I recently saw a post on a local sex work board from a client who felt stupid when he learned that most sex workers feel that the "I want to please you [the sex worker]" attitude that some clients have makes their job harder. I don't think anyone should feel stupid about assuming that attitude would please a sex worker; after all, it shows that you likely want your provider to have a good time and enjoy her work. However, an often unexamined angle of that attitude is that it also has a lot to do with a person's own sexual ego, and the idea that to be good in bed means that you must possess a skill set that can get anyone off. While it seems like it's coming from a well-intentioned place, it can often come off as sexual machismo and, frankly, creates an atmosphere where orgasms will be faked which will lead to some sex workers feeling frustrated about the amount of effort that they had to put into your session in order to stroke your fragile ego.
The phenomena of orgasm expectation in the context of partner sex, and especially heterosexual partner sex, is something that has already been addressed by several people on the Internet- and probably addressed in a much better way than how I am about to address it. But I wanted to take a moment to try and explain some things about it that are specific to the dynamics of full-service sex work sessions (these are the sort of sessions that I do; where people meet in person and get it on). It would be impossible for to talk about this without talking about it from a perspective of personal experience, so let me start with some basics about me and my oragsms.
I am one of those fortunate female creatures who finds it relatively easy to orgasm during partner sex. However, this is a skill I built over years of sex with a lot of different people. Not trying to brag on that point; I'm only including it because I think it's an important distinction on why I was able to attain this ability. When I started having sex, primarily with cis-gendered men for the first 6-7 years of being sexually active, I would rarely orgasm during partner sex. This included during manual or oral stimulation. I do not believe that this was because my lovers were not skilled, but rather because I had to reach a place of comfort with myself, my body and it's reactions to being touched by others.
Also, and this is perhaps the most important point; I never touched myself during partner sex for the first many years that I had it. Why? Well, it all goes back to the point of the way our culture builds expectations around what partner sex should look like, and I didn't want to hurt those fragile egos of my male partners by making them think that they weren't getting me off, or that I had to get myself off. It was around the age of 25 or so that I had finally read enough articles and watched enough porn to realize that it was, indeed, ok to touch myself during sex- and that was when I finally started to orgasm with more regularity.
I believe that by regularly touching myself in front of my partners led me to a place where it was easier to orgasm through the touch of my partners. I began encouraging mutual masturbation frequently, because it is hot but also because we could then see how we touched ourselves and learn from it. I began fingering myself while receiving oral sex, or rubbing my clit while getting fingered. And I always, always try to find a way to rub my clit or use a vibrator when being penetrated by a cock, be it a toy or one that is attached to a body. So, already, I am actually technically getting myself off half the time, even though my partner is definitely helping. When a partner actually is the one who gets me off, I think it is a learned response from being able to get myself off in the context of partner sex so frequently. What I mean by that is: having been in a scenario where someone is penetrating me and I am rubbing my clit and getting off so often, I now find that sort of thing so hot that having someone else rub my clit (or lick it, or use a vibrator on me) makes the orgasm easier. My body has also become accustomed to a lot of different types of touch in a lot of different situations, whereas it all seemed rather foreign or different from my masturbation before.
This, however, does not mean that I prefer the orgasms my partners give me. They're great, I love getting orgasms from partners, but the ones I give myself tend to be more powerful and satisfactory. For me, no two orgasms are ever really the same, and the intensity can vary quite a bit. That, right there, is why I always feel like my orgasms are my own to have. Someone else can give me a ton of orgasms, and it will make me very happy, but in the end I always prefer to also give myself several during a partner sex session.
I have talked to many women who have a similar orgasmic response to me, and usually they have a similar sexual background to me (though not always). I have also talked to many women who find it difficult or impossible to orgasm during partner sex. I have talked to many women who must do a very specific and certain thing to themselves for a long time in order to orgasm. I have talked to women who can only orgasm through penetration, and women who can't be penetrated at all when they orgasm. I have talked to many men who have similar orgasmic responses; this is not just a phenomena that affects women. It really affects people of any gender, and can have some to do with sexual experience, or nothing at all to do with sexual experience. Everyone is just so different in their sexual response, and this is one the first thing we need to understand and respect about people when we consensually chose to have a sexual interaction.
In the context of sex work this fact is really no different. Many people seek out a sex worker because they want to realize a fantasy, and many sex workers are in the business of providing fantasy fulfillment. I do think it's important to understand that fantasy is it's own thing, though. If you're looking to authentically please a sex worker, the best way to do that is not necessarily to ask them what is pleasurable to them and expect that it will work. The best way to please a sex workers is to not put expectations on their orgasmic response; rather, focus on sensation that is pleasurable and focus on feeling good. Always allow for lots of self-stimulation, and be happy to witness an orgasm however it occurs.
Orgasms are wonderful, but they are not always the purpose of partner sex. To me, partner sex is about connection; emotional connection through the physical, a shared experience of pleasure. While I always want my clients to get what they want out of session with me, I personally never expect to be the one who gets them off, or for them to get off at all. In an ideal sex work world, clients should hold the same attitude toward their providers. A lack of expectations placed on both parties always creates a more relaxed, happy and enjoyable experience for everyone involved. This is my firm belief after many years of fooling around with as man people as possible.