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I am a 19 year old woman in a relationship with my awesome boyfriend. We are pretty much satisfied in our sex life, mostly because of all the cuddles and love. There is a question that I have, though. Usually we go at it (and do many types of sex) for a couple of hours, and then when we are ready to finish things, we both touch ourselves until we climax. (And give ourselves a great show.) I was wondering if there is supposed to be a point in the relationship where we transition from mutually masturbating to making each other come? I feel like this is something he wants since he keeps telling me to keep going until either I come or he comes. However, it is then frustrating because I know it doesn't happen. Are there some techniques you can give to help us maybe transition from mutual masturbation to partnered orgasms? Thank you :)
There's no type of sex or orgasm that's "better" or more appropriate for a certain point in a relationship than another. So if you're happy with how sex and orgasms are happening between the two of you right now, that's 100% ok.
There's no point at which people in a relationship have to change from having sex one way to another; the "right" kind to have, in any relationship, is really only going to be the kind that makes the people involved happy. Doing things the way you do right now doesn't reflect poorly on your relationship at all; in fact, it sounds like you have things figured out pretty well in terms of what feels good for both of you.
Keep in mind, too, that orgasms don't have to (and really, in my opinion, shouldn't) be the main goal or focus of sex. The intimacy you have with your partner and all those great feelings before and after you have orgasms (or that you may experience without having an orgasm at all) are still important, and I'd encourage y'all to look at your sexual experience together as something much bigger and richer than just "stuff that leads up to orgasm."
I think it would be a good idea to take some time, ideally not when you're having or about to have sex, to talk with your boyfriend about your shared expectations and desires around this. Maybe you can ask him what's on his mind when he's asking you to "keep going" during sex - is he wanting to continue what you're doing because he might reach orgasm that way? Is he thinking you will, if you continue? Is this even something that is frustrating him at all? I'm going to leave you with some articles about orgasm and sexual response, and they may be helpful to share with him as well.
If you or your boyfriend are interested in exploring other ways to have sex that might allow orgasms during partnered activities, then by all means, go for it! It could be a lot of fun to do that exploration together.
One first step could be showing each other how you touch yourselves when you're masturbating. It may take some experimentation to be able to explain or demonstrate what you do to your own body so that someone else can understand it, but it could be an easy place to start if you want to try something different.
You don't need to think about this in terms of transitioning from one set of sexual activities to another, though; different kinds of sex, whether or not they include orgasms, aren't arranged in some secret hierarchy that reflects well or poorly on someone's relationship or sexual ability. It's certainly fine to branch out and try other things if you are both into it, but that doesn't mean you have to leave other enjoyable types of sex behind! Also, I think it's important to note that if what you're doing right now, sexually, is working for you, you don't have to make an effort to reach orgasms through partnered sex at all.
I'd really encourage you to approach any experimentation, if you do get into it, as something that's fun and mutually enjoyable to try and not something you and your boyfriend are doing because you think it'll be "better" in some universal way.
There just isn't one right way for a couple to experience orgasms together, and mutual orgasms from the same sex act isn't any sort of goal or benchmark you need to push yourselves toward if it isn't happening right now, or if you give it a try and find it doesn't work for you. Orgasm is so far from a one-size-fits-all concept that trying to fit into some supposed platonic ideal of a "proper" orgasm is likely to cause a lot of stress for both of you.
Also, I'm not sure what kinds of sex you're having other than mutual masturbation, so this may not apply to your situation, but I do want to point out it's pretty common for us to have users coming here referring to only vaginal intercourse as "sex" and treating that as the ultimate sex act, or the only "real" kind of sex, which we very strongly disagree with.
Hand-in-hand with that idea is often the thought that orgasms that happen during intercourse are more valid than others. So I want to remind you that many people do not reach orgasm through receptive vaginal intercourse or other vaginal stimulation. We have a great article about this topic that may be helpful for you and your boyfriend to read: The Great No-Orgasm-From-Intercourse Conundrum
I'm going to leave you with some links about orgasm, pleasure, and sexual response you may find helpful: