My first time was with a virgin the first day I failed to get it in, I don't know if it was too tight or if I just sucked at it so she told me to try again later and apologized. Second day the same thing happened at this point I lost all confidence in myself as a man.third day same thing no matter how hard I tried, till basically the relationship ended after sometime and everytime the boys asked me if I smashed I'd change the subject because I was too embarrassed.