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A reluctant cuckold watches as his partner transforms into a sissy, following an online guide to feminization. The sissy, now wearing lingerie and makeup, begins their training by sucking their cuckold's cock, taking it deep and gagging. The cuckold, hard and leaking, watches as the sissy moves on to strapon play, pushing a massive dildo into their ass, fucking themselves while moaning and begging for more. The cuckold, humiliated but aroused, watches as the sissy brings themselves to the edge of orgasm, only to be denied, their body shaking with need. The training continues, the sissy becoming more and more feminine, more and more of a cum slut, all while the cuckold watches, helpless and hard.