Q: I’m newly divorced and have started a relationship with a man I’ve known and deeply cared about for decades. The 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 is a very generous lover—he turns me on like crazy, and I regularly come while sexting with him. But I have yet to have an orgasm with him. In the past, I’ve had an orgasm with a partner only from oral or very occasionally from digital clit stim. My ex-husband was not skilled at oral, so I always had to fantasize pretty hard to get there (and regularly chose not to bother). My new partner has amazing moves and amazing oral skills. And he’s willing to keep at it for as long as it takes. But regardless of how amazing I feel when he’s going down on me, every single time I eventually hit a wall where I am just done. That said, I haven’t had a single session with him where I’ve been left feeling unfulfilled, despite 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.) 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’m 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
You aren’t able to pull away from your current partner in the same way. Nor do you want to. And, hey, wanna know why you come when you sext with him? Because sexting is assisted fantasizing. You’re alone when you’re swapping those dirty messages with Mr. AmazingMoves, NOPE, kind of like you were alone when you were having sex with your ex.
Q: I’m a 24-year-old woman, and three weeks ago I got out of a long-term relationship with a guy in his mid-30s. Over the last few months of the relationship, I started falling for someone else and began dating the new guy pretty much immediately after the breakup. When should I tell my old boyfriend? We agreed to stay friends, and we still talk and see each other at least once a week. I want him to hear it from me, but I’m not sure how much time is appropriate/respectful. —Don’t Wanna Be an Asshole
