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See more by tags PervTherapy Winter Flynn

Winter Flynn - “My Therapist Taught Me To Love My Titties” Winter’s Positive Affirmations

Released: November 3, 2025

Winter may sparkle on the cheer squad, but behind the pom-poms, she’s drowning in peer pressure and brutal bullying. She’s one trooper when she smiles and does her routines, but deep down inside that cute body, a wild girl is screaming to show her real self to the world. The first one to notice this is Dr. Fitzwell, her insightful and unconventional therapist, who realizes it’s time for a wake-up call. It is his mission to help Winter find the confidence to finally stand up for herself, or else her truth will come out in the worst way possible. Through a series of experiments, the therapist manages to make Winter speak highly of herself, boasting her confidence while touching herself in the middle of the session. However, for the experiment to be successful, Dr. Fitzwell will have to be more participative and play with every part of Winter’s body to help her get her groove back.