First Two of Each Gen?

[Shaz]

G1: My pony collection began with Baby Ribbon, who was a gift from my girlfriend because I liked her childhood ponies so much. She was followed by a deflocked Magic Star, who I bought after ogling ponies on Strawberry Reef and deciding that Magic Star in a rearing pose looked awesome. Both came from eBay; Magic Star came all the way from America!
G2: Clever Clover was first, followed by Star Swirl. EBay purchases.
G3: A beaten up Petal Blossom rescued from a charity shop, followed by Moondancer bought online (because Petal Blossom needed a friend!).
G4: Ty Rainbow Dash (an Easter present) followed by a sparkly blind bag Fluttershy (an impulse buy in Tesco). My first brushable was Cheerilee.

Asked my girlfriend what her first ponies were:
G1: Wind Whistler and Sweetstuff (probably) - from charity shops in the 90s
G2: Light Heart and Sunsparkle in a playset with a birthday cake, little party hats etc. She thinks she got them for her fifth birthday in 1998. We still have the ponies and one party hat!
G3: McDonald's Spring Treat (found in a charity shop c. 2004), Spring Fever (found in a charity shop in Cornwall in 2006)
G4: Sparkly blind bag Sunshower Raindrops (bought at the same time as my sparkly Fluttershy) followed by the three-pony set with mini Octavia, Lyra and Lyrica.

[Shaiyeh]

g1: Tuneful and Bridal Beauty.
g2: Morning Glory and Berry Bright
g3: Petite Petunia and Fairy Dust (FD isn't my original FD, I've sold and repurchased that pony three times, I think.)
g4: I got the entire "mane 6" when they first came out but only have 2 of them now: Pinkie and Twilight. (Twi isn't my original one, recent thrift story find. I don't collect g4 ^^')

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[The_Loner]

What a fun topic! I enjoy seeing peoples pictures!

I just moved and my ponies are packed at the moment so I can't take a group picture but I'll add pictures from my archive for each generation.

G1: Cotton Candy (my very first pony ever) and Liljekonval (Lily of the Valley in English)

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They are sisters

G2: Clever Clover and Princess Crystal

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They are a couple

G3: Kimono (got her as an extra surprise in a trade from someone in the US before they were out here) and Dazzle Surprise (got her from Hasbro Nordic after sending them a fan letter)

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G3.5: Super Long Hair Rainbow Dash and winter Sweetie Belle

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G4: Rarity (regular Pony Friends with pet friend) and Fashion Style Rarity

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They are mom and daughter

G4.25: Big McIntosh, as second I got Ocean Gem, Crystal Pearl and Sun Twist at the same time

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[Carrehz]

Oh, I forgot about the G4 reboots! My first were Big McIntosh and Starlight Glimmer Haven't got any of the newest ponies (yet? Never say never, I guess).

First two EQGs were Rainbow Rocks Trixie, then the CMC set.

[Harmonie]

I only have G1s and G3s.

G1: Pony Bride and Merry Treat (who came with a lot of mostly winter G3s)
G3: Jazz Matazz and Wave Catcher. Technically I got Wave Catcher only because she came with Jazz Matazz. My second G3 I got by herself was Candy Cane.

[tailrustedtealeaf]

I actually got quite a few ponies altogether so it's hard to say.
G1: I got four at the same time: Baby Milkweed, Powder, Cotton Candy, and Baby Moondancer
G2: I got three: Sky Skimmer, Clever Clover, and Petal Blossom
G3: My sisters had some for their birthday one year that we've had: Gem Blossom, Sweet Breeze, Baby Romperooni, Baby Pink Sunsparkle, Triple Treat, Honolu-loo, and Hidden Treasure
G4: I got three! Twilight Sparkle, Starlight Twinkle, and Blossomforth
G4 Reboot/Movie: I got the Rarity Boutique playset first and then the Fluttershy with the clippy dress!
G4.5/Pony Life: That would be the Magical Mane Rarity I got a few months ago, and then Pinkie or Fluttershy dressup size or Twilight Sparkle normal size.

[flutterscotch]

G1: Twilight, Firefly
G2: Clever Clover, Berry Bright (who I need to replace)
G3: Kimono, Minty
G4: Applejack, Fashion style Applejack (they were purchased the same day, still have them)
G4 Reboot/Movie: Luna and Celestia...I am not even sure if they're legit ones. Weird pre-release ebay purchase.  If not, Twilight Sparkle and Applejack
G4.5/Pony Life: None yet, but it is probably going to be, let's face it, Applejack.  And probably Trixie, she looks funny and cute in that reboot mold.

