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Your older sisters’ single trans friend, Alexis, is in a bind. She won a sales contest at her work and is being treated to a ‘Winners Club’ couples retreat in Hawaii with the company executives. The only thing is, in order to attend, she must bring along something she doesn’t currently have— a significant other. As a favor to your sister, you agree to pose as Alexis’s boyfriend for the event. It’s a free trip to Hawaii and all you have to do is share a room with her and pretend to be her boyfriend. How bad can it be?