I love the butt plugs with the tails and I'm just getting my wife comfortable with anal, is there...
Sir here:
I recommend starting small and having a ramp plan with beginners. I’ve found this to be a good ramp progression:
Small Starter:
Cal Exotic BOOTY CALL BOOTY ROCKER BLACK
http://www.amazon.com/Exotic-BOOTY-CALL-ROCKER-BLACK/dp/B00GIXCQUU/
MED:
California Exotic Novelties Booty Call Booty Beads, Black
http://www.amazon.com/dp/B00725VCKI/
Bigger: Tantus Neo Anal Butt Plug, Black
http://www.amazon.com/dp/B00AG591PO/
For tails the crystal delights plug tail size is a good smaller size that is still big enough to stay in:
https://crystaldelights.com/shop/
Comfort is of course going to be relative when it comes to anal :) but all of these designs are smooth without any extra irritating features.