Thanks for your query.Based on the facts that you have posted it appears that your friend has sustained injury to his urethra
during sexual encounter.
Since this has happened during intercourse possibility of fracture
penis can not be ruled out.
He has to consult qualified Urologist
for clinical assessment and has to undergo tests like Ultrasound
scanning of the penis and colour Doppler study of the penis to rule out fracture of the penis.
The future course of action will depend upon the findings of these tests.