Without simply copying and pasting another persons answer here, cuckolding is when a married women has sex with one or more men with the husband's knowledge. The husband may not only be aware, but may encourage this and even find it stimulating. In other words, she is screwing other guys and he knows and likely even likes it. He may get off on the "badness" of it, the humilation of it, watching it or simply hearing about it. Some men are aroused at the idea their their mate prefers the other guy especially if he is better endowed. He may want to be made to feel like a women while she gets a "real man". Other topics that may be related to this are: male chastity feminization small penis humilation femdom
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Strictly speaking, a cuckold is a man whose wife has illicit sexual affairs. In contemporary usage it is sometimes applied to non-married couples and is sometimes used (incorrectly) for women in the analogous situation (who are correctly termed "cuckqueans.") It is also used today to apply to men and women who experience a masochistic sexual excitement at the idea of their committed partner having sex with someone else.
This later BDSM fetish usage is the most common today. The fetish is generally referred to as "cuckolding." Linguistically this term is incorrect since cuckolds are by definition deceived and unwilling (willing or accepting cuckolds are technically "wittols,) but the pose of reluctance is integral to the fetish thrill.
The term was widely used in medieval European society and literature where fidelity within marriage was strongly propounded by religious leaders and the center of morality tales. In the very patriarchic society of the day, a man who could not dominate his wife at least to the point of sexual exclusivity was seen to have failed on a fundamental level. "Cuckold" enjoyed wide use in Elizabethan and Restoration drama, when the figure and fears of the cuckold was used for both tragic and humorous purposes. The word appears less frequently today outside the fetish usage, although it is still seen in newspapers and legal proceedings as well as artistic criticism and novels.
Plural of 'cuckold." A cuckold is, strictly speaking, a man whose wife has sexually relations with other men without his knowledge and/or to his chagrin. In the fetish sense, it can mean a person (male or female) who gets sexual satisfaction from watching their intimate relationship partner have sex with other people.