Sissy's Intimate Anal Initiation

A hooded sissy crossdresser, anonymous and vulnerable, begins a private anal training session, the room filled with the soft hum of toys and the scent of fresh leather. A custom-made penis gag, thick and veined, stretches her jaw, forcing her to drool and moan around it. She lubes up her tight hole, teasing the sensitive skin with the tip of a petite anal plug, before slowly pushing it inside. Her moans deepen as she fucks herself, the plug's ridges massaging her inner walls, driving her closer to orgasm.

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