Three insecurities men (may) never admit during sex

Taken & Claimed
3 min readMay 7, 2024

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Oufffff! That’s right, turning the tables from a society overly focused on women’s imperfections. The truth is, regardless of our gender stereotypes, we all have insecurities that don’t end at the workplace.

It’s time to talk about both sides — and in bed.

This article contains the results of my well-researched, non-scientific survey of men in their 30s to 50s to clarify this critical conversation. I’ve also interviewed selective women to get a sense of how well each side of the equation might (not) understand each other.

The results can be found below.

  1. Men fear being unable to please their woman — this is listed first because it is THE top thing on their mind. Pleasuring a woman’ hard-coded biological drive they have to perform. Think about the competitive aspect of men; yep, that’s what I’m referring to. Their ability to get you off is some measure #girlmath of how manly they are. Please indulge yourself knowing this.
  2. Men are insecure about their bodies — Cosmo magazine brought up this concept 10 years ago when they wrote a similar piece on insecure thoughts men have during sex. They cited a dozen reasons for insecure thoughts men have from “Oh, man, how is my body this weirdly shaped?” or “I hope she doesn’t look at my balls.” In a personal interview, a female friend cited a man outright saying, “I’m so fat right now”.
  3. Men are insecure on where their penis stacks up — essentially, is the dick enough for her? In my male interviews, it came up that they want to know where it stacks on the spectrum of other men came up as did. For others, it was just about whether it was “good” for the woman. Of course, no man would ever ask this so we often fall in the silent dance where the dick becomes almost a third party in the scene. In my female opinion, I also never share kudos to a man’s penis size early on because there’s no win. If you tell him it’s big, his ego gets too big. Meanwhile, you never tell a guy it’s too small or he’ll be in therapy. Focus on telling him about YOU and what you FEEL. Tell him what feels good or really fucking good.

So now what?

If you’re a hetero-women reading this, a few tips:

  1. Men have feelings too. Realize (if you haven’t already) that men have insecurities naked and, in general, just like women. Despite the external layer men put off to society, they have a higher need for connection, but it takes a lot of excavation, trust, and potential therapy to get there.
  2. Depending what stage of your relationship is, evaluate how to communciate with your partner. Personally, I would wait until you’re in a committed relationship to provide that level of support and encouragement because those are girlfriend things to offer, i.e. #knowyourworth. Meanwhile, I would consider it awareness and confidence that you aren’t the only one that feels on stage and harbor a little soft spot for your man.

If you’re a hetero-man reading this, a few tips:

  1. Get Out Of your Head. Women will love the sexual experience more when you can connect with them and make it about their pleasure. If you feel small, find ways to improve your foreplay game.
  2. Personal Gut Check. Time for a litmus test. Ask yourself if you are insecure because 1) it’s your issue of self-worth and body image that you need to work out OR 2) is it your partner making you feel insecure by their comments or being. This is then a chance to re-evaluate why you are with a partner who makes you feel lesser than.
  3. Get Smart. Learn other ways to take charge of sex and intimacy and make suggestions. Like public speaking, it’s hard at first, but once you do it, you look confident AF and hone a whole new skill and layer of opportunity.

At Taken & Claimed, we exist to provide practical tips and conversations we all should be having to support healthier, more playful, sexual lives and relationships.

Our list of sex resources has just started, and you can access our Play Resources on our website. We also welcome hearing from you, and email hello@takenandclaimed to tell us what you want to know. You can also follow us on Instagram @takenandclaimed.com.

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Taken & Claimed
Taken & Claimed

Written by Taken & Claimed

T&C was created to help you with your romantic relationships by creating more moments of play, connection, and intimacy.