Cuckold Dilemma #1
Indulging
The mood in our bedroom beguiled and terrified me. Cuckolding was the most extreme kinky bedroom play my husband Simon and I ever fantasized over. He’d pushed me for months, and now, I broke, agreeing to do it while he gave me head.
I was a sucker for being agreeable when my husband plowed his flattened tongue along my creamy furrow while thumbing my sticky, swollen lips apart.
It was a moment of madness, but a deal was a deal. Simon got me off, sucked my orgasm clean out of my shuddering pussy, and I must deliver my end of the bargain.
As I rolled in our bed, snuggling him while my body still shuddered in post-orgasm, I wagged my finger by way of a loving warning.
“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 want to be a cuckold. I would rather not do this at all, as I have repeatedly said. I’m not interested in swinging, but if you want to be cuckolded, I’ll do it, and we can see where it takes us.”
“Ah, okay. I understand.”
I wasn’t sure my husband adequately understood, and that worried me. After months of talking me through how much Simon wanted to watch another man fuck me, now he was asking for his sexual freedom. He noticed the doubt in my expression.
“I was probing, Jess.”
“Do you want to sleep with other women?”
“No… absolutely not, but if you were willing to let me, it wouldn’t be cuckolding. We would be in an open marriage, and that’s not what I want.”
“You asked me to cuckold you, honey. I’d rather not, but it seems the only way we’ll stay happily married because you’re hinting daily at me to fuck other men.”
“I’m sorry.”
“There is no need to apologize. I’ve told you I’ll do it only on my terms. Do you agree I can play while you stay?”
I held my breath, thrilled and terrified. Agreeing to set aside my marriage vows had not been easy, and there was considerable angst between Simon and me on the subject. I did research and read about cuckolding from reputable sources, and I knew the fantasy, turned into reality, was a rising fetish desired by many men and their wives.
I am not coercive, nor do I wish to be my husband’s dominant other, but slowly, I’d grown more convinced that trying the lifestyle was worth a shot to avoid a slow decline in our marriage.
“Yes, Jess… I want you to fuck other men as and when you wish. 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 to fuck any guy I choose, Simon?”
His eyes smoldered, and I saw the cuckold dilemma I had grown to recognize. My husband’s nostrils flared, his cheeks rippled with sexual tension, and when I glanced down, I saw an erection begging to be sucked or fucked.
“Yes, I give my consent. I bought you a gift. Would you please wear it?”
Simon handed me a small box. My heart leaped upon opening the small, blue velvet color box because I love jewelry. I extracted his gift carefully and laced it securely around my ankle, branding myself a Hotwife.
“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 containing 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 inside 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 both need to sign for a full-blown lifestyle change.”
“What about tonight?”
I slid onto our bed and into Simon’s arms. My lips merged hotly with his like fire and ice, steaming and bubbling. He reached his tongue to mine, entwining, before biting my lower lip and kissing me deeply.
I slid Simon’s cock out of his pajamas 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, sticky, salty 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 my husband before sharing his salty cream 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 lawyer’s document is agreed, signed, and notarized.”
“And you’ll wear the bracelet tonight?”
“Of course, but nothing happens until you permit it, and I agree. Do you understand?”
“Completely.”
“Would you rather I stay here, suck your cock, then fuck you later? This is your last chance to change your mind before I leave.”
I held my breath again, surprised by how willing I’d become to participate in Simon’s fantasy. Our marriage was strong, communication was excellent, and my love for him grew daily. While he agonized, balanced on the edge of some kinky precipice with pleasure to one side and despair to the other, I momentarily considered that maybe it was the good health of our marriage that encouraged me to step over a boundary into taboo territory.
“I want you to go out with Hannah and enjoy yourself while I review these documents.”
“Okay. I’ll shower and get dressed, hun.”
I took my time, selecting my most alluring underwear and squeezing myself into a figure-hugging dress before asking my husband to zip me up before inspecting me. He approved and drooled over the woman he was foregoing, so another man could fuck and fill her with his semen.
As I stood in Simon’s arms for the last time as a faithful wife, unsullied by other men, I checked his soul through the sparkling, excited eyes that offered me a perfect view.
“I won’t fuck a guy using a condom, Simon.”
“I want you to fuck your lover raw. I need to know he came inside you.”
“Taking everything about me that you own?”
