Possibly the only behaviour more fraught with potential disaster than sex is talking about previous sexual experiences. At least sex usually feels good and is fun for both; confession only geels good for the confessor. Blabbing about your sexual past is a good example of trading off short-term comfort for long-term pain - not such a terrific idea.
If you want to confess past indiscretions, find a priest or a therapist, not a date. Thinking that "I'm just being honest" is a terrible reason to inflict past experiences on a date. Confession is only good for the soul of the sinner, and it can wreck a perfectly good relationship. If what you want to confide is a problem, solve it yourself; if it's guilt, get over it; if it's bragging, tell your friends or your diary. Anything else will come back and haunt you.
If you are about to do something that would be hard to confess, you may want to consider not doing it. This isn't to say you have to pretend that you've just sprung fully armoured from the brain of Zeus or that you're the last Vestal Virgin, or that you have to lie. It's time to adopt the Clinton plan: Don't ask, Don't tell. Anything you are or aren't sexually is about here and now. If there is baggage, find a therapist, find a priest. It will not only add absolutely nothing positive to your relationship, but it will come back to haunt you. Comfort yourself with the thought that between honesty and duplicity is silence.
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