What's the hardest you've simped?

>I became betabux inlcuding putting her through college (She's talented and it would still, to this day
Nigger you aren't some 60 year old philanthropist you just did it because you're horny and pathetic. You would NEVER have done that shit if she wasn't a she

Responding instantly while she leaves me on delivered for hours

i bought gifted subs because streamer was cute and having financial troubles. i make 100k a year so $25 doesnt seem like much but it was def a moment where i realized im so fucking lonely

>to autistic too know that was the one
holy fuck user im sorry

I gave a girl online $100 for her to call me a loser. It felt wrong, but the orgasm I had after jerking off felt so good, the best coom I had in a long time

Paid 40$ for a bunch of really fucking expensive flowers and asked a girl on a date, she said no but we still hung out. Still pissed at how expensive the flowers were.

no she was fat and borderline

Paid 10$ for 2 months of subscription to a local part time escorts onlyfans. She only fucks certain guys for money and is very low key. She's sexy as fuck, I plan on paying her to send me a personal strip tease video. After that I'm gonna work my way to paying her for sex. Can't wait till that ass is bouncing on my cock

wrote a 2 page love letter to a girl i knew loved middle school in my sophomore year of high school.
she rejected me by returning my letter and the chocolates i had given her. nothing written, nothing said. just that. the worst part was that i still loved her lol.

Used to waste hours with a girl on phonecalls so she could use me as an emotional tampon. At least it was her calling me so it didnt cost me shit, but it was precious mmo hours