Samir Mathur gives a very accessible (heuristic?) account of Hawking radiation and why it leads to the black hole losing mass. You can access the page here. It's a work in progress and is updated about once every couple of months.
To summarize, the lifetime of particles is dictated by
$\Delta E \Delta t < \frac{\hbar}{2}.$
Normally this means that the more massive the virtual particle-antiparticle pair, the shorter lived it is.
However close to the horizon of a black hole, the gravitational potential energy is so negative that the total energy of the pair (rest energy plus gravitational potential energy) is essentially zero. So the pair can become long lived. Of the pair, one of them escapes to infinity, and the other falls in past the horizon. The one that falls in will have a total energy that is negative, because the negative gravitational potential energy outweighs any positive rest mass energy or kinetic energy. As a result, negative energy goes into the black hole and positive energy comes out. From a distance, we see it as the black hole losing mass. Note that it doesn't matter whether it is the particle or the antiparticle that escapes - the negative energy happens because of the very negative gravitational potential energy, no matter whether it is a particle or anti-particle that falls in. After all, both particles and anti-particles have positive rest mass energy.
So that's a rough (hand-wavy) explanation of how Hawking radiation leads to a black hole losing mass.