Good Luck to You, Leo Grande (2022)

In a hotel room, 55-year-old Nancy Stokes welcomes a young male sex worker named Leo Grande. Anxious, she explains that she has never had an orgasm, and has vowed never again to fake one after the death of her husband two years earlier. Nancy is insecure about her body and age, and embarrassed at having hired Leo, who tries to put her at ease. Leo expresses no shame about sex work, but he reveals that his mother believes him to be an oil rig worker. Nancy shares that she is disappointed in her adult children, adding that she is a retired religious education teacher. Her husband was her only sexual partner and found oral sex demeaning, and they never deviated from unfulfilling missionary sex with no foreplay for thirty-one years together. Nancy recounts her most sensual experience: as a teenager on a family holiday in Greece, a hotel worker took an interest in her. Alone in the garden, he began kissing and fingering her before being interrupted, and she left the following day. Seeing Nancy aroused and relaxed by her own story, Leo kisses her and initiates some form of sex. A week later, Nancy meets Leo in the same hotel room for a second session. She has prepared a bucket list of five sexual activities to experience for the first time, beginning with oral sex on him. Nancy remains business-like and tense, worsened by a phone call from her daughter, but Leo relaxes her later through dancing and a massage. Fearing that she sacrificed her youth and potential adventures for her family, she is overwhelmed after touching a shirtless Leo, who encourages her to embrace her own body. Nancy talks about wanting to feel 16 again, and mentions her old teaching job. She remarks about how outrageous some of her girl pupils were and how she opposed their shortening hemlines, remarking that "some of the male teachers were like lambs to the slaughter". Leo thinks those men might have been in the wrong job and defends the girls' rights to wear what they choose. Nancy says maybe his generation need a war to use up their energy. Leo reveals he has a younger brother in the army, from whom he is estranged. When he suggests Nancy book more sessions, she accuses him of trying to make more money. He tells her about his other clients, explaining that he obtains genuine pleasure from seeing their pleasure. Nancy sees Leo becoming aroused as he describes his work, which in turn arouses her, and she finally performs fellatio on him. Nancy books Leo for a third session in the same room. He performs oral sex on her, the second item on her list, which she enjoys, saying her body "is now a wonder" and "a pleasure playground", but does not bring her to orgasm. She admits to cyberstalking and uncovering Leo's real name, Connor. Upset that she hasn't respected his boundaries, Leo tells her not to book him again. Nancy suggests her looking him up is because she thought he was proud of his work and that they were getting to know one another. Leo asks how would she like it if he were to expose her as a client. Leo leaves but returns for his forgotten mobile phone and throws bedding about in his search. Nancy encourages him to tell his family about his work, even offering to speak to his mother. Leo reveals that his mother tells people he is dead and disowned him when he was fifteen. He restates that he believes Nancy wants the nice version of his life not the truth, and leaves once more. Nancy books Leo for a fourth session, arranging to meet in the hotel's cafe where one of the waitresses, Becky, turns out to be one of Nancy's former pupils. Nancy thanks Leo for her newfound confidence and sexual awakening, and has discreetly recommended him to several friends. She admits her real name is Susan Robinson, and that he is the only true adventure she has ever had. Becky interrupts with a story about Susan shaming her and her friends for their short skirts, calling them "sluts". Leo has revealed his job to his brother, reconnecting with him. He also explains that his mother disowned him after catching him and several friends having group sex; she no longer acknowledges his existence, even walking past him in the street. Susan apologises to Becky for her past judgmental behaviour, confessing her real relationship to Leo and recommending his services. Susan and Leo enjoy a final session in their room, passionately engaging in all the remaining acts on Susan's list, but she is still yet to orgasm. While Leo looks for a sex toy, Susan watches him walk around naked and masturbates, giving herself her first orgasm. She thanks Leo, telling him this will be their final session, as she does not need him anymore. They part amicably. Alone, Susan appreciates her own naked body.