I met my boyfriend in high school and we’ve been together since. I was never good at the whole relationship thing, but ours was so natural and I didn’t have to think to make it work.

I waited until I knew he loved me before I gave him myself – nearly eight months.

We’ve been having sex for several years and know everything about each other. Then he dropped the most unexpected question I never wanted to hear.

He asked me to have anal sex.

I was horrified.

I needed some input, so I called my friend Jessica who has a lot of expertise in this domain.

She told me it’s painful at first, but now she enjoys it.

Another friend opted to try it because pregnancy isn’t a possibility. It almost appears anal sex is the miracle women have been looking for: being able to enjoy someone else and a built-in birth control without marking up a calendar?!

How did we get here?

How did sex go from oral pleasure to penetration to “from behind”?

Anal sex goes back to before the ancient Greeks. They were the first to really objectify love, idolizing the ring finger because it was the only finger with a vein that runs directly to the heart. It’s hard to prove the Greeks are the first to have had anal sex, but it’s a decent starting place.

The Greeks also gave us the phrase “speaking Greek,” which is code in the escort industry for willingness to perform anal sex.

I talked to my friends and they collectively felt the same way about anal sex: NO!

I think there are a few reasons for their overwhelming opposition.

My first “regular” time was painful enough; I can’t even imagine my first time having anal sex. I don’t care what Jessica said, it seems painful.

Then again, maybe anal sex is like every other activity women have to do – it just needs accessories to make it bearable. Anal sex is like driving a car, but instead of a lei hanging from the rearview mirror, it’s KY lining the rear.

Anal sex has to be something both partners want to do. I think that’s the problem most women have – they don’t know what they want. I have a hard enough time deciding what shoes to wear, let alone anything more complex than that.

Picking out the right lubricant is also burdensome. There are so many different brands and types. Do I want a warming sensation with my lube? Maybe something scented or glowing. The only thing harder than this is shopping for shampoo; I don’t have time to sit there trying to read the fine print on the bottle, but at the same time I don’t want to have to explain the results of a sticky situation, so I attempt to.

For women, orgasms during vaginal sex are rare. (Sorry boys, most of the screams you hear are screams of pure boredom and pleas to stop.)

Even though I haven’t built up the courage to try anal sex, many of my faithful readers have and elected to share their thoughts with me.

From the female end, a few women claimed they absolutely loved it, April wrote: “An ex introduced me to it and it was the only way I could get off.” Nevertheless, most agreed it’s too painful and they didn’t have orgasms.

Men who wrote in said they love it because it’s a tight sensation and they had orgasms.

The truth is anal sex is natural. It’s not barbaric and several heterosexual couples do it, but it has a discouraging stigma attached to it. My friend Jessica gave it a rave review, while other friends who haven’t tried it only assume the worst.

No one wants to be judged, especially by something as fragile as sexual exploration. It’s one thing to have a reputation as a good kisser and quite another as a good lay from behind.

I want to hear from you. How much does size really matter? E-mail answers to me at [email protected].