For the past couple of years I’ve seen an amazing escort about once a month, and early this year she let me start contacting her via text. This past summer, I developed deep feelings for her and began to text her frequently just to see how she was doing; I also expressed my affection via emails, cards and gifts. Two weeks ago she cancelled a session for a reason which sounded good at the time, but I couldn’t get in touch with her for the next four days; we rescheduled, then she cancelled again five minutes before our appointment time. We rescheduled again, and again she cancelled and has been impossible to reach since then. I have a feeling she doesn’t want to see me anymore, but why not just tell me? I’m hurt and angry, and I realize now that I can never have anything serious with her, but is there anything I can do to regain her trust?
It’s not at all unusual for a client to fall in love with a whore; sometimes, as in my case, that can actually go somewhere. But there were a lot of men who fell in love with me before Matt, and every one of my sex-working friends has had clients fall for her; it’s a natural outgrowth of a situation in which a lonely man spends a lot of time in the company of a beautiful, alluring woman who only shows him her best side. Sometimes she’s able to manage the situation so he can continue enjoying her company and she can continue enjoying the income, but at other times the situation spins out of control; he may become obsessive and begin to stalk or harass her, and might even become violently jealous. On rare occasions, an unstable client’s infatuation with a professional can even lead to murder. Now, I’m sure you’re protesting that you would never hurt a woman, and maybe that’s true; however, it’s equally true that most of the whores who wind up dead didn’t think their murderers would go that far, else they wouldn’t have been caught alone with them in the first place. The fact of the matter is, all any woman has to go on when deciding whether to be alone with a man is her gut. And though the instincts of most sex workers eventually become far more finely-tuned than those of our less-experienced amateur sisters, there is no such thing as an infallible cognitive process. When you started straying out of bounds, wasting the lady’s time with non-appointment-related texting and violating her professional boundaries with excessive courtship displays, her alarm bells started to go off; it’s even possible that the first couple of cancellations were tests to see how you’d react. And how did you react? By repeatedly calling her and trying to reschedule multiple times in a very short period of time (your email to me was dated only 16 days after the date of your first cancelled appointment). And given that you openly admit to being “hurt and angry”, I can imagine what some of your (probably dozens of) texts or voicemails to her during that 16 days sounded like.
You ask if there’s anything you can do to regain her trust, but there’s no way I can answer that because I’m not in her confidence and I don’t know how badly you’ve broken it. It may be that if you let her alone for a few months before sincerely apologizing and asking for an appointment, she’ll give you another chance; most of the whores I know have “fired” clients before, and sometimes they’ve taken them back later. Before you could violate her trust she had to grant it, and she let you overrun her boundaries for months before doing anything about it; that tells me she was reluctant to end your arrangement, and perhaps that will play in your favor. But I’ve lived in the demimonde far too long to believe that your repeated attempts to reschedule were anything other than highly alarming, or that you’re as contrite as you represent yourself to be; it’s possible that she will never even speak to you again (much less agree to be alone with you). Your only chance is to back off and thereby show her that you’re not a deranged stalker; that may not return you to her good graces, but it may at least keep her from adding your name to a blacklist.