[starbritesprinkles]

G1: I believe CF Blossom and Starshine were my first. My earliest pony picture from childhood has Blossom in it, and my earliest pony memory is of getting Starshine at the flea market. I could have had others before, but I don't remember.

G2: I really don't know since I don't really collect them. I bought the first few releases in a lot, and I think those came after I found Dainty Dove at a church rummage sale.

G3: Kimono and Pinkie Pie. Bought them at Kay-Bee Toys at the same time.

G3.5: Again, I don't really collect them but have ended up with a few in lots. I think NC Star Song and Sweetie Belle (2009 "Twice as Fancy").

G4: The collector set with the molded hair. Then Twilight Sparkle with balloon and Fluttershy with tree nursery.

G4 Reboot: All About Big Mac and All About Soarin.

[flutterscotch]

G3: Kimono and Pinkie Pie. Bought them at Kay-Bee Toys at the same time.

  Kay-Bee Toys crew!  That's where mine came from too.

[dragonfly]

Bowtie and Windy

Minty and Sparkleworks

[SilverLinedStars]

I don't have pictures but:

G1: I know my first one was Night Glider. I want to say the second one was Boysenberry Pie but it's been so long now I can't remember.

G2: Sky Skimmer and Ivy. I really thought their color schemes were beautiful. I wasn't wild about the G2 design but they grew on me over the years.

G3: Pinkie Pie and Kimono. It's kind of odd seeing these on the shelf again since it seems not so long ago they were brand new!

G4: Applejack and Fluttershy.

[kingluke]

I misread the question....

First g1s: Seashell and Im gonna say pony bride. (not sure)
g2: night shine (my only g2)
g3: triple treat and merriweather
g4: sunset shimmer and rarity

[goddessofpeep]

G1:
Lemondrop - The Show Stable was a very well received Christmas present. 

Moondancer - She was waiting for me in the room we were staying in during a visit to my Aunt’s house.  I was a wee thing, but I knew I wasn’t allowed to touch anything that didn’t belong to me, so I sat and stared at her.  For hours.  Eventually someone noticed, and she was officially given to me:)

G2:
Berry Bright - I went to the mall to see Titanic, and stopped in the KB.  They had just gotten in the brand new ponies, so I got one to check it out.
I didn’t really like it that much. Oh how things would change...

All 4 wave one G2 baby sets at once -  A friend of mine was in a 2 month long trip to Europe she had planned for years.  She kept sending me emails about finding ponies, and I was super excited. She was in Greece!  She was in the UK!  She was in Italy!  She was in Spain!  I finally got the box - it was filled with MOC G2s in all different languages.  A gift is a gift, and I was touched she did so much hunting on my behalf.  I knew about the baby sets, but hadn’t seen them in person before.  They were a lot better than the adults, and they came with outfits!  That was it. I was in love, and that was the start of 20 year collecting quest which finally ended 2 years ago when I finally got Springly and Springdy, completing my G2 collection.

G3:
The entire first wave of G3s - I was an active collector at this point, and I was prepared for the release of the G3s.  I lived near a TRU, and had been checking frequently.  I found the entire first group of G3s at TRU which included the 4 Glitter Celebration, the 4 Rainbow Celebration, and the Cotton Candy Cafe. 

A bit of a twist on this question - I lived near a TRU which was pretty much the first store in the world to get some things. It wasn’t anything special, just the way the distribution went.  Because of this, I had been the absolute first person in the pony community to get certain ponies.  Some of these were totally out of nowhere(Sparklesnap).  I’d find something, rush home, photo it, and report it to the community.  I was the “first finder” of several ponies including Sparklesnap, about half of the birthflowers, the first wave of scooter ponies, Star Catcher, Hidden Treasure, and Penny Candy. 

G4:
No idea about this one.  Possibly the balloon set with Twilight Sparkle. 

[Taffeta]

I lived near a TRU which was pretty much the first store in the world to get some things. It wasn’t anything special, just the way the distribution went.  Because of this, I had been the absolute first person in the pony community to get certain ponies.  Some of these were totally out of nowhere(Sparklesnap).  I’d find something, rush home, photo it, and report it to the community.  I was the “first finder” of several ponies including Sparklesnap, about half of the birthflowers, the first wave of scooter ponies, Star Catcher, Hidden Treasure, and Penny Candy. 

<3.

[Tropical_Sunset]

I love hearing everyone's stories! And the collection pics, especially the multi-generational ones, are so heartwarming to see. 

How could I forget about half-gens and reboots?  Here are my firsts for that:
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