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Urban Dictionary says a sissygasm is a "hands-free orgasm" (HFO) usually obtained "exclusively through anal stimulation." Sex columnist, Zachary Zane, author of 'Boyslut: A Memoir and Manifesto,' defines a sissygasm as "when a sissy (often, a crossdressing man who likes to be feminized during sex) orgasms through anal stimulation ...
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Most would define a true sissygasm as a hands free type of orgasm (aka HFO). The tricky part, is that there are different ways for a sissy to achieve a HFO. Nipple play is one way. Anal or perineal stimulation, without involving the prostate gland, is another.
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When stimulated correctly, the prostate can provide intense hands-free orgasm, often called a "sissygasm." To reach the prostate, you'll need to access it anally.
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