G2 Optimus Prime (G1 mold). I was shocked to see him on the shelf at Toys R Us and bought him immediately.

 

Classics Starscream & Rodimus

 

I hadn't given a thought to TF collecting since I was a kid, and I was randomly in Walmart at one point and saw the RID 2001 firetruck Optimus Prime. It looked awesome, but buying a toy when I was an adult was weird...right? I left it at the store, but thought about it some more and went back a few days later and grabbed it anyway. That is still a fantastic figure. I later found Ultra Magnus on clearance to form Omega Prime.

 

with my first paycheck...Car robo Black convoy, i think i did good  

 

MP-01 about 3 years ago of kijiji. Now I have 3 detolfs full of TFs. So much fun.

 

Generations Kup. What a cool mold, and loved the matte detailing on the truck bed.

 

A long time ago...cybertron downshift

 

Alternators Smokescreen. At the time I was collecting Marvel Legends primarily and hadn't bought any Transformers since Beast Machines. I had a thing for WRXs at the time as well. Now my collecting is primarily Transformers and creator owned properties.

 

Generations Drirt

 

Exactly the same here!

Went back the next day to the TrU on Broadway, in Vancouver, for Bumblebee and Astrotrain. Been chasing that dragon ever since.

 

Classics Bumblebee. It wasn't intentional, but I realized later that my very first TF purchase back in '84 was Bumblebee as well.

 

Waaay back in 1997...........it was Beast Wars Fuzor Silverbolt. An it was all down hill from there..

 

Mp-04 iirc

 

US Mp01 or the 1st Unicron, whichever came out first

 

For me it was G1 Soundwave in 2000 when I was ~25 years old. I had just discovered Ebay, and noticed folks were selling a lot of original transformers on there. I still had all of my G1 TF's from when I was a child, so I decided to pick up a few more on the cheap that I never had, starting with Soundwave, then Slag, Sideswipe, Mindwipe, etc. Once R.I.D. hit, I was hooked on the new stuff and it went like crazy from there.

I even bought a sweet custom engagement ring for my lady largely through buying and selling Transformers on Ebay in 2004. She was pretty impressed at my industriousness, considering I was a poor church intern at the time. It was also good validation for her that collecting Transformers can be a worthwhile hobby, and she (now my wife of 10 years) largely supports me in it to this day.

 

Well, I was out of my parents house when I was 18 ... so that puts me around the 2008-2009 timeframe. I can't recall specifically which toy it was, but I do recall buying Encore Sky Lynx around that time. I also remember buying a bunch of ROTF toys ...

 

Mine was Binaltech Prowl, the blue colored version. Saw it on a local hobby shop and have been eyeing it for a few weeks, going back and forth on whether I should get it or not because I wasn't into toys during that time anymore. It was pure nostalgia that made me decide to get him. Just one I said. Was in awe with all the details and the complex transformation Takara engineered. So glad I pulled the trigger on him. It's the figure started my collection. Never looked back since.

 

Beast Wars Optimus Minor and Sonar. They were selling them for £1.99 each in my local Poundstretcher circa 2000, and the rest is (expensive) history!

 

Energon Silverbolt in late 2005

 

g1 trailbreaker