I reached out to an escort, with it being my first time I completely fucked up my introduction. I reached out a month later, and she still remembered me. I reintroduced myself and apologized for the weird.
She decided to graciously gift me with another chance. And I figured as a token of appreciation, besides being the perfect gentleman of course, I wanted give her something. I don't know if that's a good idea and what I could get her. Any thoughts on this?
Congratulations!
Okay, I know that might seem like an odd response. Making a mistake is supposed to be bad, right? But I'm genuinely delighted to get your message, because it's lovely to hear from someone who's so eager to learn from their missteps. Getting something wrong is a very human thing to do...and mistakes are simply how we learn to do better.
Unfortunately, there's a lot of pressure when it comes to sex. There's this idea that sex and dating are 'instinctive' social behaviours, and that if we're decent people we should simply know what to do and say on dates, and in the bedroom. If things go well, we might feel validated...but when they don't, we feel as though we've failed.
Often, this pressure affects sex work clients too. Even though spending time with an escort is a very specific situation, with specific rules, many people feel as though they should get it right the first time. If they say or do something wrong, or have an awkward moment, they often feel ashamed.
Here's your reality check: great sex is something we learn. From the first conversation to getting your partner off, there are dozens of skills to practise. If you're new to sex workers, it's definitely possible to be less than perfect.
You haven't said what it was that you specifically got wrong - and there are a lot of ways to mess up a booking request! Let's focus on the positive - you tried again, did better, and were finally accepted. That's a great outcome.
Note that it doesn't always go this way. A serious misstep when approaching an escort, such as getting too explicit or refusing to give screening information, often does result in that worker refusing to see you again. If this happens, it's not a disaster - it just means you'll need to move on. If an escort says 'no' to seeing you, it's important to respect their decision. You'll be able to adjust your approach and try again with the next worker you contact.
Now that your escort has said 'yes' to a session, you're wondering how to make it up to them. I think that's lovely too. As a sex worker, I deal with a lot of time wasters and offensive emails, and it's a huge drain on my time and energy. It sounds like you realise you've inconvenienced her and you'd like to acknowledge that. If she's anything like me, that gesture will be appreciated.
I can't speak for everyone, but in this situation I suspect a cash tip might be most appropriate gift. Dealing with difficult booking enquiries takes time...and as they say, time is money! By giving a little extra, you're demonstrating that you understand the value of her time and effort.
As with all cash payments, make sure your tip is left somewhere discreet if you're in the USA. Avoid handing over money directly.
If you're in a location such as Australia where it's okay to be more direct, place your tip in an envelope and present it to your worker at the end of the session. You could even add a card: "Thanks for giving me a second chance! I'm really glad we finally met."
Georgie Wolf
