Cuckold Archives - Seductive Gypsy https://seductivegypsy.com/category/cuckold/ My Twisted World Thu, 27 Feb 2025 23:27:25 +0000 en-US hourly 1 https://wordpress.org/?v=6.8.1 230881278 My Secret Desire: A Cuckold Confession https://seductivegypsy.com/2025/02/27/my-secret-desire-a-cuckold-confession/ https://seductivegypsy.com/2025/02/27/my-secret-desire-a-cuckold-confession/#respond Thu, 27 Feb 2025 23:27:25 +0000 https://seductivegypsy.com/?p=1678 I was given permission to tell this story from a long time cuckold. For this story we will call him Brian. “I don’t even know...

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cuckold

I was given permission to tell this story from a long time cuckold. For this story we will call him Brian.

“I don’t even know how this all began. One day I was living the perfect marriage, or so I thought, and the next, I stood in the middle of my bedroom while my wife cheated on me. Well, looking back at it now, I guess it wasn’t cheating. She was feeding her soul what it had lacked for so long. A real man. I’m a big guy, but lacking in one thing. Cock size. About 4 inches, I’ve had girlfriends in the past complain, but I leaned how to become orally gifted. Sex was quick, but I could always get them off with my tongue or toys. It was that way with my wife too, well, until it wasn’t. And so it began.

I never thought I would be here, confessing this part of myself. It started as a whisper in the back of my mind, a fleeting thought I quickly brushed aside. But over time, the thought grew, and soon, I couldn’t ignore it.

My wife, Emily, is breathtaking—smart, confident, and effortlessly beautiful. From the moment we met, I knew I was lucky. But deep down, I carried a secret, a craving I didn’t understand at first. It wasn’t until I stumbled upon a forum discussing the cuckold lifestyle that I realized there was a name for my fantasy.

At first, I was ashamed. What kind of man wanted to see his wife with another? The idea should have filled me with jealousy, but instead, it thrilled me in ways I couldn’t explain. I kept it buried, afraid of what Emily might think. But secrets have a way of eating at you, and one night, after a few glasses of wine, I confessed.

She stared at me, silent. My heart pounded. Had I ruined everything? Then, a slow, knowing smile spread across her lips.

“So, you want to watch me with someone else?” she asked.

I nodded, barely breathing.

“I’ll think about it,” she said.

Days turned into weeks, and I convinced myself she had dismissed the idea. Then, one evening, she dropped a bombshell.

“There’s someone I’ve been talking to,” she said. “If we’re really doing this, I want to do it right.”

The moment was surreal. I expected jealousy, but instead, I felt something else—excitement, arousal, anticipation. The night arrived faster than I imagined. Watching Emily with another man was both torment and pleasure in its purest form. I had never seen her like that before—uninhibited, free, lost in pleasure. And though I was an observer, I had never felt closer to her. He was 3 times my size and though I should have be intimidated, I’m on the edge of excitement.

The way he touched my wife made me feel a pang of guilt. Never once had she used that language in the bedroom with me. All I could think was “Had I ever satisfied her?”

Afterward, she curled up beside me, tracing her fingers over my skin. “Are you okay?” she whispered.

I smiled, kissed her forehead, and nodded. “More than okay.”

Some might not understand, but for us, it brought a new level of intimacy, trust, and passion. And in the end, that’s all that matters.

 

 

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A Cuckold Story; BE careful What You Ask For https://seductivegypsy.com/2023/08/13/a-cuckold-story-be-careful-what-you-ask-for/ https://seductivegypsy.com/2023/08/13/a-cuckold-story-be-careful-what-you-ask-for/#respond Sun, 13 Aug 2023 18:25:43 +0000 https://seductivegypsy.com/?p=816 With the permission of a client, I am going to share his cuckold story. Well, part of it. I don’t know if even I could...

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cuckold

With the permission of a client, I am going to share his cuckold story. Well, part of it. I don’t know if even I could do this justice. No names used to protect my client. He knows who he is.

What is a cuckold? A man who encourages and excepts his significant other having sex with another man. There are many levels to this and each one is different. Some enjoy knowing that she is cheating, and others enjoy watching and participating. Either way, the woman is getting sexually satisfied by someone outside of their relationship. The degree of cuckold depends on the man and what he wants and enjoys. Each one is different.

Small penis? Does this define you as less of a man? I hope that you say no, but sadly for the majority of men out there they find themselves stuck in a cuckold world. For most it’s not the woman who can’t accept it, but the man. Boys are taught growing up that the size of their penis defines where they land on the sexual food chain. Little does most know, but they are not alone. So many try creams, pumps, and even hiding in the dark so no one can see. This can and will spiral you into a world that you may not recover from. Beware of what you ask for. Sometimes it will bite you in the ass.

A Cuckold Story.

