Casey took extra care shaving that morning, since the blackmailer seemed to have such a problem with seeing any stubble. It was such an unfair expectation. With her fair skin and dark hair, the best she could hope for was maybe half a day or so before the five o’clock shadow effect started to become visible again. Then she wrapped the butt-plug and lube and placed them into her bag. She knew that her blackmailer expected to see it in place when he inevitably asked for an upskirt but cycling with it in her butt just seemed out of the question. Every little bump would ram it into her tight butthole. The downside of that plan was that she would have to insert it before class, not just for the damn photo that she had to get Greg or someone to take of her wearing it. As if dealing with her period wasn’t enough already. Now she had to push and pull things in and out of her butt as well. It was also terrifying to consider wearing it under a skirt without underwear as well. What if her skirt blew up? Or much, much worse, what if it fell out and rolled across the floor in front of someone?

Just as she arrived at Tech, her phone dinged. Thankfully it was only Jolene.

“All ok?”

“Yes fine. You?”

Ding.

“Yes, fine here too. I guess he’s gone. Well, that was weird.”

Casey knew very well that he hadn’t gone, but she didn’t want Jolene to know that. It wasn’t like Jolene could do anything to help anyway.

“Yes, very weird.” Casey texted back.

Ding.

“Ok. Let me know if you have any more trouble with him.”

“I will. Thx. See ya.”

Later in class she felt even more conspicuous, having both no panties and wearing the butt-plug under her skirt. She kept feeling the need to keep everything clenched in case it fell out. By the time morning teatime came around she was feeling more than a little tired and cramped from the constant clenching, but then she found a way to relax by sitting back on it, so her body weight kept it pressed into her. It wasn’t comfortable by any means, but it meant she could relax her muscles at least.

The upskirt request finally came as expected, and she dutifully sent it. There was no comment afterwards, so she assumed she had passed muster. Then at last it was lunchtime and the moment she had been dreading was about to happen.

“Greg!” Casey shouted when she spotted him. “Come here, I want to show you something!”

Greg immediately approached, hoping the “something” would be one of Casey’s naked body parts. The thought of it piqued his interest in no uncertain terms. They were more or less alone, so he began by kissing her passionately.

“What is it, Casey? Another nude picture?” he finally asked as he stopped kissing her, hoping that would be the case.

Casey groaned inside. Her nude missions were becoming predictable to the people closest to her.

“Actually, um... I’m trying some new um... jewellery and I want to see what it looks like. Can you take a pic for me?” she requested while handing her phone to him.

“Sure! What is it? Where is it?” Greg asked as his thoughts immediately started going to body piercings at Casey’s mention of jewellery. Maybe Casey had her belly button pierced? Maybe something else? He started feeling an erection forming.

“Come with me,” Casey commanded, while dragging him into an empty classroom.

“Okay, ready?” she asked, while turning her back to him.

“Go for it,” Greg replied, wondering what the hell he was about to see.

After a quick look around to make sure they were alone, Casey bent over and raised her skirt. There was silence. She looked back at him and saw that his mouth was wide open with a stunned but pleased expression on his face.

Okay, so he likes it at least...

“Take the shot already, for fuck’s sake! I can’t stand here like this all day!”

“Okay, okay. Just ‘miring for a sec,” he responded, clearly enjoying the sight.

Click.

“Finally!” Casey breathed in relief as she took her phone back from him, glancing briefly at the doorway to ensure they were still alone. She feigned interest in looking at the shot for the sake of appearances but was totally repulsed by it. “So, what do you think?”

“Well, it’s different… Slippery Sam definitely likes it,” he added, gesturing to the obvious bulge in his pants.

Casey laughed. If nothing else, she was at least glad that it hadn’t sent him running.

At the end of lunch, they reluctantly parted again, and she sent the image to the blackmailer.

Ding.

“Thank you. Don’t forget to wear it to Mark’s later”

Oh crap! Mark and Gillian are going to see it too? How do I explain it? What will they think of me?

She continued trying to come up with some way to explain it to Mark and Gillian as she made her way to class, when she passed a group of students looking at their phones and giggling to each other.

“So, there’s two girls doing it now? I wonder who they are?” Casey heard them say.

“Yes, this one’s shaved while the other one was really hairy.”

“I dunno. They could be the same girl. Maybe she just shaved it. Look, they both have the same kind of meaty lips. Although, it’s hard to tell in the first picture. You can’t really see anything through the hair. Oh my God, what a Wookie!”

“What’s it all about, though? What are they trying to say by sending pictures of their cooches out to everyone?”

“Yeah, it’s weird. It must be some kind of joke or dare maybe? Or they’re getting off on it?”

Casey realised they were talking about her and started blushing like crazy. She just hoped the wrong person didn’t see the pictures and link them to her.

