whether it was to conceive, or to just have pleasure.
How did you decide it was worth the risk?
Not sure if this is what you mean, but I gave in after almost 15 years of having sex with condoms with my wife, and decided to let her try to get pregnant.
It was coming home from visiting her family for christmas, and we stopped at a day's inn in a large city, since we had a freebee coupon to use up before the end of the year. As I recall, I was sitting proped up in bed wearing only a black bowtie around my neck. She came over and knelt on the bed, giving me a big deep kiss, as she realized I wasn't moving to put a condom on. It was one of the most intense orgasms I can recall, because it was the first time in almost 15 years that I had come without a condom on, and was pretty intense, since I was pretty passive in that position. It was sort of a cowgirl position. And we both really got off on it.
Was this what you were looking for?
We had decided to have a child... although it took almost a half year or more for her to get the timing right.