Best ponytail, EVER, has to go to, SURELY, Ariana Grande!
I get a MASSIVE stiffy just THINKING about wrapping her ponytail around my cock in a soft hair-cocoon...and holding it with both hands (my fingers wouldn't even be able to touch with the size that it would be with all that hair!) as I slowly jerk off into it double fisted...
Oh, and I always had a thing for Melody Thomas Scott in her younger big hair days.