First
Dona Olga: The Married Domme
She was my first. A married domme with two kids, older than me, whom I met online on FetLife. She loved poking at my masculinity. We met twice: in one she took me to a motel, in the other she invited me to her house, as a friend, with her husband and children around. It was creepy, and I was barely 22.
Shana C.: The Big Mulata
Everything she lacked in her face she made up for in her body. We walked around downtown Rio and everyone stared, maybe at the contrast between the tall black woman and the skinny white guy next to her. She was a swinger, insanely hot, and possibly my first civilian encounter. I was full of pornographic ideas back then, we talked about inversion, but I had never actually experienced any of it — using panties, swinging, all that. I think it was fashionable then, that thong thing with Beckham.
Shana was one of my biggest failures. She had that clipped hip-hop black girl hair and the body to match. When the opportunity finally came, I disappointed her =). She even surprised me by buying a thong for me, which was quite exciting — not only did she make me wear it, but she pulled it up so it was really tight, like a hussy, and it made my dick hard. But maybe because it was the first time, I let myself be delivered to passivity and couldn’t flip the switch to be active with her.