First:Maglite… if you want to call it a ‘real’ flashlight… 6 D cells,soon after,I did the TerraLux LED upgrade.
Last:(maybe not last,but)Nealsgadgets LEP.HB
My first real flashlight was a Zebralight H600Fw Mk III.
My first ‘real’ led flashlight was Zanflare F2.
I had read review on BLF and imediatelly purchase it.
Before that I have numerous chinese no name led flashlights and Zanflare was big step up over in every aspect.
Last purchase is Convoy L21B sft 40 and I bought it after reading review from BLF forum member Funtastic.
If I don’t consider the Nebo Micro Redline a “real flashlight”, I guess a Convoy S2+ (black, 3/5 mode driver, XML2 U2-1A, 6500K) was my first real flashlight!
My last real flashlight purchase was the Lumintop Frog!
First purchase - Solarforce L2
Last purchase - Noctigon KR1, although the last one I received was from the Cyansky headtorch GAW
BLF A6 I think it was an XPL HD 1A
Emisar K9.3 Cool white on one channel and yellow on the other. Works great for mountain bike trails at night.
Petzl Myo 5 headlamp, or possibly Fenix LD20, this would have been c.2010/2011.
Most recent Emisar DW4.
First was a TerraLux Prostar 100
I still have it, wouldn’t mind an update if the host were more suited.
I think my last was a Convoy M21F
First was TrustFire TR-801.
Last is Emisar D2SV2
First: JetBeam Jet I
Last: Nitecore NU32 headlamp
In the 1960’s I bought a Boy Scout angle-head flashlight (2xD cell), and in the 1990’s I bought a mini Maglite (2xAA), but I don’t know if those qualify as “real flashlights” according to the op.
Mine was this Nitecore MH12S, which came with a tactical nylon holster. First real purchase for me, because Nitecore Singapore was having a Lunar New Year Sale in February 2021, offering a 40% discount.
That was before I discovered this BLF, Banggood, and Ali Express, from where I have bought cheaper flashlights. Can no longer afford Nitecore anymore. Astrolux, Sofirn, Wurkkos and Convoy are my favourite brands now. Good and affordable.
My latest purchase is Astrolux EC06. Still waiting for its delivery.
In 2009 I was determined to buy a "real light" and spent a whopping $12 .
3AAA's . I'd seen someone selling $25 Fenix AA lights and wondered why someone would spend so much on such a little light .
last light purchased was a >>> Sofirn SP10 Pro (AA/14500/Andúril 2) - now available! | BudgetLightForum.com
Yeah, when I first started doing research on flashlights over a decade ago, I was looking at terrible ones for like $5 or $10 
Now, spending $40 or more for one flashlight is no big deal for me. 
After a lengthy afternoon power-outage extended itself toward evening, I spent a hectic couple of hours trying to piece together a working flashlight. All my old ones had been ruined by alkaleaks. Fortunately, by the time I finally got one sort-of working, the lights came back on.
That experience sent me to interwebs to search out a decent replacement, where I landed at CPF. There I found a great review by a fellow called selfbuilt for a flashlight called the Nitecore P36. Although it has been discontinued, I still like it today. 2000 lumens, 10 output levels, perfectly neutral tint, and an artifact-free beam from it's Cree MT-G2 emitter are a few of the reasons why.
So that was my first.
Can't remember my last, but it's been a while.
First was a right angle, brass AAA from Maratac. “Personal spot light” they call it. Most recent is a D4V2 in the new Nichia E17a Azure led. Its a really beautiful ocean blue-green color.
First : ITP A3
Last : One of the Kaidomain S2 clones with one mode and a high CRI emitter
( I’ve only bought one mode lights for years now other than the BLF-designed lights )
Back in the day, when plastic-body 2-D-cell hotwire-bulb flashlights ruled the earth, Mags of all sizes were The Shiite.
So, yeah, a Minimag in my denim jacket’s pocket made me envied by men, and pursued by women.
The multicell Cs and Ds were just stoopit-expensive, and usually relegated to professionals like cops and security-dewds who wanted a club as well as light, and who could afford it (or at least write it off as an expense).
First some maglite c cell
First Led light Ultrafire wf-501b
Last fwaa copper
First - Ultrafire XML-T6 with 2 26650's
Latest - GT Nano Pro, if you can call it a "real" flashlight. It at least looks like one.
I don't think anyone here has purchased their "last" flashlight.
I have bought my last flashlight many many times.