Anal Only Underwear

When Cassie arrives home that evening and shows you her butt plug, you bite your lip, knowing what you're supposed to request, but having to wait a couple of moments for some hesitation to pass before you can bring yourself to say it in a convincing tone.

"Don't you think it would be easier if you didn't have to pull down your panties?" You ask gingerly.

Cassie frowns. "Are you asking me to stop wearing underwear? Because I don't think that's-"

You interrupt her. "No, not no underwear. Anal underwear."

"Anal underwear? That's not a thing, is it? ...Oh."

You are holding a box full of a special type of sexy briefs where the crotch fabric parts after the section that covers the vagina, leaving the asshole always exposed and available, with delicate white frills decorating either side.

"What do you think?" You press her for an answer.

"Let me try them on first!" She protests.

"So... you'd want me to wear this sort of underwear when I'm arriving home?" Cassie ponders.

"I'd want you to wear this sort of underwear always." You clarify. "You'd never wear a normal pair of panties again. For the rest of our lives your butthole would only have a maximum of single layer of fabric between itself and me. And that's only when you have to wear pants for uniform reasons. When you're wearing a skirt or dress, which would be almost always from now on, your asshole would be exposed to the fresh air at all times. You also won't even need to take them off for anal sex or your daily anal training."

"What if my plug were to fall out?!" Cassie complains, with concern in her voice. "What about the vibrating thing in the Monday Morning Meetings?!"

"You'll just have to get really good at holding it in with your butt muscles." You say, as uncaringly as you can bring yourself to.

If she thinks it's impractical, she'll finally say no! I need to drive this home.

"And when you're wearing a dress or a skirt, a trip or stumble, or a stiff breeze could expose your secret to the world."

"This is becoming a significant part of the excitement for you, isn't it? The small risk I get caught and exposed." Cassie is more thinking to herself than looking for a response.

You're trying to work out what to say next that both increases the chances of her saying no but doesn't break the blackmailers' rules. Cassie seems to be thinking hard too. After some pause, it's Cassie that speaks first.

"Our wedding is just over two weeks away, and our stag and hen parties are this weekend. You want me to wear asshole exposing underwear to those too?"

"...Yes, I want you to wear them every day, including special occasions."

Forgive me, my love! This is the last thing I'd want to wear for our wedding!

"This anal only thing is getting pretty serious, isn't it."

"Yeah, it really is." You admit. You don't think that's against the rules.

Cassie takes the box. "Well, I'm serious about this relationship too, so I guess I'd better get used to this."

"...Yes, I guess you should." You say as neutrally as possible.

Nobody in the world should ever 'get used' to something this outrageous!

Cassie has one final thought.

"You know, the dress I've picked out to wear when partying this Saturday is pretty short."

"Oh yeah..."

"I was going to wear bike shorts under it, to avoid flashing everyone my underwear."

"Not allowed, I'm afraid."

"What should I do if someone sees my new fetish panties?" Cassie sounds less scared now, and more just curious.

It's difficult to know how to respond.

"I guess... it's up to you. You could tell the truth and explain that it's a request from me, or you could just say that it makes you feel sexy, if that feels simpler."

Cassie seems satisfied by this. "I guess maybe it won't be too big of a deal."

There's one thing she may have forgotten, so you decide you better make sure.

"Your daily porn watching and anal training shouldn't stop just because you're going for the weekend." You remind her. "You need to pack the dildo in your luggage, and find the time to have your usual 10 minute session."

"But I'm sharing a room with Amanda!" Cassie complains.

"Then you'll have to use the bathroom or something, or try and sneakily do it after she falls asleep." While you feel like you're being a bit harsh, your hope is still that you can get her to say no by overwhelming her with ridiculous demands.

"Fine." Cassie seems a little put out by that, but she is also being way too stubborn to say no right now. "Now if you excuse me, I'm going to take this plug out. And then I guess I have an underwear drawer to rearrange."