In 1998, I started a little on-line magazine to showcase the world’s most beautiful dominatrices and my abilities as a graphic designer, Heartless Bitch. I have always had a soft spot for women in form-fitting latex and high heels. The site was an almost instant (small) success. It not only rescued me from boredom, pennilessness, and despair, but also got me my first important design clients, one the (avidly submissive) founder of a DC-based think tank, the other the American southeast’s most notable dominant, Mistress Antoinette.
She turned out to have nothing to do with the Orange County-based Mistress Antoinette I’d interviewed a year or two before for Spin, and to be one of the most charming people I’d met in years — funny, self-effacing, generous, and even more deeply appreciative of the work I did for her than Mr. Thinktank had been. I dared imagine that I had a new career.
We became actual friends, Toni and I. We confided in and encouraged each other. She’d married very young, because pregnant, and then discovered that her charismatic bad boy young husband was a far badder boy than she’d bargained for — an abusive monster. Now she was married to her second substance-abuser. She found solace in the work of Tool, whose music didn't speak to me personally, but which I recognized as brilliant on its own terms.
I succumbed to her siren song after about a year and a half, and flew to Tampa to meet her. In person, we got on as poorly as we’d gotten on terrifically on the phone. I don’t commonly give people second chances to hurt me, so the fact of our friendship eventually being revived was a testament to her determination. She was the best woman (I had no best man) at my marriage in London to the former Mistress Chloe, and the only other American in attendance.
I stopped charging her to design new stuff or her Website. She was gigantically appreciative. You may imagine that, as a dominatrix, she enjoyed being horrid, or even cruel, to men. In fact, she enjoyed being horrid, or even cruel, only to men who adored beautiful women being horrid or even cruel to them. She was devoted to her son, who was beset by mental health problems. She wasn’t a loyal and generous friend only to me, but to many others. When a rich solicitor flew her to London, she brought me a new iMac.
I flew down to Tampa again, with the same result. Within around 12 hours, we weren’t speaking, but once more we somehow managed to resuscitate our friendship, more quickly this time. I was going to ghostwriter her autobiography, the cover I designed for which is at right.
But then some boastfully self-nicknamed air conditioning (or something) magnate from the Midwest hired her to oversee a sex shop in Miami for him. I found him sort of Trumpish in his defiant tastelessness. (I have lived in London, and know there’s such a thing as a sublimely tasteful sex shop.) Thinking that it would somehow put more money in her pocket, she hired some hack who's better than I at coding to design a new Website for her. I found it grim and soulless.
We kept in touch for a while on the strength of my calling her, almost always to find her too busy to talk for long. We now haven’t spoken in something like four years.
It’s bad enough when a friendship dies on the battlefield, if you will, with much shouting and rancor. It’s even worse when it just seems to evaporate into thin air, with no goodbyes said and no explanations offered.