Quote:
Originally posted by analog
One at a time: Pinky, ring, middle... then thumb... all very slowly, lots of lube, get it ready. After thumb, go to two fingers if need be. If you take your time, it will stretch for you. Take your time...
Take your time. 
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I have to agreewith analog on this one..
Another thing I find helpful is if I just hold a finger or two against her anus and let her push ata rate that is comfortable for her.. or use a small dildo (made for anal) and let her insert it and get used to it while the two of you do other things.. Once she's comfortable with something else in there you can hold yourself against her and let her push until it's in.. then go slow.. slower then you ever thought necessary..