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I would never have sex with an actual man but if it was a shemale who looks and talks like a women, I wouldn't hesitate to have sex with her. Just the thought of having sex with a shemale in the arse and making her penis cum turns me on. Emotionally a shemale enjoys having a man treat her like a woman - and having sex and penetrating her is the ultimate expression of that for many shemales. Physically they enjoy anal sex for the same reason gay men do and most women don't.
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