You’ve mentioned several times that you’ve never really “amateur dated”, but you’ve also said you were promiscuous before becoming a pro. Those seem to contradict each other; could you explain?)
By the standards of the 1970s, my mother was quite overprotective; her level of caution would be considered fairly low in these days of bubble-wrapping and helicopter parenting, but 40 years ago she was definitely on the strict side. Like modern parents, she “seemed bound and determined to control my natural free-spiritedness and to delay my sexual maturation for as long as possible“, and part of that was “she did not allow me to date until I was 16, and even then only in groups to chaperoned events.” Of course, that backfired (as authoritarian prohibitions generally do); all it did was to stop me from dating, but not to stop me from having sex (especially since nobody bothered to chaperon me when I was alone with other girls). It did, however, mean that I never developed the weird habit of going places with guys I barely knew and then letting them grope me. By the time I was out from under my mother’s roof I had already had my heart broken once and wasn’t exactly eager to experience it again; I had a few long-term arrangements with women, including my second heartbreak and my first sugar mama, but until Jack started pursuing me my relationships with guys were largely pragmatic rather than based on mutual attraction. After he left me I didn’t want to be with anybody for a long time, and by the time that feeling faded I was already a pro and had no interest in giving away that which I could sell. So even though I had sex with a lot of strange men in my teens, they were all guys I met via my social group and my motive was profit or some other practical thing rather than auditioning partners; the majority of girls who hit on me were already partnered with men and were only interested in experimentation (except for that second heartbreak, about which the less said, the better). Therefore, even though it wouldn’t be accurate to say I’ve never been on an uncompensated date, the idea of making a regular practice of going out with strangers of either gender and giving them sex for free, and of wanting to do that badly enough that I actually take the time & trouble to create an ad on a website and somehow work out how to decide which messages are even worth answering (again, without profit in mind), is so alien to me that it’s like an outlandish custom practiced by some exotic culture I read about in National Geographic.
(Have a question of your own? Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)
