Your anecdotal arguments are just that, and can easily be refuted. The fact that you lead with an educational argument about the girl that allegedly get pregnant and caught an STD her first time is as silly as your shoe argument. If you had the choice between new shoes and those that had been worn by 20 barefoot men before you for the same price and for forever, who would you and anyone else choose? See, anecdotal arguments can always be refuted because they are stupid.
Jesus is truly accepting and that is the most important part of your argument. The human feelings of betrayal related to a soiled partner though are real and would not be part of perfect human condition. I am a man with regular male feelings toward women. I would never choose a woman that had the sweat, saliva and semen of other men on and inside her as a life partner. My wife being a virgin has always given me tremendous trust in her and our marriage. I know that she values herself enough not to sleep around with men who are not her husband without even having a husband back then. So, her spending a year in Europe while I was at war allowed me to fight without concern about what was going on back home. People who have slept around can get married to other sexually liberal people, but they will never have the same level of trust that I get to enjoy. That is how Jesus would want it for all of us if it was a choice. I encourage people to be true to their bodies so they can experience what true love, in the biblical sense, is supposed to feel like. I can tell you that it is the greatest gift God has given me in my life.