Casey decided that the best way to deal with the turmoil she was feeling inside after the weekend’s events was to do something normal and go for a run. Instead of running on campus, though, she decided to just run around her neighbourhood. That way she could shower and shave at home rather than doing it at Tech where someone might see her doing it.

The run cleared her mind, and she started formulating a plan to achieve the day’s mission. She decided she would be bolder, and just wouldn’t tell anyone what she was going to do beforehand. If she just wore a simple dress that she could get off quickly with nothing on under it, then once she had everyone in position, she could just quickly whip it off, get the shot, and laugh off any comments afterward.

She knew where Cassandra usually hung out at lunch, and it was reasonably secluded. To get Greg and Amelia there at the same time, she decided she would invite them for a walk and just “happen to bump into” Cassandra and her crew, then ask everyone for an impromptu group shot.

The morning passed with just one “upskirt” text from the blackmailer, which she managed without a hitch, but as lunchtime approached, her heart started beating so hard she thought she might have a heart attack. It got even worse when she had Greg and Amelia in tow according to plan and could see Cassandra and her crew in the distance. There were some boys with them and a few other people nearby. Casey couldn’t come up with an excuse to get everyone to clear the area, or get everyone to another location, so she decided there was nothing for it. More people were going to see her nude, and that was that, but hopefully, she could at least pull this off fast before anyone really got a good look at her.

“Oh, hey, Cassandra. How’re things?” Casey asked.

“Hey, girl,” Cassandra replied. “I see you decided to dress today. I almost forgot what you looked like with clothes on.”

Everyone laughed, including Casey.

“Say, speaking of that. Can I get a group shot with everyone who was there yesterday?” Casey asked.

Without giving anyone a chance to say no, she herded them all together and handed her phone to another girl called Brigit who hadn’t been at the party.

“Okay, everyone say ‘cheese’,” Brigit requested.

“Oh, wait a sec,” Casey interrupted, and then without giving herself a chance to think about it, she took her dress off and got back into position.

“Ok now!” Casey instructed.

Brigit looked stunned for a moment, but Casey heard the camera’s shutter click nonetheless. At that, she immediately put her dress back on.

“What the fuck, girl?” Cassandra asked. “We just can’t keep clothes on you these days. Do you get off on this shit or somethin’?”

“Um... err, no. I just wanted a shot for my scrapbook to remember yesterday,” Casey responded. She could see other bystanders had seen the whole thing as well. She was humiliated, but at least thankful she had fulfilled the mission, knowing the consequences might be far worse if she hadn’t.

Greg high-fived her, laughing. Amelia looked puzzled.

“Sure you did,” Cassandra added. “You sure you ain’t plannin’ to rub one out to this later? You got somethin’ going on with me I should know about, Casey-girl?”

Casey’s mouth dropped open, but then caught on that Cassandra was actually just using homophobia to gain the upper hand in the situation by trying to humiliate her, assuming that Casey’s act of exhibitionism wasn’t humiliating for her already. Well, two could play at that game.

“Yes, Cassandra,” Casey answered sarcastically, “I have nothing else to get hot over than your fine ass.”

“Eww!” Cassandra scowled in response, and Casey knew she had hit her mark.

As the group split up, Greg left to attend a class on the other side of campus, leaving Amelia and Casey alone.

“What is going on with you lately, Casey?” she asked. “There was no need for you to do that. Is there something I should know about?”

“Err no,” Casey replied. “I just thought it would be funny after yesterday. Was it not?”

“Um… kinda, but not really,” Amelia answered truthfully.

“Sorry, Amelia. I didn’t mean to upset you. I just have a sick sense of humour, I guess.”

“I’m not upset, Casey. Just confused and worried about you.”

“I’m fine, Amelia. Really. I suppose I’m just trying a few things on for size at the moment.”

“Ok then. But I’m here for you if you need to talk anytime.”

“Thanks, Amelia, but honestly I am fine.”

Casey hated lying to her friend, but she had no other option in the circumstances. She needed to deal with the blackmailer on her own. If anyone else got involved and he found out about it, the consequences could be very bad for her and her sister, and that kind of stuff tended to follow a person around for life too.

