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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.

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Winter Flynn - Case No. 8004401 - Her Pussy for a Pair of Shoes (Winter Flynn's Debut)

Released: September 27, 2025

All I wanted was to fit in. I didn’t think that stealing a pair of sneakers would end with a security guard fucking my brains out. When he asked me to take off my clothes, I thought he was only going to make sure I didn’t steal anything else, but he took his sweet time touching every inch of my naked body. He stopped at my tits and squeezed them really hard, as if I could have hidden anything there. Then, he made me bend over his desk, and I felt his fingers slowly sliding into my pussy, deeper and deeper.

Should I have stopped him? Maybe, but I wanted to get out of trouble, and he knew how to use his hands. Besides, it was my last year of college, and law school was on the line, so if the prize of those sneakers was having a cock in my mouth for a while, I was going to suck it until I had swallowed every drop of cum. His dick felt even better than his fingers when he shoved it inside me, and I rode it so well that he let me keep the shoes.

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