Dress her

John got out a chest full of costumes and took out one befitting a secretary. It was a reserved, form-fitting business suit (sans bra and panties), with heels and glasses. The buttons were unbuttoned just enough to show her cleavage.

"Now to press your forehead..." John said.

"Mr. Doe, your 4 o'clock seems to have cancelled," Jessica said in a sultry, seductive voice. "Perhaps I can keep you company in the meantime?"

John was enjoying this. And he had the whole day to play with Jessica and use her triggers.

Speaking of...

"Sexy shy secretary!" he said, wanting to see a shy, flirty side of Jessica.