The Uncertain Cuckold Ch.01




I lay under the duvet and watched my fiancée stride naked into the bedroom, her body fresh from a bath. She approached her drawer of sexy underwear and peered inside. Her figure was insanely gorgeous. She was slim with a voluptuous ass. Her legs were beautiful, her waist tight and her tits small and perky. She hated me calling them small, often threatening to save for a boob job, but they were perfect for fitting in my mouth. She was 31, two years older than myself.

“I wonder what I should wear,” she said, turning to face me with her hands on her hips.

Her pussy was shaven bald, something she had obviously done in the bath. Something she had done without my prior knowledge. And certainly something she had done without my consent. I loved her pussy in all kinds of fashion, though. Whether it was bald, hairy or cropped.

Jill’s blonde hair cascaded down as she pulled out a pair of boy shorts. She slipped them up her legs until they clung to her hips and accentuated her magnificent rear.

“Do you remember that guy on the internet who bought me these?” she teased.

I was erect. Her history of male admirers on the web was something we rarely talked about anymore. She had never met up with any of them. Instead, she had engaged them in back and forth e-mailing, swapped photographs and even sold some pairs of her used panties. Many of the men posted her lingerie and chocolates as gifts. Jill’s self-confidence had soared, and the rewards were all mine in the bedroom.

“You may masturbate over me,” she said, eyeing me through the mirror. “But do not cum.”

My cock strained against the duvet. My bulging balls ached and indulged by her dominant tone. I was suffering the effects of her enforcement of a sex ban which had lasted for several days.

“I’m saving myself,” she had said.

I seized my cock in my hand.

That I was not the man my fiancée was saving herself for sent shock waves to my loins.

“What about these?” Jill was holding up the skimpiest of g-strings with a pink garter attached.

I nodded, almost begging for her to wear them. I had tried to touch her several times all week, but each time I was dismissed and teased that her body temporarily belonged to someone else and only when that someone else had enjoyed the pleasure of it would it be returned to me. She enjoyed mocking and playing with me. And I too was addicted. “I’m going to be for him everything you wish I’d be for you,” she promised.

The sperm in my balls warned they were rising. My resolve was tested. The moment of no return agonisingly close. My hand slacked, then fell altogether into an excruciating, static slumber.

Jill watched, understanding the agony of my actions, and laughed. “If you dare cum, Matt… I mean it.”

We had a great relationship. One which few could appreciate or emulate. Neither of us had ever been truly unfaithful. Everything we had ever done had been either with the other’s approval or so small it wasn’t worth the hassle. We had occasionally swung with another couple. A married couple. The ladies would sometimes do things together, my fiancée once even going as far as to 69 the wife. But it was her lust for the husband, and him for her, which truly turned me on.

“Is this cute?” Jill asked, giving a twirl.

“Very,” I croaked, concentrating on the garters. “You should put on your matching stockings.”

Jill paused, then clasped the g-string with her fingers and pulled it off. “I’ve got a better idea.” She looked at me, a devilish smile on her face. “You’re going to hate me when you see this.” She disappeared to the spare bedroom.

The man she was dressing for was called Gary. He was the husband of the couple we had previously experimented with. For years he had told me how he desired Jill, complementing her often and reminding me how lucky I was. His wife was attractive, but she wasn’t in Jill’s league. I couldn’t help passing Gary’s words on to Jill, nor to control my stiffness when she would reveal how she often fantasised about having him to herself for a night. It was only since Gary’s marriage had hit a particular rocky patch, the depths of which we were unsure, that he and Jill had begun texting on a regular basis. They did it only during the day, when both were at work. I got to read the messages – after all, it was I who had first suggested the contact – and the arousal was tremendous. There was a hint of jealousy within, but I embraced it. This was one of my all-time greatest fantasies, and the doubt only served to strengthen the severity of the reality.

“I’m doing this for you as well,” Jill had insisted earlier in the week, after they had made the final arrangements.

I nodded. The rules had been proposed and agreed upon. Gary understood and agreed to them every part as much as Jill.

She stood first on one foot, then the other.

My heart sank. “What is it, Jill?”

“There’s something else, Matt.”

The blood rushed to my balls as I sensed a darker requirement in her. A need. A lust. The beginnings of a runaway train Ataşehir Öğrenci Escort I might never comprehend how to control.

“You have to let me do this thing,” she insisted, twirling her little finger in a strand of her long blonde hair.

“Tell me what it is first.”

