Actually, doubling up on ray of enfeeblement would fall under the rule that says "Spells that provide bonuses or penalties on attack rolls, damage rolls, saving throws, and other attributes usually do not stack with themselves."Patryn of Elvenshae said:To respond to the above: Penalties of all forms stack. So, you could hit someone with two Rays of Enfeeblement. Note, however, that the spell cannot reduce a target's effective Strength score to less than 1.
So sure, you could hit someone twice with ray of enfeeblement. The result would be that he'd take the worse penalty, not both (and to a minimum of 1).