Cuckold Dilemma Ch. 01

"I'll do it for me, not you. That means I choose who, when and how to involve you."

"What do you mean, involve me, Jess?"

"Sometimes you may be in the room, perhaps taking part, but other times you'll be excluded."

"That's cheating?"

"No, that's me telling you I won't be your slut to command. Trust me, and you'll get what you want, I will too and our marriage will thrive."

"What about me, Jess? Do I get to fuck other women."

"If you want a divorce, Simon, yes."

"So you can fuck anyone you like?"

"Only if you agree."

"Ah, okay. I understand."

"You asked me to cuckold you. I'd rather not, but it seems to be the only way we'll stay happily married because you're hinting at it daily."

"I'm sorry."

"No need to apologise. I've told you I'll do it, but only on my terms. Do you agree I can play while you stay?"

"Yes, absolutely. When do we start?"

"I'm going out tonight with Hannah. I'd rather my first time was without you in the room. Do I have your permission?"

"Yes. I bought you a gift. Will you wear it, please?"

Simon handed me a small box. My heart leapt on opening it because I love jewelery. I extracted his gift carefully and laced it securely around my ankle.

"It's a symbol of my trust, Jess."

"We must trust each other completely for a cuckold lifestyle to work. I have something for you as well."

I handed Simon an envelope, inside was a draft document I had our lawyers prepare. He skimmed the papers, glancing occasionally at me while I adjusted my new ankle bracelet, letting it fall deliciously and cold against my skin.

He replaced the document in its envelope, and looked at me, nodding.

"These are the terms and conditions of your rights to cuckold me?"

"Yes, Simon, I want full indemnity and agreed-upon rules. You can take your time reading and we can discuss variations, but we'll need to sign for a full-blown lifestyle change."

"What about tonight?"

I slid onto our bed and into Simon's arms. My lips skimmed his, once, then again, until he reached his tongue to mine, entwining, before biting my lower lip and kissing me deeply.

I slid Simon's cock out of his pyjamas and slipped my lips from a passionate kiss down to the solid veiny shaft I'd already started wanking. Pre-cum fully loaded the folds in and around his foreskin until I pulled back, licked the glistening glans, then sucked the top few inches of his knobbly shaft like a jackhammer.

"That's enough, babe, you'll make me cum."

I stopped and eyeballed him before sharing his salty slime through a deep kiss with tongues entwined.

"Tonight is up to you, babe. If you choose to send a voicemail with permission later, I'll consider it. If not, we'll wait until the lawyers document is agreed, signed and notarized."

"And you'll wear the bracelet tonight?"

"Of course, but nothing happens until you permit and I agree, understood?"

"Completely."

"Would you rather I stay here, suck your cock, then fuck you later? Last chance before I leave."

"I want you to go out with Hannah and enjoy yourself while I review these documents."

"Bye, hun."

I left our apartment and took a taxi to the Piano Jazz bar where I met Hannah. We sat amid a nest of leather chairs, with gin and tonics, and kicked off our heels.

I felt my phone vibrate and knew it was a voice message from Simon. I let it go; my husband must agonise and think things through carefully, so I could be certain he wanted our lifestyle transformation.

"Your phone is active tonight, babe."

"It's Simon."

"Trouble in paradise?"

"He wants to spice things up. Simon asked me to cuckold him."

"Oh."

"What do you think I should do, Hannah?"

"Well... James and I recently joined Freedom Club, so swinging is a regular thing for us."

"Oh, fuck. I didn't know. Does it work for you?"

My best friend took a long sip of her drink, weighing a response. While reading her eyes and expression, I moved one step closer to fucking someone other than my husband. Hannah's next words were crucial in my decision-making process.

"Yes, it works, Jess, but only if you trust each other and put rules in place."

As I thought her advice through, I casually scanned the room, catching sight of a guy watching me intently. It happens to me as much as any woman and I usually ignore voyeurs, but this guy caught my interest because he was gorgeous. Beautifully chiselled features complimented his powerful physique evident through a well-cut suit.

We held eye contact for longer than a passing curiosity allows, and I smiled when he did. If I were single and he followed up, I'd court temptation, at least for a drink.

He's a maybe.

"You have an admirer."

"I know."

"He's coming over. I'll leave you to it."

Hannah shot off like a guided missile, leaving me alone for the thirty seconds it took my gorgeous admirer to cross the floor and plonk himself down in her vacated chair.

"What next?"

"I'm Jess."

"Paul."

"I'm married?"

"Oh, I never bombed out so quickly."

"Have you given up already?"

"Umm, oh, err... I."

I'd won our psychological battle, having derailed his standard approach. He seemed unsure.

"You need to keep going, Paul, or leave."

"I'd like to take you home."

"For tonight or forever?"

He leaned forward to the edge of his seat. The colour in his face drained slightly, and he got serious, with a determined expression. Paul looked desperate, but aware he was losing our mind chess game. He looked me up and down and gave an impression that he liked what he saw.

"Just for tonight."

"Okay, let me ask my husband for permission."

The colour drained absolutely from his face and his arms folded, a clear sign of insecurity, something my husband has never shown me. It suddenly struck me how grounded and confident Simon was.

I checked and sure enough, I'd received a voicemail. I opened the message and listened to my husband's voice.