She breathed quietly. “I might want to be alone with him at some stage in the evening.”

“To do what?”

Jill looked at me like I was an idiot.

“Okay,” I agreed. “That should be okay.” My cock was pulsating. It was more than okay.

“I’ll let you know if and when that time comes,” she had added.

Jill entered the bedroom again.

My eyes darted to her lingerie, mesmerised by her cruelty in choosing my most favourite of outfits.

“This is what I’m wearing tonight,” she said. “And that’s final.”

Jill admired herself in the mirror. Her purple basque corset, black stockings and suspenders and a g-string. There was a matching thong for the corset, which she had evidently decided wasn’t revealing enough. The g-string was cleverly worn over her suspenders for easy removal. She completed the look with a pair of red stiletto heels.

I was jealous. My contempt boiling between desire and deception. Pleasure and pain. Attraction and abhorrence.

Jill sprayed the most delightful and tantalising of perfumes on her neck, and rubbed her skin with the backs of her wrists.

“Please jerk me off, Jill… Please.”

She laughed at me. “I’m not yours and I’m not cheating on him.” She came to the bed and pulled back the duvet, her eyes feasting on my fingers wrapped around my shaft. “If you dare cum, Matt…” There was a silent threat. “I’ll not be happy.” Her words promising a punishment of more depth if I dared.

I couldn’t help myself, the sight of her before me and the thoughts of the night ahead. I was overwhelmed, and came hard in front of her. She watched each spurt, staring and smiling at the end of my cock.

“You can’t say you weren’t warned,” she said, and turned on her heel. She picked up a short denim skirt and a black cardigan. “Just something to wear over my lingerie… For a short while.”

As my orgasm subsided, I was almost instantly clouded by doubt. Was I really going to stand back and watch another man fuck Jill? It was insane, surely. What had I been thinking to initiate this?

I noticed the smile on her face as she gave the mirror a final glance. A fantasy I had conceived and convinced her to chase. How could I cancel now and contribute to her disappointment? What if she lost her confidence altogether?

I swallowed hard, downing my pride and my uncertainties, and attributed my doubts to my climax.

I reasoned that sooner or later my arousals would return. They always did.


Jill had told Gary to arrive at 8 o’clock. She and I sat waiting in the living room of our terraced house. Restless. Nervous. Each in trepidation of the evening ahead. To swing with another couple had been an enormous step in our relationship, but in some senses it was a safer risk. We had both stood to endure the jealously. We had both stood to enjoy the pleasures. But now… To accept that Jill was to have sexual intercourse with another man while I watched quietly and respectfully was very different.

It challenged everything.

Our composures almost collapsed when the front door was knocked suddenly at 7:45pm.

“It can’t be him,” I said. “It’s too early.”

“Whoever it is, get rid of them, Matt. I don’t want anyone to see me in this skirt.” She disappeared from the living room into the kitchen to hide. “Except him,” she giggled.

I left the living room and opened the front door.

Sixteen years older than my fiancée, Gary was well-dressed, smiling and mannered as he handed me a bottle of red wine. His eagerness to enter was obvious, and I welcomed him into our home.

“Jill,” I called. “Gary’s here.”

She appeared in the doorway from the kitchen, blushing, and they kissed on the cheek.

He feasted his eyes upon her. “Wow,” he wheezed, as if suddenly short of breath.

I had deliberately laid the remote controls and a newspaper beside me on one of the sofas, indicating it was my seat and leaving them to sit together on the other. Jill smiled at me as she sat, and crossed her legs. Gary’s eyes drank in every inch of her stocking-clad pins on display.

An awkward silence ensued. The grateful relief coming only in a succession of positive sighs as I poured the first glasses of wine. We had more bottles under the stairs and I expected there to be plenty drank before the night was out.

Gary and I talked about the day’s football results. Jill poured herself more wine. There were a few jokes. No one mentioned his wife, despite our suspicions they had separated. The atmosphere changed slowly as the alcohol began to fuel the mood. Jill placed her hand on Gary’s knee, her red nails dazzling under the light. While his eyes lingered on her longer with each additional stare.

