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dated a girl in college who didn’t want to try anal, which I love. she said that I wouldn’t ask if I knew what it felt like. I accepted the challenge and when we met up on the agreed upon night to settle I brought a strapon. she had taken the bet a different way and had invited her gay friend. long story short, we both lost/won. I had gay sex, and she also got ass fucked. after that she was into anal and I was into strapons.