Bought my first pipe April 15, 2011 from the local tobacco shop (Paul's Cigars) with 2oz of Lane RLP-6, a nail tamper and some pipe cleaners for $35. It was a Czech made bent brandy basket pipe. It had a stinger, which I removed after a handful of smokes. It smokes okay, but it develops a gurgle at times. I still smoke it a couple times a year.
In December 2011, I ordered my first "good" pipe, a Savinelli 645 bent apple short pipe, which arrived just after the new year of 2012. It's still one of my favorite pipes.
Below are my "first pipes," which I've had for the last 10+ years, and still own and smoke all of them.
Top to bottom:
First Pipe: Czech - Bent Brandy Basket Pipe
First "Good" Pipe: Savinelli - Bent Apple Short Pipe
First Meerschaum: Mini Bacchus - unknown carver
First Corn Cob: Missouri Meerschaum - Bent General
First Handmade Pipe: Straight Billiard - Made by me and Sparky's Pipes (I call it the "Reigning Blood Billiard.")