What is the first thing you think about when someone mentions anal sex? Is it untold pleasure? Is it sensuous closeness? Is it discovering unknown intimacy? Could it even be the best orgasms you can have?

Probably not. If you've never tried it, you've probably been told it is going to hurt. If you've seen it in porn, you probably think an insane acrobatic session is about to unfold. And, if you're like most people, you probably think bum loving is a real, actual pain in the butt.

And this is fair enough. I've never been one to sugar-coat the fact that anal sex might hurt and we all need to know that. Yet, let's remember that, despite common thoughts and porn's obsession with stretching ass limits, there is unlimited potential with ass play. The fact that it might hurt doesn't mean that it will - or that it has to.

Pain-free anal sex is not a fantastical oxymoron. It is not a fairy tale (tail?). It is real and it is awesome. Check out these seven tips for having anal sex that doesn't hurt and get down to the bottom of bottom fun.

Experiment with Self-Pleasure

There is only one person who can determine if your anal experience is going to be pain-free: you. If you are curious about exploring ass pleasure, the best way to experiment is on your own, in your own masturbatory bliss, before anybody else gets into your butt business. If you want to get a sense of what it feels like to be touched between the cheeks, reach down while you’re already enjoying strong sexual feelings. It is important to get a lay of the land, a true idea of the shape and texture of the anus. Experiencing these sensations on your own will allow you to control the speed and depth of touch and penetration. You’ll be able to teach yourself how to relax your muscles, learn when to slow down when needed, and get a sense of how far you think you can push yourself. Some homeschooling will eliminate one of the biggest sources of anal sex pain: surprise. (Learn more in Guys, Here's How to Hit the P-Spot Using a Toy.)

Talk About It

After some self-exploration, the most important activity you can do to prepare for and enjoy anal sex is to talk about it - before, during and after the act itself. Some folks really love the spontaneity of sex, but bum fun really should be something that is discussed beforehand. Anal sex can only be pain-free when everybody is on the same page. Knowing that your playmate has heard and understands your needs will help you relax. This is one of the most important factors in taking pain out of the equation.

Don’t just stop at an initial discussion. If all signs point to yes, you really should remember to check in throughout the ass action. Anal experiences can vary greatly, so there really is no way to anticipate how you or your partner will feel during anal play. If you’re giving, be ready to hear directions and needs such as "go slower" and "more lube." If you’re receiving, it is critical that you speak your needs - even if it breaks the flow

Set the Scene

There are a lot of factors that go into deciding to have anal sex, never mind also trying to ensure it is pain-free. In fact, if there is any doubt in your mind that this moment won’t be right for bum fun, the best option is to decline and play in a different way. The term “uptight” is often thrown around as a pejorative for somebody who can’t relax. In respect to anal sex, uptight could be a real problem! If you are too nervous, being uptight could be quite painful.

One of the best ways to move from stressed to relaxed is a massage. A long, luxurious massage that warms the skin and muscles can help you or a nervous partner relax. A back massage also sets the stage for a slow trail down to the bum! Have those fears and muscles worked out of your back muscles and feel them melt away from other areas as well. As your partner moves closer to the epicenter between your cheeks, you'll feel more turned on and open.

Focus on Sensuality

If you look at how most porn depicts anal sex, you’ll notice a trend: Ass sex is hard, fast, rough, and more about a show than the experience. Porn is great in many ways, but it has not done butt sex any favors in diminishing folks’ fear of pain. If that portrayal is your first exposure to anal sex, you’d be completely justified in turning tail and running away.

So, if you’re still interested, the best advice in working past anal discomfort is to unlearn everything you’ve seen in mainstream porn. Sure, there are some good, hot scenes out there, but let’s start from scratch and bring back the sensuality of the act.

Having a shower together is (literally) a hot way to bring sensuality into your anal pleasure. This also helps with the real fear of cleanliness. Many shy away from anal sex because they don't want to encounter (or expose their partner) to poop. If you're really worried about this, it may also help to perform an anal douche beforehand. If you’re confident in your body’s sensations (and your own dietary choices), this could be skipped. Instead, getting all soaped up under steamy hot water with your partner while your hands roam over each others’ bodies can set a relaxed, worry-free, and sexual mood.

Make Things Slippery. Very Slippery.

There may be lots of “S” words floating around here, but the most important word when it comes to painless anal sex actually starts with an L. It’s lube! Lube is the best friend of anyone who wants anything to do with your butt - and this includes you! Remember, the anus does not have natural lubrication like other orifices do. You really need to add some slippery stuff to the situation. Trying to penetrate your own or someone else’s bum without lube significantly increases the chances of anal tearing and pain.

There are four main types of lubricant you can use: water-based, silicone, hybrid, and oil. Everybody has their preference in lube, particularly when it comes to ass sex. And really, whatever works for you and your partners is important. However, it should always be noted that oil-based lubes breakdown latex condoms and silicone lubes can damage silicone sex toys.

Size Up the Situation

Usually, when it comes to sex, we try to say that size doesn’t matter. However, when it comes to bum fun, size absolutely matters. One of the most frequent sources of pain during anal sex is from trying to play with something you’re just not ready to use. This is particularly true if what you’re trying to play with is a rigid penis or toy. Even in the height of excitement, you have to temper your expectations of what you can fit inside you. If it is your first time enjoying ass pleasure, you and your partner need to start off small - and maybe not even take anything inside at all. Concentrate on the many fantastic sensations that can be felt on the outer part of the bum cheeks and anus through rimming, fingering, vibrators and more before even diving inside. It is important to get these good physical and mental associations in your body so that you’ll have something to come back to if you do experience discomfort. After you’ve driven each other wild on the butt porch, you can move on to inserting something - something very small - through the backdoor. Maybe a pinky finger? A tiny dildo? Whatever you choose, this is as much about creating that good feeling again. Sure, it is possible you might be able to take more, even during your first time, but starting small and working your way up to bigger sizes will heighten your excitement and lower your chance of pain.

Take It Slow

Finally, patience is the best virtue when it comes to anal sex. Everybody always wants to rush to dessert, even though we know we should enjoy the full meal first. Slowing things down is one of the keys to eliminating pain during anal fun. When ass is offered up, it can be hard to resist the temptation of getting right down to business. However, anal really shouldn’t be a quickie type of sex, so try to keep your excitement in check and let the bum fun progress naturally and slowly.

If penetration is the ultimate goal of your anal adventure, whether with deep fingers, a sex toy, or a penis, it is important to pick a position that is both comfortable and practical. Anal sex can be enjoyed in many different positions, but there are a couple that stand out when trying to avoid anal pain: on top and spooning. Being on top allows the person taking the penis to control the depth and speed of penetration. If there is any hint of discomfort, you are in complete control and can back off until good feelings return. Spooning is a wonderfully relaxed position that allows the anus to open and accept penetration quite nicely.

One last note: These suggestions offer an ideal, but we must remember that everybody's body is different. Fingers crossed these ideas will help you experience pain-free anal fun, but if other things do better, please share!