I guess this belongs here, because it would have been about 1950.
My recollection is a little vague, but what I remember is my parents used this baby sitter who was probably about 16 or so. I know she didn't drive because they would pick her up and take her home. I don't remember how the conversation came up, maybe because she saw the equipment in the bathroom. As I remember this was not the first time she sat for me, and I'm sure glad it wasn't the last.
Somehow the subject of enemas came up, I really liked Carol-Ann, and I really liked enemas. So when she did ask me if I liked them, I remember when I said yes, she got all giggly. Then she started to tease me about liking them. I didn't like being teased, but I liked talking about enemas, and pretty soon she asked me if I would like her to give me an enema.
With me you didn't have to ask twice, I said I would, and since I was already in my PJ's, I pulled them down. I got a bit of a startled reaction, and then Carol-Ann said she would like to give me one, but it had to be our secret, I could never tell anyone, ever, if I did we would both be in a lot of trouble. Because I got so many enemas I didn't understand why anybody would be in trouble, but I wanted one, and she extracted my vow of silence. She even said if I was good I could get one whenever she was my sitter.
I probably almost blew it by being too anxious, because Carol-Ann was starting to hesitate. But at last we went into,the bathroom and she got a bag of water ready. At this point my mom always gave them to me face down, sometime knee chest. But Carol-Ann wanted me on my back, so I complied. We had a Davol Comfy open top fountain syringe, and I believe mom was already using the adult rectal nozzle.
It seemed funny at first, because I was so used to having the insertion from behind, Carol-Ann had me pull my legs up over my head, spent a long time lubing me, and then put the nozzle in. Mom was pretty business-like about this, so I was enjoying the attention. Looking back Carol-Ann knew what she was doing, so I guess we can assume she might have been on the receiving end a few times. I wish I had asked.
Unlike mom she didn't hang the bag on the door high in the air, she started low and slow. She was giving me lots of encouragement. Now I do know I had taken the entire bag on many occasions, but not without some difficulty. I know I tried real hard to please my mom, and I also knew being really full felt really good. With the bag much lower and Carol-Ann's encouragement I was doing really well, at about the point I'd be hearing the bag gurgle empty when hung on the door it was about half full. Carol-Ann would move the bag up and down, a feeling I remember really liking. When finally it was empty, Carol-Ann had asked several times if I wanted her to stop, I think she was very surprised.
At this point mom would have me on the toilet, she wasn't one for telling you to hold it in, and besides there was always enough Ivory Soap in the first one holding it for long wasn't an option.
Carol-Ann closed the clamp, but didn't take the nozzle out, she laid the bag down and the started to rub my stomach, that rub included brushing my penis, but not actually playing with it. I loved the belly rub, but after a few minutes I told he I had to go. She helped me on the toilet.
Now at this point mom would usually leave the bathroom for a few minutes. Then she would come back and inspect what I had done. There would always be a second enema, usually a third. As long as there were chunks in the toilet I got another enema. I think the most was 5 or 6.
I expected Carol-Ann would leave to, but she said I should lean forward so she could watch, I used to do this anyway so I could turn and see what I had done, so I moved forward, leaned forward and let go. Carol-Ann moved her face in very close for a good look. I found it very exciting. She was talking to me about how well I was doing.
I never had much trouble emptying, and all too soon it was over, I was empty.
Mom never asked if I wanted another enema, but Carol-Ann did, and of course I said yes. She must have been pretty knowledgeable because she had me rest before we repeated the procedure. Again a slow fill and a tummy rub followed by helping me to the toilet. Carol-Ann asked me if I could hold this one a while, something mom never did. Then she said she would help me and this time she kneeled down and reached around and put her finger in me. A little bit at first, then in as far as it would go. I was startled at first, then I liked it. She wiggled it some and pretty soon I told her I needed to go really bad. I expected her to take out her finger, but she said push, and started to wiggle it some more. "Push, Push," she said, and pretty soon I could feel it squirting around her finger, it was a wonderful sensation. When I couldn't squirt anymore she took out her finger and the rest came out.
She helped me clean up and was starting to put the bag away when I told her mom always gave me three. Without hesitation the bag was refilled but this time she asked me to show her how my mother did it, so the bag was hung on the door, I laid face down on the rug and took my enema. After that she cleaned up and sent me back to the living room to rest. I remember she was in the bathroom quite a while, with the door closed, before she came out. Now I realize she was probably masturbating.
When she did come out she again made me promise never to tell anybody, and after I had, she said as long as I didn't we could do it again. She asked me lots of questions about how it felt.....
The next time she came to sit my folks were barely out of the driveway before Carol-Ann asked me if I wanted an enema, to which I of course answered yes. The procedure was much the same, but this time the well lubed finger went up inside with the first enema, and with the chunks and all it really felt good exploding around her finger. It became routine, the first two enemas on my back the third face down.
After a few of these sessions Carol-Ann decided she should check out my bum by inserting her finger before the first enema, she'd tell me what she felt, and once even asked me to push it out for her. As I pushed, she fingered. I guess she turned me from a little boy who liked enemas to an anal erotic, because pretty soon I was doing this to my playmate from accross the street, Janet.
After a couple of the push out sessions Carol-Ann started giving me enemas in me knee chest position, still reaching around and rubbing my stomach. This was great fun, and since my folks went out most Saturday nights, and Carol-Ann was usually my sitter I was in heaven.
I guess being young and being the center of attention it never occurred to me to ask Carol-Ann if she wanted an enema. But as it turns out I didn't have to, one night when we got into the bathroom Carol-Ann asked me if I would like to watch her give herself an enema. I think I said if I could have one, too. She agreed, and got everything ready. Then as she laid down, I expected to put the nozzle in and I though she was going to help me lube it. To my surprise she covered my entire hand with Vaseline and then guided me into her anus, like she did with me I could feel pooh in there, and she took my arm and guided me in to my elbow. She told me to move it around, and while I did she started to moan. I was afraid I was hurting her but she told me not to stop. Then all of a sudden she went rigid then relaxed, and she slid my arm out and cleaned me up. She let me give her an enema, and like her I got in close to watch it all explode out.
She said if I was going to have my enemas she only had time for one, so I was next, and we kind of hurried through mine. I loved them, and while I liked playing with her, I was really more into her giving them to me.
Again I got a lecture about never telling anyone, especially about what I did to her.
She sat for me several more times, and I got my enemas, she never volunteered to take one again and I never asked.
I remember how disappointed I was when my parents said she had a boyfriend and wouldn't be sitting for ma anymore. I often wondered if she really did, or just got concerned or felt guilty about what she was doing. If she had a boyfriend I wonder to this day if she was playing with him. I never saw her again, I know she got married a few years later. Then about two years ago a family friend told me she had died, guessing she was about 10 or 12 years older than me that would have made her between 78 and 80 or so.