Sex With Dr. Jess

Does Size Matter?


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TL;DR: Penis Size ≠ Pleasure
Does size matter? Not in the way culture tells you. Most penis anxiety stems from social comparison, not partner dissatisfaction.
Better is better, not bigger. Pleasure is about communication, creativity and presence, not inches.
Confidence starts inside. The average penis is totally normal. You’re not too small you’re too hard on yourself.
Where size does matter? Condom fit! myONE Condoms offers 60+ custom sizes for safer, more pleasurable sex.
Product recommendations:
We-Vibe Pivot for vibrating partner play
We-Vibe Verge for perineum pleasure
Last Longer in Bed Course for sexual self-regulation & confidence
Reframe your worth. You are not a measurement. Your penis isn’t a performance. You are worthy of pleasure, connection, and adoration.
Explore more:
Multiple Orgasms – Part I
Quick Connection Exercise for Couples
Penis Size, Pleasure & Confidence: Let’s Talk About It
Does size matter?? I receive so many messages and they often open with questions that dive straight into penis size, frequency of masturbation, and a plea for reassurance. And my response is almost always the same: You’re fine. You’re more than fine.
We live in a world obsessed with comparison and false benchmarks. Penis size is one of those cultural yardsticks, and for many, it’s a source of unnecessary shame and silence. But let’s be clear: Bigger is not better. Better is better. And better is about connection, pleasure, presence, and feeling good in your own body.
Brandon and I sat down to talk about the social pressure around penis size, locker room awkwardness, middle school posturing, and the assumption that bigger automatically means better in bed. Spoiler: It doesn’t.
The Social Side of Penis Size: It’s Not About Sex
Let’s talk about locker room syndrome. There’s real research, like the multi-country study by Annabel Chan, that shows most people with penises aren’t concerned about size in the bedroom. They’re worried about what other people (especially other men) think outside of it. Penis size has become a bizarre social status marker and a way to signal masculinity, not necessarily to enhance sex.
And the data backs this up: while over 85% of women say they’re happy with their partner’s penis size, only 55% of men say the same about themselves. That gap isn’t based on pleasure, it’s based on social messaging.
Positions, Pleasure & Personal Preference
If you’re wondering whether you need to adjust your sexual positions based on penis size, the answer is: not really. There’s no universal rulebook. For some, shallower penetration can be more pleasurable. Reverse ride, lap dance grind, vibrating penis rings, these can all enhance sensation regardless of size.
If you’re worried about going “too deep” and hitting the cervix in uncomfortable ways, look into options like a penis bumper, a stackable buffer that allows for full thrusting with a shallower feel. Pleasure doesn’t come down to length, it comes down to care, communication, and creative curiosity.
Penis Anxiety Is Real, But It’s Not Inevitable
One listener messaged to say he was afraid to reenter the dating world after a breakup,
...more
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Sex With Dr. JessBy Dr. Jess O'Reilly

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