Anal Sex First-timer

For anal sex newbies, patience, planning and communication are key. Oh, and lube. Lots and lots of lube.

Schedule Time

You can't start your exploration into anal sex with a short time limit. You just can't. Trying to speed-run through anal is what's going to cause pain. Unfortunately (and fortunately, if you like experiencing as much pleasure as possible), anal sex is just one of those things that takes time. And that means you need to have the time.

Making sure you have an hour or two of uninterrupted time is going to give you both the reassurance you need to enjoy that hour or two without worrying about something getting in the way.

Be Aroused and Relaxed

Arousal can come from flirting and teasing leading up to the time and place. Sexting can be a lovely tool for foreplay.

There's nothing wrong with spending some time touching one another and making out before you begin your anal sensation experience, though. A good, old-fashioned make-out session can be amazing for getting the juices flowing—literally and figuratively.

Not only does arousal help all of the other sensations feel even better, but being aroused can help relax the body—which makes anal penetration more comfortable and easier to do.

Warm Up & Use Lube

Before you attempt anal intercourse, you're going to want to warm up with something smaller than the eventual size of what you'd like for intercourse. If you have sex toys, those tend to be the first choice; but a lot of people choose to go with fingers as well.

The important thing is: The anus requires a lot of gentle stretching before you jump into full-on penetration. This gradual, gentle stretching relaxes the area, adds to the arousal and makes it easier for the anus to stretch wide enough for a penis during the eventual intercourse.

If you're using fingers, start with one—and slowly move on to two fingers. Consider three or four; but, as always, communicate with your partner and see where they're currently at comfort-wise. Ensure your fingernails are trimmed down to the quick, with no sharp edges or hangnails. If you want to earn brownie points, after your fingernails are trimmed and washed, run each one over the broad side of your tongue with a bit of pressure. If anything hurts the tongue, you need to retrim it. Remember: The anus is just as sensitive and delicate as the tongue!

If you're using toys, start with a slim toy—and consider using a second toy, slightly bigger than the first after the slim toy. If someone is a complete beginner, aim for an anal toy diameter under one inch. If someone has used fingers before, a toy diameter under one and a quarter inches is generally a good goal. Ensure it's anal-safe with a flared base.

The goal is to gently stretch the butt open—so be gentle, move slowly and leave the finger/toy inside of the butt to allow it to gently relax the area for future penetration. If things feel a bit too slow to you right now, consider using a butt plug to enjoy other types of foreplay while you're using the sex toys or your fingers. You also can adjust your positions for making out or other types of pleasure (like oral or manual pleasure) while simultaneously doing this.

 No matter what you're using, ensure you're using lots and lots of lubricant. Unlike the vagina, the anus provides zero lubrication. You read that right: zero. There is nothing to slicken things up and make things pleasurable. This means you need to BYOL: Bring Your Own Lube. Coat your finger or sex toy in lube and, for good measure, use your finger or the tip of the sex toy to coat the entirety of the entrance as well.

Regularly reapply the lube. If things feel a bit less smooth than they used to be, reapply. If ten minutes have gone by, reapply. It's hard to overapply lube*; but it can be really painful if you underapply.

Happy Anal-ling!