The unidentified woman later showed symptoms of the disease and tested positive for it.
Raymond, 38, is accused of "consciously and purposefully" withholding knowledge that he had the disease and continuing to have unprotected sexual relations with the woman.
Court documents, dated 2012, showed that the singer paid $2,754.40 to the woman to cover her medical bills.
According to documents published by Radar Online, the woman "feels that her health and body have been ruined."
“Getting infected with genital herpes from Raymond has devastated (the victim),” documents said. “She ... has suffered severe emotional distress and has been extremely depressed ... Not a day has gone by where she does not feel desolation and despair about her herpes infection knowing that there is no cure. Her infection has destroyed her sense of self, wholeness, health and beauty and she fears that she will never be able to have the type of relationship she had hoped for.”
The complaint was filed in at the Superior Court in Los Angeles, California, where it is illegal to knowingly or recklessly transmit a sexually transmitted disease.
According to the Centers for Disease Control and Prevention, one out of every six people aged 14 to 49 has genital herpes.
Raymond, who remarried in 2015, has not commented.