[Matt Harty]

No matter how you go about it, I suggest using a finger first, without warning, and during a time when she's extremely aroused or while she's busy sucking you off. And don't just jam it in either. Just rub the hole first and look for a reaction. If she doesn't slap your arm, yell, or pull your hand away, put your finger in a LITTLE bit and move it around. If you go too far, you might touch shit and it'll get awkward fast. You might hit the wrong spot if you go too deep and she'll think she's gonna shit on your hand, etc. Or she might be loaded already and you put it in at a really bad time.

Either way after doing so ask he if she liked it. If she said yes, do it again a few more times and then start discussing whether you should go deeper or sticking alternate items up the chute. She SHOULD come prepared cleaned out for you if she knows you might do it. Otherwise, she's dirty and you should probably stop having sex with dirty girls. They carry aids yo.