My scrotum has never been too tight for a testicle exam. I'd have to say the most recent thorough exam was 1.5 years ago when I was pre-surgery examined for inguinal hernia repair. The pre-surgery area was very warm to me, so scrotum was very loose under a couple layers of sheet & blanket. After male surgeon examined me while standing, (he examined me previously in clinic but scrotum was tighter). He asked me to get back into bed/gurney, palpated my lower abdomen, then felt each testicle between thumb & finger, quickly checking left then right nut. I caught a glimpse of his facial expression...he was fixated on scrotum, then my eyes darted back to catch the right testicle being examined. He grabbed a blue surgeon's marking pen and made an "X" around the herniated spot on my lower left abdomen.
Shortly after surgeon left the anesthesia people visited, after they left, the male Resident surgeon came in behind curtain, went over all the surgery details, what they'd be doing, how they would do it, explaining they may have to revert to "open repair" method versus laparoscopic method, etc., had me electronically sign something, popped on disposable gloves and said he would examine me, while I was laying down. He felt region surgeon marked with pen, confirmed the spot, then as he gently felt each bottom of my scotum & testcles. I really, really enjoyed being examined with a loose scrotum!
Since then, I have asked my primary care physician for testicle exam, but his don't seem as thorough...maybe because it's colder in the clinics. I've always been too timid to ask for testicle / genital exams during Doctor visits if they are not offered, but ask for them now.