This...

The second watch I ever owned:  1970 Hot Wheels (Swiss made by Bradley) boy's wristwatch, a small stainless steel watch made in the diver's watch style w/ black, plastic rotating bezel and rubber diver's strap; had date function, hour and minute hands that were painted in black and white checkered flag fashion, the second "hand" had a green and a red car that revolved around the dial in imitation of a car race, the yellow and black dial had the classic flaming red "Hot Wheels"-Mattel logo.  I received it as a birthday gift I think.  I beat the watch and I don't remember what exactly happened to it.  But several years ago I had the good fortune of coming across the same watch at a collectibles show in near mint condition.  I paid $175 for the privilege of re-visiting my childhood.

I would say two watches:

1. A Timex my father brought me from the states. I was sround 8 or 9 and asked him for a Casio with all the functions. Instead he brought me a Timex, which he said was better and had a SS case.....man that watch was big and heavy for a 9-year old wrist! I kept it for 7-8 years, until some crapy watchmaker that changed the battery broke something and there were no spare parts in Greece for that watch back then. So it retired, as it did not work anymore. However I still have it, as it was my first "proper" (i.e not Mickey Mouse!) watch.

2. In 1994 my second cousin gave me a SS Tag 1500 as a present, since I became the godfather of his daughter. I still have it and as you realize has a sentimental value for me. It keeps time quite well and has been service only once, and that was my fault, since I did not screw the crown tight enough and water entered into the watch.

My Cartier Santos ss/yg automatic. Bought new from Hettich in St. Helier, Jersey, Channel Islands in 1989 while on holiday. Was there for R&R had been working v. hard and earned some decent money debt collecting.
It was my first "proper" watch and I chose it over a Rolex Datejust which at the time I thought was too large! Anyway, quite a few of my (male) celebrity clients were wearing it at the time and I got a great deal on the price.
It has had just one service at Cartier in Bond Street last year and came back like new, cost £80.00 including new seals AND a new winding crown with a pale blue sapphire inset.
I will never sell this watch because of its history, the places we have been, things we have done, etc.
I am very disappointed with the current Cartier line up, the Santos has a simplified bracelet its too shiney and often sported by chip shop workers, the Roadster is pretty dreadful - the bracelet & crown, I would'nt touch any of the quartz models as a service seems to consist of simply fitting a recon movement. The Tanks are everywhere in Essex.
So now I wear the Santos for "best" and my Sub for "Play".
Btw Hettich are the best watch shop I have ever dealt with, are they still going?
 

Good thread, JJ!

For me, it would probably be my dad's SS white face Seiko Automatic c.1975.

It was heavy, I was mesmerised by the way the seconds hand swept and I learnt to tell the time on it!
The flip-lock style clasp was cool and I was forever asking him if I could wear it. Obviously, it was far too loose so I would put it on over my shirt/jumper/jacket and anything I could get to pad out my wrist so it wouldn't fall off!

During the day/date change, there would be a period when the day would be written in Arabic script. I was pretty amazed at how it would do that, and then go back to English!

My dad would always wear his watch loose on the wrist - I basically copied that style and that is exactly the way I wear my Rolex now!

a TIMEX IRONMAN !

My most memorable watch ever was back in 1970 which my Dad wore most of the time.  It wasn't mine but since I saw it on him, I wanted it back then when I was only 6 yrs. old.  I played with it, pushing those chrono buttons and was amazed how it functioned.  I thought it was a great watch!  I also loved the color match of red and blue.  He lost the watch eventually through the years (who knows what happened to it?), but the image of it stuck in my mind.  I have forgotten about my desire for it through the years until I was already in my mid-thirties when the Internet age came along with Ebay.  As I was searching among the Seikos, I saw a familiar image of a watch which I desired so long ago.  Suddenly, memories flashedback to me like a flood about my Dad and his beloved Seiko.  I said, "I have to get this one now!"  (Being already the age of my Dad when he first had it.)  And so, I got it for $157.00 in excellent mint condition.  I still wear it from time to time.   

A nice Seiko I got for my HS graduation gift ... actually when I got the present, before opening it, I assumed it was a Rolex and was pissed that it was only a Seiko ... but that watch ended up being a daily wearer for about 3 years plus I still have it plus it definitely brings back good memories of when I was young.

I'd have to say 2 watches , The first being a ladies watch that was given to me by my Oma in Vienna when I was approx. 9 , I'm pretty sure my passion for watches began with this watch , unfortunately I had taken it to Birk's for a stem repair and cleaning , and in my ignorance at the time , they replaced the movement on me without giving me the original back , it was many years after that I became somewhat fluent in watches and discovered this , I still get very upset about this as I can remember her telling me it came from her Oma , this would have made it approx. 150 years old or more !! I still have this watch even though it is but a shell , as a memory of my Oma it is irreplaceable even though it is not complete .
The second watch would by my G.P. Gyromatic , this was given to me for my 21 Birthday by my Stepfather and my Mother and is engraved on the caseback accordingly, I'm not sure I appreciated this watch much when I first received it simply because of it's style , it looked like an oldtimer's watch to me back then and I was somewhat embarrassed to wear it , at the time I was enamored with Movado and as soon as I bought my first Movado , it languished in my drawer , back then style was everything !!
Fortunately I have grown wiser as well as older and in the last ten years or so have truly immersed myself in this passion we all share , I now have many more watches , some very valuable , some not , all have a special place in my collection , none more than these two .   

I've got lots of them that have fond memories!

Timex Marathon that I wore in my high school pictures (just got it working again tonight!), Seiko Sports 150 Chrono I bought when I got married on St. Thomas island, Seiko Sports 150 Chrono I bought after I got divorced when she wouldn't give me my other Seiko back (6 years later she gave back my original and had "Love you Mis" engraved on it!), the Citizen Aqua Duplex dive watch I bought on Great Bahama Island that went with me when I first scuba dived to the bottom of the ocean, the "Superman watch" my dad bought me for X-mas (looks very similar to a Rolex Daytona!), the Rolex TT DJ Thunderbird I bought in Las Vegas (first Rolex ever) on the first real trip I had with my current girl friend, the Rolex Sea Dweller I bought the same day my god child was born (my best friends first child which I will give to him someday when he's old enough), the Casio calculator watch that a co-worker and good friend bought me years ago, the Casio Riseman that went with me to the top of mountains for the first time, the Citizen titanium chrono that went with me the first time I skiied down a mountain, and the Casio camera watch that has lots of memories stored on it. 

I've gotten a number of watches from my uncle over the years, back when I was 12 or so he gave me a seiko auto chrono that he had tired of.  I wore it for several years, it was huge and heavy and the resets never went back exactly where they belonged.  Unfortunately it died during the digital quartz era and was discarded.  He recently asked if I still had it, I had to say no it was gone.