Have you ever had painful lessons from demons?
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No, I have not.
Once, Lucifer taught me a tough lesson on taking a stand, even with spirits, through a sexual experience
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One core “painful lesson” memory of mine goes along the way of Don’t do business with people you’re not willing to drag to court. Not exclusively business related (but its super useful in that field!), I extend this rule of thumb to many social contracts by now, as well. Its painful because I -very often- thought I knew better. Of course I was taught otherwise, eventually 
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I don’t need that SP like I thought I did, the obsession was not healthy.
I need to learn to let go of grudges, especially after they were already cursed and dealt with.
To value myself more.
I have had many lesson but I think it’s more to do with ascend and being your beter self
Lesson are a way to reach your own godlike powers and learn from human mistakes and grow over it
The demons in my opinion have helped me so much to see the darker aspect of my self and to embrace it like most people don’t dare to look
Like crossing the Abbys
Hail Lucifer that he shine 
bright on your path
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Yeah I second what Esmee said.
Most of my lessons by demons where painful, my own “fault” for asking Lucifer to guide me on my path to knowledge, wisdom and power on my very first ever invocation .
The most painful ones are where stuff from deep down in your unconscious surface and you have no other choice than to deal with it. Even more painful when in that deep dive, you are forced to recognize the things you always blamed on others (like traumatic experiences) are your own responsibility and at least for some part your own damn fault as well.
For anyone struggling with the harsh lessons and challenges given to you by your demon mentors.
This pressure is needed to be able to form your very own black diamond. The bigger the challenge the more power you gain when you get through it, process it and integrate what you’ve learned.
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I will be making note of this!