10 Things You Should Know Before Trying Anal Sex For The First Time

Do it properly.

Matt Branhamby Matt Branham

When it comes to anal sex, it seems as simple as just sticking it in. But there’s a lot of things you should know before trying this position for the first time: nerve endings, proper lubrication and the general dos and don’ts of bending over or entering in the rear. They didn’t teach you this stuff in sex ed.

Make sure you’re into it or don’t bother
10 Things You Need To Know About Anal Sex
It’s not a prerequisite for the human experience, not like taking driver’s ed or learning to chug a beer, for instance. Generally things come out of the outbox, so if you don’t feel the need to shove junk mail up in it, no harm and no foul. The general rule of thumb in this life is to try everything once, but if you don’t, it’s not likely someone’s going to call you out on this particular one.

It’s best to prep way, way in advance
10 Things You Need To Know About Anal Sex
Ever hear the story about the girl who got her O-ring popped while her parents were at church and ended up in the hospital after they came home early and her boyfriend abruptly pulled out? That’s because it’s no joke. You shouldn’t just rush in without preparation, but rather go slowly to start. There are two sphincter muscles, and both have to be relaxed for anal sex to feel good. Take a little finger pressure to see if you like it, then work your way up to a finger, maybe two and — who knows — maybe you can keep going from there.

“With anal sex, I suggest you start gently. Find a slender midget. Or a member of Congress.”
Jarod Kintz, “$3.33”

Clean your playground before and after you play
Just as you might wash your hands before putting them on something about to go in your mouth, so is the same when it comes to shoving a pecker into a delicate flower, err, the other flower. According to WebMD, “the anus is full of bacteria.” So when we say “cleaning the playground,” we’re not talking a light graze with a bar of soap — that stuff is unsavory even for a cleaning product — we’re talking in-depth scrub-down, ridding the body of any unsightly smells, dead skin and all else on the spectrum of bacteria. Just because you’re playing with a butthole doesn’t mean it’s okay to smell like one (unless you and your partner like that sort of thing).

Get wet — and stay wet
10 Things You Need To Know About Anal Sex
Never go in dry. The ass has no natural lubrication. It’s likely similar to being entered by a corkscrew, using no lube, or so we imagine. The thicker the lube the better, and this is very important: no oil-based lubricants are welcome, as the oily parts tend to rub condoms the wrong way, sometimes rendering them defective. The water-based lubricants, like K-Y gel, as well as silicone-based ones, work best as they are thicker than most water-based lubes. There’s nothing worse than forced anal, unless it’s accompanied by rap music.

“The four most over-rated things in life are champagne, lobster, anal sex, and picnics.”
Christopher Hitchens

Prep the oven — It’s rarely the first stop
10 Things You Need To Know About Anal Sex
Piggybacking off the “get wet, stay wet” step, prepping the oven is the best natural form of staying wet. You never just shove the turkey in the oven dry and unstuffed without at least — yes, “literally” is actually the appropriate word — preheating the oven first. Start with a little foreplay to get the love juices a’flowin’, and then have a bit of some old fashioned sexual intercourse, too. There are many sexual positions to choose from beforehand. Anal is rarely the first base for anyone. In fact, it’s usually somewhere close to rounding third and heading home.

Don’t tense up, especially at first
10 Things You Need To Know About Anal Sex
When plunging someone’s toilet, you don’t want to make any hasty gestures, at least not at first. There’s a world of nerve endings to consider, not to mention the tensing up of muscles at first makes it more painful. You always plunge slowly and see if you can get it to work subtly before you get pissed off and start jabbing that thing in there, tossing out curse words and eventually calling in a professional. Speaking from personal experience, I also know it’s improper to set your dirty plunger on the floor without cleaning it first. We’re not speaking metaphorically, but now that we mention it, this reminds us to clean up after.

Don’t worry, you’re probably not shitting
The first time you came, you were probably terrified you were going to piss yourself. Well, the same goes for most women when it comes to anal. And guys, it won’t break or get stuck, so don’t be hasty with your jamming and ripping. All this is to say it’s not definite you won’t see shit. Just don’t be paranoid about it or you’ll miss out on the whole party. But just a word of advice: It’s more pleasurable if the rectum is empty to begin with.

Angles are everything
You can use a lot of the same positions as regular sex, but in the case of anal insertion, missionary is actually the least practical for once, as doggy-style and flat from behind take the cake. According to The-Sexperts.org, it’s “not nice to jam your cock or dildo in somebody’s ass.” You don’t have to be a mathematician, physics professor or an architect of any kind to know what angles work, but some light trial and error never hurt either. When it comes to popping the cherry on a trusting new anal attendee, slow and steady wins that race.

Beware the anal aftermath
Monogamy isn’t the only sure-fire way to avoid anal aftermath. According to the Mayo Clinic, any man or woman who engages in anal activity is more subjected to anal cancer, just saying.
Practice safe keeping with condoms and lube (again, beware of oil-based lubrication), and never, ever use the same fingers that were in one’s butt immediately in another sexual orifice for fear of infection.
And when you’re done, go to the bathroom, just as you would for regular sex, to avoid a urinary tract infection (UTI) or other not-so-fun bacterial mishaps. And like regular after-sex bathroom breaks, it may take awhile and come out in more than one direction. Don’t shoot the messenger.

“Nowadays, you can do anything that you want — anal, oral, fisting — but you need to be wearing gloves, condoms, protection.”
Slavoj Žižek

Be glad you did it once, but don’t feel like you have to do it again
10 Things You Need To Know About Anal Sex
It’s not necessarily for everyone. Unlike original sex, it’s not something that typically grows on people, but that’s not to say it won’t. Well, guys will likely want to do it more after their first time, but girls who don’t enjoy it probably won’t grow to love it, even if the guy thinks he’s clever when he tries to convince her otherwise.

Worse case scenario: you get laid in other ways that can be satisfying as well. Anal sex doesn’t have to be a requirement if you don’t want it to be. And always be aware of sexually transmitted diseases and be sure to practice safe sex.

Related: Girl Discovers Boyfriend’s Love Letter Is Actually Code For Anal Sex Request