I personally enjoy it on a regular basis by that I mean once a week and most of the time only during DP. Whether it's my husband and a dildo at the same time or two dildos the most important thing is being properly prepped. A good anal clean out with an enema or bulb with warm water works just fine. Also important things to remember are plenty of lube, good communication with your partner and take things slow until you are completely relaxed and opened up. For me the more I do it the easier it becomes and I guess that has to do with training, relaxing and stretching the anal muscles. Just let things fall into place you'll know when it's time for another try.