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Chapter 5 by aika092 aika092

What does the rest of the fortnight look like?

Daily porn and weekly sex

When Cassie returns from the bathroom, you have an 'aftercare' discussion about how that went. You admit you really enjoyed yourself, which was supposed to have to be a lie, but is actually just the truth. Cassie was in pain at first but then found the feeling rather manageable if somewhat intense. Towards the end it felt... sort of good, maybe? She definitely felt a weird competitive drive to see what she could handle, and got some deep satisfaction from feeling you cum inside her. So... overall, this first night was less horrific than you were anticipating.

Next, Cassie asks you how you want things to proceed from here. You subtly clench your fist again, as this has already been decided for you, and you are **** to give Cassie the instructions as provided to you by your anonymous blackmailer.

Cassie is to search for "0% pussy" porn on free tube sites, and watch at least 15 minutes per day whilst holding one of her fingers from each hand inside her butt.

"Every day?"

"Every day. Unless you don't want to."

"If you want me to, I want to."

Fuck. This is so wrong.

You are to have anal sex once per week, every Sunday evening.

"Fine with me."

Is she looking forward to this?


Towards the end of the next week, you sit down to review how things have gone. The anal sex itself has been wonderful for you and still just "manageable" for Cassie, but she seems more than happy with this as the status quo, as long as you are happy.

She has taken an almost academic approach to the porn watching. She has made several notes and observations about the Anal Only fetish world.

"A lot of this is focused on the man's pleasure, isn't it?"

"...Yes, I suppose it is."

"I see. And the woman is allowed to experience pleasure, but only if she can derive it from anal stimulation."

"That is the long and short of it I guess, yeah..."

"And if not, if she just finds it uncomfortable, too bad. She's almost just an object to be used, her experience is mostly incidental and of little importance."

"That's not... it's much better if the woman enjoys herself..."

"But if I just find it uncomfortable? Would that make you upset and want to stop?"

You clench your fist.

"No... I would still want to keep going..."

"Interesting. Don't feel ashamed. From what I've seen, this is rather common. Possibly even how the majority of Anal Only men feel. I don't mind. I love you, and I just want to fulfill your fantasy. I'm still open to trying to make it feel more pleasurable for me, but if I'm struggling, it's actually reassuring for me to know that your sexual gratification doesn't rely on me enjoying it."

"I... I love you too." It's all you can think to say.

"Now, do you have anything else you want to request? Or change?"

"Ask me again on the 15th. I have a suspicion I'll be feeling braver then."


The morning of the 15th, you check the website again. Sure enough, some new options await you. You look at the list, dumbfounded. Some are just insane.

But maybe that's my ticket out of this madness, you think to yourself.

If I choose one that's just so outrageous that Cassie says no, we wouldn't have to do anything...

Which option do you choose next?

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