Starting At The Bottom: An Intro to Anal Play, Part 2

Earlier this month I ran a workshop on anal play for a local toy shop.  Since the class turned out so great and people had so many great questions, I decided to share my handout with our HM4Her readers to make sure that you guys are getting the best of the best when it comes to sex education.  There was so much info that I had to break it into two parts (check out Intro to Anal Play, Part 1)! What what in the butt, let’s get to it!

In the first section I covered all the basics of why people have anal sex, the fears surrounding anal play, the expectations involved with anal sex and all of the basic anatomy of the butt.  Now we get to talk about safety, prep, techniques and toys – all the super sexy good stuff!


Safety Basics

Anal sex should not hurt. If it hurts, you are doing something wrong.

– Lube, Lube Lube, Lube, Lube! When it comes to butts, you can never use enough lube! Your ass does not self lubricate (like a vagina) so lube is super, extra important. For anal sex, thicker lubes are great. Your best bet is either silicone or water-based lube (as oil-based lubes can weaken condoms, if you are using them), but remember that you cannot use silicone lube with silicone toys. Also remember to add more lube frequently. If you think you’re using too much lube, add some more.

– Whatever you put up your butt must have a flared base that is bigger than the object, keeping it from going all the way in and getting stuck in your rectum. It is no fun and usually ends with a trip to the ER to get whatever it is extracted.

Never go from the anus to the vagina or mouth without first washing off the toy, penis, finger, what have you. You can go from vag/mouth to butt, but the other way can lead to all sorts of nasty infections that you don’t want.

Patience! Start slow and keep communication open throughout the experience. Make sure the person attached to the ass is doing alright and feeling good.

– Desensitizing lubes and gels that have a numbing effect (like Anal Ease) aren’t the answer to pain free anal sex and they can actually cause more injury. What you can’t feel can end up hurting you. Plus, if you can’t feel anything, what about your pleasure? Pleasure is the point.

Keep your fingernails short and clean with smooth edges. The butt has delicate tissues that don’t like to be scratched or torn. If you want to finger an ass and also maintain your mani, try wearing latex gloves. They aren’t just for doctors! Also, if you do have long nails that you want to keep, put a cotton ball in the fingertip of each glove and get to business.

Preparation for Anal Play

Make sure you are turned on. Get yourself in the mood and get comfortable. Maybe even have an orgasm first to relax and get your blood pumping!

– Take lots of deep breaths! Play some calming music to get relaxed. Anything that gets you comfortable.

Clench and release your sphincter muscles a few times to get to know your body and how it feels. Try doing it fast and slow to see how it feels.

Explore yourself. Get to know what’s back there! Start by feeling around the outside of your anus with your finger and when you’re ready, try inserting a well-lubed finger inside your anus.

– Take advantage of shower time and explore while you are nice and soapy.

– Speaking of soap. If you are nervous about dealing with feces, go to the bathroom prior to anal play to clear out anything in your bowels. You can also shower first and insert a soapy finger into your anus to get rid of anything additional. Some people prefer to do an enema before anal sex, but it is not a necessity. You/your partner can also wear a latex glove and/or condom to make clean up a snap.

Techniques & Tips

– Start with a butt massage to get your partner in the mood and relaxed. Begin with kneading the cheeks and running your fingers along the crack before you even reach for the butt hole.

– When you do get to the butt hole, spend some time on the outside before heading straight in. Trace little circles around the opening to the anus with a well-lubed finger. Press the puckered opening (like you would a doorbell) without inserting your finger. Ask your partner (or you, whoever’s ass is being played with) to clench and relax their sphincter muscles while you play with their anus.

– Use your fingertips to press along the butt crack, including the anus.

-Lube up your thumbs and press the pads of them against the anus, switching off in a circular motion – kind of like you are twiddling your thumbs slowly.

Don’t forget about the genitals too! Just because you are having fun in the back, you should still remember about the vagina, clit, penis, testicles, breasts, kissing , etc. Have your partner play with their own genitals while you have fun exploring their butt!

-When you are ready to go into the anus, have your partner breathe deeply a few times and the last time they exhale, insert your index finger (well-lubed!) into their anus to the first knuckle. Go slowly and be sure to ask your partner if they are ok, if they want you to slow down, go faster, add fingers, etc.

– Once your finger/fingers are inside your partner’s butt, don’t just start thrusting in and out. Stay still for a little bit to get them accustom to the feeling. Have them clench and release a few times to see how they are enjoying it.

-Some people really like when you explore them by pressing your fingers along the inside walls when you are inside their ass. Try up, down, left and right. Go slow and don’t push too hard.

-Once they get comfortable with your fingers and are having fun, maybe incorporate a toy into the experience. A butt plug is always fun because it is designed to stay put while you have fun with other parts of their body (just wash your hands/take of gloves).

Anal sex can be done in just about any position that vaginal sex can be done. Some people really enjoy the access that they have with doggy style (entering the ass from behind while the recipient is on their knees, bent over), while other people prefer the “bottom” to be on “top,” as they can control the speed and depth of the penetration better with that position. You can also try missionary, spooning, standing, legs over the head, whatever! As you as you can reach the butt you need!

– Remember, the first few inches of the butt are the most sensitive, so you don’t need to go in super far to have a pleasurable experience.

Don’t forget about the G-Spot and P-Spot, which are both accessible from the anus.


 Here are a few tips of anal toys, including some we have reviewed!

Flexi Felix Anal Beads:A series of small beads that are attached by a string or a stalk. Sometimes the beads are the same size and sometimes the increase gradually in size. (Flexi Felix is pictured)  
Little Flirt Butt Plug:Diamond or mushroom shaped anal toy with a tapered neck and a flared base. Designed to stay put in your butt. (Little Flirt is pictured)
Compact Anal Beads:Usually a smaller, thinner dildo with a flared base. Great for thrusting in and out. They can be used in a harness as well. (Compact is pictured)  
Waterproof P-Spot Vibe Anal Vibe: A toy that vibrates to stimulate sensitive genital and anal tissues. Lots of butt plugs and dildos come with vibrating bullets that can be inserted into the toy. (Waterproof P-Spot Vibe is pictured)
Aneros MGX Prostate Toy: Toys that are specifically designed to stimulate a man’s prostate gland and can intensify orgasm. (Pictured is Aneros MGX)

Now that you’ve got all the sexy, sexy info, go hit those sheets!

Remember to enjoy yourself!  It’s sex, it’s supposed to be fun!

-J.D. Bauchery 

Find out more hot butt tips from the Instructional Queen in Nina Hartley’s Advanced Guide To Anal Sex For Men And Women:

9 thoughts on “Starting At The Bottom: An Intro to Anal Play, Part 2”

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