I recently started wearing a condom to masturbate.
After 30+ years of marriage, during which we used hormonal contraception, then went bareback to discover there were fertility issues, I lost my wife a little over a year ago.
Decided that if I'm going to re-enter the dating pool in the 21st century one day, I need to get accustomed to wearing condoms.
Right now, the novelty of the latex sliding down my shaft, and the different feel from barehanded, result in a somewhat more brief duration than I (and likely any future partner) would like.