When was the first time you put something up your butt and what was it?

When I started getting in medical play and play exams, my first play doc did a rectal temperature and prostate exam. Back then, I wasn't as open with myself, and I sort of initially shunned it as "awkward" and didn't really give it too much a chance. It wasn't my specific interest in the play exam, but still let it happen as it was something they enjoyed. As time has gone on I have found prostate play to be very erotic; just took me a bit to get there!

Probably around 11-12 years old I developed an interest in inserting things back there. I used some child size suppositories from the bathroom cabinet to begin with, but was worried my mum would notice their disappearance. Got a bit more adventurous with hazelnuts, fingers and the smooth handle of a brush (quite a stretch!)

My fingers when I was around 12 years old making sure I was nice and clean up inside, and it felt so good 😊

When I was 5 years, old a boy I sometimes played with asked me “It feels good when you play with your butt. Want me to show you?” I declined but I was already imprinting on my mother’s black nozzled red rubber douche bulb. Later as a horny Catholic raised teenager I had an “aha” moment and took my 1st enema with, well, mom’s Davol Comfy” bag with a white douche nozzle ( the bag died in the nineties ) but I still have that classic😍I read about enemas in Penthouse Variations and that’s when my enema and anal play journey began😜😍😜

I was around 17 yrs old when my girlfriend made an off hand comment about some guys liking a finger in their ass while masturbating. I said I would be willing to try it. We had talked about anal sex and she had said that she was not ready for it so I figured if I went first, maybe she would be more willing. She ended up sticking her finger in my butt while jerking me off and I had an amazing orgasm! We never did have anal sex!

It's how my interest in enemas began - by sticking the douche nozzle up my butt when parents were working... My age? - just when puberty was beginning.

I don't remember exactly, but I was probably about 6 years old. I saw my younger brother or maybe a cousin get their temperature taken rectally and a little later while coloring with crayons in my room I got an idea. I took a crayon color I didn't like and peeled off the paper. I was totally surprised how good it felt as I slid it in and out. I may have slid in a finger in the bathtub before that, but that was the first time I used an object.

I was 13 and it was a vibrater that I was given by one of my moms friends.

@ilovetosub I'd like to know the circumstances under which this lady donated you such an object at that age…

Our 1950's era home was that of ' enemas and rectal temperature taking ' from my infancy , according to my mom , through my university grad-school days so ...... I did not have ' far to go ' for object access for my budding rectal pleasures . All was from my boyhood and all was long ago . My mom understood and she often indicated to me that ' all you have to do is ask ' and ' ask ' I did . How I wish that I could again receive one of her loving , caring and ever so well administered enemas . As I matured , the home enemas became most erotic as to anticipation , experience and desire especially as I returned home from my studies @ our state university after a much to long abstinence from my mother's ' TLC ' enemas and ' RT ' activities . Yes ...... I really miss those days . As to the thread , the first self-insertion I recall as a young kid was that of the ' adult rectal ' pipe attachment in our home enema - douche combination syringe .