Yes, milk in the udder is sterile.
Milk producers send in milk samples routinely that are hand milked from alcohol-wiped teats into sterile vials, then chilled and shipped. The lab cultures the milk sample and the only result you want is negative for all bacteria. ANY bacteria in the udder is a sign of mastitis and the SCC (somatic cell count) will raise immediately. The lactic bacteria all come from the teat end, hands, the air, etc.
It's quite safe to play around with culturing raw milk for several reasons. One, if it acidifies (which it most certainly will), you're quickly out of the danger zone for Salmonella, Listeria, Staph A, etc. You know what cultured milk smells like? You will know if it does not acidify. Two, virtually every sample that has been contaminated by manure will display coliform growth by developing bubbles in a relatively short time. If it bubbles, it's bad.
So the only instance where your milk can turn into something tangy and nicely cultured would be straight lactic-acid bacteria culturing, with no interference from pathogens and coliforms.
The best way to develop your own culture would be to set a container of warm raw milk out and let sit until it curdles. Take a spoonful of that, and add it to a fresh warm jar of milk. Let culture. It should happen a lot sooner this time. Repeat once more. Then use it in a cheese recipe. The only problem is that you're restricting yourself to one certain set of cultures. You then have to find out which cheese should be made from that culture.
Also, if you make a lot of cheese already, using bought cultures, those are the cultures that you will most likely end up propagating anyway. They tend to jump around.
One more thing... it's not uncommon for coliforms to show up if your milk isn't pristine, unfortunately.