I can't use the ones that go into the ears, either (my ears are freakishly tiny!). Transcription isn't a service I provide, so I'm not sure if a USB headset would work with your equipment, but I do use a headset all the time for calls and video conferencing. I
my Logitech ClearChat headset. It has padding on the earpads and on the headband, it has volume control on the cord, and it plugs into my USB port. Blocks out almost all background noise, and it's very comfy. Not very expensive, either.