Closely Watched Trains (Jiri Menzel, 1966) 
For its time, this film could have been considered on the cutting edge of addressing sexuality in a real and frank manner on celluloid. Unfortunately, it hasn't aged particularly well and is definitely a product of a different place and era. The plot centers around Milos, an apprentice train dispatcher who becomes wrapped up into losing his virginity to his conductor girlfriend. Initially, he has some, um, difficulties, and compensates by trying to commit suicide. The rest of the film concentrates on Milos getting some practice before finally consummating his relationship with Masa. That description sounds fairly crude but Menzel handles the material with enough wry humor and respect for his characters that it comes off as harmless and sweet. This isn't some raunchy numbskullery like American Pie. The film has a poignancy to it that isn't often seen in American cinema dealing with this subject matter. But the operating world of the film is weirdly disjointed, as the film is so engrossed in Milos and his quest that everyone is completely oblivious to the fact this is occurring during World War II and the Nazi occupation of Czechoslovakia. The war and its effects pop up sporadically, especially the end, but it feels like the reality of the world at war is being repressed. Sex is probably one of the only topics that could supersede war in a person's mind. It paints a quaint story for this film, but something, that sadly doesn't translate particularly well over the years.