I am a massage therapist of over 20 years experience and would like to offer a treatment to a lady with whom I have made an appointment (at a time other than that which I booked). I know it's something that is on her wish list; I'm just not sure if it's appropriate for her to know that much detail about me, or if it might seem weird.
So here's the situation: You've been seeing, or are planning on seeing, an escort. Because professional massages are on her wish-list, and you're a professional masseuse, you're thinking of offering her a massage treatment outside the paid time you have together.
Firstly, is this question really about your escort knowing too much about you? I don't think so. Most of my clients tell me what they do for a living, it's not a big deal.
Here are some more relevant questions: Would an escort want to avail themselves of your professional services outside of your paid time together? And would it be appropriate for you to offer? I can't answer for everyone, of course...but I suspect that for most workers, the answer is 'no'.
If a gift comes with hidden obligations, it's not a gift.
Sometimes, when we give things (or offer to give things), they're not really free.
This often happens in the context of client/escort relationships. For example, a client might present their escort with some sexy lingerie or a sex toy - but then expect that those items be used during their next booking together.
Or they might offer a free trip trip overseas, or a booking at at their escort's favourite restaurant. But when the client also invites themselves along on these expeditions, it becomes clear that they're really just wanting to spend unpaid time with their worker, while also feeling like they're doing them a favour.
Who benefits in this situation?
Would your offer of a massage benefit only your escort? Or would it benefit you too?
It sounds like it might be the latter. You may enjoy a bit of eroticism, sneaking your regular lady into your place of work...you may fantasise that the two of you might get up to something sexy mid-session. Even if your intentions are completely innocent, you may still be looking forward to your escort appreciating your skill as a masseuse and thinking more highly of you as a result.
Getting sexy, feeling an erotic charge, and feeling appreciated are all services you pay for when you see a sex worker. They don't come for free.
Even if you have no expectations at all, it's still unfair to ask your escort to interact with you outside of your booking time. If your escort came to see you for a massage, she'd be forced to switch into 'work mode' even though she wouldn't be paid for it. I suspect that this massage would become a chore for her, because she'd feel pressured to maintain the client/provider vibe the whole way through.
If you really care, give her a gift that can be enjoyed privately.
If you really care about spoiling your escort and you want to give a gift that doesn't come across as self-serving, buy her a massage voucher for a day spa.
Or, if you'd like to show off your professional expertise, offer her a treatment as part of your paid session together. In that setting, it's sure to be appreciated.
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My guide 'Getting Started with Escorts' explains how to arrange a session with a hands-on sex worker.