Losing the Bet: The Harness

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“What’s that?” I asked, though I knew exactly what it was, and so did she.

“That,” Elena said, lifting it out of the bag by its harness and letting it dangle between us, “is Mr Plum. I bought him eight months ago, the night you said you were curious. I’ve been waiting for the right moment.”

I had said I was curious. After a bottle of wine and a very good film. I’d honestly assumed she’d forgotten.

“Do you still want to?” She sat me down on the bed, kneeling in front of me, hands on my thighs. Her voice dropped out of the game and into something warm and real. “Properly. Tell me now, because there’s no shame in no. We go as slow as you need. We stop whenever you say.”

“I want to,” I said. My voice cracked. “I’m scared. But I want to.”

“Good. Scared is allowed.” She kissed my knee. “On your front. Hips up.”

I lay face down with a pillow under my hips, my cock trapped hot and heavy against the duvet, and heard the click of the lube bottle. Cold gel, then her fingertip circling me, patient, teasing. I clenched.

“Breathe out,” she murmured. “Good boy. Let me in.”

One finger slid inside. The stretch burned, then softened, then turned to something deep and dizzy. She curled it, found a spot that made me see white, and I groaned into the pillow.

Behind me, I heard the buckles of the harness.

→ I tell her I’m ready, and ask her to go slow

→ I get overwhelmed and say marmalade

Losing the Bet: Cuffs

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I held out my wrists like I was being arrested, and Elena smiled like I’d given her a present.

“Up on the bed. On your back.”

The leather cuffs were soft inside, lined with fleece, and she buckled them snug with a care that made my throat tight. Then she clipped them to the slats of the headboard, one, two, and tugged to check. I couldn’t move my arms more than an inch. I’d never felt so exposed, or so hard.

“Colour?” she asked.

“Green. Very green.”

“Good.” She took off the hoody. Underneath she was wearing the black lace set I’d given her for her birthday and she’d never worn for me, until now. “I’ve been saving this.”

She straddled my chest and kissed me, slow, biting my lip. Then she reached into the bag and came back with a single ice cube, which she ran down my sternum, across my belly, round and round my nipples until I was gasping. She followed the water with her tongue.

When she finally took my cock in her mouth, I nearly shouted. She was slow, wet, merciless. Every time my hips lifted she pulled off and blew cool air over me, and my whole body strained against the cuffs.

“Do you want to come, Mark?”

“God, yes.”

She laughed, low in her throat, and licked one slow stripe up the underside.

“Then you’ll have to decide how to ask,” she said.

→ I beg her politely

→ I smirk and tell her she’s not even close to breaking me

Losing the Bet: Not Tonight

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“No,” I said. “Not tonight. Sorry. I want it to be just us.”

I braced myself for disappointment, or an eye roll, or, worse, a very long, level look. Instead Elena put her phone down on the cushion beside her and let out a long breath, as though she’d been holding it for a full minute.

“Thank you,” she said. “That’s exactly what I hoped you’d say. Well, not exactly. But it’s the right answer.”

“You wanted me to say no?”

“I wanted you to feel that you could.” She leaned over and typed, read it aloud as she sent it. “Change of plan, Z. Sorry, big love, rain check. Nothing wrong. Another night.” Three dots, a thumbs-up, a row of aubergines. “She says you’re a sweetheart and she’ll be keeping the prosecco.”

She crossed the rug and sat down in front of me, so we were eye to eye. Her hands cupped my face.

“I’m serious, Mark. If a game like this only works when you say yes to everything, then it isn’t a game. It’s a trap. I didn’t want a trap. I wanted you to trust me, and I wanted to be someone you could say no to.” Her thumb stroked my cheekbone. “Which, by the way, is rather sexy of you.”

She kissed me. Slow, warm, tasting of wine. Her hand slid down my chest and into my boxers, and my whole body answered at once.

“Now,” she said against my mouth. “I’m still the one who won. So I’m still giving the orders.”

→ I ask her what she’d like me to do

→ I joke that Zoe can come for pizza instead

Losing the Bet: Prosecco

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Zoe arrived in nine minutes with a bottle of prosecco in each hand and a tote bag over her shoulder, looking delighted.

She’s twenty-eight, small and curvy, with black curls, a dusting of freckles and a laugh you can hear through two walls. She kissed Elena on the mouth, a quick, familiar peck, and looked me up and down. I was in my boxers on the rug. I wanted to die.

“Hello, Mark,” she said. “You look nervous. That’s nice.”

“Zoe,” I said.

“Safeword?”

“Marmalade,” Elena and I said together.

“Brilliant. I’ll keep it in mind.” She poured three glasses and handed me mine without taking her eyes off my chest. “So Elena tells me you got the Tigris wrong.”

“Euphrates.”

“Idiot.” She said it fondly. She curled into the armchair, and Elena sat on the arm beside her, one hand resting on Zoe’s shoulder. The two of them looked down at me, flushed and fond and wicked, like cats with a mouse. “Elena says you’re going to be good tonight.”

“I’m going to try.”

“Good. We’d like to see you try.” Zoe nudged me with a bare foot, and slid it slowly up my thigh, until her toes brushed the front of my boxers and found how hard I was. She smiled.

“Elena,” she said. “Do I get to touch?”

“That depends on him.” Elena’s eyes were on me, bright and steady. “Mark? Where do you want Zoe tonight? Hands on, or just a very good view?”

→ I ask Zoe to touch me

→ I say she can watch, but not touch

Losing the Bet: Banked

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“I’ll bank them,” I said. “Save them for later. Make it a long weekend.”

Elena stared at me. Then she started to laugh, a real helpless laugh, and sank back onto the cushions with her hand over her face.

“You’ve won ten minutes of absolute power over me,” she said, “and you want to save it. Like air miles.”

“I want to use it wisely.”

“Oh, you are such a Libra.” She wiped her eye. “Fine. Banked. But banked time earns interest, Mark. Look it up. That’s how banks work.” She stood, stretched, and the hoody rode up over her stomach in a way that I tried, and failed, to ignore. “Every minute you hold back, I get two. Which means you’ve just given me twenty.”

“That’s not how interest works.”

“It is in this flat.” She picked up the black holdall from beside the sofa, where it had been sitting all along. I hadn’t noticed. She unzipped it and tipped out a set of cuffs, a blindfold, a little bottle of oil. “I’ve been very patient. I’ve been planning this since the day you mentioned wanting to try something.”

“I mentioned it once.”

“After a bottle of wine. Which I wrote down.” She held up the blindfold and tilted her head at me with enormous kindness. “So. You can ask me exactly how much interest, or you can use your ten minutes right now, while I’m gloating. I’d say I’m at my most beatable.”

She was. She was flushed, grinning, off balance, and holding a blindfold in one hand.

→ I ask her how much interest I owe

→ I use my ten minutes right now, mid-gloat

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