B/L yellow areola discharge, What can this possibly be? (photo)

Hard to say via the internet. But most likely some serous discharge that can be corrected by a minor therapy. I doubt this is a "bilateral" herpes issue. But taking acyclovir could either clear it or have no effect.  

Your history of recurrent bouts of pain and rash of the nipple and areola and could suggest a Herpes Zoster infection.  Your plastic surgeon can do a test to see if you have herpes.  If you do Acyclovir or Valtrex can control outbreaks.Herpes zoster infects the nerve roots and causes pain and rash in the distal distribution of the nerve.  The nipple areola is innervated by the fourth intercostal nerve which could be septic to herpes zoster virus infection.

Spontaneous discharge from your nipples or areola should be evaluated by a doctor who handles breast disease. Your best bet would be to have your plastic surgeon refer you to a dedicated breast surgeon (general surgeon not plastic surgeon). The breast surgeon can do an examination and get the appropriate study such as an ultrasound, mammogram and/or MRI. Call your PS Monday and get set up with an appointment.  You might also talk with your PS about referring you to an infectious disease specialist.