How do I build his confidence back up

[JuliaGallo]

Me and my boyfriend have been going out for about six months and have been official for exactly three months today.
About two months ago we were on vacation with his parents and my phone was playing music on the speaker as we went to bed, he said he went to turn it off because he couldn’t sleep but then found himself looking trough my messages with my BFF in WhatsApp (keep it in mind that we hadn’t spoken to each other there for months, so the messages there where from four months before it happened) and saw a comment of mine about our first time where me and my friend more or less made fun of the fact that he couldn’t get hard and I said I thought his penis was kind of small (which now I know for a fact is actually quite big but I was used to seeing penises in porn) this crushed him and he cried to the point of having a nosebleed.
The next morning he didn’t say anything to me about what had happened because he didn’t wanted me to feel dislocated in the trip but at night I confronted him (because I clearly could see something was off) and he started saying how sorry he was about reading my messages and how what he read had hurted him badly.
Keep it in mind that at this point the sex had become amazing (as it still is) he always makes me finish and I genuinely feel a connection to him during it that I didn’t even thought could be possible to feel for someone. But the problem is that (by the point he saw the messages) he stopped saying I was the best sex of his life and I feel like he genuinely doesn’t enjoy it as much as he did before because he constantly worries that I am not “enjoying it” (in the beginning of our sexual relationship I was a virgin so I didn’t really enjoyed it the first few times but now I do love it and love him very much).
I can still tell he feels like he is being held back from pleasure because he always worries that I am not feeling any; the other day took me a little longer than usual to finish during oral sex and he nearly had a panic attack remembering what he read.
I really don’t want this to ruin our relationship, I love him very much and have fully forgiven him for this one invasion of privacy and just want to help him cope with this and reassure him that I do enjoy sex with him so so much.
Another issue is that I have a higher sex drive than him, and he has expressed multiple times how he feels “insufficient” for me because of this which couldn’t be more wrong because he literally gives me more than two orgasms every day and I do feel completely satisfied with him in every aspect.
I just need help, how can I help build back my BF self esteem? I compliment him on every single chance I get and try to make sure he always knows how much I love him but I am so afraid this won’t be enough and a stupid comment I made to a friend when I didn’t knew nothing about sex is going to ruin us. It just almost physically hurts me to see someone I care about so much hurt I just want to help him please help me do that.

[Emily N]

Hi JuliaGallo,

I agree that he definitely violated your privacy by going through your messages, and should not have done so. I’m glad he apologized about this. I want to check in, do you feel like your privacy is being respected now?
But I can also understand that for him it could be very hurtful to see a message where your body and sexual experiences are made fun of, especially by someone you love/trust.

It sounds like you might have already talked about these feelings, but it sounds like this is affecting your relationship and it would be worth having an intentional conversation. It might be helpful to acknowledge that the messages you sent were harmful and apologize. You can also reiterate that the messages you sent don’t reflect how you feel about the sex you are having together now. Thinking about what you said about when it takes longer to orgasm, you can remind him that orgasm is not the only goal of sex - sex can feel good for so many reasons, and you can talk to him about this, too. Orgasms and sex can feel different to our bodies on different days, and doesn’t always reflect what a partner is doing.

I’m also hearing that you are already actively complimenting him and validating him, that’s great! Have you asked him if there are other things you could do that would be helpful for him? I think it’s also likely that there are other things that could be affecting his confidence, not just the messages you sent. Have you had a broader conversation about whether other factors are influencing his confidence?