a couple of months ago

6 Ways to Make Anal Sex Fun, Sexy, and Pain Free

Backdoor Fun

Curious about the exciting world of anal sex? Want to try it but scared that it'll hurt, be too messy, or not your cup of tea?

Before you poo-poo it altogether, these six tips can help you have a fun, sexy and pain-free anal experience...

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It's Hard to Know What You Don't Know

I didn't have my real first anal experience with a woman until my mid-twenties.

I'd had one foray into the world of rear-end exploration with an ex-girlfriend before that, but it was awkward, painful, and she ended up getting hemorrhoids from it.

So needless to say, that was that.

Now granted, I didn't know then what I know now, but we all have to start somewhere.

It wasn't until several partners later that I learned how different people feel about anal sex. 

You Either Love It, or You Hate It

Or you're kinda meh about it. Or you're scared to try it. Or you're a dude that thinks anything coming near your booty hole will make you gay. 

Some have tried it, and either didn't like the sensation or experienced pain from it.

Others love it and know that anal sex can be incredibly sexy, intimate, and doesn't require any pain at all. 

And others are terrified that it'll be way too messy.

Come on in, the water's warm!

Whatever your fears, judgments, or feelings towards rear access rumpus, here's a deep dive guide on preparing for exit only exploration and how to have a booty banging bonanza of a time!

6 Ways to Make Anal Sex Fun, Sexy, and Pain Free

1. You Can Do Me if I Can Do You

Sorry gents.

I'm a fan of doing unto others as you would have them do unto you, or however, that saying goes.

If your lady partner says that you can stick "it" in her if she can stick "it" in you ("it" being an appropriately sized object such as a dildo or penis shaped veggie of your choice) then you have a serious decision to make.

You can either pony up and give it a shot, or pass on the whole situation and perhaps never get to experience the bliss of a backdoor bonanza.

If you choose option 1, then read on because these tips are going to help you as well!

2. Warm It Up for Anal Sex

By “it” I don't mean your rear exit.

I mean build up the sexual tension. Lots of foreplay and lots of arousal will help the situation immensely. When we're turned on, we're more open, excited, and receptive to new experiences.

Just like when you're cooking Thanksgiving dinner, you don't just turn on the oven and slam that turkey in. You gotta preheat the oven, cut up the veggies, make the stuffing, and butter up that turkey.

3. Butter up That Turkey

The bigger the object, the more lube you'll need

Lube is key to an enjoyable experience. I can’t stress this enough.

You can buy specific anal sex lube which is thicker than regular lube and stays in place better than the thinner stuff.

Don’t have any lube on hand? Resist the urge to use household oils like coconut and olive oil. Oil and latex condoms don't mix, and you risk condom breakage. Use only water or silicon-based lube when using condoms.

Speaking of condoms, use ‘em when having escape hatch escapades, it’ll protect you against any bacteria and make cleanup a breeze.

4. Slow Is the Way Go

OK, now we can move on to warming up the backdoor for anal sex. That particular door is very accommodating, but you need to work up to it.

Start with one finger (don't forget the butter), and work your way to two.

I like to use butt plugs because you can buy a few different sizes and work your way up to one that is about the same girth as your member.

Gently insert a buttplug, and let your partner get used to it. Take this opportunity to also focus on other parts of her body as she gets used to the foreign object in her out hole.

If there is any pain at all, back off and try again.

Go slow. Keep moving up in size until your partner is ready for you, and remember, slow is the way to go.

5. Positions Matter, a Lot when it comes to Anal Sex

At this point, you're probably fantasizing about entering your partner doggy style.

In my experience and studies suggest, that there are better, more ergonomic positions for this kind of play.

Believe it or not, the missionary position is one of the most accommodating positions to enter your partner from. It's easier than doggy style, and you have the added benefit of tons of skin on skin contact. You can really connect with your partner and check in on how they're feeling.

Once they're comfortable in this position, you can try switching to others.

6. How Clean Do You Feel?

Your backdoor area is a self-cleaning ecosystem.

Well, not the door itself, but what the door leads to. As long as your diet is clean, and your stools are solid, then you should be good to go.

Some people like to do a quick enema beforehand (I've had good luck with this $10 kit from Amazon) but aren't necessary if you're feeling clean and confident. Knowing that your backdoor situation is as clean will help you feel more relaxed and comfortable, which are key to enjoying this kind of play. 

Oh yea, lay a couple dark colored towels down, just in case

Oh yea, lay a couple of dark colored towels down, just in case

If you had a burrito for lunch and Indian for dinner, maybe skip this whole situation and stick to more traditional forms of pleasure, for now. 

A Side Note Worth Exploring​

Some years after that first traumatic experience with anal sex, I met a lovely women. She was a doula and midwife and had a technique that she used to make childbirth less painful.

It turns out that technique also works to make anal sex less painful. 

When your partner is going to penetrate you for the first time, push out like you're trying to poop. 

Don't worry; you won't poop (well, I can't guarantee that, but you probably won't). 

Pushing out relaxes the sphincter muscles making anal sex much more comfortable. It's counter-intuitive, but it works. 

Check in Often and Have Fun

Check in with your partner often about how they feel before you increase the size, depth, and tempo of your object of choice.

Keep it light and playful. Sex is supposed to be fun, and if it stops being fun at any point, it's always OK to stop. 

Anal sex can be stimulating, intimate, and adventurous. It can be an opportunity to bond with your partner, as long as you're both in it for the right reasons. 

Pain is not a required part of anal sex, but pleasure and intimacy are! Find your favorite partner and talk to them about trying anal sex.

They might just be up for it and following these tips will help you both have an excellent, playful, sexy and pain-free experience. 

Check out the podcast with prostate pleasure expert Charlie Glickman

EP20 How to Get Freaky with Charlie Glickman
Thank goodness Charlie Glickman is on the show. It's post #metoo and I'm more aware of how I approach women,[...]
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Shaun Galanos

Shaun Galanos is The Love Drive. He believes that talking about sex and love isn't always easy, but it doesn't have to be awkward. He lives in Montreal.