Dec 11, · Then, put your hands on his hips and pull him toward you, guiding the tip of his penis into the condom. Have him use his hands to steady the base of . Sep 27, · Actually, this is known as one of the great ways on how to put on a condom without being awkward that you should try out! Wait until the penis is fully erectile and then put on a condom. If you put on a condom on your non-erect penis, it can cause the condom to slide up, down, or off your penis. Wear the condoms the whole xmilf.xyzry: Sexual Health.