Being well endowed was never a worry for him. He was small, but for the most part, women accepted that. Maybe it was his personality, or that he made up for his short comings with oral skills. When he found the perfect woman who loved him for who he was, he made the fatal mistake of asking her about her ex-boyfriends penis size. It was big, but that didn’t keep her with him. After being told to fuck him too many times, she did. Of course this was a turn on for the him because he got all the juicy details and loved that when she fucked him after, she couldn’t feel a thing.

Riddle me this, I grew thinking no man would ever want to be teased about their manhood?

It wasn’t that he wanted to be taunted, but that he wanted her to be happy. Sadly, most think that the only way to a woman’s heart is through their dick. Wrong! As a woman I have had all sizes and the shorter to average ones have always been the best.

The adventure lasted awhile, well, long enough for him to watch from the closet. He wanted to see his girlfriend in the act with another man. Jealousy can do strange things to men, but he was more mad that she fucked him with such intensity than being jealous. That’s where she thought his “Kink” ended, but not even close.

Settling into being married a few years, the itch began again. He wanted her to fuck someone else. This time when she agreed, she told him it would be different. It would be on her terms and not his. He agreed and that was his fatal mistake. Sometimes things should remain a fantasy. This was one of those times.

She met the perfect man in a bar, and after that, nothing was ever the same. She stopped intercourse with her husband, she spends most of her time in the arms of her lover, and she’s sexually satisfied. Not that she wasn’t with her husband, but he made sure to ruin that with the whispers of infidelity.

Where does he go from here?

There is no happy ending to this story, but there is a moral to it. Hold on tight to the one you love and cherish what you have, not what they had. The life of a cuckold can be exciting, but for some, it’s devastating. I adore my client and love spending time with him. I hope that if he ever finds love again that he never shares it with another man or woman. Love is to be treasured like a rare gem. Sometimes we only find it once in a lifetime.

 

Disclaimer: I had permission to write this story. No names or places were used.

 

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Cuckold, could you watch another man? https://seductivegypsy.com/2023/03/14/cuckold/ https://seductivegypsy.com/2023/03/14/cuckold/#respond Tue, 14 Mar 2023 17:04:28 +0000 https://seductivegypsy.com/?p=37 A cuckold isn’t such a nasty label, but could you watch? Are you man enough to listen to your woman fuck another man? Better than...

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cuckold

A cuckold isn’t such a nasty label, but could you watch? Are you man enough to listen to your woman fuck another man? Better than that, are you man enough to watch?

“I have a secret desire, but I don’t know how you will react,” he said.

“You know you can tell me anything, so why would you hold back now?” asking, her tone hurt.

Can you imagine having this conversation with your significant other? I couldn’t until I did a little self exploring in the world of voyeurism. I’ve always been the person who peeked out the window when I heard a loud noise, or watched from the porch as the neighbors fought. It might be wrong, but inside of all of us, we love to look into the twisted lives of others. How would you respond if your husband asked if he could watch you with another man? No, he is not a cuckold, but a simple voyeur who has always dreamed of seeing the woman he loves being stretched open by another man.

Imagine bringing another male into your bedroom, never telling him that the man whose ring you wear is hiding in the closet. His breathing is slow and steady, but his cock rock hard the moment he hears the voices. Peeking through the little slats in the door, all he can see is the other man and the massive bulge in his pants. His wife has touched no one else since the day they met, but tonight, she was going to be filled with the cum of another. Playing in his mind was, what if she got pregnant? How would they explain a child that looked nothing like him? God, this was such a turn on that his hand went to his pants and released his cock. He was stroking his cock, and his wife, well, she was on her knees gagging on the stranger.

Do you have what it takes to be a cuckold?

This scene played out in my mind the moment I heard the word voyeur. My mind travelled to the dark side, a place that I thought I escaped from long ago.

Bent over the bed, the woman’s eyes never left the closet. She knew he was watching, but did he enjoy what he asked for? When the male pushed the huge cock head against her velvet lips, did he stroke harder and wish he could lick it first? One stroke and he was inside of her. Their monogamous relationship ended with one thrust of a cock against her willing core. She screamed at the size. After all, he was much larger than her husband. Why downsize? The scent of the fuck filling the room. The man in the closet pressed his nose to the whitewashed slats, inhaling the scent of her pussy. It smells pungent when another man is inside of her. Almost unpleasant. Did they smell it, or was it just him?

That cum is not yours!

Perched against the door, the man pumped his dick with increasing fury. He was mad. Or was it that his wife was enjoying the cock of another more than she ever enjoyed him? He listened to his wife beg for it harder, deeper, and then she asked for the man to cum inside of her. God, he listened to his wife beg to be soiled so deep that she would never rid herself of the memories. At that moment, he hated and loved her more than he could ever imagine. She did all of this for him, and yet, he was crying in pain with every stroke of his cock. When she came, he came. They always came together even now. This time, though, the cum that ran down her legs was not his. It was the lover who tainted marital bed.

Would you do this? Can you imagine burying your face in the woman you love and cleaning her freshly fucked cunt? Now imagine that the cum is not your own! Does this make you a cuckold?

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