All the group sex experiences I've had have been with people I've known for a while. It was something that we all talked about beforehand. Safe sex should be important to all members of the activity and if it isn't you probably aren't with someone who you should be including. They should be just as concerned as you are. So it shouldn't be an issue.

Talking about STDs doesn't have to be business-like but it definitely should be discussed. If someone doesn't want to discuss their sexual health but, wants to play with others, that is where trouble happens. People on the dating/swingers sites should at least be more comfortable discussing sexual health than someone who you meet in a bar. I always try to ask well before getting into the heat of the moment because that can be a downer of sorts and possibly lead to an uncomfortable situation.

When I find someone who is serious about meeting to see if the mutual interest in playing is really there, I just lay it out for them. I tell them I play safe and ask if they do too, and I ask if they have been tested for STDs and their status. Just remember, if you are going to ask, make sure you can answer about your status as well! If someone is uncomfortable talking about their sexual health, then find another candidate.