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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 fetish cuckold bbc trainer story high definition porn that is 1920x1920px in size. This image is listed in define cuckold definition category. What does cuckolding mean in Urban Dictionary, 1920x1920 in 729.14 KB.