With that history, you have to be clear with him that this is about having fun, not a romance. Like most here, we suggest you meet at a bar for a drink, not a date, just to meet. You should all look your best though! As for that first play we suggest you share a hotel room; offer to split the cost. Have a few drinks to ease the tension, maybe put on some music. We find doing own partner same room the first time is fun and sexy and if everyone is feeling it, then maybe softswap. That depends on your limits, which everyone should know. And it's ok for your limits to evolve.

Be safe and clean! We prefer bareback but always start out with condoms.