With all the nerve endings in the anus (and for men, the prostate), it is completely natural to take pleasure in anal play. However, that doesn’t mean that doing it comes naturally. In order to maintain bowel control, we have all trained since childhood to keep the dual sphincters of the anus clenched at almost all times. Retraining those muscles to allow insertion takes, above all, the ability to relax.
Don’t ever proceed past the point where your body is telling you to stop. Your anus will remember, and it won’t be willing to relax the next time.
If you have difficulty relaxing your sphincters, try some anal stimulation after having an orgasm. At that point, your entire body can’t help but be relaxed.
To find your PC muscles (the muscle group to which your anal sphincters are connected), imagine you are trying to stop the flow of urine while you are peeing. You can practice by actually trying to stop the flow during urination. Those muscles you are clenching are the ones you need to pay attention to.
Inhale, and pretend you are pulling water up into your vagina (if you have one) and anus. When you breathe out, bear down and push out the imaginary water. For strengthening, try 10 to 30 reps per day.
Inhale deeply and contract your PC muscles, holding them for a few seconds. Relax the muscles when you exhale. This pattern of clenching/inhaling and relaxing/exhaling mimics what your body does on its own. Do 100 reps per day for increased strength and tone.
Inhale deeply, and, as you breathe in, quickly clench and release the muscles repeatedly. Do this about 10 times as quickly as you can. Relax as you exhale. Perform 20 to 50 sets of 10 per day.
Another way to help gauge your overall level of relaxation is by making it a habit to insert a soapy or lubricated finger into your anus while showering or bathing. You can practice squeezing and releasing your PC muscles at this point as well, and this provides immediate feedback about your level of relaxation.