Losing the Bet: Small Print

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“Wait,” I said. “Before I agree to anything, I’d like to review the terms.”

Elena raised one eyebrow. She did it slowly, with enormous pleasure. “Review the terms.”

“It was a bet. Contracts have clauses. I’d like some say in how this goes.”

“Mark.” She leaned forward, elbows on her knees. “You lost. You’re negotiating from your boxers. Well, from your jeans, but we’ll fix that.” Her mouth twitched. “Go on, then. What do you want?”

“A rematch,” I said. “Double or nothing. One question. If I win, the bet’s off. Or at least reversed.”

“And if you lose?”

“Then I’ve lost twice.”

She laughed, properly, head back, and I felt that familiar flutter of pride at having made her do it. Then she went quiet and looked at me with her head tilted, the way she looks at a spreadsheet that’s about to surprise her.

“You’re nervous,” she said. “That’s why you’re talking. That’s fine. It’s allowed. But you should know every bit you bargain away goes on the list for later, with interest.”

“There’s a list?”

“There’s always a list.” She picked up her phone and began typing. “Two options, because I’m kind. One, I give you your rematch, one question, my choice of category. Two, you ask me what else is on the list, and I tell you. Honestly.”

Her phone buzzed with a reply. She read it, and her smile did something complicated and delighted.

“Either way,” she said, “I should mention that was Zoe. She knows all about the bet.”

→ I take the rematch and demand a fair question

→ I ask what Zoe knows, and what else is on the list

Losing the Bet: On My Knees

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I stripped. Jumper, jeans, socks, everything but my boxers, which were already doing a poor job of hiding how I felt about this. Then I knelt on the rug at her feet and said, “I’m all yours, Elena.”

“Good boy.” She said it softly, like she was testing the words, and I felt them land low in my stomach.

She stood, walked a slow circle round me, and trailed one finger across my shoulders. She was in her grey leggings and my old university hoody, dark hair loose, bare feet, and somehow she’d never looked taller.

“Hands behind your back. Eyes down unless I say otherwise.” Her fingers hooked into my waistband. “Look at you. Hard already, and I haven’t even started.”

“Sorry.”

“Don’t be sorry. Be useful.” She slid the boxers down, and my cock sprang out, flushed and ridiculous in the lamplight. She wrapped her hand round it, one slow stroke, then let go. I whimpered. Actually whimpered.

“Bedroom,” she said. “Crawl.”

I crawled down the hallway behind her, watching her hips sway. On the bed sat the black holdall she keeps at the back of the wardrobe, the one I’d never been allowed to ask about. The zip was open. I could see leather cuffs. A bottle of lube. And something long, purple and silicone, coiled in its harness.

Elena sat on the edge of the mattress and crooked a finger at me.

“Choose,” she said. “Cuffs first, or do you want to ask me about the rest of the bag?”

→ I hold out my wrists for the cuffs

→ I ask about the strap-on in the bag

Losing the Bet: Zoe

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“Zoe?” I said. “Zoe, your best friend Zoe? The Zoe who does my taxes?”

“She’s a freelance accountant, she doesn’t do your taxes. She did look at your receipts once.” Elena showed me the screen. A string of messages, a lot of exclamation marks, and the final one: On my way. Bringing prosecco. Tell him to be good.

“She knows about the bet?”

“She knows everything. She’s twenty-eight, she’s very discreet, and she’s been curious about you since the barbecue.” Elena put the phone down. “Don’t look so scared. You’ve got a safeword, and so does she, and so do I. Nobody does anything you haven’t said yes to. But you asked what’s on the list, so here it is. I want you tied up. I want you teased. I want you on your knees. And I’d quite like to watch somebody else enjoy it too.”

My brain, and several other organs, went entirely blank.

“She’s ten minutes away,” Elena said. “This is the part where you decide. If you say yes, I’ll tell her to come up, and she’ll be as gentle or as filthy as you like. If you say no, I’ll text her now, and she’ll go home with her prosecco, and I won’t think any less of you. Not one bit.”

She said it so simply that I knew it was true. The doorbell was ten minutes away, and so was a very different version of my night.

→ I tell her yes, Zoe can come up

→ I tell her no, not tonight

Losing the Bet: Tie Break

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“Rematch,” I said. “One question. Fair category.”

“Fair,” Elena agreed, to my surprise, and picked up the card box. “Sport. Since you love it so much.”

I do not love sport. I watch it, mostly for the snacks. She shuffled a card, read it, and her eyes flicked up at me with something close to mischief. “Which country hosted the first modern Olympic Games in 1896?”

My mind went blank. I could feel her watching me, her foot nudging my thigh.

“Greece,” I said. “Athens. The Olympics were in Athens.”

For a long, glorious moment, nothing. Then Elena put the card down, folded her arms and glared at me with enormous dignity.

“Fine,” she said. “That’s right.”

I punched the air. I actually did.

“Don’t get cocky. Here’s what happens. I’m a woman of my word, and you’ve won the tie-break. But you’ve only won ten minutes.” She picked up her phone and set a timer, turning the screen so I could see it. “Ten minutes of me doing what you say. After that, the bet resumes, with interest. And I told Zoe not tonight, so you’re welcome.”

“Ten minutes,” I said. My pulse was going. “Anything I want?”

“Within the limits.” She leaned back against the sofa cushions and spread her arms along the top, like a queen daring me. “Clock’s running.”

→ I order her to the bedroom and take charge

→ I bank the ten minutes for later

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