1996-1997 or so with a Yomega Firestorm Wing.
When I actually “got into” yoyo though was years later in late 2011 or so. First “serious” throw was a Yomega Maverick, followed shortly after by a Dark Magic 2.
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2006 with a Speeder that only lasted month or two
2014 Oct YYF Fast201
September 2013 yoyo jam dm2
I’m amazed at how many people have said around 1998. I’m also one of them.
My dad bought me and my brother a Playmaxx Proyo 2 each in around 1997-1998 (I was around 7 or 8-ish). I guess I owe it to him as thats when I started my fondness for yoyoing.
Since then, yoyoing was just always a part of my childhood. In the years following I took up the hobby and dropped it a number of times. I bought a Duncan Glow Imperial and Butterfly when I was about 10 or 11, a Yomega Brain about a year later, and took up yoyoing about in about 2005 with a Yomega Xodus 2. However each phase didn’t last very long and I never got beyond the bare basics (zipper, brain twister, etc).
I truly started throwing properly at the beginning of last year. Got my first unresponsive (YYJ Dark Magic 2), and the rest is history.
Isn’t it weird… So many of us playing with yoyos as children around the same time, only to take it up fully as a passion so many years later. Who’d have thought eh? 
Knock off Yomega around 96 or 96, but oh how I remember salivating over those bright shiny plastic Yomegas. Got a Team Losi Da Bomb around 99.
It was probably a year ago today or tomorrow. One of the last days of November 2013.
YYF One
2005- A Bandai Super Yoyo transaxle
This was my legitimate first yoyo I’ve ever played
2009-ish - Duncan Speed Beetle
I tried to pick one up and re-learn my old tricks, but i did not know how to maintain a bearing yoyo and I ended up losing motivation pretty quickly after breaking it,
2012- Yomega Raider
I decided to give it another try and this time I’ve successfully dedicated to it
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Yah man, it is peculiar how most of us stopped for a while that used to throw and picked it backup…the Yomega Raider and the Bumblebee were really the best you could hope to get when I was a kid. I guess I didn’t really do it for about 10 years, then I got a Maverick. I mean, as often and frequently… I still always had Yo-Yo’s but that Aluminum Maverick really opened up my skills and got me back into it. I am now working on Kamikaze and Spirit Bomb with a Torque, where as I was really stonewalled at tricks like Hydrogen Bomb, Atomic Bomb, and Split The Atom way back then. To really even be able to do those tricks at all In the 90s, you were in a diff class of Yo-Yo’rs. /not to toot my own horn or anything.
My fifth birthday in 1985 I got one of the half red half blue light up yoyos. I can remember my dad showing me walk the dog and rock the baby for the first time. I’m sure it was probably broken two days later. Then lots of random duncan butterfly’s over the year. In middle school I got my hands on the Smothes Brothers Yoyo man video. I was hooked for quite some time. Then who knows what happened, probably girls or something like that. Fast forward to May 2013. I was walking through the toy section with my son and I impulse buy a duncan butterfly. I got home, tore open the package, threw a hard sleeper and the string breaks and the yoyo explodes on the floor. So angery that my fun times had been denied I go straight to the duncan website for some complaining. First thing that pops up is a video for the duncan flipside. I knew I was hooked before that flipside was ordered. My yoyo collection keeps growing and with new tricks comes more fun. I’m in it for the long haul.
I originally wanted to start in august of 2010, but didn’t think I could be as good as my idol at the time, Marcus Koh, now im the Kansas state champion XD (not saying im at all better than anyone btw, just wanted to make that clear lol)
anyways, I OFFICIALLY started in September of 2012, when I got $15 for my birthday, ordered a YYF WHiP about a day later, and its all uphill from there 
you can find a more detailed story on my Quotev page,
my name is wYOYOw if any of you are interested (the story is not quite done, but I will be working on it throughout the next couple of days)
I started this year with a YYJ Classic.
First yoyo: Wooden Duncan Imperial, a long long time ago in another place and time. Sporadically off and on until about 1999, then all was lost.
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Hmmm… That sounds really cool! Any pics of this alleged “Wooden” Duncan Imperial? I’ll buy it right now from you for a $100! 
Yomega gamabrain in 2010? or 2011.
Ummm, the last time I saw it was in the teachers desk with all the rest of the confiscated stuff.
Haha, yah… Lost a few X-Brains and Fireballs that way. If you ever find a Wooden Imperial, I’ll pay big money for that one. My research has led me to believe that the Imperial was Flambeau’s first plastic Yo-Yo. Are you sure it wasn’t a wooden (Imperial shaped) Duncan Tournament?
~2002 with a crap clutch yoyo called “loops lite”. It was destroyed in first 24 hours ;D
1997 or 1998 (I was 16 or 17), I bought my first “real” yoyo, a Playmaxx Bumble Bee GT (aka Butter Bee) from Doc Pop at the dearly departed “Yo Momma” store in Chattanooga. He taught me barrel rolls that day, and then wound up working at the shop the summer of 99.
I lost all my stuff (SB-2s, Customs, Cold Fusion, etc) in a house fire; everything except that first BBGT with some Spintastics sides. When I came back to it when my little boy started last year, my “new” first was a Magic T5. Then I got a mystery box last year, and hundreds upon hundreds later, I’m still looking for my “last” yoyo.
BRENT