This will be harder, just stay focused on those muscles. Press the next object gently against that gaping hole and feel where the resistance starts to build up.
Slide the object back out and try to close that hole by contracting your anal muscles. While it's on tension push it back in till the sensitive part.
While pulling it out, push out aswell. Do this very slow, really let that hole have a hard time getting it out.
Do this 10 times, each stroke should take 1 min.