Aug 11, - Losing your virginity can seem scary, and the range of myths surrounding it doesn't help. While some women may experience pain during their. Does it hurt to lose your virginity? The first time you have vaginal sex, it may hurt, or feel good, or both. If pain and bleeding doesn't get better after the first time you have vaginal sex (penis-in-vagina), you can slowly stretch your hymen tissue with your fingers over time to make it less painful.