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What does cuckolding mean in Urban Dictionary?: cuckold: a man married to an unfaithful wife.so, cuckolding is whne the partner is doing the cheating. What does cuckolding mean in Urban Dictionary? Please note: You are currently browsing img interracial cum eating cuckold captions 1 high that is 960x982px in size. This image is listed in define cuckold definition category. What does cuckolding mean in Urban Dictionary, 960x982 in 163.90 KB.