Square peg, round hole?

Master and I have reached a meeting of the minds, as it were, with our old friends Ume and Gene, and now we swing together* whenever our schedules allow.

We have a planned rendez-vous later this month, and last night I chatted with Ume about what we'd like to do the next time we meet. Eventually he brought up that, though this month's meeting would be too soon for comfort, sometime in the future he'd be interested in perhaps trying pegging.

I've considered whether I'd like to try pegging before, and I must say that I find the idea a little weird, though not so much that I'm unwilling to try it. However, I'm trying to determine what the source of my disinterest is.

Part of it is that I'm not confident in my ability to avoid hurting Ume - it's the same reason I'm hesitant to anally penetrate anyone, male or female. However, there does seem to be something to woman-on-man penetration that I find mildly off-putting in a way that man-on-man, woman-on-woman, and man-on-woman penetration are not. This makes me think that my discomfort is a result of socialization.

This doesn't quite make sense to me, even though that's where the evidence points; after all, I enjoy fem dom/male sub as much as any other permutation of genders and power dynamics. And even then, penetration doesn't always equate with domination anyway - so why does the specific scenario of a woman penetrating a man cause this reaction?

My frustration with the irrationality of the whole thing makes me more keen on trying it at least once, to see if I can overcome the socialization that I believe is affecting me. However, I think this does raise a larger question: how do we find the balance between owning our sexual preferences and working to undo sexist/racist/whatever conditioning? For example, while it's okay to find, say, Asian women attractive, it's not okay to fetishize them as "exotic" or anything like that. How do we discern what is a genuine and/or benign preference and what is a problematic mindset? (And that doesn't even get into the post-structuralist idea that there is no such thing as "genuine" sexual attraction or gender expression. (Yes, I've been reading Judith Butler lately, how did you guess?))

In any case, as I said, pegging is something I'm willing to try. Maybe once I'm actually performing the act I'll find out it's actually awesome; maybe I'll grow to love it, like I did with spanking. Or maybe I'll just be "meh," but at least I can say I tried it. There are very few sexual practices that I'm willing to dismiss offhand.

*I get the impression that "swinging" as a concept has something of a sour flavor for the poly community in general, but that really is the best way to describe what we do, I think. However, I'll save that for another post.