I am newly divorced and have started a relationship with a man I’ve known and deeply cared about for decades. I am more open and honest with him (both about sex and in general) and trust him more completely than my ex-husband or any prior partner I’ve had. We are in a long distance relationship which means we’ve only been able to fuck a dozen or so times, but our sex is amazing—from start to finish I feel better than I ever did even in the best moments with my ex. And in the most intense moments? He makes me see stars. He has remarkable oral skills and is a very generous lover—plenty of foreplay and great communication. He turns me on like crazy and I regularly cum during sexting with him. But contrary to all this, I have yet to have an orgasm with him.
In the past I have only had an orgasm with a partner from oral or occasionally digital clit stim (but even when it worked, playing with my clit during sex was rarely appealing). My ex-husband was not skilled at oral—very lackluster and repetitive. I always had to fantasize pretty hard to get there (and regularly chose not to bother with an orgasm during sex with him). My new partner has amazing moves I didn’t know existed and has me screaming out pretty much nonstop. He has made it very clear that he is willing to keep at it for as long as it takes to get me there, and I believe him. But regardless of how amazing I feel when he’s going down on me, every single time I eventually hit a wall out of nowhere where I am just done with oral and want to fuck. (And the fucking is absolutely incredible, too.)
I haven’t had a single session with him where I’m left feeling unfulfilled, regardless of the lack of orgasm. In contrast, any sex with my ex that didn’t end in an orgasm left me feeling frustrated or worse yet, bored. (There were also times when I’d ask my ex to leave the room so I could masturbate after sex. It was easier for me to do myself. But I have no desire to to that with this partner, because the orgasm isn’t the fun of our sex—being with him is.) I don’t necessarily feel the need to cum. He isn’t pressuring me or making me feel guilty for not getting there—he gets that responding that way would only make it more unlikely. But I feel like an orgasm is the gold standard for sex. It feels almost disingenuous to say he is the best I’ve ever had if I’ve never managed to get there.
Do you have any ideas as to why I can’t get over that hump? I wonder if I just need him to be more boring and repetitive so that I can focus, but if that’s the case, is it even worth it? Why would I want to make the sex worse to make it “better”? Or should I just be satisfied with the mind-blowing sex I am having, even if it means I don’t have an orgasm? Is it ok to give myself permission to give up on partner-based climaxing?
No Orgasm Possibly Ever
Beware those self-fulfilling prophecies! If you sit there—or if lay there—telling yourself that being with Mr. AmazingMoves means giving up on "partner-based climaxing," NOPE, you're increasing the odds that you'll never have an orgasm with this guy or any other guy who's better at sex than your ex.
Here's what I think the problem is: you had tons of shitty sex with your ex—but you could climax with your ex so long as you "focused," i.e. so long as you were able to fantasize, "hard enough to get [yourself] there." Your ex provided you with some half-assed oral and/or uninspiring digital clit stim that didn't interfere with your ability to focus/fantasize. In other words, NOPE, with your ex
you were able you had no other choice but to retreat into your own head. You relied on your own erotic imagination to get you there; you may have been physically present during sex, NOPE, but you were never emotionally or erotically present.
Because Mr. AmazingMoves' moves are so amazing—because he turns you on like crazy, because whatever he's doing feels great, because sometimes you see stars—you aren't able to absent yourself, NOPE, you aren't able to retreat into your own head. For years, for decades, you had to essentially remove yourself from the room so you could focus/concentrate on whatever it was you needed to focus/concentrate on in order to come; sometimes you even asked your ex to literally remove himself from the room so you could get yourself off. You created a powerful association between going to that private place—pulling away from your partner emotionally, erotically, and sometimes even physically—and climaxing.
But you aren't able to pull away from your current partner in the same way. Nor do you want to. And, hey, ever wonder why you're able to come when you sext with him? Because sexting is assisted fantasizing—you're in your head when you sext with Mr. AmazingMoves, just like you were in your head when you were literally having sex with your ex.
It's going to take some time to carve a new groove—it's going to take some time for you to make a new association that allows you to be fully present (emotionally, erotically, physically) and able to climax with Mr. AmazingMoves. The trick is not to rush it and, again, not to box yourself in with the kind of self-fulfilling prophecies you ended your letter with. Relax and enjoy the amazing sex you're having with Mr. AmazingMoves, NOPE, and instead of telling yourself you're never going to come during partnered sex again, tell yourself that your orgasms will come again. It may take some time, sure, but trust that your body and your brain are already hard at work carving that new groove.
One practical suggestion: the next time you have sex with Mr. AmazingMoves, let him go down on you—but tell him in advance that you're going to ask him to stop long before you hit that familiar wall. Then stimulate yourself, either digitally or with a vibrator, while he holds you. If you need to lean back and close your eyes, lean back and close your eyes—but don't retreat into your own head. Ask him to talk to you while you get yourself the rest of the way there. A couple of dozen self-administered orgasms with both of you in the room—in the room emotionally, erotically, and physically—will speed up the new-groove-carving process along.
UPDATE: Raindrop is a little more concise...
Relax, it will happen.