Men will bear many things from a kept mistress, which they would not bear from a wife. - Samuel Richardson
A complex reader question which needed a complex answer:
I’m a highly-educated girl from a well-to-do background, with a blossoming artistic and academic career. I have absolutely no real economic need, but I have a fierce desire for financial independence and a sugar arrangement seems to me the best option. I’m not ashamed of it but I am deeply concerned about possible repercussions. On the one hand, I don’t care if people are shocked, but on the other I don’t want my loved ones hurt by gossip and slander, and I’m worried that I’d be denying myself a chance in highly public careers, lest my youthful ‘activities’ be outed. Worse still, I live in Asia – where norms governing sexuality are even more stifling than in the West. How did you deal with the judgment from family and peers, and how do you explain your job to people? On the practical side, would you advise against juggling more than one sugar daddy at a time? Are there terms and conditions I must look out for? How do I ensure that transactions are processed, that I’m legally protected, and that there are medical precautions beside testing, condoms & pills? Finally, the few friends I’ve talked to strongly advise me against being a sugar baby, and I’m concerned that I’ll lose my self-respect; do many sex workers face this inner conflict all the time? How do they resolve it? Can sex and love be completely divorced – even for a sex worker?
Sorry for asking so many questions, but I don’t know anyone else to ask; I sincerely believe that your advice immensely helps a hidden generation of young workers like me.
Your first concern is a very real one: if you think you might want some sort of public career in the future, sex work of any kind presents a considerable risk to that plan. Even totally legal forms of sex work such as compensated dating carry a social stigma, which as you rightly observe can be powerful enough to derail a reputation even decades down the road. If you sugar-date under your own real name, it is an absolute certainty that the arrangement will come back to haunt you; even if you use a carefully-guarded alias and post no face-showing pictures on the internet there is a chance of later exposure. In my case, I wasn’t concerned about what strangers thought because I had no plans to ever return to a “straight” career; furthermore, I was estranged from my family, and prepared to lose the goodwill of any friend who could not accept my choices. So in my case, I could simply be honest about my career with friends, and had a plausible cover story for neighbors and casual acquaintances. But if you’re not prepared to risk that (and I certainly don’t blame you if you aren’t), maintaining a strictly-segregated double life is probably the only way…though of course that carries its own costs and risks. I suggest you read my essay “Coming Out”, which discusses the pros and cons at some length.
In answer to your second question, I don’t think it’s ever wise to bite off more than one can chew. Were I you I would start with only one patron at a time, get used to that, and then when and if you feel ready to juggle a second gentleman you can do so then rather than rushing into it now. I would be very clear with the patron on how many hours a week you’re willing to give him; that way if he later tries to overstep his bounds you can remind him that this was discussed at the outset. Other issues will certainly arise just as they do in other types of relationships, and just as in those cases you’ll have to deal with them as they appear and learn from your mistakes. As for the rest, I’m not entirely sure what you’re asking; in the absence of an ironclad written contract there is always “wriggle room” for both parties, so any legal issues, like time allotment, should be clearly discussed at the beginning. It might be a good idea to insist on payment in cash until you learn to trust your patron, but medical concerns are a different matter: those are present even in monogamous romantic relationships, so I would advise never letting your guard down on that front. Always use condoms, stay on the pill (or get an IUD) and discreetly check him for signs of disease every time you’re with him.