“Casey, have you seen these?” one of them asked her. “We’re trying to work out who they belong to, and what their game is.”

“Err… no. No idea,” Casey replied, and then pretended to be in a hurry to get to class.

The rest of the day passed with her unable to concentrate on her classes as she frantically wondered what to do about the upskirt pictures of her being circulated around campus. She couldn’t come up with anything at all by the time she had to cycle to Mark’s, and commencing that journey presented another embarrassing problem. She couldn’t decide at first whether to remove the butt-plug before she got on her bike, or just leave it in. Since putting it back in once she got there might seem the weirder of the two options to Mark, she decided she would just keep it in and see how he reacted. The drawback in that was the fear that she might drop it while hitting a bump, but she got around that by sitting on it. Now it just pushed harder into her with each bump - the very reason she had decided against wearing it on the ride to college that morning. Sigh, and ouch.

Mark was his usual cheery self when she arrived.

“Hi, Casey, good to see you again. All ready for another shoot?”

“Hi, Mark. Hi, Gillian. Yes. Um... I have my period, though...” Casey informed him.

“Oh okay. Um... No problems. I think we can work around that,” Mark replied, frowning slightly as he considered what he was going to do in lieu of what he had planned. “We’ll just avoid the big spreads this time, I think. Um... I have an idea. Gillian, could you get Casey ready with a micro bikini? We’ll shoot outside on the pool deck today.”

Gillian led Casey out to the dressing room and got her to undress. She noticed the butt-plug right away.

“Ooh, nice butt-plug. Mark was thinking about getting you to wear one of those maybe in another week or two. He’ll be thrilled to see you already have one. Oh…we might need to give your shave a touch-up. We’ll need to shorten the string and tuck it away so it’s not so obvious too. Will you need help with any of that?”

“No, I got it,” Casey replied, embarrassed out of her mind to be standing naked in front of someone while discussing her pubic hair growth, her menstruation, and a foreign object sticking out of her butt that she had apparently voluntarily inserted.

She quickly took a shower and gave her pubic area a re-shave. Then she took a pair of scissors she got from Gillian to cut off her tampon string, hoping that it wouldn’t make it too difficult to get out later. Then she returned to the dressing room wearing a borrowed robe.

“All clean?” Gillian asked. “Okay, we’re running a bit behind. Let’s quickly get your makeup done and then pick out a bikini.”

After Casey’s makeup was applied and hair dried, Gillian took her to a rack and picked out a blue bikini for her. Well, it technically fitted the definition of a bikini anyway. The material in the cups would barely cover her nipples, and the bottoms… well, Casey decided she might look less naked without it. There was only enough material to cover her inner pussy lips. Her outer lips would still be clearly visible. After she put it on, she hoped she hadn’t accidentally put it on backwards or upside down. She was somewhat relieved about that when Gillian nodded her approval and then led her outside to the pool area, but she still felt awkward in the tiny outfit as she clip-clopped along behind the fully clothed woman.

The pool was basically just a spa, but impressively decorated with wood panelling and stainless-steel rails and wires. Several studio lights graced the outside, with Mark peering into a camera on a tripod as he twiddled with various knobs and dials.

“Ah, Casey,” Mark began, looking up on seeing her. “Wow, you look sexy as fuck! I’ll get you to stand over there in between the rails and put a hand on each one. Ooh, nice butt-plug. It even matches the bikini.”

Casey smiled, not knowing how else to respond to someone complimenting her on her choice of butt-plug.

Click.

“Okay, now knees together and just kind of twist down like a go-go dancer. That’s it.”

Click.

“And back up again. Lovely.”

Click.

“Now turn around and stick your butt out.”

Click.

“That needs a few close-ups. Hold it there.”

Click. Click.

This went on for fifteen minutes or so until Mark asked her to remove the bikini, and she was being photographed nude once again. He didn’t ask her to spread quite as wide as usual but there was still plenty of normal spreading. Casey loathed every moment of it. She loathed having to smile through it all even more.

At last, it was over.

“Thanks, Casey. Same time Thursday?”

“Sure, Mark. I’ll be back,” she replied, knowing damn well that she didn’t have a choice about coming back.

She started putting her ordinary clothes back on while Mark was still talking.

“Tell me, Casey. Does your period usually last long?”

“Oh ahh. Nah, not really. Usually, three or four days. It should be gone, or close enough to it, by Thursday.”

Casey found it abhorrent to talk about her menstrual cycle with a man she barely knew, and who wasn’t her doctor or boyfriend.

“Oh, that’s okay. That’ll be good. I was wondering if I’d need another plan for you on Thursday as well, but it sounds like we should be fine. Okay, see you then.”

