Typically that would hurt but when sexually aroused, the vagina can basically extend to accomidate any size within reason.
The first is that first or one of the first few initial thrust into her, The second is when I'm just about to orgasm.
For Above Average Players with medium to high club speed.
Plenty of control for you to work some magic near the hole.
Fortunately, Haskins was there to provide enough attempts to qualify.