My boyfriend (19M) and I (19F) generally have a really good relationship, I’ve been with him officially for a few months now. There is nothing I can complain about and the sex is great, not to mention how he is as a person too.

I know this problem has probably been discussed hundreds of times on this subreddit, but my boyfriend has some insecurities he just cannot shake.
Firstly, despite me saying it’s big often and telling him how much I enjoy sex with him, he is convinced he has a small penis and it hurts his self esteem. It’s just slightly above average and like I said it’s great for me, but he just cannot get rid of that thought no matter how hard both of us try.
Secondly, he can’t stop thinking about “lack of experience” and comparing himself to my past partners. He is my first official boyfriend but I’ve slept with two other men in the past, I’m his first sexual partner and official girlfriend. Just because I have 3 bodies and he only has 1, he feels like he is significantly less experienced than me. I messed up in the early stage of our relationship by telling him both of the men I was with had big dicks with lots of partners, and I regret that heavily. As far as I know he has never seen either of them but that doesn’t change how he feels by comparing himself to them.

TLDR; Great relationship, great sex, but my boyfriend feels insecure and inexperienced.
Does anyone have similar experiences to share or advice about this problem?

6 comments
  1. **How** and ***why*** is he able to compare himself to your past partners at all in the first place?

  2. Honestly, he will feel like that, till you’ve had enough sex . Nothing you say will convince him. But, he needs to know that he’s making progress in sex and feels like he got the hang of it.

    Review his performance. Tell him he was better than the last time …. Make him come up with some raunchy sexy moves .

    The more he fucks, the confident he gets. Then he won’t worry about the other men!

  3. I had a lot of casual sex and ONSs but didn’t have my first actual GF until I was 22. I can honestly say that I was probably not a great lover at first with my GF. I’ve found that having a deeper relationship allowed to me to explore more and become a better sex partner. So I don’t really think it matters as much as he thinks it does. The only way to gain more experience is by letting go of the insecurity and trying to get better.

    Is there something you could explore together? Are there any kinks/positions/sex acts that both of you would like to try? Maybe try doing something your both new at so you’re on the same playing field for a change. It might help with his confidence. But you can’t change dick size and it’s not worth worrying about unless he plans on only dating virgins

  4. Do some napkin math and let him know once sex with him comprises 90% of all the time you’ve ever spent having sex. Point out how ridiculous it is for him to feel unequal in terms of experience when it’s a difference of less than 10%.

    Regarding dick size, I’m afraid there’s nothing you can do about that. All I can say is that once you two are having consistently great sex, concerns about dick size typically fade.

  5. compliments. whenever he did something during sex that make you feel good, tell him that or even exaggerate a bit so it will build his confidence.
    if he asked stupid question “am i better than your ex?” then you gotta tell the white lie when he’s not.

  6. Without knowing him it’s hard to say anything authoritatively. It’s possible this isn’t your fault at all and completely beyond your control and even if you had said nothing you’d still be in this situation.

    Maybe if you get to know him more you can understand what makes him feel more confident and satisfied during sex other than just physical pleasure. Maybe he’ll grow out of it eventually.

    Spend more time with each other doing romantic things and maybe you’ll learn more about each other.

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