Help me set up my 1st CCW

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Lol. And just to twist things up. Last month bought a New Kahr and a half dozen magazines and a new holster. And already looking for another Kahr. Maybe one in 45.cal. or a S9 or ST9. Yes, I sink a lot of cash into guns and ammo.
I figured. Was more just teasing.

Sometimes there is something to be said for getting exactly what you want.
 
Over thinking it? Can't you simply open your hand and allow whatever is in it to drop as you're reaching for your firearm?

Try it. Go to a range with some tennis balls, have someone else blow a whistle as a starter (or just yell go) and try it. Then put the tennis ball is your off hand and try it some more.
 
If your going to tuck your shirt:

Smartcarry holsters: I think they start around $55, have a breathable material and the design stays put better than a belly band. Downside is the draw speed.

tier 1 concealment mini or micro axis with the clips. This is a tuckable aiwb holster that is quick to draw from. They are spendy at around $125. Downside is they can look frumpy on some body types. If your athetlic, it should work fine.

for a pistol, I would first recommend training or at least renting/shooting a few guns. You may find with familiarity, you don't need a safety. This would open more options as the industry, generally speaking is moving away from them.

If you need a safety, the Sig 238/938 may be up your alley.

If your worried about your primary hand being occupied, start incorporating off hand training into your training. Then, decide what options you want available to your off hand. You can pocket carry a 380 or maybe a knife.
 
That image is a complete no go; revolver is exposed. Also, I always, universally, wear shirts tucked in.
I want a carry method that quickly allows a full shooting grip on the draw which doesn't look possible from the picture plus it's not concealed. An inexpensive used Bianchi IWB appendix carry is what works well for me. It conceals an SP101 2.25" (26 oz) comfortably under an untucked Tshirt.
 

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