Re: transvaginal ultrasound
I do have a high and tilted uterus, and my c-section made things more challenging too. My annual, while not as bad as you describe is always a full 10-15 minutes of pressing, pulling, repositioning, more pressing, etc. just to get the pap sample. It's apparently a whole lot more invasive than what most women I know describe. It's not "a breeze" or "no big deal." It's not even merely "uncomfortable." It hurts!
Transvaginal ultrasounds were, for me, much easier. Some pressure, the tech might push on your belly while moving the probe around, but no pain.