Here's what you said that kinda brings that out...
"What are the risks associated with each choice? You have to admit that the latter girl has a much higher risk in many areas: potential STD's, loyalty issues, commitment issues etc. etc. Frankly I can't see how a person doesn't have at least some negative thoughts when honestly assessing if they want a relationship with a woman like the latter."
Why do you think loyalty and commitment issues are something that directly tie into sexual activity? To piggyback off of what marathonfool said, they've got nothing to do with one another. Also, if anything, the person who is that much more socially experienced will have a better understanding of themselves and their needs when stepping into a relationship.
Its a bit of a joke to say that people who have more sex are more likely to have fucked up relationships.