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Cuckold Sugar Daddy

You have to read this pathetic confession from a Cuckold Sugar Daddy emailed to me here at Mistress Cuckold…

Sara, I had a much younger girlfriend who used me as a Cuckold Sugar Daddy. It happened so gradually, I didn’t even notice At first, I felt like such a lucky guy that I had snagged this 20 something hottie when I’m 40 something and not hot. I’m a lawyer and work in a specific field where I make nice money. My friends warned me that Melissa was only after my money, but she never really asked for any money from me. She did have the expectation that we would only dine out at the nicest restaurants. She would leave expensive things on layaway for me to pick up for her, typically designer handbags and shoes. I didn’t complain because I would see her wearing the shoes and carrying the bags when we were out on dates. Then she told me I needed to put my credit card on account at her salon, so she could get her hair and nails and waxing done at my expense and I should be happy to make sure she always looks beautiful. Of course, I agreed because I wasn’t giving her money directly and I wanted her to look beautiful. I thought since I enjoyed her beauty, this was only fair. Now I have to reveal something embarrassing. I’m not very well-hung and don’t last that long in bed, maybe 5 minutes. I’ve never been married, although I came close a few times. I broke up with my fiancees for cheating on me. I didn’t realize at the time, because this was back in the 90’s before cuckolding had become popular, that they were only getting the hot sex they needed, which they couldn’t get from me. I kept thinking to myself: how could Melissa think I was satisfying her if all of my previous relationships had ended due to my sexual inadequacies?

My relationship with Melissa went on for about 6 months. I was beginning to get the feeling she wasn’t that into me and that she was just using me for a Cuckold Sugar Daddy, but I had no proof. Then one cataclysmic night, I found her phone at my place, it had fallen out of her bag. It made my penis hard to even hold her phone and go thru it to read her text messages. There were so many text threads from her girlfriends, but also from other men. From their photo icons, it looked like they were all younger guys, way younger than me. Finally, I found this one thread where the guy, Cale, was in a convo with Melissa about ditching the old lawyer loser, stop fucking that dickless douche, didn’t you get enough swag from him already, does he love licking your pussy after I fuck you… and on and on. I thought reading these texts would make me mad or feel humiliated, instead it made my little dick harder and I jerked off. Then I got a phone call and saw it was Cale’s icon on the incoming call screen. I picked up. It was Melissa. She asked if I was having fun going through her phone. I played stupid and said I’d just found it. She laughed. She said have fun with it, she was reporting it stolen and that she was never going to see me again. She said there were plenty of nude pics of Cale for me to jerk off to in her photo albums.

To top it off, I forgot that my credit card was on file with the salon till my next credit card statement came in and I saw multiple visits to the salon after our “break-up”. I wanted to call the salon and tell them to take my credit card off Melissa’s account, but I didn’t have the balls to do it. So my credit card is still on file there. And I jerk off to my credit card statement when it comes in the mail. I am such a pathetic Cuckold Sugar Daddy.

Cuckolding History

Cuckolding history… in Europe and old England during the Middle Ages, men who had been cuckolded and shamed by their wives and the superior males who were taking their wives sexually, were often led down the street on a rope with horns on their head to symbolize their cuckold status. This public humiliation put cuckolds in their place. Public cuckolding illustrated to everyone in the town or village that the cuckold’s wife sought sexual satisfaction from a man with a larger cock, with more manlier attributes or with more powerful status. Unlike other cultures, where there was a stigma on those who dared to commit adultery, the English and European cultures indulged cuckolding. Cuckolds were often forced to wear a hat with horns in public after the initial cuckold public humiliation parade. And cuckolds were often thrown the sign of the horns by townspeople. In Europe, the sign of the horns is still used to throw bad luck on others. This bad luck sign is why you see some Europeans, mainly Spanish or Italian men or men of European descent, wear the gold horn pendant. This pendant wards off the bad luck of the horns. In the U.S. we know this hand sign as the popular “hook ‘em horns” bullhorns with the index and pinkie finger raised. Centuries ago, this sign was thrown to mock the cuckold and remind him of his cuckhold humiliation.

Today, men can still suffer the shame of being cuckolded, but typically by their wife or girlfriend and her superior lover who might put the cuckold in panties or humiliate him for being less than a man, ridicule him for his lack of penis size or for being a wimp or loser.


In general, there are more men who fantasize about being cuckolded than there are women who can cuckold them in a relationship. This is where a Mistress Cuckold or Cuckoldress can fulfill the role and collect cuckolds as submissives who worship their Mistress and who desire her to cuckold them. Often this cuckolding is remote via cuckold phone sex or cuckold cam chat or in prodomme sessions which the Mistress arranges and has the cuck serve her and another male. Or the Mistress encourages her cucky to seek out a real cuckold relationship. In the latter instance, the Mistress will also give advice to the cockold on how to be the ultimate cucked partner or how to serve a couple. But the Cuckoldress will ultimately still lay claim to her cuckold, regardless if she sexually or psychologically cuckolds him.

Until there are more women who find a Cuckoldress lifestyle appealing for long term and not just a sexual adjustment they have to make in a particular unfulfilling relationship, there will be a need for the Mistress Cuckold. Many cuckolds consider their Mistress to be a Goddess and worship her above all women, even when and if they do become involved in an actual cuck relationship. Some cucky boys also look to Mistress Cuckolds for cock control and being their cockhold.