“Yes. I’ve become complacent and inattentive, and I know it. I want to feel desperate to have you like when we dated. I need the chase, the hunger for you, and that comes from my need to compete for you.”
There was some truth in what my husband said. I was as engaged in our marriage as the day it began, whereas Simon’s attention waned slightly. There were fewer bunches of flowers, cheaper cards, or no restaurant dates on special days, like when we once marked the day we met.
Simon was by no means a bad husband, but he wasn’t as hungry for me as he once was. As I studied his soul, mine settled, knowing that cuckolding was a step we must take to resurrect what we both enjoyed most in each other.
I left our apartment aroused, with a warm feeling in my panties that would only get worse as the evening advanced. I took a taxi to the Piano Jazz bar, where I met Hannah, my best friend. We sat amid a nest of soft, cream calf leather chairs with gin and tonics and kicked off our heels.
I glanced around the bar, eyeing up the male talent, of which plenty was in supply.
My phone vibrated on the glass table in front, and I knew it was Simon’s voice message. I ignored the message; my husband must agonize and speculate about what I was doing so he could marinate in torturous images and thoughts, thinking this cuckold dilemma through carefully. There was no other way I could be sure he wanted our lifestyle transformation.
My phone buzzed again; it was a text message from Simon. Hannah nodded at my phone.
“Your phone is active tonight, babe.”
“It’s Simon.”
“Is there trouble in paradise?”
I sipped my G&T, smiling mischievously. I had not mentioned Simon’s and my marital problem to Hannah previously, but now, since she would witness my perceived infidelity, I burst to share my tawdry secret.
“My husband wants to spice things up. Simon asked me to cuckold him.”
“Oh wow.”
“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.”
“I’ve wanted to tell you for a long time, Jess.”
“Does it work for you?”
My best friend shivered excitedly and took a long sip of her drink, weighing a response. While reading her sparkling eyes and naughty expression, I fed from her confidence and moved one step closer to fucking someone other than my husband. Hannah’s following words were crucial in my decision-making process.
“Yes, it works so well you cannot believe it, Jess, but only if you trust each other and put rules in place.”
“Is your marriage suffering at all?”
“Quite the opposite. I don’t watch James fucking my lover’s wife, but he studies me, and the look on his face when another man creampies me is priceless. I think he loves the competition. When we get home, I get so much tongue and cock for days, it’s like being single again.”
“You were always a slut.”
We laughed, and Hannah’s relaxed demeanor showed she felt unburdened.
“I love having fuck buddies, Hannah. I don’t care about them, and they fuck so hard, like you couldn’t believe. If Simon says you should cuckold him, I think you would be foolish not to. He’ll get plenty of fun from this lifestyle, too.”
“That’s what he says too.”
“Has Simon properly consented?”
“That’s what the messages and voicemail are.”
I nodded at my phone, raised my right eyebrow, and grinned disgracefully before descending into a fit of giggles.
When I recovered and thought my best friend’s advice through, I casually scanned the room, catching sight of a guy watching me intently. It happens to me as much as any attractive woman, and I usually ignore voyeurs, but this guy caught my interest because he was gorgeous. His beautifully chiseled features complimented a 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 before glancing away. 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, Jess.”
“I know.”
“He’s coming over. I’ll leave you to it.”
Hannah shot off the sofa 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. My pussy bloomed, wet and sticky rather than damp, and I needed a cock to part my swollen lips before sliding balls deep inside.
“What must I do to acquire a creature as wonderous as you are, dear lady?”
“I’m Jess.”
“Paul.”
“I’m married.”
“Oh, I never bombed out so quickly.”
“Have you given up already, Paul?”
“Umm, oh, err… I.”
I’d won our psychological battle, having derailed his standard approach. He seemed unsure and vulnerable, adding to my sexual frenzy that elicited goosebumps all over. My body chemistry took me to a place before marriage where I felt horny and without inhibitions.
I smiled encouragingly, uncrossing and crossing my legs to ensure my hotwife anklet was adequately displayed, revealing my slutty availability.
“You need to keep going, Paul, or leave, so someone else can try harder.”
“I’d like to take you home.”
“For tonight or forever?”
My heart pounded, and my head ached from the tension. My vision blurred as my body went into absolute overload. It felt like the moment I walked down the aisle to meet my future husband. I was free of all thoughts aside from Paul and imagining him fucking me.