I took the initiative to leave them alone and excused Ataşehir Çıtır Escort myself for the toilet. I took my time climbing the stairs, a distant memory of the first night of our swinging together flashing before my eyes. We had been drunk and playing a stripping game. All four of us were finally naked, giving each other dares, but I badly needed to piss. So I went upstairs. After I had pissed, I took the time to clean my cock at the sink. Gary’s wife had been crudely declaring her need to suck it and I was desperate to suppress any chance she had of complaint. I took at least five minutes, nervously trying to pull myself hard again. I was young, anxious and naive. When I returned to the living room, my girlfriend, as Jill was at the time, was on her hands and knees, sucking Gary’s cock like a porn star. His wife was next to them, watching and encouraging her. Jill stopped only when she realised I had retaken my spot on the floor.

I pissed in our bathroom, stopped, pissed some more and flushed. I washed my hands thoroughly. If something was going to happen between Gary and Jill, I figured it was best I left them alone for as long as possible. The night was young and, if they were feeling half as nervous as I was, a few more drinks were going to be in order.

I headed back downstairs and opened the door. Gary and Jill were still sat together, quietly. Apprehension accentuated the air. I flopped onto the sofa and made a comment about a referee’s decision in the early kick-off. My fiancée leaned forward and set down her glass on the centre table. I noticed the fixture list for the following day in the newspaper and composed a comment in my mind. When I looked up, Jill’s lips were against his. Gently touching another man. Kissing. Devoid of tongue. She was smiling, somewhat placated by his obvious nervousness. Gary pulled away first, and reached for the bottle. He poured more wine.

They both drank.

Jill giggled, smiled again and leaned back in to him. She placed her arms around his neck and met his mouth in the middle. Their lips opened. Their tongues entwined. Smooches and saliva were swapped. Gary’s lines creased as he grinned. Jill’s skin relaxed as her smile faded to a pleasurable moan.

I was straining in my trousers. The sight of my fiancée enjoying a most intimate experience with another man was swiftly defining. I had no woman there to enjoy. No partner of his to take as my own. I was not part of their equation. It was both different and exciting.

Their lips smacked. Their eyes occasionally opened. Snatched a glance. Closed. Her fingers roamed his hair. His knee rose nervously, clashing with Jill’s, then fell. His hand reached out, found her waist and clasped. Jill’s smile widened. His tongue brushed the outside of her lip.

Several minutes passed before they finally broke the kiss for another drink. Exhalations marked their excitement. Repercussions faded in lieu of recurrence. Gary’s boldness grew. His hand wandered, grazing the outline of her figure, tracing her skirt from its beginning to its end. His fingertips rubbed her stocking tops. Her eyes lit up. Their attraction heightened. Her legs dutifully parted, and she smiled to me across the room.

I returned it as Gary’s hand passed her stocking to her naked thigh.

Jill gasped.

His palm travelled higher.

Her breasts heaved as she breathed.

His hand disappeared altogether under the denim of her skirt.

Jill’s eyes and mouth opened. She leaned towards him as his hand moved between her legs.

I quietly moved for a closer look.

Gary gently caressed her cheek and brought her mouth to his, kissing her gently. Jill panted suddenly.

I looked down. He was rubbing the outside of my fiancée’s g-string panties, pushing the material into her pussy.

“Fetch my mobile phone, Matt,” she ordered suddenly.

“What?” I asked.

Gary stopped touching her.

Jill’s fingers wrapped suddenly around his arm and pulled him back to her pussy. “Get me my mobile… Now.”

I was confused, but saw little reason to disobey her.

“Touch it like it belongs to you,” Jill said to him, as I entered the kitchen.

When I returned with her mobile, they were kissing with a fiery passion. Her fingers hauled his head to hers. His mouth ravished the lips of hers. Jill’s g-string was pulled to the side. Gary inserted his first finger.

I stood unnoticed, with her mobile outstretched in my hand, for over a minute while he manipulated her most delicious of inner sanctums. Her beautiful eyes were shut, lost in her growing lust. Shame shook the steadiness in my knees and threatened the balance in the balls of my feet. I was reduced to a mere servant, forced the indignity of watching another man pleasure my wife-to-be. Pleasures which she herself had refused to permit me for days on end.

But it was what I had wanted. What I had encouraged. What I had practically begged for. To watch my Jill with another man.

“Thank you,” she said finally, and took the mobile phone. Her fingers Ataşehir Elit Escort scrolled downwards, hit a contact and put the phone to her ear. Several seconds passed without explanation. “Hello, I’d like to order a taxi.”

Gary and I looked at each other as she called out the name of a local pub. The arrangements had been made for a night in. A kinky night in. What was she planning? The frustration on Gary’s face was a match for my own as she ended the call.

