Seducing a Straight Man (Feminization, Crossdressing)

Craig can’t believe it! He’s a contestant on the Impossible Challenge TV show, the show where you win big money for completing crazy challenges.

His first challenge is a piece of cake. All he has to do is run out into the street and get an unsuspecting stranger to cut off a lock of his hair. He wins the six hundred dollars easily.

The second challenge, however, is worth a lot more money and is going to take a lot more work: He has to seduce a straight man. Craig’s a straight man, and he’s got to seduce one! It really is an impossible challenge!

The show will help him: they’ll dress him up as a woman and feminize him, but he’s on his own for the rest of the challenge. Craig’s conflicted, but the challenge is worth a lot of money. There’s no way he’s going to fail…

Author's note: This is a crossdressing and feminization story with a happy ending!