Yes trim the nails...!!! They hurt!
Be sure you get him good and wet or use some KY or olive oil, don't take much.
I love it, when my wife gives me head and she will at times when licking and sucking my balls lick and get my ass all wet (oh man that drives me nuts) and insert a finger and just as I cum pull the finger out!! WOW what a rush!
This guy loves the anal, we have many toys and I love it when she uses them, I'd let her us a strap-on on me if she had one!

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GirlWatcher......;-)
Love Them Little Tits

Pixie's Wildland Fire Fighter
Find'em HOT and Leave'em WET!