We study analogues of classical Hilbert transforms as fourier multipliers on free groups. We prove their complete boundedness on non commutative $L^p$ spaces associated with the free group von Neumann algebras for all $1<p<infty$. This implies that the decomposition of the free group $F_infty$ into reduced words starting with distinct free generators is completely unconditional in $L^p$. We study the case of Voiculescus amalgamated free products of von Neumann algebras as well. As by-products, we obtain a positive answer to a compactness-problem posed by Ozawa, a length independent estimate for Junge-Parcet-Xus free Rosenthal inequality, a Littlewood-Paley-Stein type inequality for geodesic paths of free groups, and a length reduction formula for $L^p$-norms of free group von Neumann algebras.