I'd been touching and exploring it myself before my teen years but only 'learnt' the true potential in the early teen years when i started to see men! Never doubted it since, although they do need to be quite big now lol

I'm str8 but a little curious and I knew it was a thing when I was younger but never tried it.
I only recently got a little more adventurous when I was jerking off and decided to try it and now I do it regularly. I don't think I'd want anything bigger than a finger but I do enjoy it

First ass play for me was when I was as sophomore in high school. Started rubbing my hole while jerking and loved the feeling. Then started fingering it, stretching it, and massaging my prostate while jerking later that year. My gf my senior year would suck me and stick two or three fingers in while doing so and would rim me. College was when I started using toys and have continued to this day. Love playing with it, the stretch and full feeling is amazing.

In my late 40s I started experimenting, wife was going off sex & I wanted to make the wank go that bit better. Moved from caressing under the balls to rubbing the perineum and eventually letting a finger feel around the hole.

Then one day I let a well lubed finger slip inside - wow! That was it a whole new journey.

I don't do it every time but is one of those for that special undisturbed wank. I feel around with a finger in a latex glove, then I slip a finger in and out; I then replace the finger with a Sharpie pen in the glove, lube it up a bit more and away I go. Great thing with the glove, no residue on the pen and no risk of it getting stuck.

It is!