What is your biggest Chastity regret?

Not starting with it sooner in life

 

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You cannot get them anywhere now, and I know it’s a outdated device now, but it just fits me perfectly in every way.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

 

I think my biggest regret was not being serious about chastity and initially treating it as just another kinky fetish that would get me off.
Sometimes I would use convoluted methods to keep myself from getting the key with a high degree of risk of loosing the key. I would then snap off locks if I lost keys and run 1 out.
If I had been more genuine and less about getting my orgasm I would have been a much better partner in the beginning of my relationship with my current KH.
I was never disobedient with them and I always did my chores and looked after them but we did not have the close bond we share now and I was more about my own pleasure instead of theirs.
I wish when we were long distance I was more up front about wanting and needing to be in chastity so I could have been a better partner and submissive.
I guess my biggest regrets are always going to be about the time I was not as well behaved and investing in my KH's emotions and pleasure as I am now, I wasted so much time and contentment.

 

Still just a few months into our FLR. I regret not starting sooner.

 

My thoughts are similar to others. I regret not searching and finding chastity devices sooner in my life than just two years ago. I could have saved myself a lot of frustration and disappointment.

I chose to be self locked permanently. My wife's health issues destroyed her desire and ability to enjoy intimacy. It is uncomfortable and painful for her.

For more than 15 years, it was one issue after another. It was very frustrating to see your special love suffer from multiple issues. At the same time, I was struggling with my needs not being met. Had I found chastity way back then, life would have been much better for me.

Since I made the decision and am now locked for life for my love, I no longer have to fight the frustration that I had for well more than a decade. I have surrendered myself to my chastity cage. Nobody made this decision for me, I did it of my own volition.

She is not involved in my locking at all. It is painful for to think about it because it represents that which she is not able to fulfill as a wife. So I am content with her gratitude and spoken words of appreciation for that which I have surrendered in her behalf.

The regret over not finding what has become a wonderful solution to this problem is that I have had a lot of personal frustration for too many years, and it could have been avoided if I would have dedicated more time to research, and having an open mind to what would help, and then follow thru on it.

Better late than never. What a difference it has made. I absolutely love being locked and do not wish to be free, ever. I didn't know. No one told me it would actually feel good. It has an amazing feeling that gives you some sustained satisfaction that gets you through.

I was able to make a firm commitment of lifelong permanent chastity to her that I could have made long ago. But, I can't look back, only forward. I feel great about never being let out ever again. We have both found contentment with this decision.

 

The two greatest injustices in life are not getting what you wish and having all your desires fulfilled.

 

Same here, wish had we started it much sooner.

 

I would have to say that if we'd discovered good quality strap-ons for me to wear while locked, we could have gotten my wife off the pill way sooner. Having gone a month or more without any relief, the pleasure from what amounts to dry humping while caged and in a harness, is as good as the pleasure from regular sex for me. I would not have guessed that one, but it took having a friend enforce my chastity/denial, to keep me in a state where I can enjoy what pleasures I have. Still, if we'd known how much we love it, I would have been able to give up my dick at 40, instead of 50, and not had to wait till I had a vasectomy at 45.

 

Someone recently posted or said something that is so true. When we vow "in sickness and in health", we are usually healthy at the time.

It is kinda nice to look back at that most sacred vow, and meditate on the meaning of that, and other things like, "for better and for worse", "til death do us part".

A side note is that "til death do us part", someone said to me recently that you might say, "for as long as both shall live". Some would change it to, "as long as we both shall love". In other words, if it ain't working for ME, then sayonara!

For some reason, though I am not into kink, it would appear that, from the personal comments of many, you have used your kink to draw you closer with your wives, rather than be self- centric. That is refreshing when you consider how most view marriage and commitment theses days.

I would keep my vow anyway, I am absolutely true to every word of it, to the death. However, a chastity device has been a vital aid in helping me to avoid the aspect of pursuing my one's own selfish desires and focusing on what really matters, which is, true love.

 

My biggest regret is like most, not discovering this sooner. And l have the same problem as DoseasTold, it's so hard to enjoy the lifestyle and kink when you have a 3 yr running around. I love my son to death and wouldn't give him up for anything but it makes it challenging to our chastity and kink life. But when he goes to bed the kinky side comes out

 

We don't use the hollow ones. They were either stupid solid, or crazy squishy. We use a roughly 8.5" Doc Johnson dildo with the vaccu loc on a leather harness. I stay locked in a micro cage. It's pretty accurate for sensation I'm told. I was 7.5", but the 8 inch model is way bigger than me. My parts are too sensitive now to do much thrusting, and if we go super slow, it tries to go soft, so we are committed to the strap-on now.

 

Regrets? Nothing really permanent, but I often have moments that I wish I hadn’t started all this. Sometimes looking down seeing all that steel and knowing you are done touching it. Being sick and having no interest in sex and going through the inconvenience of being locked. Looking at porn and wanting desperately to just cum, and knowing you can’t and she probably isn’t going to unlock you. Going to a bar and needing to sit(I hover squat) using a stall instead of just whipping it out at the urinal.

Of course like I said, I wouldn’t say I regret anything permanently, but I have my moments of “wtf was I thinking!”

 

Not finding it earlier, or at least, not broaching the subject with my loving Wife earlier....

 

Abso-bloody- lutely

 

Not finding chastity sooner seems more like a life regret than a chastity regret.

Anyways, here is my biggest regret.

My wife was out of state recovering from plastic surgery and I was home alone. At one point she brought up she was a little worried I would get into trouble so I suggested I could wear a cage until I saw her again. She agreed so I set it up that she had one key with her and the other key was locked in a safe that only she knew the combo to. So I wasn't unlocking. Anyways during my time alone I decided that it was time to start exercising and losing weight. Well walking with a cage is no problem but I was a little worried about running with the cage. So I convinced my wife to give me the combo to let myself out so I could run. Now she doesn't seem to be into it much.

I have continued my weight loss and did stay out of trouble but I haven't done chastity since and she hasn't really brought it up.

 

This

 

Wish I would have met my wife 20 years ago and started on this journey . The one thing I regret the most was making excuses for not doing things she wanted done. Because of this , she lost interest in being a Dom. I just learned of this last week and now I have refocused on her needs and wants , and she is starting to be more controlling over me again. Only a man in chastity would say Amen to this.

 

Not starting sooner. It has only been a year, but my Wife(KH) and I both wish we would have found MC sooner...Better late, than never, I guess...

 

I honestly wish we could have exchanged marriage vows with me locked up and her in control. We have been playing with chastity for the last three years but imagine "would could have been" for the 27 years of our marriage.

I think of all those business trips where I had solo session in a hotel room, the days when the kids where tiny and needy but she still felt the need to please me, sex was one more chore she had to do before she could sleep.

I doubt she could have handled the concept in her very conservative and very early 20's when we married but what if...?

 

I wish we had got this sorted before I was paralyzed. It's the one good thing that's come out of my disability.

 

I should have been locked permanently when I was 12. This all came along way too late for me. It would have saved a great many women lots of frustration and resentment by now.