A New Personality

(You handed Finn a bag of clothes and instructed him to change into them in a connected room. You heard a bit of shuffling and a small gasp while he was changing but eventually her exited the room feeling quite self conscious.)

(He wore clothes that you'd expect to be worn by a beautiful young coed. A tight thin white shirt and a skirt so short his penis would keep popping out despite how fruitlessly he tried to cover it.)

Finn: I feel ridiculous.

You: I think you look beautiful. (Finn blushes at this.) I want my office to feel like a safe place to continue discovering the sissy version of yourself. To do that, I have two rules. #1 During our sessions you are only allowed to wear feminine clothes. #2 In Femboi mode your name is Rose. Understand Rose?

Rose: Yes sir. I just feel uncomfortable sitting her with my cock out like a weirdo.

(You shrug and take out your cock as well. Enjoying the shock and blush on Rose's face.)

You: There now you're not the only one.

Rose: Wow. You're like twice as big as me. That's insane

You: Would you like to touch it? It may help you understand your urges more.

Rose: (takes a deep gulp) Um... If you think it'll help I guess so.

(Rose lowered herself in front of you and poked at your cock. Building up confidence until she was wrapping her hand around your shaft. Slowly pumping it up and down. Blushing more as her hands harden your cock.)

Rose: Sir you're so hard.

You: So Rose here's a good chance to show me what kind of Femboi you are. What do you think a girl in your position would do after making a man hard?

Rose: She'd..... She'd make him cum..... She'd..... She'd suck his cock.

You: So what are you going to do Rose?

(Rose stared at your cock conflicted for a few moments. But eventually she gave into her temptation and slowly wrapped her mouth around your cock.)

(Rose started very shy and slow. But eventually she started to enjoy herself. Bopping up and down faster and deeper. The pleasure eventually overwhelmed you. You grabbed her the back of her head and pushed her down as deep as she could take you. You came down her throat and gave her **** but to swallow. You cleaned yourself off while rose caught her her breath and tried to make herself presentable.)

You: You did great Rose. Good girl.

Rose: Thank you daddy

(Rose covered her mouth as soon as she realized what she said and rushed to the side room to change. After changing Finn rushed out the office with a quick goodbye and a bright red face. You chuckled to yourself as you started packing up for the night.)