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28 Aug 2026 #1

member_2b7ce21282

  • Posting sinceAug 2026
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I want to start by thanking Mistress Watchful for creating this amazing website. I wish you well and hope the future brings great joy your way. I discovered this place through a Yahoo group, and so far, I am quite impressed with what I’ve seen.

After numerous delays and false starts, the date is finally set for my chastity journey to begin. Next weekend, which coincides with Memorial Day here in the US, marks the start of the end for me. My wife/Mistress has decided that this coming weekend will be memorable for many reasons. On Saturday, she plans an evening filled with erotic lovemaking. I am permitted to use my cock on her however I wish. As she puts it, it will be a three-hole affair. The only rule is no orgasms allowed on Saturday. On Sunday, I will be tied naked to Her bondage horse. She will stroke my well-lubricated cock while explaining how much pleasure I am going to get from being her chaste, cocksucking cuckold for the rest of my life. She tells me that Saturday was the last time my cock would ever enter a woman’s body; henceforth, all cocks will be inside me. She promises that as I feel myself starting an orgasm, she ensures I understand it is the final one because I am being locked permanently in chastity from that moment forward.

My path to this point and what lies ahead are the reasons for keeping this journal.

Thank You again, Mistress Watchful, for this wonderful opportunity. mantoy (a soon-to-be sex toy for men)

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Where this goes next

Every thread on this board is somebody in the same few months of their life, told from different ends of it: the conversation that has not happened yet, the one that ended in tears, the drink that went well, and the weeks afterwards. The site has a page for each, and one account of an evening written while it was still fresh.

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