zero2010,
Go for it, and be sure to tell us how it goes.
From your description of your relationship, I would think the worst that could happen would be that the reality doesn't match the fantasy and you choose not to pursue it. More likely it'll make her hot and wet as hell, and you'll love the way it feels like I do (the anus has an incredible concentration of nerve endings, and the rectum has the prostate to bump against, which also feels great.).
As Ms Athena would say, it is an incredible mind fuck, and likely very hot for her to be the aggressor, yet seeing you moaning with delight, as you should if the two of you do it carefully with lots of lube, and loosening up with fingers before moving to a strap-on. I find that it feels great, and the role reversal taboo feeling of the whole thing is delicious. Both the penetration and her hips slapping against my ass are very erotic. I like mish best for this, though doggie is fine too, and might get her off visually. Combine that with a nice hand job for an explosive ending.
Have fun, you lucky guy!!
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