Big difference in the world of motorcycle riding today compared to when you were 16. I'm 68 and I started the same way you did, but we didn't have the hazards then we have today. You can't tell me if you had a 15 yr old with no experience, no license or insurance, you would allow him on the highway for a 500 mile round trip? If I had a 15 yr old son that wanted to ride, I would insist he take the MSF course and have plenty of practice in parking lots and off road to build his confidence and experience in handling the bike. I would probably start him on something smaller than a sportster. I don't think a lot of the posters here really read the OP's statement. as I understood him to say, He found out the guy was bringing his 15 yr old son whom had no license or insurance. He told his buddy...not the parents, He was not riding! Am I right?