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Is it possible to cause damage by squeezing penis while trying to urinate?

My ex girlfriend used to hold my **** tight while I tried to pee and it hurt sometimes bit never cause immediate problems. It's been a few years since then and I'm having problems with my bladder like completely emptying and I always have the urge to pee. It's also important to mention. I have spinal stenosis in my l5 s2. I've seen a urologists and he said my prostate feels normal but has no idea what might be causing this. I'm currently on Flomax and it seems to help but I've been on it a few months and it seems to be working less and less. Can someone give any advice?
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