In Freeside, near the gate to North Vegas Square, you will find two bodyguards for hire and a Kings gang member standing on the street. Pay the bodyguard for hire 100 caps and he will follow you through Freeside until you leave. The other one is Orris, who charges double. You are required to expose Orris' scam or kill him in the quest G.I. Blues.
Killing a bodyguard will have a negative impact on your Reputation in Freeside.
The bodyguards rotate, changing which bodyguards you will see upon entering Freeside. It will, however, always be one Kings gang member and Orris until you complete G.I. Blues, when another bodyguard will take Orris' place.
"Ah, my friend, believe me when I tell you that this place, while quite nice when you know your way around, can be very, very dangerous. There are those who would hinder your every step with requests for your money, your business, or even your life. With your permission, however, I would be happy to stand between you and those people. How does that sound?"