Black Tie Sissy (Reluctant Feminization, Crossdressing, First Time)

Brian has really done it this time! His practical joke results in his roommate Carl missing an important meeting at work, and Carl has had it.

After giving it some thought, Carl figures out the perfect way for Brian to make it up to him. There's an important office gala dinner on Saturday night, and Carl's date backs out at the last minute. It doesn't take him long to figure out that Brian would be the perfect replacement. He just has to turn him into a beautiful woman in time for the party.

After the gala dinner, Brian (Brianna now) finds out that the after party at the hotel is really a party for 3 - her, Carl, and Carl's boss!