Saturday, June 14, 2025

Diary of a Cuckold – Part 6

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Hi, I’m Jessica — a wife, a hotwife, and someone who has fully embraced the beautiful journey of a female-led, cuckold relationship. I’m in my late 30s and happily married to Martin, a devoted, self-aware man who has come to not only love but thrive in his role as a cuckold.

I’m so incredibly thankful for Emma and the thoughtful, empowering blogs she writes. Honestly, many of her articles feel like she’s narrating chapters of my own life. It’s rare to find a space that gets it — the complexity, the love, the surrender, the power, the fire — and Emma captures it all.

I’ve poured my heart (and some of my wildest nights) into my writing. Diary of a Cuckold is deeply personal — it’s erotic, raw, emotional, and very much based on my real experiences with Martin. If you’ve ever wondered what this dynamic feels like from the inside — from my side — I think you’ll find a lot to connect with.

And I’m thrilled to offer my book, Diary of a Cuckold, to the readers here. If you enjoy what you read, I’d love if you would check out this title and more of my work.

Just getting started with this series? Check out Part 1


March 16

Jessy and I went shopping, groceries for everyday life… and yet there is something more to report. Jessy wore the key to my penis cage openly around her neck like an exquisite piece of jewelry. It humiliated and excited me immensely that she displayed the little key so openly, while I wasn’t even allowed to lay a hand on my own cock. Jessy was also wearing a light-colored blouse whose most important feature must have been the unreliable buttons: all it took was a gentle tug and they popped open.

At lunchtime, we drove to a furniture store outside the city. A place that was anonymous and safe for our little game. No familiar faces, no judgments.

Jessy picked out an attractive employee and engaged him in a technical conversation about pleated blinds. She flirted with him charmingly, not too intrusively, and when she casually ran her hand down her neck, the top button of her blouse popped open and gave the employee – ‘Friendliness has a name: N. Ardeler’ – a glimpse of her cleavage so deep that the poor man could hardly concentrate on pleats.

I stood at a distance, a manager, a man in control, and yet at that moment nothing more than a silent witness to her art of seduction. Jealousy gnawed at me, a burning feeling that mingled with arousal. I saw it in his eyes, the greed, the desire, and I knew I was sharing it with him at that moment.

As we drove home, we both giggled excitedly, laughing freely about the experience and Jessy realized how much fun she had had flirting and I realized how much fun I had had watching. When she released me from my cage at home, I felt the painful pressure on my skin for a long time.

It was agonizing and exciting at the same time.

March 21

Last night, Christian, an old school friend of my Jessy’s, came to visit. He’s a doctor, a damn good one it seems, and only recently moved back to our hometown. I remember Jessy talking about him: they had gone to school together and had spent one or two honors classes together before losing track of each other after graduation.

Christian is a really nice guy. And I say that without any sexual reference: he’s polite, charming and interested. He asked me questions about my job and how we got to know each other and told me funny anecdotes from his life. I liked him right from the start.

We had food delivered, Thai food, Jessy’s favorite. The scent of lemongrass and coconut milk mingled with the joie de vivre in the air. We drank, first one glass of wine, then two, and at some point I stopped counting. The alcohol loosened our tongues, and we joked and laughed.

I have to admit that I sometimes wondered what he was like in bed. Athletic figure, tanned face. He was a heartbreaker from the catalog. I was excited by the thought that this man could sleep with my wife – but at the same time I felt uncomfortable with the idea: I didn’t want to be in competition with this doctor. It would have destroyed the lightness of our adventures.

With unknown, nameless bar patrons – yes. A quickie with N. Ardeler from the DIY store – the thought had excited me. But Christian? There was a risk of them falling in love with each other and I didn’t want to jeopardize my marriage.

“Jessy, you haven’t changed a bit, still that gorgeous laugh,” Christian said with that charming smile that men like him have perfected. She blushed and I felt a painful tug in my stomach.

“Martin, I envy you your wife!”

