You have not reached a ''sticking point'' in your journey. It is your mind that might still be trying to tell you you are stuck, because it does not understand what is going on (it has been exposed to the consciousness). But the opposite is true: you are not stuck, you are finally getting out of being stuck all your life, you are awakening. And it is very beautiful to read you because your awakening shines through every line you write.
That ability you have to clearly and fully understand what has been happening to you in the past and how to get rid of it (the painbody, the lies, the fears) IS awakening......
You are in a state where you are fully conscious of how ridiculous it is to try and live up to societies expectations but still think you need to do it in order to be part of society (you are still looking for ways to enhance your dating life as though it was your duty in order to be accepted by society).
Remember this: having had your first sexual experience at a certain age, dating, marriage and so on are norms of society (just as there are another billion, moreover differing from one culture,nation, country to another).
But YOU, as an awakened being, are free of that now, liberated (or are soon gonna be).
Your painbody lies in the dating life....but it could be just as well any other area where society has put invisible ''boundaries'' that make you appear ''not normal'' when you do not have this or that at a certain age (first sexual experience with 14-20 / marriage with around 30/ children from 30-45 years old and so on, depending on society of course).
Does that not seem ridiculous to you? And then of course it goes ''Ho hoooo, Oh my god, you are over 20 and still a virgin, that is not normal". What else can you expect from our ''little minds''. A person in the egoic state of mind, and those are most of us, will do anything to annihilate what is different. They will lead you to believe YOU have a problem, YOU are not normal, YOU are a failure.
GermanEnlightenment, believe me, you are not. My first time was a disaster and certainly not with the right person but I too felt like I'd be an outcast if I didn't do it. Sadly, many of us have a similar story. To be honest, that first time when I was eighteen , I am not even sure it was my first time. I am still horrified even when thinking of it. I prefer never to.....but Id like to share my story with you so that you realize just how ''insane'' those norms are. I was in love with someone but because of the pressure I would get, Id feel like I have to have my first time to fit in. I was desperate about life and found it hard to believe the first sex could ever be with someone I love and meaningful (how can it when you force it?). Well, I then would get drunk at parties and remember myself waking up next to men without knowing what had happened at all. I was so ashamed I never dared to ask. This happened twice and probably nothing happened because I fell asleep or wouldve felt it if something did happen.....the truth is, I dont really know. But how insane was this: I guess I preferred THAT to ''being a virgin''. That way it felt as though I had my first time even though I had no idea what I have had because I was sh**drunk and didnt remember. But everything was better than ''not being the norm''.
Can you feel the deepness of the insanity here? By the time I was eighteen, I wasn't even sure whether my first time was my first time. And it was anything else but glorious either. The sexual act is no pleasurable thing if the want does not come from deep within, from your being, from that place underneath the million labels and confinements. It can be to a certain extent, when you lose yourself for a couple moments (just as you get glimpses of awakening in your sleeping ego possessed state of life from time to time), but most "ego possessed " people cant lose themselves in sex just as they cant in life, they cant just be........let it be......let themselves go.....experience those many orgasms in a row. Anything is possible but it comes with how deeply you are connected to your being, how peaceful you are, how awakened you are.
What I am trying to say is that if you force your first time it will maybe be ''real'' because it happened and it will be no more ''lies you invent'' to fit in but it will be NO better. It will not be the pleasurable, enlightened sex you can enjoy. It will be the bland one you have to ''undergo'' to be the norm or it will be with the wrong person and your awareness will be asking you ''why am I doing this'' etc. I am sure you understand............You can only feel true pleasure doing the right thing at the right moment. Whether you decide to let things flow and have the woman of your dreams come to you in the right moment or whether you decide to sleep with someone more experienced just for the teaching and pleasure, do it fully, meaning: dont let your ego torture you with its little ''rights'' or ''wrongs'' , the only thing you should listen to is your intuition, your heart. Consciousness is going to give you the answer, all you have to do is let life live through you.
GermanEnlightenment wrote: the fact that some random guy could just sweep her off her feet for one night while I "worked" on her for months, not getting any sex.
If you reconsidered this statement of yours in the light of what I just wrote and would remove labels such as ''getting sex'' or ''working it'' by ''LIFE'', meaning: if you would SEE IT ALL AS A WHOLE instead of labeling, you would realize that what you have with this girl is infinitely greater than anything anyone could ever put a label on. The label sex is : ''genital contact, especially the insertion of the penis into the vagina followed by orgasm'', as defined by dictionary.com. This is what western society expects us to do before the age of twenty (even earlier) or else we are seen as ''not normal''. This as well as a million other things ,our society expects us to do or be, keeps us in confinement, on ALL levels.
YOU are given the unique precious chance to finally get out of that confinement, find true love, pure joy, liberation ......the chance to awaken. I am so happy for you. Enjoy it and always remember: only good can come from it. Our lives purpose is to awaken and in that state....everything is possible.