Failed simp attempt

NSFWSimp Perspective

This was a failed simp attempt. I know this woman through mutual friends. She's petite with a great, athletic figure and a beautiful face (think Alan Rickman's secretary in LOVE, ACTUALLY, but much better-looking and with a similar naughty energy). I'd been fantasizing about simping for her for about a year, when one night (while drunk) I grab her number from a WhatsApp group we're both in and message her.

I've deleted the messages since, but I basically propositioned her right off the bat. It went very like this (name changed):

"Hey, Kelly. It's John Madeupname. It was great seeing you the other night. Listen, this is probably going to sound incredibly weird, but would you like it if I sent you a treat some time or bought you something? If this is wildly inappropriate, I'll stop immediately! :D"

"Hi John. :D Emmm... it is a bit of a surprise. What do you mean exactly? I'm lost."

"That's understandable! It's a thing I like to do. I like to send women who are completely out of my league gifts, just for being themselves. I know it's weird, but I just had to ask. What do you think?"

"I'm flattered and also intrigued by all this. But I have a boyfriend who's very jealous, and I wouldn't lie to him."

"Tell him if you like. :D I don't want anything back. It's just a real rush to treat really attractive women."

"It sounds like a compulsion, and I wouldn't want to make it worse..."

"It is a bit, lol, and I do send random people money, but if I had one person I could spoil a LOT, that would be more manageable (and also amazing!)."

"I don't think so, John. I don't want to make your situation worse, not to mention the money involved!"

"I see. Look, I'm sorry I messaged you about it and I'll be mortified when I run into you again. I hope you'll think of it as just an amusing little moment and nothing more... :D"

"I will. Haha. You certainly have a big kink, you know? Ask me again when you win the lottery maybe! :D Still friends?"

"Absolutely!"

And that's how it played out. Embarrassing? Certainly. But you miss all of the shots you don't take, right?

Posted Sep 13, 2025, 10:53 PM UTC

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