Ever since I can first remember, I've always had a severe constipation problem. Since I was a little kid, I got enemas every Saturday morning from my Mom, to clean me out, plus enemas during the week, when she felt I needed one. When I was very young, she'd use a squeeze bulb type, with a regular enema nozzle. Shed have me lie down on my belly, on a towel which she'd put on my bed, and she'd fill the bulb from a pitcher of hot water with Ivory soap in it. Shed keep refilling the bulb, and me, until I couldn't take anymore, at which point she'd usually coax me into taking another bulb or two. Then, I'd lie there holding it in as long as I could. After the first enema, I always had to take at least one more enema, of clear water, unless she thought I needed another soap enema, or I asked for one. I enjoyed the feeling of being penetrated, and loved the way the water felt going into me, so sometimes I asked for another one, even if I didn't think I needed it.
She was always very open about giving me enemas, and had no compunction about relatives, neighbors, friends, or anyone knowing that I needed one, was going to get one, or was getting one. Frequently, she'd just tell whoever was with her to come into my room while she gave me an enema, so they could keep talking. While I was always embarrassed about my enemas, I remember kind of liking that feeling, so I never protested. My sister, who was several years older than I, was a frequent viewer in those days.
When I was young, I remember taking my usual soap suds enema from the bulb, and that day it was a particularly large one. I was very plugged up, so I needed it, and Mom kept coaxing me to take another bulb every time I told her I was full. She had me hold it in longer than I ever had, before she let me go to the bathroom. When I came back, she told me I needed another one with soap, which I was glad to hear. She then told me that I was big enough to use adult equipment, so I'd be getting it from the bag. At first, I didn't know what that meant, but I didn't mind trying something new. So, I laid down on the bed, and she left to get the equipment ready. When she came back she was holding an open topped red bag, with a large, black, douche nozzle on the end of the tubing, which was shiny with Vaseline. I knew I wanted all that water in me, and didn't mind the idea of a larger nozzle, either.
As soon as I felt the nozzle pressing against my ass, I instinctively lifted my hips up to meet it. She told me I was a very good boy about taking my enemas, and how much she appreciated that. I was in Heaven as she slid the nozzle deeper into me than anything had ever penetrated, and I loved the snug fit when it was all the way in. A minute later, I heard, for the first time, the most wonderful sound in the world: an enema clamp snapping open. I really enjoyed the way the water just flowed into my ass, pouring inside me, without the stop and start of the bulb. I took the entire bag without once asking her to stop, which got me a lot more praise from her. When I heard the bag gurgle, and saw that it was empty, as she shut the clamp, I told her I liked this way of taking enemas much better, and asked if I could take all my enemas this way from now on. She smiled, and told me of course. I lay on the bed holding it in and feeling wonderful, especially when I realized I still had to take a plain water enema after this one!
Over the next few weeks, I made sure that I got lots of enemas, and even started asking for them when certain people were in the house, in particular some cousins of mine who were grown women. I was always very embarrassed about having them see me take my enemas, but I found I couldn't resist having them see me take them. Also, I noticed my sister, who was well into puberty by this time, rarely missed one. In fact, after a few weeks, my mother told her that if she was always going to be there, she should make herself useful, and hold the bag up. She always held it up very high, and would sometimes stand on the bed and have the tubing going straight up, if I was plugged up badly, and the water wouldn't go in. She loved to see me get my enemas, and was always telling Mom that she thought I needed one, which was fine with me.
When I hit puberty, my enema experiences changed radically: I noticed that my cock always got hard from two things, pretty girls and enemas. I had no idea why, at first, but I realized that I always got hard as soon as Mom slipped the nozzle into my ass, and while it felt great, I didn't know what to do with it. The first time I got up to go to the bathroom with a hard on, I remember my sister giggling at me, and my mother telling her to stop. After a week or two of this, Mom made a change. Years later, my sister told me that Mom had always gotten turned on by giving me enemas, but felt wrong doing it once I hit puberty. So, she finally convinced Dad to let her give him enemas, and, according to Sis, they still do that frequently, and they both enjoy it. So one day, Mom told me I was too old to get enemas from her anymore, so my sister would give them to me from then on. She said I had to take them whenever my sister said to, just as if it came from her.
The first time Sis gave me one by herself, without Mom watching, she got the bag ready, then came into my room and told me to undress. I was hard by the time I got stripped, and she looked at it, shaking her head. "Don't you know what to do with that yet," she asked. I asked what she meant, and she pointed at my cock.
"Not really," I told her. She said to lie down and she'd show me something I'd like. When I was on my belly, she slid in the nozzle and told me to start rubbing it against the towel. Of course, as soon as I started I knew I was onto something great. She opened the clamp, and as the water started filling my ass, my cock felt better and better. Shed been holding the nozzle fully inserted, but then she started fucking my ass with it, slipping it in and out as I wiggled up and down. At that age, it only took a few strokes before I came for the first time, with a scream. Of course, I still had most of the bag to take, and take it I did. Lying there, in a puddle of cum, with the nozzle pouring water into me, made the warmth of the orgasm seem to go on forever. When I had the whole bag in me, my sister told me that whenever I got hard, I should tell her, and she'd give me an enema to take care of it. From that day on, I got 3 or more enemas daily.
One day, I came home from school with a throbbing erection, unable to think of anything but getting an enema. I walked into my sister's room to ask for one, but she had a girlfriend over. She asked what I wanted, but I couldn't bring myself to ask in front of her friend. She told me she knew what I wanted, and I shouldn't hesitate to mention it, just because she had company. I still couldn't say anything, so I just told her it was nothing, and started to leave.
"Wait a minute, I know that look. You need an enema, don't you?" she gloated. I could only nod my head. "Well, why didn't you say so? All my friends know about your problem, she won't mind moving into your room while I give it to you. Go get ready."
By this point, I was usually able to keep from cumming until I'd taken the entire enema, so my sister would have me roll over onto my back, and jerk off so she could watch me shoot. That was fortunate, since that's what she wanted me to do in front of her friend. In fact, that's what she made me do in front of most of her friends, over the next few months. On my next birthday, she bought me a three quart hospital style clear bag, with a larger, inflatable nozzle nozzle, and "christened my ass" with it in front of three of her friends.
By the time I went to my senior prom, I knew enough about sex to realize what I'd been doing all these years, and to keep my mouth shut about liking to take enemas. I got them every day from my sister, and once in a while she'd have one of her friends give me one. I had a few girlfriends, but I never discussed enemas with them, until prom night. The girl I went with stayed the night at my house, more or less with her parents' knowledge, and I had regular sex for the first time. When we woke up, it was Saturday morning, and I was nervous about my sister coming in with the enema bag, since I didn't know how my girlfriend would react.
She quickly put me at ease, by telling me that she envied her older sister, who was one of my sister's friends. When I asked why, she told me that her sister had seen me take my enemas, whereas she hadn't. Before I could express my joy at this, in came my sister with the bulging three quart bag, nozzle greased up and ready to go. I asked if they'd arranged this, and was told of course they had. My sister told me she hoped I hadn't planned on the beach or anything, because she had to teach my girlfriend how to give me enemas, and she figured it would take all day!
I rolled over and told them I hoped it took all week.