First time - Plan it or Leave to Fate?

Hi everyone, newbies here. Hubby is white guy in his 40s, wife is Asian in her 20s. We are both excited about trying a hotwife experience and after talking about it for a while we are getting close to making it happen. Question for you pros of the lifestyle…

For our first time, we like the idea of watching her first get hit on at a hotel bar and then going up to our room with the lucky guy that passes her tests. However, a) this strategy leaves a lot to chance and b) we over-analyze everything. Safety is our #1 concern, both overall and with STIs. So there are clear benefits to vetting the guy first. But it seems naughtier and hotter in some ways than to meet someone on a site like this and plan everything in advance. An added benefit of this approach is that it seems easy to adjust and call it off at any point (well up until a certain point of course!) vs feeling bad that we wasted someone’s time. I don’t expect either of us will chicken out but who knows. We are both as nervous as we are excited about trying this.

Any advice for us? It’s much appreciated!

C & E
 
I could have written your question myself! Basically strangers were a no-go safety-wise. Local people we knew were not good candidates for various reasons. I knew my slightly shy and not terribly experienced gf would need a safe, perfect first time.

We settled on her former boss that is also her Mom's friend. He would take my future wife to his house on Fridays at lunch before I met her. She was a late bloomer sexually and by 23 she was horny everyday. He's discreet (She worked for him for 2 years and her Mom never found out about the sex) and he is 26 years older. She said he def would not let me watch because he occasionally has ED. She did not even want to ask him about me being there.

The week before I could hardly think of anything else. On the morning of, I drove her to his window blinds shop and dropped her off. The guys in the shop must have known. They were all smiling and excited to see her. I felt a tinge of jealousy as my gf looked hot and I left her there alone. I went for a 2 hour hike nearby. I was literally shaking from being aroused. She was in the shop talking when I pulled up. She waved goodbye to the lusty, knowing crew. I drove for a few mins as she described what all had happened. She was nervous before the encounter and surprised that she enjoyed herself so much. To start he made her orgasm with his fingers and then his mouth. They had been together so much he knew what to do. She said then he mounted her and reached for a condom on the night stand. He had always been clean, but they wore condoms to keep her from getting pregnant... even if sometimes he'd go limp as she put the condom on him. I just assumed they'd use a condom like before. Looking to simplify things, she boldy (for her) spoke up. Embarrassed, she asked him if he wanted to do her without one. With a huge smile on his face, they locked eyes as he slid into her for the first time bareback. She said his cock felt really nice and big because he was so excited. Things didn't go as planned since he was so horny for her that he jizzed inside her quickly. She wasn't going home sexually frustrated, so she moved to a big chair near the bed and spread her legs resting them on the arms of the chair as she had done another time. He walked over to her jacking off and she licked his balls. He took his time as she used her tongue till he was ready. He had been hard for a while and she was craving him to be in her. He gently pushed into her wet pussy and fucked her like an experienced man should. He knew to slow down and let her massage her clit for one last orgasm. He wasn't done yet though. He rocked in and out of her for 5 or so mins like she likes. He stiffened, then grunted as she felt his juice splash inside her, adding to his first load.

She ran into the bathroom to wipe away his semen that was leaking out of her onto her inner thighs. She was excited to tell me it all went great and tried to remember details for me. They had taken much longer than planned so she hurried him up to drive her over to the shop. She didn't want me to be waiting with the guys around. This massively successful encounter tee'd up the second sharing experience.
 
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My wife plays Pokémon Go. She had met a man while playing and they would get together and walk around and play. Once I told my wife of the fantasy, she started looking at him in a more than just person to play the game with. After a little bit of time, she decided she would go through with it and she decided he would be the one. So on my birthday, she showed up dressed up to met him and explained my fantasy and that she wanted him to be the one. Needless to say, he agreed and I became a cuckold.

So my wife started off with a man she knew and trusted.