Losing your virginity can seem scary, and the range of myths surrounding it doesn't help. In most cases, though, penetrative sex should not be intensely painful, even on your first time. Follow along after the jump to learn how to mentally and physically prepare yourself. How painful is losing your virginity - How painful is it to lose your virginity? Variable. It may or may not feel uncomfortable. Jun 08, · How to Lose Your Virginity Without Pain (Girls) Three Parts: Building a Positive Attitude Educating Yourself About Your Body Enjoying Yourself During Sex Community Q&A. Losing your virginity can seem scary, and the range of myths surrounding it doesn't help%().