Do woman care if a guy lost his virginity to a prostitute?

[Jeremy]

"I lack the ability to feel shame and do not care about what others think of me."

Next sentence.

"Is this going to be a red flag for woman when I seriously start to look for a girlfriend/sex buddy?"

Thought you didn't care?

For most people, yes this would be a red flag, especially since you publicized it and posted on twitter...It shows that you can't get a woman yourself, with your looks/personality, so you paid for one. Not only did you pay for a woman to have sex with you, you bragged about it, like you actually achieved something. I know that pussy ain't free, but to actually pay a woman to have sex with her, is something i'd never do.