Are You Experienced? Escorts as Teachers of Titillation, Clients as Students of Sensuality

Posted on Posted in Ask Annie: Advice from an Escort about Escorts, Intimacy, Relationships, Sexuality, Sex Work, and "The Hobby”

This is a continuation of my responses to the long list of questions sent to me by a young newbie. Today, I’m going to answer three questions on the topic of sexual experience (or lack thereof), and the role of a sex worker meeting with a sexually inexperienced client.


  • Who makes the first move? I am a shy person in intimate matters. I have done the deed once, and that was when I was not sober. I barely remember it. To me that doesn’t really count as an experience. So how do I let an escort know about my level of expertise in general?
  • My whole goal in finding a companion is not just for my own enjoyment but rather as a learning experience for future non-companion partners. I want to learn what makes a woman tick, how to please them and give them the pleasure that I can get. How do I let a companion know that I want to learn the ins and outs of pleasing a woman in bed? You know, from beginning to end. I am weak in the “length” and physique department so I need some other things in the Arsenal until I fix the physique part lol.
  • Many guys look at companions as their brute right and for their pleasure. But, I literally want to enjoy and learn things on a woman that you could not learn without being in a relationship. Let me know if you think my views on this is achievable and realistic. I have been scouring the Internet but it’s mostly Alpha Males and they’re Triumphs. Your blog is something I have been looking for. A chance of getting info from not a client side but by the companion side.

These are all such fantastic questions, and I really hope this is indicative of a broader trend–as in, I really hope that more young men think like he does. He has no reason to put on airs for me, as I’ll never meet with him (he lives far, far away from New Orleans and doesn’t plan to visit), and plus, he let me know at the very beginning of that email that he was only asking for help, not seeking an appointment with me. I’m gonna be pretty sad when I run out of questions form this guy…

Are you Experienced?

Who makes the first move? I am a shy person in intimate matters.

Who Makes the First Move?

I touched on this for a minute in the “How to Tell if an Escort is an Undercover Cop” post. There are a lot of misconceptions regarding what to do to avoid arrest when meeting with an escort, and I know I’ve seen (worthless) advice flying around the internet about who should make the first move. I don’t really even remember what the advice was, which is fine, because it’s bullshit anyway. You’re not going to be able to use the “entrapment” defense, so don’t bother adhering to a bunch of weird rules about who should touch whom first, or who should get undressed first, or who should take your pants off or whatever (I swear I saw something that said you (the client) should wait for the escort to take your pants off because that means she’s not a cop…or something. LOL yeah, that’s bullshit).

Here’s what I said in that post:

At the beginning of your time together, as I explained in my last post, introduce yourself, be normal and nice, make conversation, and treat this as a normal date. The monetary gift should already be in place. If she likes you, things will progress. Yes, you can “make the moves” on her, as you might with anyone you’re on a date with, unless she has made it clear that she does not want you to. And an escort is not going to stick around if she doesn’t want you to. She will either leave, or she will ask you to leave. Hopefully you’ll be graceful about it and won’t just reach over and grab her boob and honk it or something totally ridiculous (though I think I would crack up if that happened). If you’re really feeling confused as to how to get the physical intimacy started, ask for a backrub. Or even better, ask to give her a backrub! If you’re not sure what to do next, let your hands wander a bit and ask, “Is this OK?” You’ll probably start to undress each other at this point. WTF, I’m actually turning myself on picturing this, LOL.

So, to answer your question, it doesn’t really matter who makes the first move. If you want to, go ahead. But, since you say that you’re “a shy person in intimate matters,” then that might not be an option for you quite yet. If you’re too nervous, then chit-chat for a while, and gradually scoot over to sit closer and closer to her until she makes a move. Or maybe just rest your hand on her thigh while the two of you are talking. Or, like I said, ask for a backrub (or to give her one).


I have done the deed once, and that was when I was not sober. I barely remember it. To me that doesn’t really count as an experience. So how do I let an escort know about my level of expertise in general?


How to Tell an Escort You’re Sexually Inexperienced

Are You (Sexually) Experienced? Sexually Inexperienced?
No, not that type of experience….
Look, different people see escorts for different reasons, and I think you’ll be happy to hear that A LOT of clients–especially the younger ones–don’t have a whole lot of notches on their bedposts. Several of my clients were virgins when we first met. I know you’ve “done the deed,” as you put it, but if you don’t remember it, then I can see why this is a really big deal for you. It’s like your first time, except this time you’ll be able to actually think straight (well, until things get going, and then maybe not so much, lol). This will be the first sexual experience you’ll remember!! And the best part is, you can be really open about that, and you can ask questions and seek guidance from someone who probably won’t pass judgment, whereas it might be difficult to admit your inexperience to someone in your social circle. That’s awesome, and I’m super excited for you.

