How should I handle an overnight meeting with an escort?

January 21, 2008
I have scheduled my first overnight appointment with an escort. What do I do now? I don’t want to come off as a sex-crazed person or as someone who doesn’t know what he is doing. How do I spend that meet and greet time together? Talk, dining, a shower - what? This will be my first meeting with an escort.—Anonymous
Congrats on taking the plunge! I hope you made a good choice that will be everything you want him to be (and more).

There is no “routine” you need to go through with an escort. Since it’s an overnight appointment, you’re not pressed for time. So invite him into your home (or hotel), sit him down, and talk with him for a little while. If you’re feeling particularly randy, go ahead and have sex with him right there on the couch (or take him into the bedroom and do it there). If you’re nervous and want to go a little more slow-paced, take him out for a light meal so you can talk and get to know each other. Either approach works fine.

With overnight appointments it is important to remember two things. First, it’s absolutely exhausting to have sex for hours and hours and hours without a break. Possible, yes. But also exhausting. Wanting a lot of sex is fine, but you may want to have a little break in there somewhere. (Perhaps for that light dinner I suggested).

Second, while escorts tend to be night people, like anyone else they become tired as the night goes on. If you’re looking for hours and hours of sex, you might want to start your night a little earlier so that he finds it easier to stay awake. Meeting at 8:00 and going to sleep at midnight may work better than meeting at 10:00 and going to sleep at two in the morning.

Either way, take a shower and brush your teeth before he arrives. (Y’all would be amazed how many clients don’t). It’s a good habit to be into even if you plan on taking a shower with the escort before you play. And if you’re a bottom, be sure to eat light the day before and to “clean yourself out” thoroughly at least 1-2 hours before the escort arrives. (Giving yourself an enema that far in advance allows your body to reabsorb any water that remains inside you. It makes sex considerably less messy).

Above all, have fun! Relax, and be up front with your escort about being a novice. He won’t look badly upon you and will take a gentle lead to give you the sort of night you want to experience. —Aaron Lawrence
Comment by Anonymous on January 21, 2008
I might say that you are nervous because you don’t know what is going to go on. Well, have something in mind like the following:

Depending on what they want, wash EVERYWHERE, inside and out. Take your time, don’t rush, and make sure you’re all ready for a good time. Light spray deodorant. Place money on the table, slightly hidden and direct the escort to it at the appropriate time (I preferred before, but whatever).

Lock up your valuables. This is not because escorts are thieves (although one of my boys did have a little problem) but mainly for peace of mind, especially if there is some nap time. Last thing you want to do is be paranoid about your wallet, watch, etc. be safe and be safe. Let the escort know you’re a little nervous, but do it in a sexy way. If he’s good, he’ll calm you down before a single piece of clothing is shed.

Once the first “round” has gone by, then take a breather, cuddle, etc. If you are in a hotel room, ask the escort if he wants room service, etc. Get foods that can be used in sex later like whipped cream and fruit. If it’s at home, put him in your shirt and head towards the kitchen... you don’t know what might get started there!

Play again, then take a second break. Cuddle. Get some fresh air. That can be fun too.

After three rounds it’s good to take a shower, though a bubble bath is nicer.

By the way, just because you have something in mind doesn’t mean it will happen... and that’s the fun of it. You have something you are thinking, but as the night goes on… well, the night will take care of itself.

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