Same, always had a thing for cute but mean/ cruel girls as well. One girl at highschool I was besotted with, would finger her pussy and let me smell her fingers if I paid for her lunch. Once I offered to pay her a whole weeks pocket money to let me suck her fingers, only to find out out she told her girlfriends the next day and thus the boys as well.It started for me back when I was 12. I grew up in a very small town with a very small elementary school. My class had 10 girls and 2 boys, and the other boy was special ed. So in my mind by the sixth grade I thought I had a harem, and in their minds I was apparently just one of the gang who happened to have a penis.
A new girl moved into town and she was gorgeous and much more mature than the rest of us. She opened up a bunch of new feelings inside me, a lot of it lust. I became obsessed and she strung me along. Then she started dating a boy in the fifth grade and flaunting it in front of my face, forsing the two of us to hang out with her together. Him angry because I was the third wheel, and I was angry because he was there at all. She loved it.
And then I had to watch them make out for the first time and something broke in me.
She moved away at the end of that same year, but she remained the model for my ‘perfect girl’ since then. Cute redheaded bad girls who like to tease and have a cruel streak in them.
And then of course all of the next 3 girls I had crushes on in middle school and high school were dating my friends... so yeah. All kinds of cuckold conditioning over here.
Everyone found it funny because they were all highly sexually active yet I was yet to even kiss a girl/ finger a pussy/ suck on a nipple etc. let alone fuck one. So the fact i'd paid money for something the other boys were getting every day and a lot more, plus everyone sucking their finger and making wanking gestures to me for the days following was not an easy hurdle in my teens. But I was hooked on that type of girl then and ever since.