I've done silicone with a print positive for a plaster mold. TPU is surprisingly soft and I hear TPE is even more so. So far with a headphone pad every day, TPU over my ears isn't terrible. I'm working on compliant mechanisms that bend into shape too... Actually working on a bistable mechanism that can lock into curved shapes but still remain soft and compliant like a headphone pad now on the laptop beside me. There is a scientific paper on sanitizing prints to medical levels effectively using 120°F soapy water too.

My last iteration of headphones pads fascinated me for the potential to create curving mechanisms like fingers that can bend in a controlled joint like motion using just a printed vertical tube... Much is possible for those that care to explore.

Like seriously, I took apart an old worn out heated massage vest thingy a few months ago and the massage vibration is just a 2in diameter heavy steel weight inside a giant coil like a subwoofer magnet. It thrusts back and forth like a subwoofer and is driven the same way by an audio signal. Something like that could do way more than a little jiggling. There is a whole different level of trepidation over inserting versus insertion with such mechanisms, but that massive driver is more than capable of fun for the full spectrum of human anatomy.