Well, Valarie, I honestly don't know what I would have done had I been in his shoes at 14 - The sex thing doesn't bother me as much as the drug allegations - those, I fear, would have scarred him for life far more than a little nookie... I had LOTS of sex at 14, and I turned out fine - faithful to my wife, not a drug addict, and I certainly am not a pig.
I don't think that having sex with an older woman would have been any different than the sex I was having with the girls in my own age group. Well, actually, the sex with the older woman would probably have been better - the experience factor, you understand...
Sex with a woman older than your mom when you are in middle school - that couldn't possibly be harmful to a boy? With whom were having tons of sex at age 14? A 12 yr old girl? A 6 yr old boy? Your Grandma?