

Michael & The Diddy Escort: “Diddy Watched the Whole Time” | Shawn Dearing
Jul 19, 2025
Shawn Dearing, a former escort, shares his jaw-dropping experiences with Diddy and the dark underbelly of celebrity culture. He recounts his journey into the escort industry, revealing the blurred lines between companionship and sexuality. The conversation dives deep into themes of power dynamics, coercion, and the moral complexities of intimacy with influential figures. Dearing also reflects on personal growth and the influence of societal norms in shaping relationships, offering listeners a candid look at exploitation and the quest for genuine connections.
AI Snips
Chapters
Books
Transcript
Episode notes
Escort Session With Cassie
- Shawn Dearing recounts being called from a party to a private session with Cassie, P. Diddy's girlfriend.
- He was directed in a sexual performance while P. Diddy watched from behind a curtain.
Control Beyond Coercion
- Though Cassie appeared authoritative, Shawn perceived her as under P. Diddy's control during sessions.
- The dynamic showed power exerted subtly without overt coercion, reflecting complex control.
P. Diddy's Power Play
- Shawn observed P. Diddy exhibiting controlling and perverse behavior, including controlling interactions between Cassie and himself.
- P. Diddy made veiled threats that conveyed his power and control over others.