If you are planning on using latex gloves for finger penetration or dental dams for oral/anal play make sure they are near you and ready for use. Nothing ruins the mood more than having to search for something in the heat of the moment. Make sure any sex toys like anal beads, butt plugs, anal probes, vibrators, dildos or strap-ons are clean and ready to go as well. Lubrication and baby wipes should also be on hand.
Read: Anal Sex Toys for Every Experience Level
Be Prepared for Poop
Here's the truth about anal: It might be the first time or the fourth time you try it, but eventually poop will become part of your anal play. It's OK. It happens; that's just the nature of the anus. Have baby wipes handy for a quick clean-up so any potential embarrassment can be avoided. Remember that any kind of sex is, by nature, messy. Don't make a big deal of it. If you do, you can be sure that future anal play will be out of the question.
Unlike the vagina, the anal canal and rectum are not self-lubricating so any form of anal penetration needs to involve a lot of lubrication. It makes the whole experience a lot easier and more pleasurable for both partners, and going without can lead to anal tears. Spit is not going to cut it; go for a high-quality sex lube. If you are planning on using condoms or latex gloves remember that without lubrication, latex is very likely to break.
If you or your partner suspect either of you have an STD you probably want to get tested and consult a physician prior to having any form of sex. However, the use of condoms during anal sex can help reduce the risk of spreading certain STDs.
Finally, make sure never to put anything in or near the vagina that has been in the anus without thoroughly cleaning it first. Ladies, this is why your mother taught you to wipe front to back - it's that important that the germs from your anus do not get into your vagina. It can mean a nasty bacterial infection. And if anything will ruin your sex life for a while - and turn you off anal sex - that has to be it.
Read: Don't Have Anal Sex If ...
Go Slowly and Keep Communicating
Before any anal action begins, start with some basic foreplay. You know what turns your partner on so pull out all the stops, leaving him or her wanting more. This will make anal penetration that much easier; arousal helps relax the muscles in your anal sphincter. (Actually, it helps relax all your muscles, which one reason why sex is so good for you!) Really learning to relax your sphincter muscles takes practice, so do not get discouraged if you have trouble doing this the first few times. Taking deep breaths can help and any penetration should occur on an exhale of a deep breath.
The anus is more delicate than the vagina, so anal sex has the potential for pain. But anal sex should not be painful; just go slowly and communicate with your partner about what is and is not feeling good. Start slowly by massaging the area around the anus, the thighs and buttocks before moving on to massaging the anus. Continue stimulating the clitoris, vagina, or penis during this time to keep your partner aroused. (Just remember not to mix genres; nothing should touch the vagina that has already touched the anus.)
Read: 7 Tips for Having Anal Sex That Doesn't Hurt
When the receptive partner is ready for penetration, starting with a well-lubricated finger is usually best. The finger should go in very slowly and not all the way - you can always save more experimentation for another day! Now is time for some of that communication we talked about. How does this feel to your partner. Do they want more or is this enough for now? If you are continuing, wait for the sphincter muscles to relax and then try moving the finger ever so slightly up and down then side to side without bending the finger, just slightly pulling at the anus to open it up. Ready for more? Try putting the finger in all the way, doing this while the receiving partner exhales helps.
As your partner wants more, you can move from one to two fingers. Once you have two fingers comfortably inside the anus, try a "come here" motion with the two fingers toward the front of your partner. This can stimulate the G-spot in women, or the prostate in men. This alone can lead your partner to orgasm.
Keep in mind that the anal opening and anal canal are more sensitive than the rectum, which is located further into the anus. This means that getting in deeper is not necessarily better when it comes to anal play.
Because going slow is so important to the enjoyment of the anal experience, the partner receiving anal sex should be the one controlling the speed. Any fear of being hurt or feeling pain will be relieved if the person at risk of these feelings leads the way. When starting out, the receptive partner can push his or her partner’s finger into the anus at the desired speed and depth. Once you move up to penile penetration, one partner can be on on top, lowering themselves onto the penis, thus controlling the experience.
If you're an anal sex virgin, don't be intimidated. There's a lot more to anal than penetration from a penis, large vibrator or strap-on, and in fact, these are probably too ambitious for a first try. Going slow is the key to enjoyment - and only going as far as feels good is the key to continuing to have anal play in the future. Also remember that starting slow with penetration should happen every time you have anal sex; going straight to penile penetration is not a good idea at any point. The more anal play that occurs, the more quickly you will become comfortable with anal penetration.
Read: Anal Sex: After the Entrance
Clean Up Afterward
You do not want bacteria from the rectum getting anywhere it shouldn’t, so be sure to clean all body parts and sex toys that were involved in anal fun thoroughly.
Also keep in mind that what goes up, must come down. If a man ejaculates inside of the rectum, it will need to make its way out of the anus. This, combined with the lubricant that you should be using, can mean a little disruption to your bowel movement the next day. Just know it's nothing to worry about.
Check Back In
After it's all over, the arousal is gone and the clothes are back on, check back in with your partner. What did you both like/not like about your anal experience and what comes next? The more you can communicate, the better the anal part of your sex life will be.
Good luck and enjoy!