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A curious, crossdressing bad boy finds himself in over his head when his girlfriend catches him masturbating. Seizing the opportunity, she punishes him by making him wear his favorite football player's jersey and a pair of stockings. She then secures a massive dildo to a chair and orders him to sit on it. He hesitates, but her stern gaze and the promise of further consequences if he disobeys drive him to comply. With a grimace, he lowers himself onto the dildo, his ass stretching to accommodate its immense size. He struggles, his body tensing as he tries to take it, but she urges him on, slapping his ass and telling him to take it like a good little cockslut.