How did you find out that you like anal play? How is your first experience getting something inside anal?

I think it all started when I was 5 or 6 when my mother gave me salt water enemas for pinworms. This went on daily for two weeks. Then when I was 8 or 9 my older brother decided we should try anal. We tried with NO LUBE!!! I screamed when the head went in and he pulled it right out. Then at about 10 or 11 I was playing with an older neighbor, he was about 14 or 15. Upstairs in his bedroom. He came in the room with a jar of cold cream and had already undressed. Before I knew it, I was naked and he had his cock in my ass. Plenty of lube this time. He was hammering me pretty hard when he stopped. He asked me if he should "Shoot the Load." I didn't know what it meant so I said go-ahead. This went on for a few months, at least three times a week. I believe I was his walking sperm bank. But as I think back on it 60 years ago, it was really fun...

I am a paraplegic born with Spina Bifida. Among other complications, it caused lifelong urinary and fecal incontinence. Throughout my childhood, my mom was my main caregiver and disciplinarian. I received frequent enemas and suppositories along with less frequent rectal temps and bare bottom spankings. I didn't enjoy enemas or any health related anal penetration or treatments until puberty when I was about 12. It was still embarrassing, but suddenly I no longer feared the process. In fact, I suddenly had a, um, hard time hiding my enjoyment. This added a new level of embarrassment at first.

Thankfully, my mom acted like it was a normal, which I learned much later was true. I mostly got gentle enemas from my strict but loving mom. However, sometimes she would make the enema(s) cramp by adding one or more "secret ingredients" that I later learned had been added to her own childhood enemas by my grandmother. She assured me she understood my discomfort (short of intense pain) because she got p.e.'s (punishment enemas), too, as a child and teenager. She also got her share of spankings, which she and I agree helped her to give safe but very effective ones to me, my two brothers and any other children, boy or girl, in her care. I didn't want the punishments as she was administering them and I rested the cleansing enemas and other healthcare more than I should have in my younger years, but as I reminisce I am thankful she cared enough to give me what I needed even if I did not want it at all. I believe my childhood experiences are linked to my decades long enjoyment of anal play, especially with a medical theme, and I don't regret it at all.

What I can remember of it, I was probably 9 or 10. I had a male neighbor that we used to play together a lot. Not sure how it even came up but I think it was his idea. We ended up playing in the back seat of his dad's old car that was in the back of a huge garage. We started putting stuff up our butts. Stuff like bits of plastic and things. It was lucky we never hurt each other. I can remember that I liked it a lot. The feeling of it going inside and then staying there. Then one day I moved away and it stopped until I discovered my Mom's enema bulbs that she had given me when I was very young. In fact, when I could, I would take out the small bulb (3 oz or so) and fill it then insert and give myself little enemas. This continued until I was 12 or so then one day I really noticed that the little "tingle" I would get was getting stronger with every insertion. One time, I was in the bathroom laying on a thick towel and with the enema inserted when the tingle started. So I started rubbing onto the towel. The tingle got stronger and stronger until all of a sudden, some stuff spurted out and I had the most extreme pleasure and feeling. At first I thought something had "broken". I tried it again the next day and sure enough, it happened again. Hence my first orgasm from an enema...or anything else for that matter.

I have been doing enemas for years

Tried a double balloon enema nozzle and liked the way it felt so I moved on to other things