Here is some more food for thought from CS Lewis, from "The Problem of Pain", the chapter called "Hell". A few excerpts.
...I would pay any price to be able to say truthfully "All will be saved." But my reason retorts, "Without their will, or with it?" If I say "Without their will" I at once perceive a contradiction; how can the supreme voluntary act of self-surrender be involuntary? If I say "With their will," my reason replies "How if they will not give in?"
...A third objection turns on the frightful intensity of the pains of Hell as suggested by mediaeval art and, indeed, by certain passages in Scripture. Von Hügel here warns us not to confuse the doctrine itself with the imagery by which it may be conveyed. Our Lord speaks of Hell under three symbols: first, that of punishment ("everlasting punishment," Matt. xxv, 46); second, that of destruction ("fear Him who is able to destroy both body and soul in hell," Matt. x, 28); and thirdly, that of privation, exclusion, or banishment into "the darkness outside," as in the parables of the man without a wedding garment or of the wise and foolish virgins. The prevalent image of fire is significant because it combines the ideas of torment and destruction. Now it is quite certain that all these expressions are intended to suggest something unspeakably horrible, and any interpretation which does not face that fact is, I am afraid, out of court from the beginning. But it is not necessary to concentrate on the images of torture to the exclusion of those suggesting destruction and privation. What can that be whereof all three images are equally proper symbols? Destruction, we should naturally assume, means the unmaking, or cessation, of the destroyed. And people often talk as if the "annihilation" of a soul were intrinsically possible. In all our experience, however, the destruction of one thing means the emergence of something else. Burn a log, and you have gases, heat and ash. To have been a log means now being those three things. If soul can be destroyed, must there not be a state of having been a human soul? And is not that, perhaps, the state which is equally well described as torment, destruction, and privation? You will remember that in the parable, the saved go to a place prepared for them, while the damned go to a place never made for men at all. To enter heaven is to become more human than you ever succeeded in being in earth; to enter hell, is to be banished from humanity. What is cast (or casts itself) into hell is not a man: it is "remains." To be a complete man means to have the passions obedient to the will and the will offered to God: to have been a man?to be an ex-man or "damned ghost"?would presumably mean to consist of a will utterly centered in its self and passions utterly uncontrolled by the will. It is, of course, impossible to imagine what the consciousness of such a creature?already a loose congeries of mutually antagonistic sins rather than a sinner?would be like. There may be a truth in the saying that "hell is hell, not from its own point of view, but from the heavenly point of view." I do not think this belies the severity of Our Lord's words. It is only to the damned that their fate could ever seem less than unendurable. And it must be admitted that as, in these last chapters, we think of eternity, the categories of pain and pleasure, which have engaged us so long, begin to recede as vaster good and evil looms in sight. Neither pain nor pleasure as such has the last word. Even if it were possible that the experience (if it can be called experience) of the lost contained no pain and much pleasure, still, that black pleasure would be such as to send any soul, not already damned, flying to its prayers in nightmare terror: even if there were pains in heaven, all who understand would desire them...
...Finally, it is objected that the ultimate loss of a single soul means the defeat of omnipotence. And so it does. In creating beings with free will, omnipotence from the outset submits to the possibility of such defeat. What you can defeat, I call miracle: for to make things which are not Itself, and thus to become, in a sense, capable of being resisted by its own handiwork, is the most astonishing and unimaginable of all the feats we attribute to the Deity. I willingly believe that the damned are, in one sense, successful, rebels to the end; that the doors of hell are locked on the inside. I do not mean that the ghosts may not wish to come out of hell, in the vague fashion wherein an envious man "wishes" to be happy: but they certainly do not will even the first preliminary stages of that self-abandonment through which alone the soul can reach any good. They enjoy forever the horrible freedom they have demanded, and are therefore self-enslaved just as the blessed, forever submitting to obedience, become through all eternity more and more free.
In the long run the answer to all those who object to the doctrine of hell is itself a Question: "What are you asking God to do?" To wipe out their past sins and, at all costs, to give them a fresh start, smoothing every difficulty and offering every miraculous help? But He has done so, on Calvary. To forgive them? They will not be forgiven. To leave them alone? Alas, I am afraid that is what He does...
http://www.merelewis.com/CSLpp08.html