by Dr. Rachael

by Dr. Rachael

Table of Contents


I get a lot of questions about how to make anal sex hurt less.  If you are familiar with my advice, you know that I always tell people to PRACTICE.  Anal sex is no different.

Your anus has a lot of nerve endings and happens to be a very sensitive area, but it is not a very stretchy area; this is why it is sometimes difficult for the anus to accommodate a big penis or dildo.  Your ability to accommodate large sized objects in your rectum (anus or butt) depends on your ability to relax your butt hole.  This is a learned experience.


Practice dilating and relaxing the muscles of your butt hole:  If you have access to an adult bookstore you can buy what are called butt plugs and use them as dilators.  If you do not want to purchase an aid, you can use your fingers.  Apply large amounts of water-based lubricant to your finger and or your butt-plug, and slide them into your anus.  Once they are inside of you, relax.  Notice how your muscle starts to relax.  After you have perfected it with one finger, try again with two fingers, and then three.  If you started with a small butt-plug, move up to a larger size.  These exercises will get you ready for the real thing.



Remember that you are going to have someone firmly placing either a penis, dildo, finger, or hand in your butt.  This is the same area that boo-boo travels out of during a bowel movement.  So do not be afraid to go to the drugstore and use an enema or a laxative the day of or the day before for bowel preparation.  Just do not overdo it.  Diarrhea is so not sexy!



So you have to bring your own.  Prepare ahead of time and bring a tube or bottle of water-based lube with you.  Some popular brands are Wet and KY Jelly.  Avoid Vaseline, Crisco, Baby Oil, or anything that is oily because it will break down the condom very quickly.


If you are new to anal sex, make sure that your partner knows and understands that they should be gentle.  Let him or her start out by penetrating you first with a finger and then a thumb.  Make sure that they have lubricant on their fingers and a GLOVE.  The glove will keep both of you from transmitting any diseases either into an open cut on his or her finger or into a cut in your anus.  After the anus has become loose from the fingers, then he or she can move on to bigger things. Start out slow.  If you start slamming away, you will not get a second chance to perfect things.

Bring Lots of Latex Condoms:  Bring at least six extra.  Do not let ANYONE or ANYTHING penetrate you without a condom on it.  Lubricated condoms will not have enough water-based lube to last a whole session, so make sure you bring the bottle of lube even if the condoms are lubricated.


Change condoms whenever your partner switches to penetrate a different hole.  This goes for your mouth and or your vagina.  Use a new condom for each hole!!!   If you have a vagina and an anus, do not let anyone dip from your anus to your vagina.  This will make it easy for you to get an infection.  Instead, have him or her remove the condom that was used for the anus and put a new one on for vaginal penetration.  When it comes to your mouth, you don’t want a mouth full of boo-boo; this can make you really sick.   Take pause and change the condom.


Afterwards it will be hard for you to hold your farts in because your bottom will be loose.  This will cause you to walk with your butt cheeks clinched tightly. Take a time out, find a private bathroom, and sit on the toilet for about 15 minutes.  During this time out, fart as much as possible.  Air will have built up in your rectum and it needs to escape.  It’s better to let it out on the toilet than it will be to do it during your business meetings.



The key to enjoying anal sex is that you have to relax.  If you cannot get your anus muscle to relax, then the experience will be painful.  It takes some practice and it will not be perfect the first time you try it, but you can work your way into successful anal sex.  A word of caution, understand that you will fart during the experience, so just be prepared.

Use the link at the bottom right hand corner to email this article to a friend!

Article by

Rachael L. Ross
MD, PhDAs a family doctor and a sexologist.

Dr. Rachael Ross has been heralded as “The next Dr. Ruth, the nationally renowned sexual therapist who pioneered frank sex talk.” Chicago Tribune. Dr. Rachael earned her M.D. from Meharry Medical College and her Ph.D. from the American Academy of Clinical Sexologists, along with a B.A. from Vanderbilt University, where she studied anthropology.

Scroll to Top