“Anything that makes you hard,” she said. She then started to massage my body with her hands, again, lightly, until she started playing with my cock. Her hands caressed me in a much lighter and gentler motion than I ever did. I fantasized, I strained, I concentrated, I sweated, and, eventually, I came. It was not satisfying. Then I put on my clothes, but the bell rang before I could leave, so she asked me to hide in the bathroom. The next patient walked into the living room, and I slipped away unnoticed.
I continued to see Tiger every two weeks or so for the next few months. Reaching orgasm was now routine. But I couldn’t connect the feeling of the personal pleasure I received from the body contact, the lotion, the massaging, with sexual pleasure.
She had me try different positions. She taught me ways to masturbate that she thought were healthier (there were several instructions, including the primary rule: Do not ever use lubricants, or you’ll become overly reliant on them to reach orgasm). She worked on my fantasies: I had a tendency to think about other people; she encouraged me to include myself in my scenarios. She was still insisting I refrain from masturbating between sessions, but I didn’t have the willpower.
One evening, we got into a terrible fight over it. She called me an idiot. I said she was cruel and heartless. She said I was weak. This continued for half an hour until, again, we showered, I douched her, we went to bed, I fantasized—including myself in them—and she then told me that she would masturbate as well. I was fascinated. I knew women masturbated. I had never thought about the mechanics involved. I ended up rolling over on my side to watch. This wasn’t sexual to me. It was more like watching a nature documentary.
By the end of winter, I was becoming impatient. My psychiatrist was not very helpful: “Why do you feel impatient? What does that mean to you?”
Tiger was more empathetic.
“I wish this were going faster,” I whispered.
She looked at me, and then she took off all her clothes, rather than have me do it, pushed me onto the bed, and began to suck my cock with the kind of force my hands could barely muster. I got hard. Then she suddenly straddled me, and sat on my cock. Me inside her. The thought thrilled me. I kept pumping for a few minutes and then lost my erection.
She slipped off me and asked how I felt. I said it was good. “I think this is the night,” she said. She starting sucking again, and when I got hard, she thrust her body onto my dick, and I worked it so intensely I was sweating and panting like a long-distance runner. Then I came. I had done it! I had sex with a woman! Isn’t that what all you men wanted, all you shrinks in your reclining leather chairs in your wood-paneled offices with the beige sound machines whirring outside? Wasn’t this the goal?
From then on, over many seasons, each time I visited Tiger, we had sex. For the first few times, she was on top. Then she coached me on how to mount her, how to best insert my dick into her vagina, how to keep a woman involved. I don’t believe she ever had an orgasm—there were days when she saw five men, and I doubt she was sexually attracted to any of them or me—but she kept her feelings so remarkably private that I wouldn’t have known.
As the sex progressed, our personal relationship changed. Often we’d gossip, or play word games, like Boggle, which she generally won. But sometimes she’d lash out—telling me that she was bored and tired of me, that I wasn’t doing anything to help myself, that I was still masturbating too much, that I wasn’t including myself in my fantasies. I’d respond with a rush of anger, calling her narcissistic and uncaring. Sometimes our fights were feverish. But I never knew how serious they were, because at the end of the first hour, she always led me into the bedroom, where we would have sex. Were the fights part of the therapy? Did she mean them? I had no idea. I knew little about Tiger, although I did eventually piece together much of her background.
She fell into sex surrogacy by accident. She had been a bartender, she’d run a boutique, and she’d been a call girl. Then a friend wanted to learn how to have sex with women and wondered if Tiger could help. (Actually, one of the first things I learned about Tiger was that her name wasn’t Tiger—she never told me her real name.) She agreed, the work went well, and the friend related this to his doctor, who was Helen Singer Kaplan, one of the country’s leading authorities on sexual dysfunction. Kaplan had founded the country’s first clinic for sexual disorders connected to a medical college and served as the director of the Human Sexuality Program at New York Hospital–Cornell Medical Center.