In 1984, Winston retells part of a memory about himself and a prole woman. What can the reader infer about what he did with this woman and how does...

In Part One, Chapter Six, Winston recalls a memory from three years earlier in which he met with a prole woman on a "dark evening," in a side street by a railway station. Attracted by her bright, red lips and painted face, Winston goes towards the woman who is evidently a prostitute. She charges "two dollars" for her services and Winston follows the woman to a nearby house where they have sex.

That this memory...

In Part One, Chapter Six, Winston recalls a memory from three years earlier in which he met with a prole woman on a "dark evening," in a side street by a railway station. Attracted by her bright, red lips and painted face, Winston goes towards the woman who is evidently a prostitute. She charges "two dollars" for her services and Winston follows the woman to a nearby house where they have sex.

That this memory is written in broken and disjointed sentences demonstrates Winston's pain and frustration in recollecting it. This is an experience that he is evidently very ashamed of, primarily because of the age and physical condition of the woman:

The woman was OLD. The paint was plastered so thick on her face that it looked as though it might crack like a cardboard mask. There were streaks of white in her hair...her mouth had fallen a little open, revealing nothing but a cavernous blackness.

Though horrified by her appearance, Winston had sex with the woman because this act was about rebellion, not about lust. Under Party rules, sexual acts outside of marriage are forbidden and, as we know, Winston's marriage to Katharine was one of convenience, not of love or desire. This leaves Winston with an intense craving for sexual intimacy. As he comments in the text:

Why did it always have to be like this? Why could he not have a woman of his own? 

In addition, the prostitute may not be beautiful or young but she is wearing make-up and perfume, items forbidden by the party, which appeals to Winston's desire for sexual gratification and rebellion. So, for Winston, having sex with the prostitute is about connecting with his natural, sexual self, which the Party has sought to control through propaganda and arranged marriages. He may not desire the prostitute but he does, in fact, desire all that she represents.