Will I ever do it? Your opinions please.

All the signs are already there. If the opportunity arises I'm sure you will dive in, honey ;)
 
No Brainer

Im surprised you haven't. I sucked plenty before my first anal experience.
 
also

Your one fortunate S.O.B. to have a woman that sexually open to try those things with you!
 
Your wife sounds wonderful! If my wife were like her I would have done it already.
 
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