Pretty sure it was G2 Sideswipe, and I played the shit outa that guy. It's a wonder that I still have his gun & that he's still alive to begin with. Well, not alive alive, but you know what I mean.
It was RID X-Brawn. Since it was also my first TF, it took me like 45 minutes to transform EACH WAY. Now I can transform ROTF Prime back and forth in 6 minutes
G1 Optimus Prime back in about 85-86 which eventually led me to become a Prime collector as I got older. One of the first things I got when I started to collect again in the early 2000s was the TF Collection 0 Convoy, which is probably the best packaging ever for the G1 Prime
G2 Optimus Prime, the one that was largely identical to the G1 version but with the black trailer and the soundbox. That was my favorite toy I had, but unfortunately I don't know what has since happened to it.
RID Optimus Prime I got him for my swimming diploma. I WANTED Ultra Magnus D: we saw him the week before, but after my diploma, gone. But then I got a Car Robots god magnus 4 years ago, and I'm a happy man ever since.
When I was 6, the older brother gave me a big transformer, already badly battered in fighting I guess he has no relation to real official Transformers (though vaguely reminiscent Predaking), but he was my favorite toy, until I grew up. Almost all of his paint got off, and his leg cracked, but I shook it by scotch and continued to play Who knew that after almost ten years I will become a fan, my room will be filled by posters and shelves will be occupied by his real serious colleagues? Perhaps I have the tendency to Transformers since childhood
G1 Scourge when I was 3 years old. Still have him- he's got no stickers left and missing a win, but we won't be parting!
07 Movie Starscream and Bonecrusher, these are the guys that started my passion for movie-verse figs, and TF's in general.
G1 Optimus Prime. Still have him at my parents house. Going to grab him over Christmas and put him back on display. Oh, and he should still be complete.
As a kid, G1 Twin Twist. Although, I think I also may have had a Top Spin at around the same time. As an adult, Movie 1 Starscream. It took me an hour to figure out the transformation. The last time I had even messed around with a Transformer was around 1993 when my parents bought me G2 Sideswipe, Jazz, and Grimlock for my 11th birthday. That's a 14-year gap of not playing with toys right there. I guess I was too busy chasing girls and playing Street Fighter.
G1 Ramjet. He taught me to never take toys to school. I still have what's left of him. Ended up buying a mint one much later.
I don't remember. It might have been g1 prime since he's the only one I clearly remember getting on christmas eve. As for collecting, alternator silverstreak was the first TF toy I ever bought with my own money, and got me hooked back into TF toys.