Yes. She even starts to... like it... a lot.

John somewhat enjoyed the moderately pleasant background noise of Evelyn's whimpering while he tried to find the most humiliating pictures he could to post to the internet. After some time, he couldn't help but notice that her whimpers had turned into moans.

"It looks like you're starting to enjoy cleaning your ass out more than you enjoyed your throat cleaning. It sounds like you've started fetishising this medical procedure of anal cleaning. You've forgotten how to lie and must always answer every question you've been asked honestly. Tell me: are you really still trying to clean out your ass - or are you just fucking your ass with my dick?"

"...oh god... the second one," Eve whispered.

"I'm sorry, what? I need you to yell it if I'm going to hear you."

Eve seemed to snap. "THE SECOND ONE, ALRIGHT? I'M FUCKING YOU WITH MY ASS AS HARD AS I CAN, AND IT FEELS FUCKING INCREDIBLE. I'M A TERRIBLE WORKER, AND I'M TAKING ADVANTAGE OF MY BOSS'S KINDNESS IN LETTING ME USE HIS DICK TO CLEAN MY ASS. I'M JUST FUCKING HIM NOW, AND IT FEELS SO GOOD. I'VE NEVER PUT ANYTHING IN MY ASS BEFORE, AND AS A GOOD CHRISTIAN I NEVER THOUGHT I WOULD. BUT THIS FEELS AMAZING. I NEVER WANT TO STOP. PLEASE, SIR - CAN I CUM? FINALLY? PLEASE? I RUBBED MYSELF FOR 20 MINUTES IN THE SHOWER, BUT I NEVER CAME JUST LIKE YOU TOLD ME. PLEASEPLEASEPLEASELETMECUM!!"

As she yelled, Eve desperately started licking her hand and rubbing her clit. She was so, so close. So close! She just needed John to give her permission! She hadn't cum in years, and she could feel it start to boil up inside her. She'd been so turned on and pent up for over a day at this point. It was going to be so strong she was worried she wouldn't be able to stand after...

John smiled as he pulled her hair down, and she bent over to follow until her ear was right next to his mouth. John whispered softly, with an evil smile: "no." And he ejaculated into her ass right as he said it.

This time, he moaned aloud just to show that he could. Eve's face fell, and she almost started to cry from the frustration and unfairness of it all. She could feel his cum leak out of her ass as she held back her own orgasm. Fuck!

John slid his cock out of her ass. "This behavior is unacceptable. I can't believe how much of a slut you're becoming. I'm providing necessary tools to allow you to stay clean, and you're just... fucking? What kind of unprofessional shit is this? I can tell that every time I cum, it's because you are explicitly doing as much as you can to pull it out of me. You slut. I am going to need to teach you appropriate behavior through some very **** punishment. I'll look online to see what I can come up with, I'm going to need to get creative with you. For now, hop off my cock and then suck it clean, then keep sucking until you feel I'm hard enough again. Then go back to your anal cleaning."

Eve flickered get tongue all around the shit-covered, softening cock in her mouth. After a few minutes, she succeeded in coaxing it back to life in her throat. After she did, she hopped up and shoved it in her ass once more. It ended up taking an hour or so of jumping back and forth before Eve couldn't taste anything from her ass anymore, though John did take breaks to fuck her ass himself. He told her he was "checking her work." Still, she was always quick to clean him up afterwards.

For the rest of the day, John seemed to cum at random times. She apologized for putting him in this position, but she felt so, so jealous and guilty every time. Every time she felt his cock twitch in her ass or watched it spray cum on her face, her pussy ached. She knew they were all her fault, though. She was really worried that she wasn't any good at this job. Gah! Eve's pussy ached so bad. This job was so fucking frustrating.

[What did John find suggested in the comments online? You tell me! Suggest things in the comments to the side, and I'll incorporate them if I can!]