Took DS to the allergist on Thursday morning, and without running any tests, based on what I told him, he said it sounds like it's only contact dermatitis. He said it sounds like when DS touches one of the overripe fruits, and then brushes his face, or rubs his eyes, that's what is making him break out... not actually eating the fruit. Yay for it "only" being a contact allergy!
The face has some of the most reactive skin on the body, so it looks that much worse when the allergen comes into contact with the skin on the face. Think about when you get a mosquito bite on your arm vs near your eye. The one near the eye looks much worse.
So, although DS' pediatrician has prescribed an epi pen for him just in case, it doesn't look like he should need it for his reactions. But, I'll take it as an insurance policy, should there be a more severe reaction. Rather, what we'll be dealing with is Benadryl to block the histamine, making him a bit more comfortable, and help reduce the redness when he gets hives. But any swelling will take upwards of 12-24 hours to fully go away when he has an outbreak. (I am all to familiar with hives, since I too have contact allergies). At least, I already know tons of tricks to help make you more comfortable during particularly bad outbreaks.

Re: Allergist update
What a relief! I think contact allergies, while super uncomfortable, are way less scary to handle. Is it something he might grow out of, or will it likely stay since you have contact allergies?
Glad you got some answers!