I’ve said it a million times, but I still do not understand the appeal of female anal penetration for hetero dudes. Women have these amazingly soft, warm, moist vaginas specifically designed to accommodate a penis, and yet men are still like “Sure, but what does the poop chute feel like?” 

That said, I have a number of female friends who genuinely enjoy the experience of anal sex, so I’ve found myself trying it out a handful of times just to see what all the fuss is about. As many sex guides as there are out there, my best advice has come from word-of-mouth over the years, and here are the little gems I’ve collected that I wish someone had told me about trying anal sex for the first time.

1. The pain may be worse than you're expecting.

I don’t care how much pre-research you’ve done on the topic (like I did because #NerdAlert), it's going to hurt more than you’re expecting if your partner is of average size or larger. I don’t care how big your sh*ts can get; it feels completely different going the other way. Yes, even worse than the first time you had regular, vaginal sex.

2. But there are positions that minimize the pain.

Oh, please don’t try it doggy-style the first time unless he’s tiny. I mean it. If you face each other, the penis will go in much more gentle (#ergonomics), and if you’re on top, you can control the depth and speed much better.

3. The right lube is essential.

Nobody's paying me to plug them, but I've been swearing by Pjur brand's Bodyglide for at least 15 years now because it's magic. However, EVERYTHING I love about it is what makes it all wrong for anal.

Because the anus does not provide its own lubricant and is not inherently designed to accommodate friction, you absolutely need to invest in lubricant that is thick, sticky, and doesn't soak into the skin easily. Think of creating a liquid cushion between the phallus and your butthole tissue. Gun Oil brand or good old-fashioned Astroglide are good places to start.

4. Your anus may require some prep work.

Look, your butthole has spent its life holding poop in and then pushing it out, so asking it to do the opposite of that won’t be as easy as pulling a “REVERSE” lever. Your anus will loosen given the right treatment, so give yourself plenty of time to warm up to receiving a whole, erect penis. This may include your partner inserting one digit until it feels comfortable and then gradually adding another.

An alternative is to invest in an Anal Trainer, which is a special type of butt plug designed specifically to help massage and loosen the muscles of the sphincter, thus minimizing your pain. Don’t feel like you have to dive into the deep end on your first go, either! These things can take time and if you work gently and slowly, you won’t be so miserable as to never try it again.

5. Only try it on a weekend.

I was discussing my frustrations with anal with a girlfriend a few years ago when she dropped a bit of wisdom on me. She said, "With anal, you need Wet Naps and a weekend." What this hilarious quote boils down to is that you do not need to start experimenting with anal on a weekday when you’re tired after work and distracted by having to wake up early again for even more the following morning.

Also, expect a bit of a mess; give yourself plenty of time to warm up, cool down, and clean up. Wait for a weekend... maybe even a long one. 

6. You can also use "poppers" to relax.

I would never, ever endorse anyone experimenting with inhalants, and I would especially never tell you to look into poppers, which have been used in the gay community for decades upon decades as a means to relax the rectum.

Poppers aren’t addictive and only give a 30-second buzz, but are usually marketed as “liquid incense” when you find them in sex shops, head shops, or online, but again, you guys, I would never publicly admit to having tried them and finding them really, super, incredibly useful at  minimizing the pain of one’s first anal  intercourse experience. So I won’t do that.

7. There are topical numbing ointments.

A second chemical option is a numbing ointment that can be applied to the anus to deaden any sensation externally. While this doesn’t do anything for the muscular tension, it does take a bit of the “bite” off the pain, but not so much that I think it’s really that necessary.

Still, though, Anal-Eze has been on the market for a very long time, so it must be working for someone. Try it, and if it doesn’t work, you can use it before your next waxing appointment for a pain-free bikini wax.

8. You don't ever have to do it if you don't want to.

I don’t care how much your partner is whining about really wanting it; if anal intercourse is something you never have any interest in doing, you do not owe anyone the right to put his penis in your butt. Period. It does not make you “frigid” or “boring” or any other bullsh*t term society likes to throw at us to make us feel guilty for not doing sexual stuff we don't want to.

If he can’t handle that you don’t want to try anal sex, that’s a "him" problem, no matter what he says. Many sexually liberated and adventurous people (like me!) can have very full, exciting sex lives without having anal on the table...or anywhere else, for that matter. And even if you don’t want adventure or wild stories, keep in mind that a healthy, happy sex life doesn’t include being miserable just for someone else’s enjoyment.