Over the years I've had an opportunity to indulge in prolonged enema sessions. Each time, these sessions were with someone I really liked and who had as much of an enema obsession as I did. The first time was when I was in college, with a friend who was a seminarian (!), and that session lasted for nearly seven hours! I think I gave him eight enemas and I got, at least, five. We didn't have a lot of equipment in those days, but it got used, as well as different solutions, amounts and positions. I think, too, that he had four or five intense orgasms and I know I had four in the course of the day. In between, and also during, the enemas we did a lot of kissing, fucking, sucking, rimming and filth-talking. It was very intense. Somewhere in the middle of the games we played we got hungry but, because we didn't want to put clothes on or go out, we snacked on what was on hand. I don't recall that either of us complained of having a sore anus by the time we were through, but we were young and tough!
Some years later I became good friends with a Mexican-American guy in Los Angeles. When we eventually began to sexualize our relationship and I discovered how he loved rimming and anal play as much as I did, I whispered in his ear one day that I wanted to give him an enema. He was astonished, but he'd had an enema or two growing up, so the procedure wasn't new to him and because we were both such anal erotics, he was turned on. He didn't have any equipment, and since we were at his place we had to go to the local Walgreens down the hill to buy an enema bag (they were readily available in drugstores then), and I made him make the purchase so I could watch his face, but he was very laid-back about it. Needless to say, after a little initial apprehension, he was completely seduced by the power of the enema and five hours and seven enemas later, we were exhausted but sated, and then went out and had Mexican food! All through the meal I'd catch his eye and would mouth the word 'enema' or lean over the table and whisper it in his ear. Luckily it was chilly out and he had a coat to hide it or the other people in the restaurant would have seen the large bulge in his jeans when we left. We then went back to his house and I had him give me an enema, which he enjoyed doing, but he preferred to get them and I was all too happy to oblige him. A couple of hours later we collapsed and slept. God, how we slept! We didn't do this often, strangely enough, but it gave our relationship a color and flavor our other friends never understood. It was a secret between only us.
There were other prolonged-session adventures after those, but I'll save them for another post.