For most of his life, Adam was your run of the mill straight guy. He was only attracted to women and when with a woman, he was always in the dominant role. He loved rough sex and being aggressive, even borderline abusive, to the girl he was fucking. He was proud to be a hard fucking, dominant, straight male.
That is, of course, until he moved to San Francisco.
Adam had gotten into grad school in San Francisco and was moving there from his home state of Iowa. It didn't take long for Adam to realize that he was in an entirely different world. In Iowa, being gay was still not a totally acceptable thing. In San Francisco, you saw men dressed as women walking down the street like it was no big deal.
Adam couldn't believe his eyes at how sexualized the city was but was also jealous because it was sexualized for men and trans, but not as much for straights.
It didn't take Adam long to let down his walls. He soon had friends in school who were gay and he was learning that they were no different from him, they just preferred cock to tits. But soon, Adam would find that he had a lot more in common with his gay friends than he had thought he would.
It started the summer after his first year in school. His friend Tony took him to his first ever gay pride part in the Castro. He went to meet his friend to walk to the Castro together and was shocked to see that his friend was dressed as a woman. And even more shocked that he found himself attracted to his friend, constantly sneaking looks at his ass in the short skirt.
The two spent the night in the Castro drinking and doing drugs. At around 3 am they decided to call it a night and head home. As they were walking, Tony told him Adam he should just crash at his place cause Adam's apartment was too far of a walk. Adam agreed, but it wasn't because of the walk, it was because secretly he was hoping he'd get to fuck his friend while he was dressed like a slutty woman.