said. No game in her voice at all. “I’m right here. You did exactly the right thing. Breathe with me. In. Out.”

I breathed. The hot stinging in my eyes spilled over and I pushed my face into the pillow, mortified.

“Don’t hide. There’s nothing to hide.” She took off the harness, the whole thing, and set it on the floor out of sight. She pulled the duvet over my shoulders and lay down against me, still in her lace, her chin on my shoulder. “Can I hold you?”

“Please.”

She wrapped herself round me, warm and solid. “Do you know I was scared, too? Not of you. Of getting it wrong. I love you, and I wanted tonight to be good for you.”

“It was good,” I said, wetly. “Then it was a lot.”

“That’s allowed. That’s exactly why we have a word.” She kissed the back of my neck. “So. What do you need now?”

→ I ask her to just hold me tonight

→ I tell her I’d like to try again, but softer

Losing the Bet: Mr Plum

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“I’m ready,” I said into the pillow. “Slow, please. Please go slow.”

“Slow.” Her hand stroked down my spine. “Always. Tell me everything.”

A second finger, then a third, patient and slick, until I was loose and shaking and pushing back to meet her. Then the pressure of something broader, smooth and firm, nudging at me. “Breathe out. That’s the head. Let me in, Mark.”

I breathed out and it slid inside. A hot, heavy stretch, burning for a second, then easing, then spreading into a fullness I’d never known. I groaned, a long, dirty sound that I didn’t recognise as mine.

“There,” she whispered. “Good boy. Look at you taking it.”

She pushed in an inch at a time, one hand firm on my hip, until I felt her pelvis against my arse. She stayed there, perfectly still, while I panted and my cock throbbed against the duvet. Then she pulled back, slowly, and pushed in again, and the angle caught that spot inside me and every nerve I owned lit up.

“Oh God. Elena.”

“That’s it.” She found a rhythm, deep, steady strokes, and reached under me, wrapping her fingers round my cock without moving them. “Feel that? You’re so hard. So hot. You’d come in seconds if I stroked you, wouldn’t you?”

“Yes.”

“But you don’t come until I say.” She slapped my arse, a firm, bright sting, and drove deeper. “Do you understand?”

I understood. I was a heartbeat from ruin, and she knew it.

→ I say please and tell her to make me earn it

→ I can’t wait and grab my cock myself

Losing the Bet: Cheek

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I smirked. I don’t know what came over me. Maybe it was the leather round my wrists, or the idea of Elena pretending to be impossible.

“Is that your best?” I said. “I’ve had firmer handshakes.”

Her eyebrows went up. The room went very quiet. I felt the first cold trickle of regret.

“Oh, Mark.” She said it with something like affection. “You really shouldn’t have.”

She climbed off me, slowly, and crossed to the bag. She came back with a long black feather and a small pink vibrator, which she held up so I could see it buzz. “I wasn’t going to use these until later. But since I’m not even close to breaking you.”

The feather came first. She trailed it down the inside of my arm, across my ribs, over my nipples, along the crease of my thigh, avoiding the one place I wanted it, over and over, until the whole of my skin was singing and I was thrashing against the cuffs. Then she put the vibrator against the underside of my cock, on the lowest setting, and watched my face.

“Still smirking?”

I was not smirking. I was biting the inside of my cheek hard enough to taste blood.

“Last chance,” Elena said, and turned the dial up one notch. “Say sorry, or say nothing. Your choice. But choose carefully, because I’ve got all night, and you have somewhere to be, which is under me.”

→ I keep up the cheek

→ I take it back and say sorry

Losing the Bet: Please

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“Please,” I said. “Please, Elena. May I come?”

“Is that it?” She propped her chin on my thigh and looked up at me, mouth shiny, eyes bright. “That was a very small please.”

“Please. Please, I’ll do anything. I need to come. Please, Elena, please.”

“Better.” She wrapped her hand round me, loose and slow, and my hips jerked against the cuffs. “Louder. And look at me when you say it.”

She edged me three times. Three. She stroked until my breathing went ragged and my thighs shook, then let go and sat back with her hands in her lap while I swore at the ceiling. The second time she added her mouth, hot and tight, and stopped one heartbeat before the end. The third time she dragged her tongue over my balls and pressed a thumb to the spot behind them, and I howled.

“You’re so pretty when you beg,” she whispered. She climbed up my body, naked now, her lace discarded somewhere, and hovered above my cock with her thighs trembling either side of my hips. I could feel her heat and her wetness, and I could see she wanted this almost as badly as I did.

“Tell me what you’re going to say when I let you.”

“Thank you.” My voice was a croak. “Thank you, Elena.”

“Mm. Or do you want to tell me what you want?” She brushed the head of me against her, just that, nothing more. “You can ask. I might say yes.”

→ I thank her and take whatever she gives me

→ I ask her to let me come right now

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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