He has to cross dress

"Oh, but I can't give you a job." she said, watching as his face fell, "I'm sorry, but I need a woman at the front desk, it puts people at ease. You're feminine, and if it was just talking on the phone you could probably pass as a woman, but not in person. You'd need to change your hair, and wear makeup and a dress. Sure, it's not hard, and you'd get more money and maybe you could finally get a date and make your mother happy, but I'm sure you'd refuse the offer outright."

He hesitated, she had made it sound pretty good, but it was true he should probably refuse. On the other hand, what did he have to lose from it? His masculinity, he pointed out to himself. But what good had it done him? It's not like he had a girlfriend who would care, and his life wasn't going anywhere. So he'd dress a little differently at work, that wasn't such a big deal. "I'll do it."

"Are you sure? I don't want you to be doing this for me or anything, I'm sure I can find an assistant."

"I'm not, I just think it's- that it's a good idea."

"Really? Prove that you're doing it because you want to. Say that you want to cross dress and work for me."

His cheeks tinged with color, but he tried to keep his cool as he spoke. "I want to cross dress, and work for you."

"Wonderful. Now, I'm going to take you to the hairdresser and fix your hair. It's far too messy, okay."

"...Okay." he said, wondering if he had made a mistake as she led him out of her office and locked the door. She took him onto the elevator, and soon they were at a Salon.

She told him to sit down in the waiting area and talked to one of the hairdressers she knew for a while. She called him up, and the hairdresser sat him in one of the chairs. Then the hairdresser talked to Wendy out of his earshot.

"Is there anything special you'd like me to do with him?" she asked.