Hmm. Well, the value of D_\lambda is a continuously defined function of wavelength for all materials relative to refractive index, and most materials (if not all) have a wavelength where the group velocity reaches a minimum, and at that point the dispersion coefficient becomes positive - i.e. for glass, D_\lambda is greater than zero for \lambda > 1.31\ \mu m.
The sign of D_\lambda just indicates what type of dispersion takes place. For a negative value, the shorter wavelengths in a given pulse travel slower than the longer wavelengths, meaning the short wavelengths are the last to arrive. For a positive value, the opposite is true.
To conceptualize it, I just imagine the pulse as a ball of uniformly distributed red and blue specks (the uniform distribution helps me to remember that despite the pulse's \Delta\lambda, they all still enter the material at precisely the same time. Then, suppose you throw the ball through the air, knowing that the red specks will always travel slightly faster than the blue specks. When the ball lands, many of the red specks will have outpaced the initial 'ball', and many of the blue specks will have lagged behind, so obviously the time between the first red speck hitting the ground and the last blue speck must be greater than if both colours traveled at exactly the same speed. Change the sign of the dispersion coefficient, and the same analogy still works, but with the red specks lagging behind the ball and the blue specks jumping ahead of it.
The only way to actually end up with a shorter pulse would be if you were to send the slower wavelengths into the material first, followed by the faster wavelengths. Then, they would superimpose due to dispersion and come out the other end closer together. Since our pulses are of uniform wavelength "content" throughout their timespan, pulse-lengthening is always required.