Self Locking: How do you know when it is time?

Then simply set a date goal. 2 weeks, a month. And go.

 

Saying an orgasm should be earned might imply that chastity is all about the eventual orgasm, and orgasm is the pinnacle of sex. You could also consider that chastity can be simply about keeping the penis separate from sex, and enjoying/learning to enjoy sex without involving the penis, or perhaps without involving the unlocked penis. It's a matter of perspective and not fixating on penile orgasm can be very, very rewarding.

 

Here are a couple of pictorial suggestions for when it's the right time to self-unlock...

 

You could always put your key in one of those kitchen safes that are meant to lock up food for a set amount of time. That way, you kind of force yourself to stay locked. I think the maximum is 10 days.

 

Why not just make a meaningful experience with a woman your goal.

 

Longer each time.

 

As something to tr for yourself. See how long you can go before it goes off on its own.
Then try and beat that
If you allow yourself sufficient stimulation of what ever kind works for you
then you can induce some leakage just pre-cum or chastity tears as is often called
this if you do it regularly before you feel the NEED can relieve the need to cum and just leave the more manageable / desireable.... desire to cum. Which helps prevent accidents without the drop or the loss of control. albeit self-control in your case.

Milking will/can produce the same effect but seems to me at times to require a lot more effort.

 

Surely there are ways in which you know you can improve.

What might those be?

 

I decided to give myself a 5lb weight loss goal
Unfortunately I like being locked up so I keep hitting the ice cream- -1lb this month
Could be in for a long stretch

 

As a fellow self-locker, I think that is a very good question!

I normally try to beat my previous record. So far, I always took off the cage once it really hurt eg red, sore skin, pain. That usually happens after 10 days of continuous wear but hope it gets better.

Another problem I have is that once I cum, I'm not anymore interested in chastity play and cum 3-4 times in a row for a few day

 

I do agree with you as far as always trying to beat previous record locked but barring any health issues I want to get back in a little quicker. Maybe just a 24hr window to do as I please. I still have 3lbs to lose before I cross that bridge

 

Being newly locked I find the topic timely. When I locked myself 2 days ago my only focus was to be locked. Never gave a thought to how long. Honestly, I don’t know if I want to think about removing it right now. But when I do, I want to tie it to a goal.

 

The original goal for this lockdown was 15 days- passing the previous record, I got to that day and set a new goal of losing a few pounds. I’ve actually started to take that goal a bit more seriously. When we get there we’ll see.
The nice (or bad) thing is there’s no rules to your timeline.

 

You might be surprised, with a little effort. Pet was rather pessimistic when we met. Of course, it's a part of his personality and I wouldn't change that for anything as it creates a distinct sense of humor. Looking at certain parts of life with a different lens, however, can make all the difference in being able to feel the (healthy) effects of positivity.

Perhaps you could satiate your need for data by measuring the steps you take while finding silver linings of life - whatever that might mean to you. You can still be a realist while improving your outlook.