Trouble adding air to my tires

Hello everyone. I have had Toyota's since I was 15. I started with a 2000 Tacoma, then a 2001 Tundra and I recently purchased a 2013 Tundra.
I have never had a problem adding air to my tires until now. The valve stem is BEHIND a cutout in the wheel and I can't reach it.
I ended up putting the chuck on the valve stem from behind the cutout, bringing the hose behind another cutout and attaching it to the chuck, all while air is releasing from the tire.
I drove my truck yesterday, no problem. This morning, completely flat tire.
Do they make chucks without an angle? Is this a design flaw or did someone modify and f*** up?

 

You have pic's of it? I'm trying to picture it, but my brain isn't computing

 

I think its obvious that we need a pic to understand.

 

Yes, you can get tire chucks and gauges with a straight head.

 

Did they put the "beans over the frank" when they installed the tire?

 

Official welcome

 

Sorry everyone. Every time I remembered to take a picture, I wasn't near my truck or my phone.
The first photo is from the top of the tire, looking down. You can't even see the valve stem

 

Rusty sitch - does that valve stem even still function properly?

 

I'm pretty good with vehicle lingo but I've never heard of a sitch. I took the cover off just to show you. My left rear tire kept going flat but my dad said it's missing an o-ring and replaced the cover and fixed that

 

I don’t know if you have an air compressor. I don’t have room for a large one so I got one of these about 10 years ago from Harbor freight. At the time it was like 35 bucks,(now $50) then I got a little hose kit to go with it. It’s been working well enough for me to get the job done and all my cars.


or even one of these

 

An O-ring under the valve stem cap? That’s the only thing I can picture from your description. If that stopped the tire from leaking air, it’s more likely that your Schrader valve inside the valve stem is leaking. You can also replace that yourself or just take it to a tire shop.

 

Your valve stem looks normal to me - and can be reached by most angled chucks - if your tire is going flat check the valve stem with soapy water to see if it's leaking after you add air. You also need to see if you got a nail or something else causing the leak.

 

I have a large compressor but I do like the last chuck you posted. I went to harbor freight and NAPA and asked if they make a straight chuck and they said no

 

I know I don't have anything stuck in my tire. Since my dad put a new cover on the valve stem on the left rear, it hasn't gone down. I will spray the stem and look for bubbles, good thinking.
The stems didn't look bad to me but the location is driving me nuts. Using a regular 90° chuck, I can't get it locked on

 

NAPA might not have it because they don’t have a large inventory of accessories. Harbor freight probably didn’t know what you were talking about LOL. But the first one I posted I got from Harbor freight in the hose kit.
Check this one out from Home Depot. Similar to the inflator chuck at a gas station.

https://www.homedepot.com/p/Husky-Dual-Foot-Inflator-Gauge-17850HOM/205331827

 

Also, if it is your Schrader valve inside the valve stem, You can get a little tool that takes out the valve with replacement pieces. Quick search brought this up. Most auto parts stores will carry something like this.
https://www.walmart.com/ip/Slime-4-...VONSzCh1ctw1EEAQYBSABEgIO9_D_BwE&gclsrc=aw.ds

And as always, Amazon will have everything I’ve talked about as well.

 

I'm pretty sure my dad has one of those. He's got EVERYTHING! Thanks