Yes, you can definitely pump both breasts at the same time. That's how most people do it to save time. (Definitely follow our silicone flange application method!)
With a bra: See our article How do I pump hands-free with the silicone flanges?
No bra: Once the first flange is on securely, hold it on your breast with your forearm (extend the arm next to that breast, then bend at the elbow and bring your arm toward your breast). You'll then have that hand free to work with your other hand to get the second flange on. Remember to change the pump setting or tubing to double-sided.
Reviewed by Diana West, IBCLC
June 10, 2021