Just a couple of changes, babe. First thing I want a clear stipulation that if you believe, at any point, our marriage might be in jeopardy, then it stops. Second, I need a photograph sent to me and at least one other person you trust of the guy you intend to fuck. That's to ensure your safety. Other than that, it's your rules and do what you want tonight. I consent to any choice you wish to make.

I snapped a quick photograph of Paul while he turned to look at the bar, then hit send.

"What's it to be, Jess?"

"Your place. Then you'll drop me off home after fucking me."

His house was enormous, reflecting on a wealthy lifestyle. When Paul tried to kiss me, I refused politely, pointing him downwards towards my moist pussy.

He knelt, pushed my dress high, then peeled my French knickers down. They didn't slide out of my crotch as easily as they would if my gusset wasn't already soaked. Paul slipped them off my heels, then held the delicate crimson lace to his face, sucking gently on the moisture laden lining that had housed my swollen labia.

"You taste incredible, Jess."

"Then enjoy a feast."

I lifted one leg, placing it gently on Paul's shoulder, twisting my hips slightly to grant his tongue better access.

He gripped my ass cheeks, prising them wide apart, and I felt a chill against my puckered sphincter. A luxurious pang of taboo slapped my soul, vibrating through my body when I glimpsed my domination of a stranger who gave excellent cunnilingus.

The flat of his tongue lapped gently, wiping my labia up one side, then down the other, collecting a copious creamy deposit almost dripping down my thigh.

He purred like a satisfied pussy, and mine did, too.

I pulled away, not wishing to stand any longer.

"Where's the bedroom?"

He pointed to a nearby door, and I strolled there.

"I'd prefer you crawl."

I felt powerful, in control of my husband's sexual kink, and that sensation bounced delightfully in my psyche, speaking to my desire for dominance. I felt empowered lying on a strangers bed waiting for him to fuck me.

Paul made the approach to fuck me, Simon had approved, but it was important to me that both men got what they wanted on my terms.

I chuckled, watching his arrival as my new fuck buddy slid both knees across his highly polished wooden floor.

Paul stood, slipped his clothes off, then crawled onto the bed, into my Y shaped restaurant, created when I spread my knees wide apart.

"Dinner is served, Paul."

I noticed his cock was a little smaller than Simon's and felt pleased. It would ensure I could end this cuckold date with my pussy benefiting from my husband's cock.

"You give far better tongue than my husband. I may ask you to give lessons."

He didn't answer. Paul was far too busy licking, lapping, then sucking and sloshing my pussy lips. His powerful arms wrapped around my thighs, pulling me towards his tongue, while his fingers stretched apart the skin on either side of my clitoris.

He flicked my clitoris delightfully, catching the tip with the slightest hint of his tongue. It was as if a hot, wet scirocco wind tantalised my love button.

Fuck, he knows how to tongue a woman.

He pressed his tongue down harder, circling it around my slimy pearl, before dragging the hard nub from side to side.

I heard someone moan like a whore. Realising it was me, I lifted my phone and recorded a twenty-second burst of my rapture, sending it to Simon.

I pulled Paul up my body, allowing him time to enjoy my breasts before insisting he fuck me.

"Have you taken a stamina pill?"

"Before we left the club."

"Good boy."

I spread my legs, wrapping both around him, gripping his ass cheeks while pulling. When I spurred my heels into his hips, forcing him further into my crotch, I felt Paul's cock slide gently into my pussy entrance.

He circled his hips, spreading my cream all over his cock, and then, with a single, delicious thrust, he buried the veiny shaft balls deep. He felt wonderful, less girth and length than my husband, but still beautifully rigid and plenty for me to massage my pussy walls against.

Paul placed both palms on the bed, each tight above a shoulder, pulling down, pinning me so he could reach deeper inside my pussy. When he began driving in and out, I felt the blood rush warmth to my reproductive organs, a sign he was hitting the right spot and releasing my oxytocin.

I scraped his back, pressing sharp fingernails into his skin, spurring both heels, while spreading my legs wide to help him reach further inside.

His fucking style was metronomic, strong, steady and amazing. He pounded me, never averting his eyes, which lit up like a New Year firework display. His perspiration exuded testosterone as the stallion lurking within leapt from his soul, driving his cock deep inside.

I felt a rising climax throb through my pussy and the muscles surrounding it. An explosion of butterflies from my stomach fired a chemical chain reaction, jolting me. I arched my back almost violently as his thrusts encouraged my nails deeper into Paul's back.

While I orgasmed, my eyes locked on Paul in a tractor beam stare. My thoughts drifted to Simon, wanking at home while my swain's semen flooded his wife's womb.

To his credit, Paul didn't stop. He kept fucking me hard, driven by a small blue pill. My pussy squelched like a monsoon in the jungle as Paul's cock slammed into my loose hole, wet from his cum.

I thrashed on the bed, pumping my cunt upwards to meet his thrusts, wanting more.

Wave after wave of orgasmic bliss hummed through me as I slid along a delicious climatic ridge staring into a taboo abyss on either side.

When I descended to earth, Paul moved in for a kiss.

"Please don't spoil it, babe."

I held my finger gently against his lips.

"May I know why?"

"You got what you wanted, my husband and I did too, let's leave it at that. I like you, love him, and that's never going to change."

"Will you come back?"

I slipped off his bed, pulled my knickers up quickly to keep his cum inside, or at least handy for later.

"Maybe. If I feel like it, my husband agrees and you want me, then yes, but those three planets must align seamlessly. Can you drive me home, please?"