"Being kept is fun!"
Despite the failure of my first attempt at being a kept woman, I decided against cancelling my date with Dennis, a sixty-five year old testicular cancer survivor. The fact that he had sent me a picture of himself dressed as Hunter S. Thompson suggested he might be an interesting person, and the fact that he’d survived testicular cancer could bode well for me. I didn’t know much about the disease, but I was pretty sure most people didn’t survive it with both balls intact. One or even no balls probably meant a lower sex drive and I dared to hope the whole relationship could be conducted by way of shopping trips, theater performances, and fancy dinners.
Dennis had mentioned a financial arrangement in his email, but insisted on hashing out the particulars in person. After the debacle with Tony the Tattoo Artist, I was wary of such an arrangement and worried that he’d bank on some sense of delicacy preventing me from bringing the matter up. I had already ignored the dictates of good manners and asked directly about money once; I hoped I wouldn’t have to do so again.
I met Dennis at a nearby restaurant. It was a place I’d been many times before, but always with friends. The food was terrible, but there was something about the old-timey freak show posters on the walls and the servers who engaged everyone in too-lengthy conversations that made me love the place. It was strange to be there while the sun was up, even stranger to be meeting a client there. We exchanged pleasantries over the menu, and as we waited for our food, Dennis mentioned that he had been a sugar daddy before.
I immediately felt reassured; if he’d already had experience as a sugar daddy I probably wouldn’t have to deal with any awkward misunderstandings or navigate the social minefield of a discussion about money.
