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Well, if Efim wants to get her into trying anal sex, then what he needs to do is the next time he is going down on her, start fingering her to get his finger nice and wet, and then casually slip that finger down to her anus and just rub his fingertip around in light circles.  If she likes it (and I have never had a girlfriend who didn't - even though a few of them swore they would never try anything anal), then Diana will push against that finger and allow it to penetrate a little...but don't let anymore than the first segment of his finger enter her...and don't let it go any further than that...the first time.  That will be enough to tease and have her thinking about trying it again.  And, all he needs to do is repeat this process during the next few sex sessions (allowing her to push on his finger for deeper penetration).  Before he knows it, he won't be the one asking for anal sex.  She will. 

This has worked every time I wanted to have anal sex with a girl and I thank the girl, who was a good friend in college, who taught me this strategy.  Angie! Wherever you are in the world today, THANK YOU SO MUCH!  That was one night of homework that I will never forget.

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