1 & 2) Still, yes, on occasion. Whenever I am stumped by a new thing to have to figure out how to handle. This summer, it was getting back into mountain biking for the first time since surgery, trying to figure out what protection would keep me dry while not getting shredded from the physical activity. Plastic diapers of any thickness: no. Pull-ups: sadly, no, wouldn't stay in place. Abena pads with cotton fixing pants: not bad, but made too much laundry; would be fine if I had a washing machine. Solution: Tena Super Stretch. Problem solved, I moved on. Another bugger: amusement parks and water parks or just swimming. That I haven't quite mastered yet. I need a way to keep water from flushing back up my urethra and causing an infection, but haven't found a 'water tight' swim diaper yet. There have been many other instances over the last 3 years: flying and the TSA, road trips with friends, camping. There is trepidation before each new experience if I'm not sure how to handle it or how it will go. I've found a little planning and forethought goes a long way. So does privately disclosing on a 'need to know' basis.
3) I've not had a professional massage ever, but I'd imagine they would be just that--professional. If it was me, I'd probably wear a loose pair of boxers over the diaper (modesty about being obviously wet) and go in as clean and dry as possible.
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