I'm sorry for the loss of your little companion.

Sounds like he was similar to my old girl, she showed up as a feral in the garden eating what the dog had left over, we would throw the left overs out for the hedgehogs to eat (thanks to slug killer, and pesticide they can't bulk up like they used to), it took five years to be able to pet her without getting torn up, or swatted at, and an additional two years before she got tired of living on the bottom shelf of the BBQ under a tarp cover (and I still think she only changed her mind because something tried getting her).

I don't know how old she was exactly but easily in her 20's from the year we first noticed her showing up, since I left my home country almost a decade ago, I had only seen her twice, and made the most of the time with her, when it was time for her to see a vet, they had to come and see her as she wouldn't let you pick her up (be prepared to lose some blood in the process if you tried), I wasn't there for the end (that part still hurts the most), but I know my parents and my sister said what needed to be said for me.

Don't know if it is because she was my first cat, but I think that's why it hurts so much, it get's better over time, it helps if you have something to take your mind off of dwelling over those last moments. Between hobbies, and work, I have our cats to deal with, if I haven't got my youngest boy snuggling up where ever I am, it's the little tortie sneaking onto my lap and passing out, or my old stray boy, decides he is hungry, again...After just eating his afternoon meal (they got grilled salmon last night, as a treat...It was half of my salmon).