Have one of the masses a massless spring attached in the direction the collision takes place. So now when they collide, the spring compresses and then expands back. Momentum is conserved during this process.
While they're colliding, the spring compresses. The compression applies forces on both the masses, slowing both of them down.
When the masses were moving with -v and +v : The total momentum is 0. When they collide, the both come to rest at some point (total momentum is still 0). Their total kinetic energy ($=mv^2$) is now stored as potential energy in the compression of the spring. This potential energy is a function of the compression of the spring. The force applied by the spring at any instant is also a function of the compression at that instant. So we can say that throughout the collision, the spring force (and hence the force at the masses) varies between the force corresponding to a potential energy of 0 (no compression) to a potential energy of $mv^2$ (maximum compression). Same goes for when the spring is elongating.
When the masses are moving at $-2v$, $v$- The total momentum is $-mv$. During the collision, the spring force first slows both of them down until they're moving with the same velocity.
This same velocity can be found by conserving momentum: $-2mv+mv=(m+m)v_{const}$, giving $v_{const}=\frac{-v}{2}$.
So, in this case, both the masses are still moving at $\frac{-v}{2}$ when the spring compression is maximum. Their initial KE was $\frac{1}{2}m(2v)^2+\frac{1}{2}mv^2=\frac{5}{2}mv^2$, while thie KE at maximum compression is $\frac{1}{2} m (\frac{-v}{2})^2+ \frac{1}{2} m (\frac{-v}{2})^2=\frac{1}{4} m v^2$. The difference between initial and final is of $\frac{9}{4} mv^2$. Now this is stored as the PE of the spring at maximum compression.
So in this case, the force on the masses varies between 0 (no compression) to the force corresponding to a compression of PE=$\frac{9}{4}mv^2$ (at maximum compression). The force varies similarly in the opposite direction during elongation phase.
You see that the force varies throughout the collision phase, the but the range of forces applied is different in both cases because of different compressions of the spring.
When there is no spring attached, the electrostatic forces between the charges on the colliding surfaces act like springs. Those forces are also a function of the distance between charges, just like the spring force is a function of the elongation/compression.