Feminize him

"Yes Ma'am, any instructions?"

"Secretaries usually call their bosses mistress," Cassandra tutted

"Sorry mistress." Jake said blushing softly.

"Come to my home at 6pm tonight so we can talk about this."

"Yes mistress"

Cassandra had gone out to get some fun things for Jake and now he was here,

"Come in Jake, and strip also, its normal for a boss to use her secretary as a mannequin for uniform ideas." Cassandra said closing the door behind Jake.

"Obviously" Jake said undressing.

Now fully naked Jake was just standing in her living room.

"Well I was going to just do something normal but since you just confessed that every night you masturbate to me making you my sissy, slutty bitch" Cassandra said sitting down,

"Uh... yes... yeah uh I was doing it just last night." Jake said adjusting to this new truth.

"Well I don't think you'd do well as a man, your penis is tiny," that wasn't true, it was perfectly average but Jake didn't need to know that.

"That's kinda rude..." Jake mumbled

"No, it's just a fact. A fact that makes your micropenis hard when ever you hear it," Cassandra saw Jake's penis standing at attention, she guessed his brain was just adjusting "But a good secretary shouldn't get hard, it's so serious that bosses are allowed to make penis inspections and spank sissies who disobey."

"I- I'm sorry mistress" he said turning around to show her his ass.

"it must be embarrassing that every time you are spanked you cum." She gave it a firm smack while Jake came on her carpet, "Probably even more embarrassing that your doctor told you to lick up your cum so that you don't lose the proteins."

Cassandra laughed as Jake got to his knees and started licking.