Gandhi said that if you want to change the world, you have to be the change you want to see. To that end, Insatiable Desire brings you No Stupid (Kink) Questions, a series of questions asked by novice kinksters around the web. If you have a question for us, leave it in comments, or send it to rayne (at) insatiabledesire (dot) com with “NS(K)Q” in the subject.

Question 67:

My Daddy is really into butt stuff. My sister sub (SS) says there are months where he only ever fucks her ass. I am a butt virgin. Like, nothing has ever been in there. I’m not even sure I’ll like butt stuff, so he’s been working me up to being comfortable trying. SS says the first time might hurt. Maybe even a lot. But the internet says butt sex should never hurt. Are Daddy and SS doing it wrong? Or do I have a lot of pain in my future?

So, okay. The internet is lying.

While ideally, butt sex won’t hurt, sometimes, it does. I mean, think about it. You’re sticking large hard things in a hole that is only supposed to expel soft stuff.

Not to be gross, but consider those times when it’s been a while since you’ve gone, and you’re a little dehydrated, and what comes out is bigger than normal, and a little dry, and maybe even harder than normal. That hurts, doesn’t it? It sure hurts me. So it makes sense that if you just ram something hard and dry into a hole that’s meant to expel soft stuff, it’s gonna hurt a little if you’re not careful, right? Right.

What most people mean when they say butt sex shouldn’t hurt is that if it does hurt, you’re probably going too fast, or not using enough lube.

It could also mean there’s something wrong with your butt (hemorrhoids, minute tears in the lining, etc.), but if you weren’t having any problems before you tried to have butt sex, the chances of that are probably pretty slim. I’m no doctor, though, so if you have some concerns about your butt, please do discuss it with your gyno or your PCP. I dunno that your gyno will do anything more than refer you to your PCP, but I’m always more comfortable asking my gyno sex questions.

The best way to go about first time butt sex is to start with lots of lube, and either a finger, or a really slim, graduated butt toy like the Tantus Little Flirt or the Tantus Ripple Small.

I’m sure there are tons of others on the market, if you don’t like the look of those, but I’m a huge, HUGE Tantus fangirl. I love their silicone so much that I absolutely hated the design of the first Tantus toy I bought (which just happened to be a butt plug), but still went on to collect far more Tantus toys than anyone has any business owning.

If you do decide to find another beginner toy, look for something in silicone, no bigger in diameter than an inch. It should have a small tip that graduates into a wider middle, and then slims down to a “neck” that allows your butt to close comfortably around it. And make sure it has a flared base so it doesn’t slip inside of you completely.

When you embark on your butt stuff journey, make sure you’re already aroused. It will help you to relax, which is important, because if you clench your butt, inserting things is definitely going to hurt. M often starts by playing with my clitoris and a little bit of PIV (penis-in-vagina) sex.

Some people like to cleanse with an enema first; especially if they have issues with IBS (irritable bowel syndrome) or something of the like. You don’t have to, but I would make sure you’ve at least gone to the bathroom to avoid the squick factor.

Start with a finger or small plug, like I mentioned. Use lots of lube. Go slow. If it hurts, stop.

People have different ways of dealing with the pain. M likes to hold still until the pain subsides, give me a minute or so to adjust to the stretch, and then push in some more. If/when it hurts again, he’ll do this over and over until he (or the toy) is all the way inside of me. This method works well for us.

Some people prefer to take the item out, add more lube, and try again. Others prefer to take the item out and stop all together and try again at a different time.

You may not be able to take a dick on your first foray into anal play. That’s totally okay. Some people try small toys dozens of times before they’re comfortable with a penis.

And you may find that you don’t like butt sex. That’s also totally okay. You don’t have to have butt sex if you don’t want to, even if you’re a submissive. Don’t let anyone tell you any different.