I was visiting a friend for a long weekend some years ago and he arranged for us to play with a very handsome younger man who loved getting enemas. He also like being tied up while getting an enema, but that proved to be too complicated, and annoying, so I told him we were going to dispense with the ropes and just concentrate on giving him large volume enemas and he had to cooperate. Over the course of an afternoon and long evening, we gave him at least a dozen enemas, using different bags (2 qt., 4 qt), nozzles of various lengths and thicknesses, colon tubes, and large bulb syringes. My friend had even modified one of those plastic water cannon toys, so that we could force very warm oatmeal up into him, to 'constipate' him, which would then necessitate large cleansing enemas to clear out the obstruction. We put him in all sorts of positions as well. Mirrors were strategically placed so he always had a clear view of what we were doing to/with him. The guy loved having his ass worked on and various items inserted into his rectum, like hard-boiled eggs (shelled, of course), and then expel them. I even made him eat a couple of them. He was running clean by then, but I don't think he'd have hesitated anyway. My friend was exhausted at one point and went to bed, but the guy and I continued to play. Needless to say, rimming, cock sucking and fucking all got worked into the scenarios we devised throughout the day. And saying the word 'enema' as often as possible, was mandatory from the beginning to the end of the evening.
The only other time I played with someone and gave them more than two or three enemas in a session, was when I was in college and had a friend who loved enemas too, and we shared them. I think I gave him eight enemas and I got six one cold rainy Saturday. And I think we both came at least four times each that day! We never managed to play that much again, but we'd give each other at least two or three when we did. Lost track of him after I graduated, but would have loved to have had it continue. He was hot!