Hi Thank you for asking HCM I have gone through your query.You should get rid of anxiety and stress including performance anxiety because those are most offenders in many people.You can try squeeze and stop technique.You can stimulate your partner before getting yourself stimulated.You can deviate your thought to something nonsexual when you about to near ejaculation.You can put on a condom or condom with anesthetic which will decrease the excessive stimulation on penis and there by prevent premature ejaculation.If all these not helping you can approach a psychiatrist for behavioral therapy and medicinal management like antidepressants.SSRIs like Paroxetine as well as Clomipramine helps in many.Short acting SSRI Dapoxetine can be used in need also. Regarding your question no 2, pain while inserting for your female partner-if the pain is while entering it can be due to lack of lubrication or vaginismus.If it is while deep penetration it can due to endometriosis or pelvic inflammatory disease.A pervaginal examination should be carried out by a gynecologist to rule out that.Hope this may help you. Let me know if you have any further query.