So here's the deal, I am the communications director for a large physical therapy conglomerate; I also have my concealed carry permit and work in an environment where it is permitted as long as no one knows about it (i.e. there are only four people in the organization who are my superiors two of which are the owners and they are very pro gun but don't want to deal with an employee seeing an executive carrying a fire arm). I also ride a motorcycle almost everyday and during the course of my day I am required to go between our different facilities regularly, and I carry with me my airbook and medical files. I have been doing all this with a backpack and not carrying my pistol at all because our dress code is business casual (slacks and a company logo polo tucked in). I have tried just about every holster known to man and, frankly, none of them will conceal my pistol without heavy printing, and that is simply unacceptable in my position. I will not carry anything smaller than a 9mm and I have several pistols that are very thin and short, including a Khar pm9. Two days ago someone (a pro bono indigent case) became irate and threatened one of my PT tech's with a knife. It was a polarizing moment... I have decided to look into a messenger bag solution. I am leaning toward the maxpedition larkspur but I have one major issue with it; it only have one main compartment where I would keep my apple and files, and this is also where the fire arm is meant to be carried. This really doesn't  work for me as I have to open the bag with employees present and if one of them sees the gun in there they are libel to freak (some of my employees are unfortunately total tree huggin hippies)

Long story short: I need a CC messenger bag with quick access top to an independent holster slot that has a waist strap so i can use it on my motorcycle. It needs to be big enough to carry medical files and my apple, but small enough  that it doesn't look like it could hold a small child... I like the look and size of the Maxpedition Larkspur but it doesn't have the independent pocket and that's kind of a must.

I use a Maxpedition lunada
Shown here

I really like it.

have you checked out the HSGI Armordilla?

the Lunada is going to be to small for my purposes as I have to carry medical files that are legal sized paper.... I haven't seen to much on the HSGI bag but I am a big HSGI fan. I have one of their vest and several tacos... i would like to see some pictures of the inside of it if anyone has one...

http://www.ar15.com/forums/topic.html?b=6&f=10&t=256446

i also ordered one a couple of days ago as a briefcase for my father, when i get it in i plan on doing a youtube vid of it as well.

this

I think you're looking for the US Grunt Gear Defender bug out messenger bag.

I have one on order, its been about 4 weeks into the 6-8 week quoted lead time.  It will fit a fullsize (5") barreled pistol, and has sleeves for pistol, rifle mags and a zippered pouch for paperwork.  It also has a seperate padded compartment for a laptop.  It will fit my macbook pro perfectly.

-Tom

Maxpedition Mongo !!!!!! It sounds like what you are looking for . Here is a good review of the bag with a lot of pictures.
Hope it helps.


http://www.britishblades.com/forums/showthread.php?99847-Maxpedition-Mongo-photo-review

Maxpedition is quality gear also. Will last you a lifetime.

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Not quite within your modern nylon design parameters, but I have one of these....



Nice wide shoulder strap - gets ALL sorts of gear in it, has built in dividers AND the outside rear pocket could be modified for quick access

just my 2c worth...

I have the U.S peace keepers bag I bought from Bravo comp. I luv it                                            

People getting off topic in a way. You need a briefcase that happens to have a good place to hide your handgun so everyone isn't freaked out, not a go bag. What about sewing palls or a hook panel in a bag to create a spot for your holster?

i was thinking of getting this one  


link to the other ones
wen site

I use a Maxpedition Malaga, because I also found myself riding a motorcycle between two locations with paperwork.  The malaga is just big enough to fit 3~ring binders and has a sleeve to hold a handgun that's easy to access.  It also has a secondary strap that buckles near the center of my chest that secures it for the ride.  It's just big enough for a laptop and paperwork, with no extra bulk.

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If you're a motorcycle rider I'd take a look at the Maxpedition Sitka (or Kodiak/Noatak) depending on your size requirements.  Both the hydration bladder pouch and main pouch have velcro for a holster and all pouches are designed to be accessed either from the top or side.  Love it on the motorcycle because I can get into it while I'm on the bike without having to struggle out of a conventional backpack with a stiff riding jacket on.  Obviously I'm not getting into it while I'm riding though  Plus the secondary strap keeps things from moving around on you.  Maybe not a big deal on a cruiser or standard where you're sitting upright but things can flop around a bit on a sportbike.  I carry mine everyday.

http://www.maxpedition.com/store/pc/Sitka-Gearslinger-12p926.htm

Disclaimer:  I do not work for nor have any association with Maxpedition.  I just happen to like their stuff!

brown truck just dropped off a sitka to me yesterday. i like it alot better than the fatboy i was carrying. two days of carrying it and i like it alot. and its slim enough to sit under my legs in my truck while i drive.

I have the Jumbo bag and have been seriously eyeing the Sitka.

Thanks for all the replies guys. I really have issues with backpacks because they fold the corners of my charts that's why I am opting for a man bag. I am all but sold on the Mongo or the HSGI bag. I like some of the others but I honestly am not going to pay upwards of 250 bucks on a purse. I'm sure they're  fantastic quality but that's just not in the cards for me.