In her comment to my Pimply-faced youth post the other day Quilzas said

But as for the first-time sex itself. Hm. Well, actually, first time for me was anal. I wasn’t quite on birth control yet and I was tired of waiting. It was fun, we had a great time. :D

She said it here.

Last spring a lot of people had fun mocking “intelligent designers” for their claims that, say, bananas are curved to fit the palm of our hand and therefore creationism is true. One twist that came up was expressed nicely in comments

Imagine that in an Australian accent:

“Now, what I’m doing now is dropping my pants and bending over. Now, look at that. Notice that my anal opening is round and roughly the width of your penis. Go ahead and show them. Stick your penis in my anus. There. See how perfectly that fits? Also notice that my anal cavity goes deep enough to take the whole shaft. Go ahead and show them how you can repeatedly move your penis in and out. Good. See how perfectly that fits?”

Source: AZImagine at RichardDawkins.net

So…

The world of heteronormativity and, especially, our now-basic-but-extremely-recent ideas about basic hygiene don’t cultivate us to see it that way, and for a lot of us age and experience tends to blur our earliest attempts, but in terms of things one can do with a penis anal penetration isn’t that much harder or often any more awkward or uncomfortable than vaginal penetration. Nor (since, upon rereading Quilzas’s comment, I notice even here my cultural conditioning is trying to take over) need anal penetration be any less than “fun, we had a great time. :D”

Except for a two-year period of surgically-facilitated fertility I’ve had vasectomies since I was 21. But several of my partners mentioned that they chose anal intercourse as an alternative to abstinence when birth control was unavailable.

Now at least according to a blogger named Mark Pincus this may be another one of those generational things, e.g.

...we found that most urban 20 something women saw anal as normal while those in their 30’s and 40’s saw it as something taboo, racy, raunchy, slutty (take your pick).

He said it here.

So… I’m curious. Assuming nobody involved is a clueless dimplick and also assuming your experiences were voluntary and intentional, and of course, assuming you’ve tried both, how would you compare your first times trying vaginal and anal intercourse? And which did you try first?

For me I think it was actually a lot easier trying anal penetration for the first time. For one thing I was older, I already had a lot of experience with vaginal intercourse, and since I was out of adolescence I think I just had a lot less of that teenage angst-on-the-line, whoa-this-is-it feeling. For another my partner was way more experienced and so was able to take the lead and tell me exactly where, when, how, and how quickly she wanted to proceed. Which is a good thing because I was so heart-thumpingly solemnly/aroused/thrilled/honored/curious, not to mention head-over-heels in love anyway, that I was practically trembling. (I think my partner and I trembled the first time I had vaginal sex as well, but that had a lot to do with our dead fear of pregnancy combined with our dodgy contraception techniques.)