As someone who used to deal with lots of repressed thoughts bc haha internalized homophobia haha purity culture haha internalized misogyny, what are your thoughts about Kaoru x repressed!reader? I see you interpret him as someone with some internalized shit in intimacy which I can see, so I wonder how it'd be a scenario of him with a partner with similar struggles as him while both of them being self-aware of this... Taking their time and being gentle while exploring their kinks and feeling more comfortable with each other... And sometimes just going wild without thinking, being too horny and repressed that they forget about being shameful... Also I think the pillowtalks with Kaoru would be the sweetest, they'd heal me - Kaoru pegger
Hmmmm well, Kaoru's internalized thoughts are primarily related to homophobia afaik. Because of that, I can imagine he often feels adverse to anything that emasculates him or masculinizes his partner. He can get over them and work through his issues one by one but time and patience is the key.
Purity culture is rough and can make intimacy very complicated in ways that are similar but not quite the same. Tackling both issues would probably be something to happen a bit independently from each other. Easing you into sex may be the first easy step then getting you more comfortable with it may be the next. You have to be able to have sex in the first place before you could tackle the issue that is internalized homophobia.
Once you are at the stage where you can have sex with ease, you can start pushing Kaoru's buttons a bit. You might have to forgive him for having a couple of knee-jerk reactions to things while you get him to open up a bit more. Maybe you can start off by taking the reigns in small things in sex such as by riding him instead of letting him do the work or by not letting him control the pace during other things such as oral sex. This step could also really help you deal with your own struggles with purity because it's building your confidence and encouraging you to be an active participant in sex
Once you get past the first barriers of both of your issues, it becomes a lot easier to deal with them. The hardest step is the first and the easiest is the second :)
pillow talks with kaoru would def hit. he's probably a bit chill in the afterglow of an orgasm but it's also probably a decent way of getting him to open up about his complexes and repressions regarding sex