Now I’m no stranger to having dates on February 13th, Mistress Day, but this year brought me good tithing on Valentine’s Day instead. Regardless of the actual holiday you chose to celebrate, the overall meaning of Mistress Day and Valentine’s Day are similar. Both are days to show appreciation of someone you either care a lot about or sleep with, even if you consider the mere act of ‘just sleeping with someone’, at least you can still appreciate the raw physical satisfaction you get.
That said, I had a very memorable Mistress Day a few years back, way before my days of experimenting with sugar daddy dating sites like SugarSugar.com…
Oh, and Happy Mistress Day to all– I hope you enjoy this story half as much as I did actually living it…
I went out on Mistress Day with a married man once, David. We had dinner reservations at Daniel, one of my favorite spots in New York. People thought I was his wife and we were celebrating for Valentine’s Day, so that was a little awkward, and he was a little shifty. We normally don’t go out in public, and in the rare instances that we do, we aren’t affectionate with each other. I’ve learned to use my periphery more than most, probably in case some crazy tow-headed bitch comes at me, I can be prepared…
I could care less about dating married men, so going out on either Mistress Day or Valentine’s Day was of no consequence. It’s wives and clingy girlfriends who get caught up in the specifics anyway. I just wanted to have a nice evening out, I could have gone out any other night too if he would have been less awkward.
After an excellent as always dinner at Daniel, David gave me a card-sized envelope to open, not without his eyes darting back and forth. I opened the envelope to a cutesy pre-fab card with a heart on the front, on a side-note, married men are not really romantic, like they’ve given up all around. The inside of the card had cash in it (a nice surprise of $1000), and was signed “Love, David”.
Fortunately or unfortunately the card was actually intended for his wife. The tip-off? Her name was on the inside of the card instead of mine—oops… I didn’t tell him he gave me the wrong card. I instead, graciously said thank you for the gift and for taking me out while struggling to choke down my surprise and scoff at his stupid mistake (I wonder who he gave more money to though). I put the envelope in my handbag and could see David squirming to end the night early. We never went out on Saturday nights, so I suspect his wife was wondering where he was or something. I didn’t ask but I saw him nervously looking at his cell phone in between his other awkward movements.
We said goodnight and goodbye before we even got up from the table, making no plans of seeing each other again soon. He patted my hand on the table and I could feel his hands were nervously clammy. I told him I hoped he’d have a nice Valentine’s Day with his wife for what it was worth, though he didn’t find that as amusing as I did.
I never heard from him again, which is fine, but I still wonder if giving me the wrong card ever blew up in his face.




TooSpoiled writes: Diamond watch from Mr. World Traveler.
SugarCookie writes: Christmas present from my sugar daddy, a diamond tennis bracelet with diamond earrings.
LatinMama writes: My first sugar baby purchase, Gucci Purse!
Hotbod writes: I love Birthday's, Louis Vuitton and purse from Mr. Beemer.
Chocolatelove writes: One of my many shopping sprees with my sugar daddy, Christian Louboutin and a diamond necklace.
Sweetness69 writes: All I have to say is I love being a sugar baby!
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