Mine might be the time when, as a teenager, I was given a surprise rectal exam by a doctor. My mum was in the appointment with me. The doctor started with saying “this might feel a little uncomfortable” as he lubed up what looked like RoboCop’s detachable penis before sticking it up my bum. Then he realised the light on that one didn’t work so he’d need to get a new one. MAYBE CHECK THE NEXT ONE WORKS BEFORE PUTTING IT INSIDE ME, EH DOC?
The embarrassing part was walking back outside the doctor’s office, still feeling the lube between my cheeks, and my mum breaking the silence with “…so, was it a bit uncomfortable then?” while barely keeping the laughs in.
Thanks mum.