1 year ago
Musing on Mistress Day: A Sugar Daddy’s Take


Holidays belong to the family and the mistress is often alone during those times, while the man is in the arms of his loving wife (well, hopefully loving wife). Mistress Day, unofficially celebrated on the day before Valentine’s Day, is when some men who are married or partnered with a steady girlfriend take out their mistresses.

There was a situation, some time ago, where I was seeing someone on the side, and that ended up developing into a full-blown relationship, i.e. it went beyond NSA or pure Sugar dating. We had met a month before Valentine’s Day and since the first meeting we had a strong connection with each other, and at the time it was almost as if I forgot I was married.

I had violated one of my “Sugar rules,” which was “No emotional attachments.”

We used to see each other on a weekly basis. Soon enough, I had violated one of my “Sugar rules,” which was “No emotional attachments. This is all NSA at the end of the day.” I remember one Mistress Day we had a date and then the following day, Valentine’s Day, I was strolling around Midtown New York in the evening with my better half, having a great conversation. But suddenly, my mind wandered off to my mistress, and I was thinking to myself: “I know she is probably seeing someone else tonight. It’s okay, I guess. After all, I am attached as well. But somehow it bothers me a little bit.” It bothered me, an experienced NSA kind of guy.

Mistress Day is fun, though. I don’t know who came up with that terminology but I am glad it exists. It’s a day that can make someone feel almost as special as my partner on Valentine’s Day, with all its commercialized glory.

On Mistress Day we can feel like we can let loose and be “single” again. I can almost guarantee that sometimes the mistress is getting a better deal than the wife. Let’s be blunt: The mistress is getting the extravagant treatment, since they often make their man feel desired and special, and the man will feel like he is on a mini-vacation. The wife will get the box of chocolates, roses, and a card. A set of gold earrings, who knows? Maybe yes, maybe no.

So what are your plans for this year’s Mistress Day?

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