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Answer by Calvin
The discomfort may be due to the head of his penis hitting the cervix
Answer by embroidery fan
He can meet girls at social events you enroll him in: church youth group, Parks & Recreation activities, community college sports classes that are open to high school students, volunteer work he can do (if he does it in girl-type places like hospital helper or with young kids, it's easier!), joining sports teams locally like youth football or basketball teams in the area, summer camps, clubs like chess club or reading club at the library. Even camp counselor at co-ed summer camp for high-school kids, if he's good at something. LIFEGUARD!!-always works!
Those are a few ideas!