How strange it was that I should be encompassed by all this taint of prison and crime; that in my childhood out on our lonely marshes on a winter evening I should have first encountered it; that it should have reappeared on two occasions, starting out like a stain that was faded but not gone; that it should in this new way pervade my fortune and advancement. While my mind was thus engaged, I thought of the beautiful young Estella, proud and refined, coming towards me, and I thought with absolute abhorrence of the contrast between the jail and her.
– Charles Dickens
Great Expectations, Chapter 32. After Pip visits Newgate Prison with Wemmick while waiting to meet up with Estella, he reveals feelings of inferiority and shame. He speaks of how his life has been tainted by criminals and prisons. He uses the simile to compare his past life to a “stain.” He imagines the sophisticated and beautiful Estella coming towards him, and contrasts her refined beauty with his tainted life. Foreshadowed here is the complex relationship he will have with Estella and his unrequited love as he attempts to climb the social ladder to win her.