Ok, really someone explain to me what the difference is?
I can only think that maybe riding refers to Reverse Cowgirl… But I’m not really sure.
My guess is that these refer to the same thing and one could (should) be removed. However, the consequence would be that a lot of topics need a tag replacement and that is a lot of work for someone with the access rights to do so (unless there is an admin feature for it).
Seems to be a lot of topics using either of these tags and there is no obvious one that should be removed. Maybe you can determine one winner if you can query the entire database and count topics and not be forced to manually counting topics using “endless scrolling” or clicking “load more” while filtering on each tag.
My votes gonna have to go with “riding”, since there’s more than just cowgirl.
Alternatively, change all of both to “woman on top” or something more encompassing.
Meh.
Riding is where the girl’s knees are on the surface in question and she’s facing forward.
Cowgirl is when she’s squatting while facing forward and her center of gravity is also forward.
They are, in fact, two different positions. Personally, I’d be opposed to combining everything into something like “woman on top”.
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The hero we all deserve. Thanks!
Probably could have been a Google search. 
It’s funny - when you Google image search it, you get the opposite.
Riding looks more like squatting, and Cowgirl is more like her knees are on the surface.
https://www.google.com/search?udm=2&q=riding+sex+position
https://www.google.com/search?udm=2&q=cowgirl+sex+position
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Even if there is a difference not many know about it. And if the difference was commonly known such distinction is too detailed anyway since there is a limit in the number of tags to use on a topic.
I see both results in both links, so I have to conclude that cowgirl is a form of riding sex position. Same for reverse cowgirl, side saddle, and everyone’s favorite, amazon 
Hence why I opt to combine them. On that note, it’s not uncommon for the rider to transition into different ‘on top’ positions.
fwiw I can’t imagine someone sifting through scripts looking for content with that position, unless they intended to script said content, but that’s just me…
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