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Jan 2, - 25 Women Describe What It Felt Like To Lose Their Virginity. By Lorenzo Jensen III, I felt bad about his sheets and carpets after.” —lasthebest “It happened so fast I don't even know if he entered didn't feel a thing.”. Apr 17, - Losing Your Virginity Doesn't Have To Hurt reaching out to a clinical sexologist, who can help you work through ways to make sex feel better.