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Strap-On Play

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24 Aug 2026 #1

member_a4d280e69c

  • Posting sinceAug 2026
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So last night, my Wife/Keyholder and I had our first experience with me using a strapon on her. We’ve both really settled into this lifestyle over the last several months, and we owned several strapons long before we found male chastity, I could never get enough of her using them on me (still can’t). That said, we’ve both been interested in trying this for a few weeks, but she was apprehensive about me going too hard because I couldn’t feel anything. Anyway, last night it all came together and she permitted me to penetrate her with the strapon. I realize this is not new to many of the members on this site, but I have to say, I really underestimated just how much of a mind fuck it was going to be. Watching that lifelike cock go in and out of her, not being able to feel anything whatsoever, while hearing her tell me how useless my real cock is, was as intense an experience as I’ve had. Watching her cum, and not be able to experience that familiar feeling of her clamping down on my cock. I had no idea just how submissive and frustrated I was going to come away feeling from this. Luckily for me (I’m already pretty lucky), she really enjoyed herself as well, which I hope means there will be much more of this to come. I’d love to hear more about others experience’s with this.

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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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