I had bounced around the idea of an anal stud, but injecting a little pragmatism:
Guy and gal dating. He's great, but has small dick. She has a hard time getting off with him. He suggests anal. She had tried it before, but her last boyfriend didnt prep properly so it hurt. With current bf, she goes ahead because even if he botches it, he Wont hurt her with that little thing. He gives it to her pretty good. She actually manages to cum. Later she and gf are talking, and she confides about anal with bf and that it didnt hurt. Gf can't stop thinking about it. Gf's own bf wants anal, so gf sneaks to small dick and seduces him. She reveals that she knows he's great at anal and she's curious. Fast forward, guy knows he is kinda small, but has had practice getting girls in the back door.
Smart is sexy!!!