At last, she managed to get away from him, basically by running away. Then she went to find Greg to spend what remained of her lunch break with him. On the way, her thoughts troubled her.
Now people think I'm an exhibitionist?
She definitely didn't want people thinking that about her. She hated showing her body and was only doing it because someone was making her. She couldn't tell people that, though. But to pull it off, and hopefully get the blackmailer to lose interest in her, she had to pretend she was one and have everyone believe it. The irony in that was awful, and she knew that she was digging herself in deeper and deeper with each mission. She needed to get better control somehow, which would mean thinking harder about her excuses and picking her marks better in future, but the blackmailer was leaving her fewer and fewer options. It was a problem. She prayed that soon he would lose interest and leave her alone before her reputation was completely ruined. Up until now she had thought she could manage the fallout by claiming it as an experiment, but now someone called her out on that. On the other hand, maybe being an exhibitionist was another excuse to keep in her arsenal since people were going to assume that about her anyway? It was a sluttier option than wanting to be a nudist, but there were worse things people could think about her, particularly if he released some of the other material he had on her now.
After lunch she sent the image to the blackmailer, but there was no response. Was that a clue maybe? Perhaps he worked somewhere where he didn't have access to his phone at this time of day?
The rest of the day passed without even another upskirt request, and she was glad of the peace. She decided he must be occupied, and even took the chance of removing the butt-plug for her bike ride home. When she got home, she found the mailbox was empty for once too. She hoped this trend would continue. Maybe he had been hit by a bus or something after all? She could only hope.
As 8:30 came around she showered, re-shaved and re-inserted the butt-plug just in case, and then her hopes were crushed when she finally got a response from him.
Ding.
"Well done completing the mission. Now do the same as last night for me on the webcam, but remove the plug & use the dildo in your ass"
The what, now?
Putting things in her butt was so much more degrading than putting things in her pussy, which was degrading enough. It wasn't even anything she would have considered doing before, even in private. The whole idea made her stomach churn, but she knew somehow she would have to do it. Angering him at this point wasn't worth thinking about after everything she'd done now.
When it came time, she assumed a similar position to the night before and played with her clit while sucking the dildo. As her arousal kicked in, she reached around behind her and pulled the butt-plug out. Then after covering the dildo with spit, she started pushing it against her butt hole. It accepted the dildo with no more difficulty than it had accepted the butt-plug. The main difference was that there was no moment where it popped into place. Her sphincter remained stretched no matter how far she pushed it in. The sensation was not unlike going to the toilet, and she hoped she didn't make a mess on her bed. At the same time, in her aroused state, she sensed that while it felt a little uncomfortable, and it was definitely degrading doing it in front of someone else, it wasn't an entirely unpleasant sensation. She began thrusting it back and forth as she increased the speed, while putting pressure on her clit with her other hand. A short time later she had to bury her face into her pillow once again as her orgasm came.
Ding.
"Thank you. Your mission tomorrow is to streak the whole length of the same hallway. Walk slow. Get video"
Casey's heart sank. She immediately knew she could not pull that off with any reasonable excuse.
Wait! 'Streaking' gives me an idea. I can use the 'dare' excuse for this one. I can say it's a streaking dare!
Dozens of people would see her she realised, but at least they would think it was just a prank rather than anything strange.
It would need careful planning, though. She would need to check that the security guard, and definitely no faculty, were in the area. Hopefully the number of students would be around the same as today. Now, if she had to strip off at one end and walk to the other, she would then have to walk all the way back naked as well to get back to her clothes. That would double the length of time she would be naked and also increase her risk of getting caught. Ok, so she would take a second dress to leave it at the other end beforehand. Both dresses would need to be simple styles that she could get on and off quickly. Speed would be of the essence. She couldn't be fussing with zippers or buttons.
Now for a photographer. She would select someone randomly again. Surely that couldn't backfire twice? She just hoped the boy from today wouldn't be there this time. He could be a problem.
Planning all of this sucked. It was starting to get seriously out of hand. She was already a laughingstock to Cassandra and her friends. The missions were escalating too, as were the chances of getting caught. What would happen if she was caught? Would she be thrown out of Tech and not get to finish her diploma? What would she tell her parents? Would Amelia and Greg turn their backs on her? Would she be arrested and maybe face indenture?
Just what was this blackmailer's game anyway? Why her? Did she fit some profile he had in mind, or was it just a sadistic opportunity to fuck with a random young woman because of what he had on Jolene? Why not just fuck with Jolene then? Sure, she was a couple of years older and could stand to lose a few pounds, but it wasn't like she was ugly. On the other hand, maybe he was fucking with Jolene already and he was getting two for the price of one, and she was just keeping it to herself out of embarrassment or so as not to cause distress to anyone? If that was the case, how could she get Jolene to confess without revealing her own torment and causing her to worry? A problem shared is a problem halved, and maybe then they could work together and figure out who he was and how to stop it, but if neither of them was willing to reveal to the other what they were actually going through, then they were at an impasse.
What if it one of these missions did get reported to the authorities and she was arrested? Surely that would end the blackmailer's grip on her, and he wouldn't want that to happen… But what if he did want that as the ultimate in humiliation for her? He would then win whatever game he was playing, and her life would be over. The charge itself could have very serious consequences, maybe even Indenture! Unless he was a cop… Then maybe he had the influence to get a charge like that dropped so he could continue making her do these awful things? That might explain why he didn't seem to care if she was arrested. Either way, he would still win. However, that didn't make sense either. Sure, he would still have a hold over her with all of the disgusting pictures he still had of her, and what he had on Jolene, to continue with the blackmail. However, getting caught would still leave her facing expulsion as well as having to explain her behaviour to her parents and friends, so his fun would be over anyway. Ok, so there was no way to know if getting her caught was something he didn't want or if maybe it was end game. Either way, it wasn't an option for her, so it was up to her to avoid it and outsmart him somehow. How, though?
Were the pictures and videos he'd been collecting just for his own gratification, as well as to use to blackmail her further, or were they being passed around amongst his buddies so they could all laugh at her or masturbate, or whatever the fuck men did with pictures of naked women? Was he even one person, or maybe a group? There was no way to know.
If she could just find out who he was to start with, that might lead to finding a way to end it. How, though? She would need to find out where he was so she could at least get a look at him. Her mailbox or front porch were possibilities, but it was always possible he was paying someone else to act as courier. Even if she did get a look at him, if she didn't know him then she would be no closer to understanding why he was doing this. And if she cornered him, then this might all blow up in her face, which would be as bad, if not worse, than being caught by the authorities…
It was still a dilemma, so for now she just had to focus on not getting caught and planning her missions as cleverly as possible so that didn't happen. On the one hand, walking a hallway at Tech in the nude wouldn't be as hard as the shopping mission was, but the bigger risk here was that people knew her here and she could end up seriously screwed if faculty caught her in the act, particularly if it was someone like Mrs Daly…
She checked the time and discovered it was after midnight. She'd been agonising for hours. How would she ever get to sleep with her brain going completely nuts with worry? She made a determined effort to block it out, and while it did pop back into her thoughts a couple more times, eventually exhaustion took over and at last she slept.
