For nearly all men, ejaculation is accompanied by orgasm and is a highly pleasurable event. However, for some men, ejaculation can be a painful event rather than a pleasurable event. When orgasm itself is painful this is called odynorgasmia. The cause of the pain typically involves some sort of reproductive tract infection or disorder such as prostatitis, pelvic tension disorder, or seminal vesiculitis. Prostatitis can cause painful ejaculation as the tender, inflamed prostate contracts during ejaculation, sending pain signals to the brain. Pelvic tension can also be painful as the tense, sore BS and IC muscles that assist with erections and ejaculation contract repeatedly during ejaculation (think of contracting an extremely sore muscle at the gym). Seminal vesiculitis can be painful as well as the seminal vesicles contract during ejaculation. Sometimes this pain can be felt as pain in the urethra and perineum after ejaculation.
Treating the underlying prostatitis, pelvic tension disorder, or seminal vesiculitis usually resolves the pain. Sometimes, taking an anti-inflammatory pain reliever like ibuprofen or naproxen 20-30 minutes prior to sexual activity can decrease pain transmission which may allow a man to feel more pleasure than pain.
Some men can also have pain elsewhere in the body during ejaculation. One of these types of pain is a severe headache that accompanies ejaculation. These headaches are called ejaculation headaches.