You may be looking for Time Trial Challenges in GTA Chinatown Wars.
“
Cross the final base with a girlfriend.
”
— In-game description
Home Run is an achievement/trophy in Grand Theft Auto: San Andreas.
Acquisition[]
Simply go on dates frequently with any chosen girlfriend of CJ. Different girlfriends take longer amounts of time to hit final base with, so CJ's first girlfriend, Denise Robinson, is probably best for this achievement/trophy.
Walkthrough[]
Grand Theft Auto San Andreas Home Run Achievement Guide