Chastity and orgasm denial discussion

So I have been wandering through my and my lovely KH/Wife Mistress Kay’s (who doesn’t frequent the site very often) journey through Chastity so far. It got me thinking about what people regret most regarding their Chastity stories. Is it that they were too pushy for their partner to play along? Were they too timid in asking for certain things? Too resistant to listen to their Domme/Dom? It made me think about my own regrets up to this point. What I figured out is that I don’t have many regrets regarding the path we’ve taken, save that I feel like I am the driving force by leaps and bounds. Though I have been reassured many times that she appreciates my ideas and it does turn her on to hear my fantasies. My only real regret would be that I didn’t meet my wife and discover Chastity sooner in our lives. I was just sitting there using the bathroom as I do now because frankly it’s easier! And I looked at my Queens Keep and thought to myself “I love being locked up!!” Then within about 5 seconds my thoughts drifted to all the kinky things I’d like to do with/to/for my wife when I got home from work, only to have those dreams smashed by the pitter-patter of little 2-year-old feet and the sweet rhythm of a 1-month-old baby crying uncontrollably with no way to communicate his life’s problems!! This is my regret: that I didn’t discover this wonderful world and my wife sooner in my life. I wouldn’t trade the life I have, my beautiful wife, and children for anything, but I wish I had more time in the lifestyle than just the last 3 years. I feel like we are just coming into it really well only to have almost no time for play between the two of us. Don’t get me wrong, I realize how selfish that sounds, but I wouldn’t trade my children for anything!! I wonder how long it will be before we get back into the groove. But suffice to say I will stay locked and do my wife’s bidding and do my damnedest to keep our kids from discovering our little secret! Anyhow, thanks for letting me get these thoughts out there. Feel free to share your stories of regrets!

Not starting with it sooner in life

I don’t really like to think about regrets, as I don’t like to dwell on what could have been. Also, I am so thankful for the amazing fetish/BDSM/FLR life I have experienced so far with my madam that I feel it’s selfish to want more. But I think my biggest regret is not buying another cb2000 (or even 3!) when I had the chance. You cannot get them anywhere now, and I know they are an outdated device nowadays, but they just fit me perfectly in every way. I have tried others (cb3000, 6000s, 6000) and other makes too, and nothing fits my anatomy as well.

I think my biggest regret was not being serious about chastity initially, treating it just like another kinky fetish that would get me off. Sometimes I used convoluted methods to keep myself from getting the key with a high degree of risk of losing it. Then I would snap off locks if I lost keys and run out. If I had been more genuine and less focused on getting my orgasm, I would have been a much better partner at the beginning of my relationship with my current KH. I was never disobedient; I always did my chores and looked after them. However, we didn’t have the close bond we share now because I was more about my own pleasure than theirs. I wish that when we were long distance I had been more upfront about wanting and needing to be in chastity so I could have become a better partner and submissive from the start. My biggest regrets will always center on the time I wasn’t as well behaved, not investing enough in my KH's emotions and pleasure as I do now. I wasted so much time and contentment.