Bound and gagged, the sissy boy is at the mercy of the dominant lady. She teases him with a feather tickler, tracing it along his erect cock and sensitive nipples. Then, she lubes up his ass and inserts a thick, textured anal plug. He moans against the gag as she twists it, stimulating his prostate. She watches, pleased, as he squirms and begs for more with his eyes, ready to take him further into his sissy training.