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

@trentd1114 same here!!! 😋

I realized that being fucked by a real cock would be fun, after using a dildo in my ass. When I started with the dildo, I was expecting pain and resistance. I found that, while resistance to penetration was there, pain was not there. In fact, it was immediately pleasurable. I tried several different diameters and lengths of dildo, however, they all felt good. At that point, I was ready for a real cock!!

What an interesting question. I have never thought that I am "into anal play," but do now realize that it is a source of medfet for me and has been over time. As I have described in other posts, the experience of receiving a rectal temperature as a child and into adolescence has now morphed into something that is very stimulating. Over time, the entire aspect of what an adult male exam may entail has only intensified my feelings both in anticipation of an exam and thereafter as a source of reenactment. The entire sequence of events from undressing and showing myself to the doctor is thoroughly heightened when receiving a genital exam and culminating in a DRE. There is nothing more intimate and I think submissive than having these parts of my body exposed for manipulation. There is no turning back as I stand before the doctor and surely no way to observe what he is about to do if made to lay on my side or bend over the table for his finger! Be it standing there fully naked or gowned with my rear on display, it is a moment of such personal exposure that is so priceless and subsequently rewarding given multiple exams over time. The first DRE around age 18 was very shocking but now it's in someways welcomed and serves for very fascinating conversations with friends here!

I was 12, neighbor kid who was 14 showed me how to masturbate. Sometime later he introduced me to putting his/our version of a toy which was usually a toothbrush or hairbrush handle to make the masturbation feel even better. I was hooked.

I was able 13 years old. I was overseas. The house we were living in was newly built at that time. The bathroom had a dedicated bum cleaner/bidet or whatever else it's called. I was afraid to use it but somewhat curious. I hesitantly sat onto the seat and expected anything to happen or go wrong. I turned the tap and felt the high pressure of the water spray right onto my sensitive anus! I was both shocked and had a delayed arousal. I dried my butt and decided it was enough for a day. A few days later, I gave it another go, but that time, there was only a bit of shock, but plenty of pleasure. I'd never felt any stimuli of my anus before and never thought I could have. I always kept it to myself and from then on, from time to time I would use my finger to circle around my anus for pleasure.

I was taking a bath and for for some reason I brought my knees to the chest and relaxed, the next moment my anus opened a bit and some water went in. It did feel interesting, so next time, I don't remember why, but I used a pen. When inserting the pen just a bit, my anus would have opened and let some water inside, so the pen it was the trigger😃

It's started out as one finger when i was 16 and now i graduated too much larger objects. I have had a lot of things in my ass ,too much to write here and always looking for new ideas.

Pooping and wiping definitely got me

Horny as a young boy and got me hard. Didn’t take much for me to get into anal after that.

Grew up with rectal temp, suppositories and enemas. The stimulative effect related to these procedures was the trigger I guess.