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A bashful femboy, adorned in lingerie and a chastity device, takes his first tentative steps into sissification. Alone in his room, he retrieves a realistic dildo, its size and texture sending shivers down his spine. With trembling hands, he lubes it up, the cool liquid making his asshole pucker. He teases his 'man-pussy' with the dildo head, his asshole lips quivering. Finally, he inches the toy inside, gasping at the intense sensation. He rides it slowly, his big ass bouncing, relishing the feeling of fullness.