Shameless Sex

#448 Bottoms Up: Exploring Anal Play, Training, and Fisting

Aug 26, 2025
Guest
Jamie Joy
In this discussion, Jamie Joy, a queer, trans, Jewish certified sex educator with over a decade of experience, breaks down the often-taboo topic of anal play. They address common fears like poop and offer practical tips for beginners, including anal plug training and techniques for smooth insertion. Jamie shares their favorite toys and introduces the art of anal fisting, all while emphasizing consent and pleasure. With humor and expertise, they inspire listeners to explore anal experiences with confidence and curiosity.
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ANECDOTE

Saved Anal For A Milestone

  • Jamie Joy waited until their 30s to have anal for the first time and treated it as a sexual frontier to keep life spicy.
  • Riley practiced patience and guided Jamie through sensations, breathing, and milestones like two fingers then more.
ANECDOTE

From Teen Experience To Professional Fisting

  • Riley's first anal experience was at 17 and later they progressed to fisting on camera for kink.com.
  • Riley found anal fisting accessible with training and has incorporated it deeply into their sexual practice.
ADVICE

Tell Discomfort From Pain

  • Differentiate discomfort from pain by attuning to pressure, burning, or tearing.
  • Breathe and pause when panic rises, and stop if sensations are sharp or tearing.
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