So, the answer is: You don’t have to admit your inexperience at all if you don’t want to. So you’re not a sexpert. Big deal. Even if you’re completely awkward and clumsy in bed, you’re under no obligation to tell her why (and frankly, given your age, if she has two brain cells to rub together she’ll figure it out on her own).

But if you want to let her know that you’re a blank slate, I think that’s a terrific idea. It’ll be helpful to both her and you. She’ll be prepared for any awkwardness, and she’ll be able to guide you through the experience so that you can get the most out of it. So how do you say, “This is pretty much my first time with a girl because the only time I’ve done it, I was too drunk to remember”?

Easy: “This is pretty much my first time with a girl because the only time I’ve done it, I was too drunk to remember.”

It really is that simple. Just tell her what you told me. Or make something up. As long as it gets your point across (that she should expect some awkwardness and/or ignorance on your part), you’re ahead of the game.


The Escort as Coitus Coach

Lesson: How to Please a Woman in BedSo you want to learn from an escort so that you can be a better lover when you sleep with non-escorts. I think that is so, so, so smart, and I 100% support that. Depending on the type of person you are, you can do this from the very beginning of that first meeting, or you can get a couple sexperiences under your belt before starting on your training. You can ask her for guidance that first time (“I really don’t know what I’m doing, so can you help me out? I want to learn.”). Or, you can just enjoy the experience that first time, and once that’s out the way, then you can begin your studly studies. Either way: how do you explain to her that this is your motivation for meeting with her?

Easy: “I want this to be a learning experience for future non-companion partners. I want to learn what makes a woman tick, how to please them and give them the pleasure that I can get. I want to learn the ins and outs of pleasing a woman in bed? You know, from beginning to end. Can you help me with this?”

(Those are his words, by the way.)

Or: “I really want to learn how to please a woman in bed so that I’ll be better prepared when I get a girlfriend. Do you think you can teach me some things?”

Remember that, even though she can doubtless teach you a LOT of valuable lessons, probably the most important thing to remember when you want to please your partner is COMMUNICATION. Different women like different things, so watch and listen to see if she likes what you’re doing, and if you’re not sure, ask. You’ll get better and better at this the more practice you get and the more your confidence improves.

Pleasing a Woman When You’re Lesser-Endowed

I am weak in the “length” and physique department so I need some other things in the Arsenal until I fix the physique part lol.

Oh honey, that is music to my ears. Some of the best lovers I’ve had were a bit on the shorter and thinner side. I can’t speak for all women, but let’s just say that the vast majority of ladies love love love to be licked. Plenty of women can only come through cunnilingus. And it’s not all that easy to find a guy who can do it well–especially not a young one. And what makes them able to do it “well”? Listening to their partner and doing what she enjoys. Learn the principles of muff-diving and a few techniques, remember to listen to your partner, and you’ll likely be golden with any girl who decides you’re boyfriend material.

Not only that, but as long as you don’t fall in love with a size queen, you cock is likely absolutely fine. An especially large penis is NOT necessary (unless, like I said, you find a “size queen”). In fact, all things being equal, many, if not most, women would prefer a lover with an “average” size penis to one with an especially large one, as the larger ones can be uncomfortable or even painful, and sometimes they make certain positions impossible.

And of course, I have to trot out the old cliche: “It’s not the size of the boat, but the motion of the ocean.” It really is true. If you’re a passionate, attentive, generous lover, you’ll be A-OK.

Don’t Listen to Stupid Douchebags on the Internet

Many guys look at companions as their brute right and for their pleasure.

Those guys are gross, and I feel sorry for the women around them. It sounds like you know better than to listen to guys like that. You know that sex workers are people, and as people, we deserve respect and basic human decency.

But, I literally want to enjoy and learn things on a woman that you could not learn without being in a relationship. Let me know if you think my views on this is achievable and realistic.

I do, 100%. I’ve had clients like you. I actually had one email me not long ago to tell me that he’d found a girlfriend and they were doing the whole meeting-the-parents thing. So happy for him!!! Of course he could have done it without me, but I think I helped him with his confidence level, and confidence really is key.

I have been scouring the Internet but it’s mostly Alpha Males and they’re Triumphs.

I don’t know what a Triumph is, but I see you’ve found the delightful gentleman on the “Red Pill” subreddit and on forum.bodybuilding.com (and by “delightful gentlemen,” I mean “scarily misogynistic Eliot Rodger-types and troglodytes”)

Your blog is something I have been looking for. A chance of getting info from not a client side but by the companion side.

Awww…ladies and gentlemen, isn’t he adorable??? :)

4 thoughts on “Are You Experienced? Escorts as Teachers of Titillation, Clients as Students of Sensuality

  1. Annie :
    Another very well done treatise. I also liked the Jimmy Hendrix reference.” Are you Experienced?”will be playing in my head for a while.
    Jim

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