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This has actually happened to me before. I have long arms so when my arm hangs off of her shoulder, it just lands on her boob naturally. Luckily it hasn't gotten me slapped yet.

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I accidentally did that to a girl once because it was extremely cold where we were so we huddled to keep warm and I thought I was holding onto part of her jacket but it was her boob and she didn't say a word for about 10 minutes until I realized what was going on.

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