Wow! Sorry to say that the Apple People conquered the world in the meantime. Where were your scroll of Rainbow Blast, eh?
Sounds like a great time 
The first RPG you ever made!
A few months ago I put together this: The Tower of Scrabbleon (And the DM Page. It’s nothing extraodinary, I suppose, but it played OK and I was pretty pleased and pretty proud. I also enjoyed designing in a space that was, as far as possible, wholly circumscribed by the rules of a pre-existing game.
I planned to take this approach with a couple of other games, but so far I only have two at the very beginning stage.
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I wrote 3 RPGs for the first 200 word RPG anthology but I think the first one was The Council of Advisors which is a simple social LARP I’ve always wanted to play but never have. I did play my other 200 word RPG Corporate Memo and it was a blast. These were my first RPGs.
Council of Advisors: https://200wordrpg.github.io/2015/rpg/2015/04/01/TheCouncilofAdvisors.html
Corporate Memo: https://200wordrpg.github.io/2015/rpg/2015/04/01/CorporateMemo.html
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The very first one I can remember might be when I was 11-12 years old and me and a friend drew maps which had all kinds of traps in them and secret passages and levers to pull. We based it off of video game maps. It must have been the year 1996.
Then next one is probably a “Fantasy Walk” or “Story Walk” I made for 3-5 year olds which was basically pure roleplay (kids style) with a few mechanics for guidance. (I think it was rolling a die, which meant pulling a picture from an envelope and interpreting it). It was fun. Kids don’t need mechanics. 
The first actual PnP game I made was one to use as an illustration in class (I teach religion) where the 6 year olds played minions trying to find bananas before the countdown clock ended and Donkey Kong came to steal them. Turns out it was a bit too scary for them. (thieves are quite terrifying to some at that age) So while I still use the system I developed, I changed it into a challenge of kids surprising mom with a surprise birthday party. (the mechanics rewarded working together and are diceless, since I did not want randomness undermining the principle that it had to teach)
I think the same year I also made a game about Care Bears working together to solve a problem. It did involve dice, but it still worked. (and the kids loved rolling hands full of dice)
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Middle school, DeD 3e just came out and a friend of mine gave me the player’s guide to read so that we could run a game. I was slow as hell, reading less than 1 page a day so, in the meanwhile, we run our own version of DeD, which was with 5 of the 6 stats and no real rule other than “roll something and let’s see what to make of it”.
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My brother heard of D&D and made a simile we played in 1982.
Three years later I crafted a magic system with words, combined into “sentence” spells, with mana segments you could arrange to maximize finesse (myriagons>>triangles) or scope - potency (number of regular figures). 9 bars made 5 triangles, with 12 bars you could make 5 squares, etc. I never used it to play, but I learned some maths.
In 2018, I did a successful façadist hack of Reve (banana challenges really).
Only this year did I complete my first TTRPG (still without theme though). Does it mean I’m late by 38 years ?
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