He leaned forward to the edge of his seat. The color in his face drained slightly, and he got serious with a determined expression. Paul looked desperate to have me but was aware he was losing his mind in a passionate, sexually charged chess game. He looked me up and down and gave the impression that he liked what he saw.
“Just for tonight.”
“Okay, let me ask my husband for permission.”
The color 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 and how lucky I was to have his permission to fuck a guy I wouldn’t care about.
I checked my phone, and sure enough, I received a voicemail. I opened the message and listened to my husband’s voice.
Just a couple of changes, babe. First, I want a clear stipulation that if you believe, at any point, our marriage might be in jeopardy, then cuckolding 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?”
“Are you an accomplished lover?”
“I’ve never had complaints.”
“Your place then, please. Then you’ll drop me off at my home after fucking me.”
Paul’s house was enormous, reflecting a wealthy lifestyle. When he tried to kiss me, I refused politely, pointing him downwards towards my moist pussy, stifled inside sticky panties.
As I stood and he orientated to my demand, my entire body shivered as I stared at the only man to ready himself to fuck me since I met my husband. My nostrils flared, and I breathed heavily, my breasts heaving.
“No kissing?”
“Not yet, Paul.”
“Do you enjoy having your pussy licked? “
“Yes… so much, and I must step across a boundary - a kiss doesn’t cut it. Your tongue worshiping my sticky hole feels so fucking right.”
“I agree.”
He sniffed the air, glanced between my legs, and smiled.
“You’re excited, Jess.”
“I’m off the charts. No scale could measure my arousal.”
“Do you want me?”
“I want you to fuck me, Paul. There is a subtle difference.”
“Not to me.”
He knelt, pushed my dress high, and then peeled my French lace panties down. They didn’t slide out of my crotch as quickly as they would if my gusset wasn’t already soaked and sticky, so he tugged, making me feel delightfully slutty. Paul eventually slipped my underwear off my heels, then held the delicate crimson lace to his lips and nose, sucking gently and sniffing deeply on the moisture-laden lining that had housed my swollen labia.
When he completed what seemed like a ritual, my lover grinned at me, temporarily satisfied and looking very excited.
“Your pussy tastes incredible, Jess.”
“Then enjoy an all-you-can-eat feast, honey.”
I lifted one leg, placing my thigh gently on Paul’s shoulder, twisting my hips slightly to grant his tongue better access to my leaking, throbbing hole.
Paul cupped my ass cheeks in both palms, prising them wide apart in clawing fingers, and I felt a chill against my puckered anal whorl. A luxurious taboo twang slapped my soul, vibrating through my body when I glimpsed my domination of a stranger who, within seconds, was giving me excellent cunnilingus.
The flat of his tongue lapped gently, cleaning the sticky veneer off my labia up one side, then down the other, collecting a copious creamy deposit almost dripping down my thigh.
When he swallowed, Paul purred like a satisfied pussy, and mine did, too. His lips clenched tightly around my quivering, creamy clitoris, and I gasped, holding his head to steady myself, bowing low to kiss his hair.
He dragged my sticky pearl from side to side, lifting me ever closer to a powerful orgasm, but I needed more. I needed Paul’s seed inside me to help sully my marriage precisely the way my husband wished it.
Simon and I were aligned. Paul dipped his tongue inside my hole, breaking the seal that held back a dribble of tawdry, sweet nectar. My knees buckled, so I pulled away, not wishing to stand any longer.
“Where’s the bedroom?”
He pointed to a nearby door, and I strolled there, followed by my super attentive lover.
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 stranger’s bed, waiting for him to fuck me.
Paul approached like a rampant lion to fuck me, Simon had approved of it, but it was important to me that both men got what they wanted on my terms.
I chuckled, watching my new fuck buddy desperately kick his clothes off before crawling onto the bed. He kissed his way up my legs, licking both silken, sticky thighs, palming them wide apart. When he descended with hot tongue and lips into my Y-shaped restaurant, 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 stretching by my husband's cock, lubricated by my lover. There seemed to be a natural balance to that vision.
“You give far better tongue than my husband. I may ask you to give him lessons.”
He didn’t answer. Paul was far too busy licking, lapping, then sucking my pussy lips before swallowing every drop of my sleazy liquor. His powerful arms wrapped around my thighs, pulling me towards his tongue while his fingers stretched apart the protective skin on either side of my clitoris.
I would report the matter of my lover’s superior tongue to my husband, forcing him to work harder. Paul brushed my clitoris delightfully, catching the tip with the slightest hint of his tongue. It was like a hot, wet scirocco wind tantalized my love button.
