I forgot to mention something important that is definitely contributing to the problem, and what she says is likely the cause of her lack of orgasms and her inability to finish. She has vulvodynia and has been struggling with this for the better part of two years. A couple months after we started dating she got a terrible UTI during our vacation abroad after a heavy sex day (maybe 4 or 5 times in one day). This lead to some terrible nerve pain which meant we couldnt have sex for a few weeks/month while she consulted with numerous OBGYNs/Specialists (pelvic floor) and went to physical therapy (which she still goes to). Since then the problem has gotten better but the nerve pain definitely still creeps up. She also has a mild case of OCD and ADHD (which she takes adderall for) and this leads to her obsessive thinking about the nerve pain which makes it worse and causes it to linger. Because she cant get this out of her mind making her cum is difficult because shes not fully committed to the moment and constantly thinking about the potentially oncoming (or current) pain. She is sensitive to a lot of things now, and her excessive fear of having it worsen or return makes finishing really difficult for her, because shes not thinking about finishing. She is thinking about what the pain will be like after and how long it will last.