Chastity and orgasm denial discussion

member_6fe1948f0f · 2026-09-06T22:06:44.000Z · 0 replies

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2026-09-06T22:06:44.000Z #1

The last few days have been eventful. I’ve started noticing a decline in my erections as time passes. Mistress is quite pleased with this, though it also led her to draw a new conclusion that I’ll share later. On day 3, she and I drafted our contract, ensuring we covered everything while still adding clauses for emerging issues. Every day, she has me performing self-pleasure via anal play under her watchful eye as she masturbates; I don’t mind this arrangement provided she is getting her pleasure too.

Last night (night 4), frustration with being locked up prompted me to tease Mistress and test her resolve. I boldly claimed that even if I removed my chastity device, no punishments would be inflicted upon me, thinking she was perhaps a bit too lenient. However, I was mistaken. I took off the cage—it’s just an inexpensive silicon one, so it wasn’t hard to remove—and started explaining how I might have overcommitted myself and gone too far with this fantasy. She went to bed angry, while I slept outside my cage.

I woke up early and messaged her, admitting I had erred in judgment; I knew deep down that I was meant to be her sissy. This realization hit me when I slid my hand down to my now-unlocked penis and gave it a gentle grasp—it felt so incorrect. I skipped masturbation for an ice-cold shower instead, trying hard to slip the cage back on while remaining locked inside. It worked! Mistress is still fuming… which brings us to that new conclusion.

Mistress decided that because I am currently secured and she has no intention of releasing me or allowing myself to cum this year, she needs satisfaction from a real man. After some discussion, I accepted the idea of giving her the freedom to do as she pleases with whomever she chooses. She plans to get acquainted with several guys and arrange meetups, eventually having them fuck her. Even though I regret removing my cage and enduring this punishment, it simultaneously arouses me. Knowing that Mistress will be happy allows me nothing but support for her endeavors.

7 days without cumming, 5 days in chastity. Be careful what you wish for..

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