“Her ex could get her off, but I can’t seem to…” | Concierge Confessional
Sex comparisons can sneak into even the most loving relationships… especially when past partners get brought into the bedroom.
This week’s Concierge Confessional comes from someone who’s doing a lot right… but can’t quite shake what’s bothering him.
Concierge Chloe breaks down why this isn’t about “performance,” and how to reconnect without letting the past steal the spotlight.
Concierge Confessional: You Asked, Concierge Chloe Answers
Arya Member:
This feels kind of awkward to admit and we’re genuinely trying to figure it out together. But… she doesn’t orgasm from penetration with me.
And honestly, it wouldn’t really be an issue on its own… we do other things, I go down on her, and that always works. But it still gets in my head sometimes. Especially because she’s told me that with her ex, she could orgasm in missionary.
Apparently, a big part of it was eye contact and dirty talk while they were in that position. The problem is, she’s a lot shorter than me, so logistically it just doesn’t work the same way for us. I can’t really get down to her eye level in missionary, and it feels like that whole dynamic is missing.
I don’t know… I’m not sure what to do with that. Before this dude, she thought she couldn’t cum from penetration, but then he proved her wrong. How do I stop it from bothering me so much?
Concierge Chloe answers:
First off, I just want to say: it really comes through that you care about her and about your connection. This isn’t a “you’re doing something wrong” situation. It’s a figuring-it-out-together situation. That’s the right approach.
When she talks about eye contact and dirty talk, it’s likely less about the exact mechanics and more about how connected she felt in those moments.
Feeling seen, desired, and emotionally in sync can make a huge difference in how easy it is to relax into pleasure.
One thing you can try is to slow things down a bit and stay verbally connected: tell her what you’re noticing, what you love about her, and what you want to do next. That kind of presence can be just as powerful as any specific position.
It can also help to get a little playful and flexible with how you’re positioning yourselves.
If the missionary position makes eye contact tricky because of your height difference, that’s not a dead end, it just means you might need a small adjustment.
A pillow or wedge under her hips can bring you closer. Face-to-face seated positions (you can look up “yab-yum”) or side-lying positions often make closeness feel much more natural.
Even simple things, holding her face, guiding her gaze, pausing to really look at each other, can recreate that intimacy she’s describing.
And it’s worth gently letting go of comparisons to the past.
Just because penetration led to orgasm for her with an ex doesn’t mean it has to work the same way forever.
Bodies change, relationships change, and what feels good evolves over time.
Inviting her to talk about what feels good now, without pressure to recreate an old experience, can actually open the door to even better sex for both of you.
The big thing here is staying curious instead of critical, of yourself and of the situation.
You’re not competing with a past partner; you’re building something new together!
Focus on what helps her feel connected, what turns you on, and what brings you closer as a couple.
When you approach this as a shared exploration rather than a problem to solve, intimacy tends to deepen naturally.
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