Cuckold Stories Archives - Seductive Gypsy https://seductivegypsy.com/category/cuckold-stories/ 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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