Thank you for sharing your problem with us. Firstly, there are many factors that result in delay in ejaculation or sometimes absent ejaculations. You need to study your boyfriend’s case to analyse the true cause of his problems. Factors that can result in absent ejaculation can be either Psychological, due to some diseases or side effects of drugs that are taken. The psychological factors that can cause absent ejaculation are performance anxiety, decreased sleep, relationship problems or anxiety. Some diseases like high blood pressure, diabetes, pelvic surgery or neurological diseases can also result in such problems. Even some of the drugs are responsible for delayed or absent ejaculation like anti-depressants, anti-hypertensive or ant-psychotics. Since your boyfriend is taking some drugs for hypertension there are possibilities of facing sexual problems. Also your boyfriend seems to show depressive tendencies and you need to look into the problems which are causing him depression. More over such problems can be caused by stds too but since you both have protected sex this possibility is ruled out.
I would suggest your boyfriend to consult a good GP who can identify the actual cause of his absent or delayed ejaculation. More over you need to tell your boyfriend that there is no need to worry and he would recover soon. Hope you got the needed answer. Take care.