I also had what I guess would be called “anorgasmia” during sexual penetration for many years, and only rarely orgasmed during sex early on. I might have had a weak/loose PF, but mostly I had mental connection problems - I just had no clue how to orgasm from sex and it didn’t happen on its own. Could orgasm from masturbation just fine, but the building feelings didn’t translate to sex.
As for how it felt, I could feel everything happening, and it still felt pleasurable, but the feelings didn’t have a high ceiling cap if that makes sense. My orgasms usually build from the base upwards, and I had to really go all out for the feelings in my base to get very intense during sex, and it didn’t cause many ik’s. For me, feelings that we’re just pleasurable and feelings that built an orgasm were two different things. Just learning how to build an orgasm from sex and especially oral was an ordeal. Was very frustrating/demoralizing.
Through communication and willing to help partners I’d say my mind-to-feeling connection has me to around a low to normal orgasm-building level during sex now though. The feelings are the same, but I can take how they effect me to a much more intense level with altering angles, speeds, and movements. Sometimes muscle memory kicks in and I don’t have to think about doing the things to build an orgasm and I have to slow myself down or do a RK to drop sensitivity if I want to prolong it. Although, my lady now also knows more ways she can move to make me build too, so she can really push me to an orgasm when she wants to. And getting into kegels has been helping a little to decrease the time to build to the ponr as well.
Have you looked into Dry Orgasms/Multiple Male Orgasms at all? You might find that helpful in getting the first sensitive orgasm out of the way without losing the erection. Doing a DO is how I combat my lady forcing me to an earlier orgasm than I want when she gets feisty and wants to take control over my orgasm
a strong upper kegel held and locked from just before the ponr all the way until the orgasm subsides is what works for me. Timed and held properly you still have the orgasm, but you don’t cum and don’t lose the erection. Sensitivity drops down to a lower level afterwords so you can resume sex after, and you can chain them for MMO’s. Just something to look into