My wife was a virgin when I married her. Didn't realize I was short in the down there way. Never got her off. She didn't understand what the big deal was about sex, wasn't all that much fun, after all. Truth be known, wasn't all that much fun for me, either, as I didn't get much friction from penetration.
Years into our marriage, we were living in a garden apartment, that is, a small one-story apartment complex surrounding a garden/patio area. We'd become friends with a woman across the garden from us and one day having drinks on the patio, my wife blurted out how sex was unsatisfying. We were into the third bottle of wine.
Our friend suggested a trip to a local swing club for some variety, told us they supplied condoms for free and not to worry. That Saturday, we went and I had never seen my wife so well satisfied by a man with a real cock. Not my pathetic nubbin.
She was quite angry on the ride home about years of disappointments and our friend, who took us there, said that she could have other lovers, and my wife said well not him again, pointing to the rear seat where I sat.
She took us to a fetish shop and bought me my first chastity cage and locked me into it. Also bought an eyeless latex hood. She had me wear the hood whenever she took a lover, having me sit in what our friend called a cuck chair she'd talked my wife into putting into our bedroom.
The day containing the moment of me becoming an ultimate cuckold arrived without me knowing about it but she put the hood on me and for the first time guided me outside to our car and drove to a motel. She guided me into the room where there was a man waiting. I sat in the chair (nice of the motel to have a cuck chair!) and she had him fuck her. He then came over to the chair and wiped his meat on my lips, having me clean him without touching him. He dressed and left and she had me come to the bed to clean her up, again, no hands.
That was my ultimate cuck moment.