First gun ever bought with my own money: .32 British Bull Dog revolver, for $10, 1968. Don't ask.
First rifle bought by me: M1896 Krag-Jorgensen, original cavalry carbine, 1968, $40. Earned the money by working part-time after school in a slaughter house. Don't ask.
First new rifle: 1972, 700 BDL .243. $130-140 or somesuch, wholesale from the LGS owner who mentored me. Put a Bushnell Banner 3-9x on it, again don't ask.