Given permission from your SO, would you engage in sex acts with another? (NSFW)

This is a quick rundown, but here goes….

I have always been interested in trying anal sex with a woman. For one reason or another, through the years and various lady friends, it’s just never happened. My current lady friend and I are well on pace to be engaged in the next 6 months or so (though don’t tell her I said that ;) ).... BUT, she has made clear she’s not keen on the idea of trying anal sex, and likely never will be.

A few weeks ago I jokingly brought up the prospect of engaging in the act, and she sat me down and told me… seemingly 100% honestly and without any malice or what not… that she would be okay with me finding another woman to try anal sex with. I tested this notion, pointing out that if I actually did it she would rightfully be upset, etc, etc…. and she assured me she would not be, as she knows this is something I’m interested in and have been for my entire adult life… and she can’t provide it. The caveat being she would never want to know about it. EVER. AND it couldn’t be someone we know or that I am friends with or what have you (basically can’t be someone I see regularly and consider a friend).

Since that talk I’ve tossed the idea around, thinking about it. By in large I am very against the idea of sex outside the confines of our relationship (unless we are BOTH involved in it, IE 3 or more-way, something else I’ve never done, but I digress…).... On one hand I even try to justify it by thinking about the fact that very early on in our relationship (ages ago), she was sleeping with another man at the same time… prior to us becoming “official”.... which has always pained me a bit. That fact, paired with her express permission…. vs my own issues with the concept of “cheating” on my g/f, even with her permission.

But where would I ever find a girl like that anyways right? Well surprise surprise there is now a girl available. One whom I know to be clean of STD’s, free of drama, trustworthy to maintain the secret, and open for the idea of anal sex…....... and NOW i am truly faced with the prospect of this being a possibility.

And I’m battling with some conflicted emotions. My long time desire to try this sex-act, my loves desire to never try the sex act, her express permission, the bitter taste from what I take as an early indiscretion, the perfect candidate to be the other girl, my own feelings about the morality of the subject…. etc, etc.

What would YOU do put in my shoes…. or what comments/thoughts do you have?