Better Sex

363: Anal Sex for Beginners with Dr. Evan Goldstein

Feb 9, 2026
Guest
Dr. Evan Goldstein
Dr. Evan Goldstein, an anal health surgeon and sexual wellness expert who wrote Butt Seriously, shares basics of anal play for beginners. He covers anatomy, muscle relaxation, preparation, and safe product choices. The conversation tackles myths, hygiene, dilator use, positions, lube tips, and how to integrate solo practice with partnered play.
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INSIGHT

Anal Problems Often Start With Everyday Bowel Health

  • Many anal problems stem from common issues like fissures, hemorrhoids, and poor bowel habits rather than only injury from penetration.
  • Addressing general bowel care and anatomy can prevent limitations to anal sex and improve comfort.
INSIGHT

Anal Play Isn’t Linked To Sexual Orientation

  • Anal play is not limited to gay men and can produce heightened orgasms via prostate or posterior stimulation.
  • Pleasure pathways and anatomy allow both men and women to benefit from anal stimulation.
ADVICE

Train With Dilators Before Penetration

  • Use an anal dilating kit for 6–8 weeks to train muscles and skin before full penetration.
  • Do two sets of 10–15 reps with the small dilator two to three times weekly and progress small→medium→large.
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