Unfortunately the stereotypical asocial shut-in types are not the only ones harboring misogynist attitudes. Unfortunately actually interacting with women doesn't always make people have respect for them. Either way, there are a bunch of loner types with poor social skills in higher education.
"Elite" institutions such as Caltech are constantly mired in discrimination issues, and frankly I think some of that is perpetuated by the whole narrative of their supposed prestige to begin with. The need to remain at the top causes such places to turn a blind eye to smart or highly acclaimed people's misbehavior and lets their biases show in selecting who to let in. Caltech in particular is an engineering oriented school and that field in particular has an ongoing history of hostility to women and minorities.
On a more personal note, I'm glad you've had the introspection to recognize your upbringing-related issues with women and that you've seemingly worked to get over those issues. That said, I'd recommend you to avoid things like using genitals as a synecdoche for gender, It reduces people to mere sex objects and bringing up people's genitals when not called for is generally considered crude and embarrassing.
Nice detective work. The second time I got one of those I figured it resembles the false flag channel ad spammers on IRC. I still wonder occasionally what #superbowl at supermets did for someone to go on a multi-year spamming campaign against them.