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So the next day while showering, I put some conditioner on my index finger and stuck it right up there. In the year since my now-ex-girlfriend helped me discover anal delights, I've bottomed with many men and a couple of women. My gay friends told me there's nothing more pleasurable than proper prostate stimulation. Evidently, I'm a vocal bottom. More From Anal Sex, Explained.

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Gwendolyn. Age: 31.
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In the year since my now-ex-girlfriend helped me discover anal delights, I've bottomed with many men and a couple of women.

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Ireland. Age: 30.
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Like a massage, except on the inside of my body. We kept it slow and shallow the first few times. Even though I was typically a top, men I'd dated had always asked me — actually more like begged me — to bottom.

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