I am not sure if I used to be intimidated by wide waistband jockstraps or if I avoided them because they appeared claustrophobic to me. Restricting, restraining and choking. Perhaps they seemed to “old fashioned” and that is what I was rebelling against when it came to my underwear.
I chose to go first off with the Classic Swimmer Jockstrap for the simple reason that my first ever proper jockstrap was a swimmer jockstrap and I have a soft spot for them.
I have the XL and it fits me perfectly but it is important to note that usually the model here, Trent, wears a size large, but due to the amazing work Trent has been doing in the world of fitness, he needed to jump up a size to XL so the leg straps were big enough to get around his meaty muscle ass and not squish the pouch down on his shaft and balls.