Strictly Anonymous Confessions

1408 - Jane is Into Gangbangs, 3somes, Foursomes, Orgies and Moresomes

Mar 26, 2026
A frank dive into a life lived on the wild side, from swinging and sex clubs to unicorn nights and organized gangbangs. She recounts intense sexual milestones, radical relationship experiments, and how those choices shaped her marriages. The conversation also covers shifting priorities, intentional monogamy in a new relationship, and zero regrets about a promiscuous past.
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ANECDOTE

First Double Penetration From A Bar Pickup

  • Jane's first double penetration happened after she and a female partner picked up two cousins at a bar, and her partner's strong squirting amplified the experience.
  • The spontaneous pickup-turned-DP illustrates how Jane and her girlfriend mixed club pickups with planned kink experiments.
ANECDOTE

Setting Up A Dying Friend's Double Penetration Wish

  • Jane organized a DP for her best friend who was dying of cancer after multiple failed attempts with bar pickups and Craigslist; she ultimately recruited people from the sex-positive community.
  • The event fulfilled the friend's bucket list wish and became a meaningful, carefully planned send-off.
ANECDOTE

How She Organized A 12 Man Bukkake Gangbang

  • Jane's 12‑man bukkake/gangbang was set up by a sex‑party organizer who screened men by Jane's specifications and even supplied two 'fluffers'.
  • She vetted photos, approved the final invite list, insisted on condoms, and directed the event to include bukkake rather than internal ejaculation.
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