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Hi,
You are right---this is a tricky conversation, but an important discussion that can ultimately lead to increased trust, honesty and intimacy.

Here are a few suggestions that I have found:
- Go Ask Alice: How do I ask my partner about his past?
- Coversation Starters: STD Testing from USDHHS

To answer your first question, there is also a Sex Readiness Checklist at Scarleteen: http://www.scarleteen.com/article/sexuality/ready_or_not_the_scarleteen_sex_readiness_checklist

Let us know how your conversation goes! You can bounce some ideas off of us on this thread, if you would like to.