I grew up as the timid little boy who was always ignored and laughed at by the girls. My early sexual life consisted of only masturbation and watching porn, i quickly found myself attracted by femdom and humiliation porn, and needed more of that, so at 16, I bought a chastity cage and started self imposed frustration and denial.

I then started to watch chastity themed pov femdom porn and since i couldn't masturbate I've looked for alternative pleasure starting with hypno porn, hand free orgasm, etc...  One thing led to another and I started to explore anal play, as a way of degrade myself and to try and have some sexual release. At the time, these fantasies were just and fantasies and i would still think i was a pretty normal boy with kinky fantasy.

The first turning point was when i was 19, i was in love with a girl, lets call her Lisa , she was a really pretty blond sexually active and liberated, never in a relationship, always a lots of boyfriends i was struggling with her and spend 1 year being in the  "friendzone" until one night after she's been drinking a little to much, she take me home to have sex, but whatever we tried, i couldn't get it up, she was disappointed and while she was trying to be nice and comprehensive about it, i could feel what she was struggling not to be contemptuous and laugh at my face and be.

She ghosted me after this night,altough we were good friend before, and all my friends covertly laughed at me whenever we were talking about her.

After this night, when I came home in the morning, i was feeling humiliated and got real hard thinking about the night, i then masturbated myself telling me i was a beta virgin loser who will never please a woman, I remembered the emasculation I felt when she smirked and say something along the lines of "dont worry, it can happen, I understand, its not a big deal", that triggered the most intense orgasm of all my life at the time. I then realised that all this wasn't just fantasy, but who i really was deep down. I then spend the following years isolating myself, focusing on depraving myself, i took a lots of drugs(psychedelic, uppers, weed, poppers...) in this time watching increasingly hardcore femdom hypno, keeping myself in chastity and toying my ass as much as i could.

(to be continued.... )