I will answer this from my perspective. I am a proud cuckold and I will try to explain what it is and why. Some things we do may not fit in with every one's thoughts but this works for us. The term is "Cuckold". Not "Cuckhold" and certainly not "cockholding".
Here's Everything You Need to Know About the Words "Cuck" and "Cuckold"
Urban Dictionary: Cuckold
Top definition. Cuckold unknown. A man who willingly encourages his wife to sleep with other people because it brings him pleasure. Cuckolds exist on a spectrum between two extremes. One on end is the masochistic cuckold who enjoys humiliations, degradation, and other demeaning activities at the hands of his wife and her lover. The alpha cuckold lies at the opposite end of the spectrum and does not enjoy any form of humiliation and often has a direct say in who his wife sleeps with and when.
Either way, what TF does it mean in all different contexts? We asked experts and found out pretty much everything and anything there is to know about the term and its many uses. That being said, Laurence Horn, PhD, professor emeritus of linguistics at Yale , adds that the way the term is used now more closely mirrors the meaning of the word "wittol.
Top definition. A man who lets his wife or girlfriend have sex with other men. Often the man lets her do whatever she wants and treat him like shit. Short version of cuckold.