He said it so freely and without falseness that I took a deep breath at that moment. He didn’t want to compete with me – and he didn’t want to conquer Jessy. He was an honest guy and I really appreciated that.

As the evening drew to a close, the bottles empty and faces red from the wine, Jessy offered Christian the guest room. “It’s so late, don’t go home,” she said with a solicitousness that excited me.

“Ah… I really don’t want to be a burden,” Christian replied and raised his hands defensively. I insisted. Christian’s respectful manner had brought back my desire and I felt the urge to add a little fuel to the fire. “Jessy, why don’t you show him the guest room?”

I heard them going up the stairs, their voices a low murmur seeping through the ceiling. I stayed behind and put the glasses away.

What just happened in this guest room, just one wall away from our bedroom? Were they giggling? Had this perhaps been a stupid idea after all? Was I a fool?

When Jessy came into the bedroom, she quietly closed the door behind her and scrutinized me with the look a lion gives its prey. It was as if the knowledge of Christian’s proximity, the awareness of his presence in the house, had only inflamed our lust. She undressed quickly and wrapped her arms around my neck in a demanding kiss. With every soft moan we suppressed, with every fleeting touch we allowed ourselves, the fire inside us seemed to grow.

“What if he hears us?” I breathed as my fingers gently stroked Jessy’s silky skin, as if to capture the heat emanating from her.

“Would that be so bad?” she breathed back, biting into my shoulder, her voice a sweet venom pulsing through my veins. Her fingers buried themselves in my hair, pulling me closer to her breath, which beat heavy and hot against my lips.

“Go on,” she ordered me, a soft laugh in her voice that made me tremble deep inside. “I want to feel you, Martin. Now.”

I slipped off the bed and knelt between her legs, which she willingly opened for me. I kissed her bare thighs and approached her lap.

She didn’t finish, I thought, but I didn’t care at that moment. I caressed her vulva with my tongue, tasted her pleasure and began to lick her clitoris. I heard her gasp, felt her muscles tense and a part of me hoped that Christian would come in now. Seeing me like this, between my wife’s thighs, her legs spread wide, just waiting for someone to open the door.

Before Jessy reached orgasm, she pulled me towards her. She quickly opened the penis cage and handed me a condom. “I wonder if Christian’s cock is bigger,” she murmured quietly as I slipped it on.

I blushed with embarrassment and at the same time the blood pulsed hotly in my penis. “I guess the thought excites you, huh?” Jessy realized with a smile. She let herself fall back and pulled me on top of her. “Come on, Martin,” she whispered softly as I pressed my penis against her hot lap, “let’s see what you can do with your little cock.”

Her words were like poison. As soon as I had penetrated her, as soon as I felt her hot lap around my cock, I felt an unstoppable pull in my testicles.

I jerked and moaned my way to orgasm, clawed at the pillows and poured myself into the condom before my wife had a chance to climax herself.

I saw her smiling mischievously out of the corner of my eye. She didn’t have to say it – I could clearly read the thoughts between us: Christian would certainly have lasted longer.

March 24

Our relationship is taking on forms that I didn’t think possible at the beginning of the year. Not only do I now hear terms in my head that I had never heard before – our bedroom cupboard is also full of sex toys that I had never heard of before.

I came home from work yesterday, tired but satisfied after a long day. I love my job, feel competent, recognized… strong and enjoy the contrast at home all the more, where Jessy is increasingly dominant and leads our marriage.

And Jessy, my wonderful wife, with her shining eyes, had a surprise for me. She met me in the hallway, again holding a small, auspicious package. “For us,” she said with a giggle that would normally have given me a thrill of anticipation.

But when I opened the present, still in the dining room, I felt my face burst into flames. A dildo… no, not just a dildo. A sleeve, transparent and shiny, designed to be slipped over the penis. Bigger, thicker – more. I could barely look her in the eye. “We’re going to have fun,” she whispered, and I… I just nodded. My cock wasn’t big enough for her and she let me know that with this gift. The humiliation of this realization was like a stone in my stomach and excited me at the same time – because surely there were men out there who could do it better than me.