“See ya,” Casey replied, not wanting to spend a moment longer than necessary in the place, and wondering just what Mark had planned for her later in the week if the shoot she had just done was tame by his standards. “Bye Gillian!”

Gillian waved from her desk.

Casey got back on her bike and found the butt-plug was getting seriously uncomfortable now after wearing it for such a long time, not to mention the bike trip to Mark’s, so she looked around for a suitable spot she could remove it without anyone seeing. There was nothing except for a few trees on the side of the path. She decided that would have to do, so she quickly ducked out of sight, extracted it, and stuffed it into her bag before continuing her journey. Thankfully no one saw her, and the rest of the journey was far more comfortable. Still, removing a butt-plug in public was something she never could have imagined herself doing in a million years.

Once home, she found her mother was there already too.

“Hi, Mum. How was work?”

“Oh, same old same old. How was your day, Casey?”

“It was fine too.”

Apart from being forced to wear a plug in my ass all day and having it photographed by various people.

“Oh, there was a package for you. I left it in the kitchen,” Sue mentioned.

“Oh thanks, Mum, I’ll check it out.”

Only one person sent her packages these days, and after yesterday’s “present”, Casey knew better than to open it there, so she took it up to her room. Just as well. It was a dildo about the same size as a banana.

“What was it, dear?” Sue called out. “Anything from anyone you know?”

“Nah, just some stuff off eBay I ordered for Tech,” Casey lied.

“Oh okay. I was just curious,” Sue called back.

Casey wondered what new hell she would have to endure now at the hands of her blackmailer. She had to wait until after dinner to find out.

Ding.

“Bring your new present with you at 8:30. Make sure there’s no stubble this time!”

Crap! I guess I’m taking another shower then... Wait, dildos and periods aren’t a great mix. Surely, he can’t expect me to use that in front of him?

She texted back.

“I still have my period.”

“I know. It’s for your mouth. Show me what you can do”

At least Casey now knew what it was for. Not that the knowledge made the humiliation of what she had to do with it any easier to bear.

She was ready, shaved, and naked with the butt-plug inserted by the time she turned the camera on at eight-thirty.

He really has me trained well now. God dammit! He has me right where he wants me. My only choice is to keep playing along until he slips up or loses interest. I gotta show him I’m not afraid or humiliated to improve the odds of one of those things happening.

“I got a new present. What shall I do with it, I wonder?” she purred to the camera while licking and kissing the dildo with what she thought was her sexiest smile. It was reverse psychology. A proud slut couldn’t be humiliated, and humiliating her seemed to be his kink, so acting like she was into it was her best chance of turning him off without making him angry.

This time she tried kneeling with her back to the camera and her legs spread wide. Then she turned the top half of her body to the side so he could see the butt-plug. Confident her ass was on full spread display while her new jewellery shielded her hole, she teased and sucked the dildo with her lips and tongue. As this went on and her arousal increased, she began to rub her clit with her free hand, while continuing to work the dildo with her mouth. While outwardly she hoped she looked like a total porn star, inwardly she felt completely degraded and humiliated, which was a feeling she realised was becoming all too familiar.

She noticed her hips had started swaying, seemingly of their own accord, in time to her rubbing. She responded by thrusting the dildo further down her throat but accidentally made herself gag several times, causing tears to stream down her face. She felt herself getting wet while rubbing her warm pussy. She knew she was beginning to lose control once again, but then considered that would work in her favour anyway so she ran with it. She took the dildo in deep, managing to wrap her lips around its base, all the time rubbing her clit hard. At last, she threw herself into her pillow and filled it with muffled screams as a powerful orgasm overtook her. She felt her body twitch several times and she continued gyrating her hips as she came down from her sexual peak. At last, the desperate haze started to clear, and shame at what she had done took over her thoughts. She bit her lip and hoped it wouldn’t be evident on her face.

Ding.

“Thank you. Your mission tomorrow is to get a nude pic in Tech hallway while it is occupied. I want to see at least 3 people I don’t know in it”

Sudden horror replaced the shame.

Someone will call campus security if I do that! Then I’ll be in front of Bernstein and the cops will be called.

“I’ll get arrested”

Ding.

“Not my problem. Find a way”

Not his problem if I get arrested? Won’t that ruin all his fun? I don’t get it. Unless the humiliation of me getting arrested is gonna give him a boner?

Casey knew this time there would be no avoiding new people seeing her naked. The only plan she could come up with was to make sure she knew where campus security was, and then use speed again like she did for the group shot on Monday. She’d need a simple dress she could get on and off quickly again, and someone teed up to take the shot. Then just do it quickly so it was all over in seconds, hopefully before anyone could get a good look at her.

Her final thought before going to sleep was the awful realisation that planning her own humiliation was becoming as familiar to her now as her friends were getting with seeing her nude.