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October 2017
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The Making of A Wimp: A Cuckold Tale – Too Late Now

The best laid plans of wimps and men…

The wimp’s wife told him on the phone that the vacuum salesman was a bit wary of her wanting her husband to watch. He was nervous that it was a set-up for him to come back and get his ass kicked or that her husband would want to fuck HIM or something like that, and so of course he did his best to fuck her right then and there. She finally convinced him that she wasn’t joking… that if he came back later when her ‘hubby’ was home, she promised she would fuck his brains out. And with that, it was a ‘date’!

Cuckolding Princess Heather

Last chance to back out… or not!

The wimp went home after work, getting there about an hour before the salesman was due to return for the fuck session. There was a bit of an awkward silence as his wife walked around their bedroom, naked, preparing herself for being fucked by another man. Finally, she broke the silence and just came right out and snapped, “Look, if you don’t really want this to happen, you need to be a man and tell me that you won’t allow another man fuck your wife! Otherwise, the next dick in this pussy isn’t going to be yours!”

The wimp was paralyzed. He could hardly breathe. He had a lump in his stomach and all he could hear were the words, “need to be a man”, ringing in his ears.  He knew he should say something, but he couldn’t. She sort of huffed under her breath, almost in disgust, and went back to putting on her lipstick. A few minutes later, when she was almost ready, the doorbell rang.

Time is almost up… what are you going to do?

The wimp’s wife looked hard at him for a moment, and then she said, “This is your last chance… if you want to back out now, say the word, and we will pretend that no one is home. Otherwise, go answer the door while I finish getting ready… but just remember that once he’s in the house, it IS going to happen… so don’t try to back out later.”

They stood there, just staring at each other for a moment, the wimp still a frozen mute.  The doorbell rang again, and he broke eye contact with his hot wife, who was waiting for him to take charge and be a man, but instead he went to go answer the door for another man to come in and fuck his wife. At that moment, he realized what a fucking wimp he really was… but he also had a raging hard-on.

So the wimp answered the door, as though walking through the arch between ‘real man’ and ‘cuckold wimp’…  and then…..   *giggle*


The Making of A Wimp: A Cuckold Tale – Fantasy Becomes Reality

Aaah yes… our poor little wimp. He had accepted the realization that his dream of being a cuckold would likely always remain just that… a dream. And then, one day, he got a phone call from his wife that would rock his world in ways he’d never imagined.

When opportunity knocks, answer the fucking door!

It seemed our wimp’s wife had found herself smack dab in the middle of a steamy hot porn fantasy, only this time it was real! A door-to-door salesman had showed up at the house selling very expensive $2000 vacuum packages.  She told him that she wasn’t interested in buying a new vacuum. He must have been able to sense something about her and her unsatisfied sexual cravings, because once she brushed off his vacuum pitch, he propositioned her with something better… sex.        Bratty Cock tease 800-356-6169

An offer that can’t be refused

The wimp’s wife told the vacuum salesman that she would be interested in getting fucked by a real man for a change, but that she wanted her husband to be home to watch.  So her question to the wimp when she called him at work was, “Do you want to make your fantasy a reality?”   He was so shocked and in awe that he could hardly talk… but somehow, he found himself saying, “Yes.”   It was almost like someone else was speaking, because his brain was saying, “Are you CRAZY, man?? You’re going to watch another man fuck YOUR wife??”  But his mouth and his raging hard-on were agreeing that this was what he wanted more than anything, to finally be a cuckold husband, even though it was the most humiliating thing he’d ever agreed to do.

His wife seemed a bit surprised that her husband actually said yes, but there it was, validated by his choked voice squeaking on the other end of the line.  And so the plan was put into place!

Do you think the wimp followed through on the plan? Only one way to find out…. *giggle*

The Making of A Wimp: A Cuckold Tale – The Acceptance

Here we are again with our Wimp and reliving the experience of his journey into becoming a lifetime cuckold. The response of my readers has been outstanding. Apparently there are a lot of small-dick cuckolds out there that can relate to the Wimp and his reckoning. Who would have imagined?    Cuckold Princess Heather

Acceptance of your inadequacies opens doors for experiences!

When we last left our Wimp, he had just realized that as far as size of his penis was concerned, he was even smaller than previously thought. The reality of this began to consume his thoughts, and everything seemed to revolve around it. When he and his wife spent time together in the bed, they naturally would play with dildos. He noticed that she always seemed to like the bigger ones the best. He also realized that the reason they used dildos in the first place was because he himself was so small. It was likely the only way his wife could obtain an orgasm!

The Cuckold Fantasies Begin

The Wimp began to fantasize how his wife would respond to a man with a bigger cock. He became obsessed with the idea of watching her with another man. And for some reason, he felt comfortable enough to share this fantasy with her. Ironically, in the beginning she thought that his newfound fantasy was merely a ploy to get her to agree so that he could have sex with other women. Even with such a pathetically small dick, his wife was a bit on the jealous side.  But soon she realized this really was a fantasy of his, and she even started talking about fucking other men while they were having sex, especially after she’d had a little too much to drink. It’s funny how a little alcohol can become a truth serum isn’t it? *giggle*  But once the alcohol wore off and the sex was over, she never brought it up again, so he figured nothing would ever come of it.

And then, one afternoon, he got a phone call that would change his life forever…..

Princess Heather
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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 😉

The Making of A Wimp: A Cuckold Tale- The Beginning

One of the most popular calls I get as your phone sex Princess is the cuckold call. I have to say that I love cuckolding for many reasons, but the biggest reason is that it embodies just about everything I love in femdom.  Of course, there are always exceptions to the rule, but for the most part cuckolding is a delicious mix. Humiliation, coerced bisexual cock-sucking, small penis humiliation, getting spoiled with gifts, using men for my pleasure, and a good bit of the time, big black cock.  Even if it’s not black, it’s always big cock for sure! *giggle*

Cuckold Princess

Cuckold Princess Heather

How does someone get started in cuckolding?

This is probably the most-asked question I get when people find out I’m a femdom. That is, if they’ve even ever heard of the concept of ‘cuckolding’.  To many, it is a foreign concept… one that most people would never admit to even thinking about, much less jerking off to, and even less actually living the lifestyle.  Inquiring minds always ask ,”How does someone even find out they are into that?”  “What makes someone want to be a cuckold?”   Well, today starts a series of blogs that will give you the unique opportunity to travel down that spiraling abyss of kinkery and cuckolding.  You’ll see what happens when an ordinary, every-day man begins to discover that the smallest chance encounters in life can lead to huge life discoveries.  They might even change your future forever.

Once you become a cuckold, there’s no turning back.

As with most sexual fetishes or kinks, once you’ve experienced them you can’t go back to the way things were before you experimented. It’s much like a child finding out that Santa Claus or the Easter Bunny isn’t real.  You can’t ever go back to truly believing a fat man in a suit sneaks in your house once a year and leaves you gifts. Nice memory of a more simple time of life, but you always know the truth.

It’s also similar to popping open a bag of potato chips. You can’t eat just one and put the bag back. Once you get a taste of such slutty sex, you crave more.  You want to see how far you or your partner will go and where it will lead to.  And the underlying danger of what may happen to your existing relationship seems to be put on the back burner while the raging lust takes center stage. And that’s exactly what happened with our case-in-point here… the Wimp.

Just an ordinary guy with an ordinary life, until one day…..

Check back for the continuation! 😉

Free phone sex and virtual world party!

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Cuckold Mistress

Cuckold Mistresses

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