“Let’s try it out,” she urged later that evening and I felt the shame paralyze me. Jessy scrutinized me closely and I could feel her trying to find out if I had reached my limit.

If I put the sleeve on, I would feel her even less than through a condom. And with the added length and thickness – I weighed the artificial dildo in my hand – would she even be able to feel me when we made love normally? “Are you in yet?” I heard her ask in amazement as I pushed her with all my strength.

Jessy seemed to sense my thoughts. She gently put her hand on my arm, wanting to say that we could throw the thing away and take a step back. But I didn’t let her get a word in edgewise.

“Do you think,” I asked, gripping the sleeve as tightly as I gripped my own cock when I was pleasuring myself, “do you think Christian’s penis is this big?”

Jessy smiled. “I’m sure you will.”

I slid the sleeve over my erect penis with plenty of lubricant. It smacked and gurgled as I pulled my testicles through the rubber ring at the end so that it didn’t slip off my penis.

Jessy reached for it, stroking my testicles, which stood out plump and firm from my body under the rubber. Her hands were gentle, but every touch burned like a stigma of my inadequacy. In my mind, I heard her voice whispering, “You’re not enough.”

The worst and best thing is that she really enjoyed it. She groaned and moaned like never before while I lay between her legs and thrust into her. I felt the muffled thrusts, but I didn’t feel her wetness or her heat through the silicone. At least I would last longer this way, I thought.

As she came closer and closer to an orgasm, she wrapped her legs around me and dug her fingernails deep into my back.

“Oh Christian,” she moaned loudly and these words, this brain fuck, also moved me forward. While we melted together in this most intimate moment, her thoughts were not on me, but on her old school friend. While she was being fucked by this thick cock that was touching places inside her that I had never reached, she wasn’t thinking about me.

We came to orgasm at the same time, panting. Jessy left red welts on my back, through the sleeve I could feel the muscles of her lap contracting spasmodically and I squirted my semen into the artificial dildo.

“Thank you,” she gasped when we had caught our breath. “I’ve never had an orgasm like this before.”

March 30

I flew to Asia for five days on a business trip. Jessy took my penis cage off so I wouldn’t have any trouble with airport security. And I have to say: I feel a bit naked without it. It’s crazy how much I’ve gotten used to living under my wife’s guidance.

Yesterday Jessy sent me a photo on my cell phone without any comment: Hands, her hands, wrapped around a penis. It’s not my penis. But are they really her hands? Or is it just a picture from the depths of the internet, chosen to torment me?  My heart is racing, my thoughts are constantly revolving around this one image.

Could it be Christian? The thought is enough to ignite my jealousy and at the same time awaken this inexplicable desire. I remember the last time he was with us. His smile, his casual manner. And Jessy? She was so… obliging.

“Come on, Christian, make yourself at home,” she had said in that sweetly seductive voice that seemed to imply that she wanted more than just to be a good hostess.

I can imagine it vividly – how he sneaks into her bedroom at night, quiet as a shadow. And me? I’m not there. I can’t hold her, I can’t touch her, I can’t feel her. Thousands of kilometers separate me from her, and yet I never feel closer to her than in these moments of agony.

Jessy remains vague, enjoying making me squirm. “You have an imagination, Martin,” she replies only when I ask for more details.

It is a test, a game that she has mastered.

But I know what I feel and what I want: I want more. The jealousy, the excitement, the lust – they are more real than anything else in my life.

Two more days, then I’ll be back. Two endless days in which my imagination is the only company I have. What will I find?

With trembling fingers, I put the phone aside and close my eyes. Images of Jessy and Christian dance before my inner eye, and I surrender to them – the pain and lust as my only solace.


To Be Continued

Emma
Evolving Emmahttps://evolvingyourman.com
Emma brings her own experiences to light, creating a space for open conversations on relationships, kinks, personal growth, and the psychology of sexuality. With insights into everything from chastity to emotional fulfillment, she’s here to guide readers on a journey of evolving love and intimacy.

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