When I was younger I spent way too much on ladies of the night. It was the heyday of craiglist hook ups and backpage escorts.
My worst experiences included aggressive rider who managed to break the condom. Still finished. (inside)
It lead to months of anxiety thinking I caught something as it burned while I pee. I got tested multiple times and it kept coming back negative until I discussed it with an urgent care dude who recommended cranberry juice/pills which cleared it up. Supposedly it was just some kind of urinary tract infection.
Another women took a phone call while continuing to ride me and having a frenetic conversation in Spanish. Still finished.
I had a couple others with just bad attitudes bad vibes that made it the opposite of fun.
I once found a beautiful girl posting in the escort section, she came over and almost yelled at me when I went to touch her between her legs. Ended up just being an expensive personal stripper, it was still fun although I wish she didn't misrepresent herself. Still finished. (In my hand while she danced naked standing over me)
My best experiences included randomly finding this gorgeous and young alt girl who was totally my style on Backpage. It seemed too good to be true but she showed up looking like an unassuming punk rocker chick you'd see at the shows. She was shy but instigated by simply undressing and then kissing me. She is the only pro I've kissed to this day. I saw her a lot and spent a lot of money, including sleepovers and getting the breakfast the next day. Probably caught feelings but it was draining my bank account. Finished (multiple times)
For a while I was desperate to try anal and randomly posted a craiglist ad looking for girls into it. A blond milf type girl hit me up and after discussing the price I went to see her at a very sketchy apartment complex. I had to park outside and jump a fence to gain access. She answered the door and looked much better than her pics (still dodged her attempted kiss)
She told me she was borrowing the room from her friend and that we didn't have a lot of time. She told me to lay down and briefly rubbed my back before she got on her knees and said I could have her ass now. I got behind her and started massaging her ass, I felt between her legs and was surprised how warm and wet she was so I asked if I could start there. I took her from behind for a little bit while fingering her butt before breaking out the lube and going for the glory hole. Not long after I got in the front door flew open and this dude came running in, saying he just got in a fight and he needed to hide out. He ran to the bathroom and locked himself in. I was freaking out at this point and she calmed me down saying he was her friend who was living in the apartment. I had deflated and couldn't get back to attention so I asked if I could take off the condom and she agreed. I hit that ass raw and I don't regret it. (Finished outside, which I do regret)
Afterwards as I was leaving there was a cop interviewing people in the parking lot about the fight, the cop looked at me and shined his flashlight in my face. I thought I was cooked but he just went back to talking to the other people.
I haven't done it in a long time, the game has changed. The quality of the girls online seems to have declined while the prices have gone up. There's mostly scammers online now too, you can spot them from the too good to be true pics and explicit ads. Reviews can help verify if someone is legit but even those are faked. NEVER make a deposit when trying to meet a girl. Be safe out there.