Once alone, Casey texted the group shot to the blackmailer.

Ding.

“Thank you. There’s a present waiting for you at home. Don’t open it until 8:30. See you then.”

Oh God, now what?

When she got home there was indeed a parcel addressed to her waiting on the front porch. She gave it a shake but was mystified, and worried, about what it might contain.

Just prior to eight-thirty p.m., she got a text.

Ding.

“Get naked and cut your tampon string off”

He remembered I’m on my period and my tampon string would be visible? This can’t be good…

Reluctantly she complied and turned the camera on at the prescribed time. It was mortifying to know she was showing her naked body yet again to this complete stranger, and while she was on her period. Perhaps it was even more mortifying to realise she was kind of getting used to the humiliation of it all now.

Ding.

“You have stubble. Your first shaved upskirt pic just went to ten people”

Oh God!

Casey knew she had fairly distinctive anatomy which several people had seen now. If one of those people received the image, she would be unable to deny it was her and would have to come up with an explanation as to why she took that picture of herself and how it ended up in their emails.

Ding.

“You may open your present”

Casey opened the parcel and found it contained a silver object with a large fake jewel at one end. There was also a tube of lube. She had no idea what it was but figured it would probably be going into her vagina. She just hoped at least that she wasn’t having a heavy flow day if she was to suffer that indignity.

She gave a puzzled look to the camera.

Ding.

“It goes in your butthole. You may want to use the lube”

The fuck, what?

Casey had never had anything in her butt before and she wasn’t about to start now, especially in front of someone else. So, she gave the camera a blank look.

Ding.

“Ten more people just got the pic”

Casey realised she was not being given an option, and she would have to comply. She was beyond appalled at the idea of touching her butt, let alone putting something inside it, but she tried consoling herself with the thought that anal sex must be popular for a reason. Maybe it wouldn’t feel so bad.

She quickly got into the spread position in front of the camera, then applied lots of lube to her butthole and also to the object. Then, holding it by the jeweled end, she tried testing it against her anus. It didn’t feel good. She was sceptical that it would even fit. She tried pushing it in, but as it started to penetrate, the sensation alarmed her, and she extracted it again. She tried several more times with the same reaction. Then, with a final do-or-die push, and more than a little wincing, it passed the point of resistance and her sphincter seemed to pull it into place by itself. It was a little uncomfortable going in, but after that, it didn’t feel quite so bad. Just weird. She hoped she’d be able to get it out again, though.

Ding.

“Now rub your clit until you cum”

Unwilling for more people to get another picture emailed to them, Casey obeyed without hesitating this time. It wasn’t long until her primal instincts kicked in again and she was rubbing her genitals with increasing fervour. She wondered about the obscene spectacle she was making, now with a jewel sticking out of her butthole. It didn’t take long for her to orgasm. Then the thought of what she had just done made her want to orgasm again, but she resisted.

Ding

“Thank you. I expect to see you wearing the plug from now on. I’ll be checking. It’s much prettier than your asshole. Just ask Cassandra.”

What? No way!

Ding.

“Your mission tomorrow is to get someone to take a picture of it.”

Casey immediately started wondering about how she could pull that one off, and what excuse she could use. The experimental nudist story wouldn’t work this time. A dare would lack plausibility. Who would wear a butt plug and ask a stranger to photograph it on a dare? The only thing she could come up with would be to use the surprise approach, as she had done for the group shot that morning, and not try to explain herself at all. The person would probably think she was a vulgar tramp, but what else could she do? On the other hand, maybe she could ask a friend again. Their face wouldn’t be in the picture so there’d be no way the blackmailer would know who took it, and she could lie if he asked. She couldn’t ask Amelia this time. She was already worried about her behaviour. This would be too much for her. Greg? He’d probably be totally cool with it, but did she want him to see it? What implications would it have for their relationship? Although, if she had to wear the thing on a frequent basis, and they were having a sexual relationship, he was going to see it sooner or later, and she would have to explain it eventually anyway. In many ways, it had to be Greg.

She had a plan.

With some force, she extracted the plug from her anus again, but she now felt like she’d been violated in a whole new way. She could still feel it in there as she cried herself to sleep again.