My best friend since childhood is gay, she came out to me when I was 23 and she was 22. I always knew but never said. Just waited for her to be ready. A few years later I was 25 and she was 24 we were sitting around drinking and just talking shit and she told me she’d never been with a guy and had thought about what it would be like. We laughed and joked about it and just left it at that but then it came up again a couple times over the next few weeks and then she asked me to be her “Guinea pig” as she put it. We would always get together at her place every Thursday night to watch supernatural together and have a few drinks and that’s when it happened. Started off just making out and she started jerking me off. She was terrible at it but she quickly moved to giving me head and at that she was amazing. It was sloppy and passionate and she kept eye contact the whole time. I let her take control of me. I wanted her to feel comfortable so I layed back and let her ride me. She was awkward at first but she started getting into it. Her hands on my chest. It was slow and but she was enjoying grinding on me. Then she stopped and just told me to fuck her. That’s all I needed. I took control and took over. We fucked like crazy the whole night and that’s all that ever happened. She’s still my best friend in the world and it was awkward for a few months after but she’s still my day 1 and always will be. We’ve talked about it a couple times and she says it’s still one of the best nights of her life but said “dick just ain’t for this chick”