Hi everyone, I’ve been part of this forum for a few years and have experimented with chastity on my own for some time. Over the last year or so, I’ve been dating someone who has gradually accepted the concept. We started small—beginning with one week, then taking a break, followed by two weeks, another break, and so forth. Those breaks usually lasted around a couple of months. Now things are becoming quite “real” for us. I have been locked up for the last two months (my previous longest stint with her was just one month, so we’ve doubled our record). About a month in, I mentioned that I loved having her power over me and would be happy to stay locked away long-term, only allowed an orgasm once every three or four months. Now she has proposed that I go without climaxing for the next three months—totaling five months, which matches my all-time personal best from when I was single. Going solo while single is one thing, but being kept in a cage with a gorgeous woman sleeping beside me each night is entirely different. She thinks I should wait until early September, right before we go on holiday. But that feels like an incredibly long time for me, especially since we’ve been approaching this gradually. It seems like a huge leap to commit to five months. After chatting tonight, we came up with these possibilities:
- I hold out until September and then allow one orgasm during our vacation before starting another period of chastity—the length will be decided later.
- I wait until September and remain unlocked for the entire holiday, enjoying lots of sex—then get locked again afterward.
- We keep going as we have been for these past two months, with some teasing and denial—and me never quite sure what comes next (whether it’s an orgasm, edging, or just teasing while in the cage). I’d love to hear your thoughts. I want to do what Miss wants—but five months is a long time when my previous longest was only one. Any advice would be greatly appreciated.