How many lines crossed before calling time?

This weekend my wife and I were attending a wedding out of town. We were in the lifestyle years ago, but since having kids it's been difficult to find the time, energy, and privacy needed to arrange and host anyone. Being that we were going to be staying in a hotel for a couple nights, kid free, and in a town nobody would recognize us, we decided to set up an encounter.

We were very up front in what we were looking for. Clean white male, shaved, comfortable with close (but straight) proximity to myself, and comfortable with pictures and video being taken for personal use only, protection a must.

We made contact with a 19 year old who had a milf fantasy and said yes to all of the above. His photos showed him as white and clean shaved down there. He was friendly, wife thought he was cute in his excitement etc etc. We chatted for over 2 weeks about the expectations and ground rules. (no kissing, nothing in the bum, no cum in mouth, no choking etc).

On the night we agreed on, we left the wedding early, somewhat buzzed and invited him to the hotel. I reminded him to bring condoms in his size.

Red flag #1: he said he didn't know what size he needed and all condoms ended up being too tight. It seemed in hindsight like he was hoping we'd say don't worry about them, but I told him I couldn't help him out since only he'd know what fit.

Red flag #2: he knocked on the hotel room door and I opened it. A clearly Hispanic man was there. He looked the same as his pictures, except he had a small mustache now, and the lighting in his photos made him seem much lighter skinned than he was. He also had a Spanish accent. I invited him in, as we had discussed him showering before hand, and him being in the shower would give my wife and I a few minutes to decide what to do. She said, it's fine, he was still attractive and it was now or never. He took almost half an hour in the shower. We have no idea what he was doing in there.

Red flag #3: he comes out of the shower in his towel and my wife lays him down on the bed. She tries to remove his towel but he refuses because I have my phone recording. He says he's just nervous at first and I can record once he's more comfortable. Okay... Fine I guess. Not what we discussed but whatever.

Red flag #4: she removes his town and he's fucking hairy. Like thick black forest of pubes. I thought for sure she was going to say no way I can't do this, but she didn't.

Red flag #5: She takes off her dress and he gets erect. And his cock is huge. She goes to put the condom on and it just won't fit. He then stretches it to fit over his cock but it won't cover the last inch or so. She tries to suck him a bit and he's alrwdy going soft again. This is a recurring issue throughout this encounter. He asks her to kiss him to try and get him hard but she says no, that was one of the rules.

The only photos or video he allowed me to take were closeups. The problem is he wasn't hard for 90% of the night. So a bent floppy dick trying to fuck my wife in close up is all I have. Anytime my dick got close to his, either in her hands or face or any position, he immediately pulled away. He tried to put his hand around her throat at least 4 times and she had to stop him. (our rule between us is that I don't intervene on her behalf unless she gives me a certain look).

She asked him if he was going to cum. His response was "tell me when, I can cum on demand"... So I'm getting close, I'm ready, she's egging us on, and I blow... He doesnt. 5 mins of him jacking it, and he still doesn't. He asks her if he can fuck her again until he's ready. She says yes, so back to the condom bullshit again. Also - I've cum already, so my hornyness filter is gone and I'm trying to not be an ass.

He asks her if he can try putting it in her ass. First of all, I barely fit in there and he's way bigger than I am. Second of all, this is literally the third rule we discussed that he has asked for anyway. So I said "dude we discussed this, no". Another 10 minutes goes by of him flopping his limp dick around and I start to say "it's fine dude, you can leave". But he keeps going. And I had to repeat myself probably 5 times at increasing levels of aggressiveness before he said it's because of the camera that he can't finish and left.

I get the risk involved in what we were doing. I get that in a perfect world we would have met before hand, but seeing as we were travelling from out of town and wanted it to be nsa, we didn't. But at what point in the night would you have said no this isn't what we agreed and you gotta go? My wife isn't upset. She says it was still fun, and his size even when soft was still impressive, but I can't help be upset. He asked me to send him copies of everything I recorded but fuck this guy. He was blocked the second we left town.