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My advice is to trust your body, and if you feel up for it, go for it! This is not an act that should ever be undertaken with a random dude or at a random moment; you both have to want it, and you both have to be prepared. It wasn't really planned, but one night after we both had a couple of drinks, we started hooking up in my bedroom, and he whispered in my ear, 'Should we try it? It takes so much time, trust, and communication that it just amplifies everything physical going on because you are so connected with your partner. Leave the place cleaner than you found it. Having the right angle of entry is important for me. At one point in high school, I was having more anal than regular sex.

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Margot. Age: 31.
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At one point in high school, I was having more anal than regular sex.

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Amy. Age: 26.
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He had slept with a lot of women in his teens and early 20s, so I loved the idea of doing something with him that he'd never done before. My advice is to trust your body, and if you feel up for it, go for it! Fortunately, I enjoyed myself and had a positive experience overall.

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