When Sex Is Painful. Gynecologic Problems. How common is painful sex? What causes pain during sex? Where is pain during sex felt? When should I see a health care professional about painful sex? What causes sexual response problems? What kinds of gynecologic conditions can cause pain during sex? What can I expect when I see my . Did he break my virginity with dry humping? Share | Anonymous. asks: I am a 23 year old virgin and have pledged to remain so until marriage. I recently had an intimate moment with one of my guy friends. I sat on his lap while he kissed my neck but he had an erection and I felt his pennis almost at the entrance of my vagina thought I had all my clothes . Sep 29, · pain after dry sex. i orriginally posted this on teens health but belive it should be on here, would appriciate any help on the subject: i was at my boyfriends house 2 nights ago and we were having dry sex, the problem was that we ended up getting quite rough. It became painful and alough we stopped, my vigina lips were swollen and .