“Oh, Gary, don’t stop fingering me,” Jill told him, and melted when he complied. “Yes!” They were kissing again within seconds. She rubbed his crotch, then momentarily broke the kiss to slip out of her cardigan, revealing the bare flesh of her shoulders and arms.

“Why did you make that call, Jill?” I asked.

She giggled, taking Gary’s tongue again, then moaned as his fingers worked deep inside her.

“Why have you ordered us a taxi?” I demanded, her ignorance affecting my tone.

Jill kissed him harder and nibbled on his lower lip.

I sighed. She was in complete control. Nothing I said, whether in defiance or subservience, would change her behaviour.

The kiss was broken. “The taxi isn’t for us, baby.” She squeezed Gary’s cock through his trousers at the final word, teasing me with a phrase she usually reserved for when we were in private. “I’ve ordered it for you.” Jill stood up and found the zip of her denim skirt. “I’m going to fuck my boyfriend, and I don’t want you around when I do it.”

My insides crashed together. Butterflies in my stomach became fireworks in my chest. My heart pounded. Amok with betrayal and with punishment. And yet there were no words of protest which escaped my lips.

Jill pulled down her skirt, revealing her g-string clad ass in all its glory. Her red heels stepped out. She was dressed only in her stunning lingerie. Lingerie I had bought her. Lingerie I loved her in. And lingerie she rarely indulged in wearing for me anymore. She straddled Gary, his legs relaxing beneath her. Jealousy pumped through my veins. Gary’s hands mauled her backside. They kissed again. She rubbed herself up and down on his crotch. His erection was poking through his trousers and she glided her pussy over it with expert precision.

“I can’t wait for you to fuck me when he leaves,” Jill told him.

“I will… I’ll fuck you really hard,” Gary replied, shedding his shyness.

My cock fought for freedom in the restraints of its coffin. My mind muddled through a multiple myriad of possibilities and probabilities. The sexual extremities of their impending night of passion was upon us. I lost myself in the impossible aftermath of my leaving. Would I seriously allow my fiancée to fuck another man without me around? Her adultery fantasy – my fantasy of her adultery – had fuelled our fantasies for years. I couldn’t. I just couldn’t. Could… I?

Her g-string stretched around the crack of her ass as she splayed her legs and invited Gary closer.

Then I was struck suddenly, shattering the charade. Of course! I was supposed to fall for Jill’s bluff. She hadn’t ordered a taxi at all. It was merely her creative attempt to turn me on. And it had worked. My suffering – my humiliation at her maliciousness – had stretched my cock to new lengths. My need for her expanding forcefully to new heights. For her sexuality. For her sensuality. For her downright degradation.

Jill malevolently swooped her tongue down from above, molesting Gary’s mouth. Her body curved and craved to his touch.

I faded further into her irrelevance, and my testicles bloated in twisted appreciation.

“I need your cock, Gary,” Jill said. “I wish that taxi would hurry up.”

I smiled. Every part of her effort for the evening had been perfect. The elaborate hoax all the more thrilling because it had been her creation alone, and never discussed nor implied beforehand.

A horn triple-blasted outside.

“Oh, about time,” she said.

My eyes darted from Jill to the curtains and back again. She was dry-humping Gary, seizing his neck and staring lustfully into his eyes.

“Are you serious?” I asked.

I was almost certain Jill whispered something in his ear.

My heart pumped faster as I stood. I crossed the room to the window, looking back at their coupling in agonising, embarrassing fury. I pulled back the curtain and peered outside. “Fuck!” There was a vehicle at the end of the driveway. A red roof light in view. “You really booked it?”

Jill sighed, her frustration clear. “Yes.” She kissed his lips. “Now get out, Matt.” Gary’s fingertips fell inside the thin g-string at her ass. “This is your punishment. You know what for.” She rubbed his cock through his trousers. “Tonight, I really do belong to Gary.”

“Yeah,” he said, and gave her ass a playful spank and a squeeze.

There was an unplanned, worthless feeling to my demise, as I stood watching him take charge of my fiancée. It was a step I had neither anticipated nor sought to indulge. Yet somehow I found myself stood at the living room door, preparing to comply with Jill’s demand that they be left alone. I struggled, yet internally acknowledged that I would do whatever she wanted. I stared, wishing for permission to stay. Preparing for compromise, willing to retreat alone upstairs while they fucked. Willing to listen and to imagine. To masturbate and be grateful.

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