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August 2017
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The Making of a Wimp: A Cuckold Tale- The Discovery

Ahh… so it seems the draw of knowing you aren’t alone in your fetish is just too much. You couldn’t help but to return and read more about the making of our Wimp. Well, I don’t blame you. It’s often comforting to know you aren’t alone in being useless in sexually pleasing a woman with your dick. 🙂

Cuckolding Princess Heather

There was always a suspicion of smallness.

To start with, our Wimp began his journey into cuckolding a long time ago.   He’s well into middle-age and began his sexuality in an era long before the internet and when sex wasn’t in your face everywhere. He says he remembers vaguely thinking he may have a slightly smaller than average penis while growing up, but nothing out of the ordinary, especially since ‘size doesn’t matter’ (or so he was told). Of course, he knows better now that size ABSOLUTELY matters, and matters a great deal! But at that point, he believed what he was told and didn’t think much about it.  This of course would come to a head in his first relationships.  Soon he would learn the truth of his lack of manhood.

Ignorance is bliss… or is it denial?

The Wimp married his first wife only a few years out of high school. Of course in the beginning, everything was hunky-dory and he thought all was well.  But only a couple years into their marriage, his wife decided she wasn’t happy and wanted to separate.  As often happens, he learned that his wife was cheating on him with multiple men. He of course was devastated and they divorced… and he was still clueless that his sexual inadequacy had any bearing on it.  Talk about being in denial!

Second time around brings reality home.

Not long after their divorce, the Wimp found another woman to make his bride. She was gorgeous and recently divorced, too. The difference was that after her divorce, she experienced sexual encounters with a number of men. The Wimp, on the other hand, was basically celibate.  For the first six months or so into their relationship, she talked openly and freely about the other men she had been with.  The issue of penis size came up, and while she admitted that her previous lovers had all been larger than the Wimp, she said size didn’t matter. Finally, the Wimp could stand it no longer… he point-blank asked her if his dick was the smallest she’d ever been with.  And without hesitation, she answered, “yes.”

Faced with your shortcomings and sexual inadequacies, what next?

The Wimp was completely stunned by her answer. It may have been painfully obvious to anyone else, but to him, this was the first time it actually hit him that even for a small dick, he was beyond the norm. Now, some may ask, why would she be with him if it were really THAT small? Well, in actuality the Wimp is genuinely a really nice guy. He is successful and has a professional, white-collar position and makes a very good living. There are a lot of great qualities about the Wimp that would make  him an excellent ‘catch’ for a woman wanting a husband. Some women are willing to overlook circumstances where a guy may be a loser in the bedroom but great outside of it. After all, isn’t that pretty much the entire definition of ‘cuckolding’ in the first place?

This realization that the Wimp came to accept turned out to be just the beginning of the long and twisted road that brought him where he is today.

 

To be continued 😉

4 comments to The Making of a Wimp: A Cuckold Tale- The Discovery

  • violet

    Thanks for these awesome posts Ms Heather, i have mostly always been single, but i am totally hooked on the whole cuck thing, especially the interracial thing, its my main turn on !!! and You are very hot and beautiful also !!!

  • OMG! Story of my life! The truth hurts but feels so good…! But I think you forgot the part about when the Wimp discovered phone sex. His first wife didn’t know about all the money he was paying…in order to get some sexual attention. Or did she?!? And what if he discovers his first wife is friends with his second wife? Oh, my! I can’t wait to see how this unfolds…

  • Michael

    Even though I am single and always have been – what you write here is amazingly close to what happened:

    “He says he remembers vaguely thinking he may have a slightly smaller than average penis while growing up, but nothing out of the ordinary, especially since ‘size doesn’t matter’ (or so he was told). Of course, he knows better now that size ABSOLUTELY matters, and matters a great deal! But at that point, he believed what he was told and didn’t think much about it. This of course would come to a head in his first relationships. Soon he would learn the truth of his lack of manhood”.

    It is exactly that – initially, a “vague” and not specific sense and you are not even sure if you are totally right. You sort of know deep down you probably are but not for sure as you are just with your own thoughts and you really don’t see a lot of other guys so you don’t know for total sure. Women “teach” you where you stand. Some women are frank and up front about it. Others are way more subtle and say things or under react and you get the picture. Sometimes it is what they don’t say that makes the impression. In either event it is those first few female contacts that let you know. You fight it but you have to accept it.

  • Sissy April Nicole

    Thanks for the post i am tiny also and have come to terms with it and know it now everytime i see a sexxy photo of a woman

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