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Winston records his last sexual encounter (with a prole prostitute) in his diary. The entry is a springboard for Orwell's consideration of sex and politics. Being caught with a prostitute might get Winston five years in a labor camp, but the real crime is "promiscuity" between Party members, which at the moment Winston finds unthinkable because of his Party conditioning. He'd like it, but thinks nobody would dare.
The aim of the Party, Winston believes, is to remove all pleasure from sexual acts. Sex and marriage are a mere necessity, like "a slightly disgusting minor operation," to be undertaken for the purpose of producing infant Party members. He understands that the Party is trying to suppress the sexual instinct-but for purposes he hasn't yet identified.
His ex-wife Katharine had a "stupid, vulgar, empty" mind and shrank from sex, submitting only for Party purposes. When it became clear that she and Winston were not going to produce a baby, they separated.
Orwell has political reasons for drawing women and sex the way he does in this chapter. He also has artistic reasons: to show us that Winston is lonely and ready for the affair with Julia. He also wants us to know that Winston has more than love in mind:
"And what he wanted, more even than to be loved, was to break down that wall of virtue, even if it were only once in his whole life." This is romantic, but look at what he thinks next: "The sexual act, successfully performed, was rebellion."
Does Winston think of women as something to be used, or is this Orwell's view? Watch the unfolding affair with Julia and decide whether you think Winston is ever really in love with her. Does he respect Julia for who she is, or is she simply the first available woman?
Back to the diary. Winston's remembered prostitute took him to her room where he discovered that she was old, ugly, and made him feel dirty. He took her anyway.