8. He has caveats.

“Sure, we’ll have her show me exactly what she did.”

You’d been hoping to be the object of the demonstration, Annabelle gave truly excellent handjobs, but you decide to let that one slide in the interest of cementing your relationship with Jack. If you had an in with the hiring office, you’d have full control.

You buzz for Annabelle and moments later she walks through the door. She looks a little afraid. You suspect she thought that by reporting she’d never have to interact with you again.

“Annabelle, Jack and I were just discussing our morning meeting.”

She swallows the lump in her throat and nods.

“And he thought it might be best if you show him what you did.”

She looks over at Jack and when he nods, moves to stand behind him.

“I… I just gave Mr. Howard a massage like this.” She squeezes Jack’s shoulders a couple times. “And then he told me to give him a hand job.”

“Annabelle, I told you to continue as you do when you usually give massages.” You speak sternly, as if chastising a school girl. “It was your choice to continue as you did.”

She blushes hard.

“Is that correct Annabelle?” Jack jumps in. “You told me he told you what to do.”

“I– well… but he did tell me! He told me to do what I do for my boyfriend. Which was that!”

“Yes but he had no reason to know that.” Jack adopts your admonishing tone. “And that matters Annabelle. I think the only way to settle this is through recreation.”

“I agree wholeheartedly. Jack, you be me so you can really experience things.”

He smiles as you follow through on delivering the teen intern to him.

“You can begin, Annabelle.” Jack sits back in his chair and waits for her performance to begin.

Annabelle tentatively moves to stand behind Jack. She places her hands on his shoulders and begins to massage the internship director properly. He sighs and relaxes into her hands. It’s not long before you notice his hands move to try to hide a growing erection. Annabelle repeats her words from this morning and you fill in your dialogue. Obediently, Annabelle moves to free Jack’s cock to continue the massage. Jack groans in pleasure as you add the next things you said. You and Annabelle trade dialogue as she jerks off her program supervisor.

Suddenly Jack grunts and shoots a load onto Annabelle’s face. The girl is shocked as two more spurts land on her face and exposed cleavage.

Jack sighs contentedly. “Well. I think we can all see that Annabelle did initiate this encounter. Richard, as her internship supervisor, you devise some kind of punishment for her.”

He stands, does up his pants and smiles at you before leaving your office with a spring in his step. Annabelle is still kneeling in the same place, glazed in Jack Warren’s cum.

What to do about Annabelle Wilson? (roll +hard)

• 2-5: She escalates the situation
• 6-9: you’ll find an appropriate punishment… but it’ll have to be later
• 10+: you have the perfect idea.