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Description:July 14, Losing Your Virginity Raised on a diet of rom-coms, we often imagine our first time to be wonderful and romantic. But in reality, our first sexual encounters are far what we see in the movies. Clueless virgins and fumbling hands can make for a messy, complicated, or downright awful experience. He was my then boyfriend and we were The whole situation was awkward and I was uncomfortable because we were both clueless. As he rolled on a condom, I remember lying flat on my back, waiting for an impossibly long time.