Is the first month of permanent chastity the hardest ?

In my experience,
If you can stop focusing on the possibility of an O, and instead focus on the hormonal cloud you are floating on as a result of being denied that O, ...then 2 months wont feel like enough. After that, you can start using a mental cost/benefit analysis to decide that 20 seconds of bliss is not worth the Drop you will feel afterwards.
Eventually, your cage will just feel "normal", and you will start to feel "naked" without it.
,,,At least that was my progression.

 

I agree with you. I started wearing a cage in July, and lasted circa 2 months before having another O. My cage felt really normal, and I loved the high I felt whilst wearing it, without release.
My wife permitted me an O, PIV, after my 2 months. It’s taken me 1-2 weeks to get back to that lovely high. I don’t feel desperate for another O soon; I really long to have elections though!

 

My situation was very similar. While it varies somewhat for every person, in general most people get to the point that the cage feels "normal." You don't want to be without it, and you get anxious about having an orgasm.

 

Every month of permanent chastity is the hardest. It's a trick question.

 

If anything it gets worse as you realize your full erections are just gone.

 

Lack of acceptance is what makes things difficult.

 

Not a “permanent” chastised guy here…

For me, actually, when (re-)starting a lock-up, the first days are the hardest… And the most exciting! Slowly getting more accustomed in the following weeks until after week 3 or so, it feels natural and without any problems I can hold for another couple of weeks or probably even months.

After unlock, there is indeed the odd feeling of missing “something”; indeed feeling sort of naked!

being unlocked for some time, which may be one or two days up to a month or so, that feeling gradually goes away as well.

and then, the sudden re-lock brings all back to life and the excitement begins again

 

My experience is that the first 10-20 days are the hardest. After that I get into the groove can go 30 days easily. I've never gone more that 45 days without some kind of release but I have gone months with only ruins which I then have to consume.

 

lol, good thinking there!!