Once again, clean wins out. I always start with three to five cleansing enemas, at least one or two with Dr. Bronner's Castile soap to clean things up. I then like to wait about an hour for any residual water to make its way into my rectum for a final evacuation. Then the fun can begin by stretching out some place comfortable. I like to load a shooter with KY and inject it into my rectum so the dildo has plenty of lube once inserted. Prior to the shooter injection, I like to smear a liberal amount of KY all around my perineal area and anus. This helps later by adding lube to the toys in use.
I generally start with one or two fingers and lazily insert them into my anus doing a in-out motion combined with rotation to liberally grease up the anal wall and conduct continuous, mild stretching. I also enjoy the feeling of my fingers touching the junction of my rectum and large intestine.
Once my anus and sphincter has relaxed, I will start with any number of toys to include double ended dildos/butt plugs/prostate vibrators or a butt-buddy.
The key is to go slow and enjoy all the sensations!