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Movies like Cherry (2005)

Meet Whipper. Cherry describes a short, but pivotal episode in the life of Whipper, a 16 year old growing up in the North East of England in the early 90's. We encounter Whipper at a difficult age - socially awkward and saddled with the seemingly impossible task of losing his virginity to his 15 year old girlfriend, Alison. This issue gnaws at him daily until he hears his mate Steve brag about his sexual encounter with an older girl called Liz. Whipper is instantly convinced that this girl is the answer to his long-standing problem. When his chance comes, though, he is led into a hilarious and utterly cruel final denouement that sees him learn some lessons about love and sex.