Dear Welcome to HCM We understand your concerns I went through your details. Painful sexual intercourse, known as dyspareunia, is rare in men. The cause is usually physical, but in some cases it may be psychological. The most common cause of painful sexual intercourse in men is an infection of the genitals, the prostate gland, or the urethra. In some instances, discomfort during penetration results from skin irritation caused by an allergic reaction to a particular brand of condom or spermicide. If you think that the pain is due to an allergy to condoms or spermicide, try asking your friend to changing to another brand. If the pain persists, consult your doctor. If you require more of my help in this aspect, please use this URL. http://goo.gl/aYW2pR. Make sure that you include every minute detail possible. Hope this answers your query. Available for further clarifications. Good luck. Take care.