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Work on building up your self-esteem. Not just for the sake of having a 3-way, just do it in general for yourself and for your relationship. In my own open relationship, jealousy has occasionally popped-up both for myself and for my boyfriend. It is not the sort of thing that causes us to go into fits, but something that we acknowlege to one another and talk about. Practicing groundlessness in our relationship has helped, not only in the realm of being open, but also in the realm of placing expectations on one another. Rather than fretting about whether he'll still be with me two years from now, I focus on and appreciate the fact that he's with me now and stay mindful that Gawd has never promised us another day. Regarding the 3-way, take it slow. Talk to your husband about it. Tell him about your insecurities, have him tell you about his, talk about what activities each of you would want to do in the 3-way, talk about what would make you uncomfortable, fantasize about WHO this third person is. Wait for the way untill you've become somewhat comfortable with the topic. RE: STD's? As Notquitebiguy stated, you're limited to hand-jobs if you want % safety. Oral only keep you relatively safe from HIV, but not other STD's. If there's fucking, use a condom. Having everyone get tested beforehand would be a great thing, but I think you'd be hard pressed to find a guy patient enough to meet with you, establish that there's chemistry, be willing to go to a clinic for testing with you, and follow-up a week later when the testing results are ready. An open minded friend who is into you would probably do this, but I don't think guys you pick-up off an internet dating site would. Sometimes, meeting with a guy and guaging his level of integrity, openness and sexual communication through having a conversation with him might put your mind at ease that he is being truthful about his stated STD status. Ultimately, though, bringing in a third always entail at least a ~little~ risk of exposing you to STD's, unless you go the hand-job route (which, I'm guessing, would be a little too limited a type of sex to hold your interest.