Hey mccainimages,
I hope I'm understanding your question correctly.
It sounds like you're using the Edit > Free Transform tool to transform the contents of a layer. I think this can help you get the effect you're looking for, but there are some pitfalls that can make it tricky.
Firstly, I recommend converting the layer to a smart object, to prevent it fr om degrading over multiple transforms.
To convert a layer to a smart object, right click the name of the layer, and fr om the menu choose "Convert to Smart Object".
While in Free Transform mode, Photoshop automatically attempts to use perspective distortion when you move the corner transform handles independently. You can move the corner handles independently by holding Ctrl and left dragging them around.
I'm going to assume you're starting with a square texture. (This is an important assumption as I'll explain shortly.)
To place a texture flat on the road in your image, you'll probably want to rely on Photoshop's perspective distortion.
There's a problem though, you'll need to know (or guess) wh ere exactly the corners of your distorted texture should go on the road to create the impression of realistic perspective.
This can be tricky because you can't just put the bottom two corners on the near end of the road, and the top two corners at the far end, (at least not if you're starting with a square texture). You'd get a stretched out mess.
So why does it look stretched out if you do that?
Well suppose your original square texture represents a 10 by 10 foot square of flagstone. The road in the image may be 10 feet across, but it looks about 200 feet long.
So if you stretch the bottom two corners of your texture to sit at the nearest two corners of the road, you just stretched the 10 foot bottom edge of your texture across a 10 foot span of road, and that's a perfect fit.
However, if you then stretch the top two corners of your texture to sit at the farthest two corners of the road, you just stretched the 10 foot side edges of your texture down a 200 foot span of road.
This means your 10x10 foot texture is now stretched over a 10x200 area.
This overstretching along the depth axis may be the cause of the extreme distortion you're seeing.
To get a 10x10 foot texture to look natural, you'll need to make sure that when you lay it down on the road, it only stretches 10 feet into the distance. Unfortunately, there's no tile floor in your road image, so you'll have to eyeball that depth distance when stretching the textures.
One trick that might help is to stand the texture up on the side of the road, wh ere it's not as squished, and size it so it looks right, then lay it down on the road. I've attached an image to show what I mean.
Also, if you want to texture a section of road that's 10x50 feet, you'll need 5 copies of the 10x10 tile. However, you probably shouldn't try to warp each one into place separately, because moving the warp handles will start getting really finicky as you get into the more distant stretch of road. Instead, before doing any warping, just create a strip of 5 tiles in a row and merge them into a single smart object. Now you can warp the entire strip as a single object, and alignment between tiles in the strip will be guaranteed. Just remember that the 1x5 strip of tiles will need to cover a 10x50 foot span of road to look properly sized.
In your case you might want to try a strip of 10 or 20 tiles. I recommend trying 10 first, and covering the first 100 feet of road, because I think the road is closer to 100 feet long than 200 feet.
(I used "200" in the examples because I thought it would be harder to read about "10x10" tiles and a "10x100" road, since all those 1s and 0s start to look the same in text.)