Fuck, he knows how to tongue a woman.
Paul pressed his tongue down harder, circling it around my sticky pearl, before dragging the solid, throbbing nub from side to side. I was in ecstasy, far more than when my husband went down on me, and I figured my lover knew it.
I heard someone moan surprisingly loudly and disgracefully, like a whore. Realizing it was me, I lifted my phone and recorded a twenty-second burst of my rapture, immediately sending it to Simon before I could change my mind.
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 wide open, 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 inside my pussy entrance.
He circled his hips, spreading my cream all over his cock, and then, with a single, energetic thrust, he buried the veiny shaft balls deep inside me. Paul’s cock felt wonderful, less girth and length than my husband, but still beautifully rigid and plenty for me to massage my pussy walls against.
It was also not my husband that added enormously to my enjoyment, much more than I imagined it could. My emotions were on vacation, enjoying unhooking love from lust, focusing purely on the latter.
Paul placed both palms on the bed, each tight above a shoulder, pulling me down, pinning me so he could reach deeper inside my pussy with his lovely cock. When he began driving in and out piston-like at a metronomic, rapid pace, I felt the blood rush warmth in my reproductive organs, a sign that he was hitting the right spot and releasing my oxytocin.
My lover fucked me far more enthusiastically than my husband did these days, and suddenly the entire cuckold dilemma came into sharp focus, and I understood. The envy that drove Simon’s competitive nature would make his and my lovemaking far more intense, especially when he knew another man’s semen swam inside my womb and ovaries, hunting down a fertile egg.
My mind drifted into a carnal place where Paul fucking me was the best marital therapy I could enjoy. I raked his back, pressing sharp fingernails deep into his skin, spurring his ass cheeks with both heels while spreading my legs wide to help him reach deeper inside my sticky, throbbing cunt.
His fucking style was strong, steady, and felt amazing as he panted, kissed my neck gently, and stared into my eyes with pure desire. He angled himself higher, arching his back while ramming his cock deep inside my tight hole. When I milked Paul’s shaft with powerful pelvic muscles, he groaned, then screamed, staring at me in wonder, just as my husband said he would.
Paul pounded my quivering hole, never averting his eyes, which lit up like a New Year fireworks display. His perspiration exuded testosterone as the stallion lurking within leaped from his soul, driving his cock deep inside my throbbing, sticky hole.
I felt a joyous rising climax ripple 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 deep inside me encouraged my nails to dig deeper into Paul’s back.
I knew he was going to cum inside me, violating the marital sanctity that I held dearly. I wanted his semen and wouldn’t leave without it, and I wrapped my arms around his neck, drawing my lover closer.
“You must cum inside me.”
“Yes… I must.”
“I am yours right now… in this moment… only yours, Paul.”
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 fucking me just because his cock jerked energetically, filling me with his seed. He kept fucking me hard, driven by a small blue pill. My pussy squelched like a monsoon puddle on a jungle path as Paul’s cock slammed into my loose hole, soaking wet from his cum.
I thrashed on the bed, pumping my cunt upwards to meet his thrusts, wanting more cock, and more of Paul. Wave after wave of orgasmic bliss hummed through me as I slid along a delicious climatic ridge, staring into a taboo abyss of unknown emotions on either side.
When I descended back 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, and my husband and I did, too. Let’s leave it at that. I like you very much, but I love him with all my heart, and that will never change.”
“Will you come back?”
I slipped off his bed, pulled my panties up quickly to retain my lover’s cum inside, or at least to soak it up and keep it handy for later. I was amazed at how detached I was from my lover, feeling nothing but gratitude for his sexual prowess.
My fears about cuckolding were finally, irrevocably and entirely assuaged.
“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?”
“Of course, Jess, and thank you.”
“No honey… thank you.”
Next Chapter:
Simple, straight forward presentation of all the complex issues surrounding the cuckold experience. Thinking twice before jumping into this is such a huge understatement. The author takes us along on the roller-coaster ride of emotional turmoil. How many time does she need a "yes" from her husband? Then there are the conditions and rules she wisely outlined in the cuckold contract. I wonder if the legal contract is used IRL. A great ending with all of the hot sexual adventures Kate is famous for. Thank you, Kate!
Much of what I would say has been said by the others. I get the impression though Jess and Simon are in for the long haul drive of their lives