Masturbation Challenge – Day 20 – Ready to Finish

  • Date: 5/21/16
  • Time: 12:29AM
  • Location: Bedroom
  • Duration: 6:58
  • # of Edges (Nearly climaxing and then backing away): 5
  • Pass/Fail: PASS

This was the shortest time it's taken me to reach my edge. I attribute this to sleep deprivation and my incredible desire to go to bed. Last night I slept poorly for a few reasons, but mainly because I was sexually frustrated. I've been fantasizing about how I'm going to finally release on Sunday. Here are a few options I've been considering:

  • The traditional masturbation session, edging a few times to make sure that it's a full release. Likely would not use pornography, so that I can remain present with all my bodily sensations.
  • Contacting the woman that hit on me last night to see, on the off chance, if she's interested in helping me eliminate 21 days of built-up semen. Is that wrong? Maybe she'd be into that kind of thing? I'm sure some people are into that sort of thing. How do I bring that up?
  • Happy ending at massage parlor. This was my friend's idea. I've never considered getting a happy ending before, and the prospect of sex work is disturbing to me. However, part of me is considering finding an old masseuse who views happy endings as just a part of the massage. I was curious about how one goes about finding said masseuse, so I spent about half an hour on (based on Christopher Smith Bryant's intel in Episode 18 of the podcast). It's quite shady and it seems like it's a big gamble. Still, it's on the table.

Tonight I watched A Dangerous Method, a movie about psychoanalysts, Freud and Jung. I was amazed by the sexual repression of their times. In fact, their societies were so sexually-repressed that Freud theorized that all neuroses stem from some sort of sexual repression. While most people believe him to be wrong these days, it still goes to show just how far we've come as a society. The fact that I can blog about my masturbation challenge and talk with my mother about sex on a weekly basis is just mind-blowing. I'm excited to see where this journey will lead.

With love,

Charleston Chew


Cameron Poter