High School Woman Blackmailed Ch. 02

Ryan was at home, laying in her bed after the day. She had stopped crying, but that didn't mean much. She still felt so disgusted, so disrespected, so... so violated by Jack. She had never had these feelings before and she hated it. And she had a feeling that this wouldn't be the end of it. She needed to think of a way out of this. But every time she started thinking about her situation too much, she got overwhelmed. It was just too difficult to think about. She wanted to just say no to him. Tell him to go fuck himself. But if he showed her parents that video, they would know she was gay. They'd disown her if they found out, and with no other close family or friends, she'd be out on the streets. She was fully reliant on her parents. Unbeknownst to her, things would be getting a lot worse.

Jack was having the best day of his life. He had been recording while in the closet with her, and now he had a nice video of the situation he could enjoy pleasuring himself too. But more than that, this video made even better blackmail. He figured the threats to reveal her homosexuality would only take him so far, so having that new video would allow him to push her even further. Something he fully intended to exploit. She had such a nice ass after all, it would be such a shame if he never got to use it.

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The next day at school, Jack approached Ryan once again.

"Had a wonderful time yesterday," Jack told her.

"That makes one of us," Ryan grumbled.

"It's such a shame you didn't enjoy it. It was so amazing for me, I barely left my room after I got home. Just sat in there, rewatching the video again and again."

"Video?!" Ryan asked with a sense of shock.

"Of course. You don't think I would just be content with what happened yesterday, did you?"

"Delete the video right now!"

"Why the hell would I do that?"

Ryan didn't respond.

"That's right. Now, unless you want both videos shown to your parents, and the second one spread across school, I suggest you follow me."

Jack headed off to the stairs, Ryan once again hesitantly following him. This time though, he led her to a bathroom that was almost never used.

"Alright, drop those pants now." Jack ordered her.

"What! No, I'll give you a blowjob like I did last time, that's it!"

"As much as I love blowjobs, I think the leverage I have this time warrants a bit more from you. Now, drop those pants and turn around, unless you want the world to see what a pathetic little whore you are."

Ryan was paralyzed, not wanting to move a muscle. Something occurred to her though, and she began looking around the bathroom.

"If you're looking for a camera, good luck." Jack said, catching on to what she was doing.

"Are you wishing me luck because there isn't a camera, or because it's well hidden?"

Jack smiled, before yanking her jeans down and turning her around, pressing her chest into the sink and pulling her ass towards him. Ryan let out a high pitched yelp, before Jack leaned in, mouth nearly touching her ear. "I think you've got other things to focus on right now," he grinned. After pausing for a moment, he decided he should reassure her. "Look, I don't mean to be cruel. I actually love you. I have for a long time. I'm going to take good care of you. And if I do hurt you, just understand that it's because you drive me absolutely crazy. Ok, Sweety?"

Ryan let out a shudder, and Jack sighed when hearing it, clearly getting some sick pleasure from it. She wanted to struggle away from him, but it was pointless. She was wondering exactly what he was going to do when she felt a huge slap on her ass. Not that hard, but still painful to someone who wasn't used to it. Jack felt a bit bad, but he really wanted to see that ass jiggle. He's been imagining it for years. It was just as delightful as he imagined. Shockwaves rippled across the slightly plump but perky booty that had just the right amount of fat on it.

Ryan tried to let out a cry but a hand around her mouth quickly silenced any noise. She began to struggle, tears starting to fall, as she tried to cry for help and get out of there. Unfortunately Jack was too strong, and as she struggled she felt Jack's cock begin to harden. She felt another slap, and she struggled more, but still, nothing happened.

A third slap followed, then a fourth, then a fifth. She was sobbing into his hand, flailing her arms, trying to put distance between the two of them. She failed.

Jack continued his relentless assault, enjoying the way her booty jiggled each time he hit it. But it was more than that. She was trying to escape, she hated this, she didn't want to do this, but it was happening. This meant Jack had power over her. And it was thrilling. Nothing excites him more than the fact that even if she hated this, she was helpless to his whims and desires. She would do whatever he wanted, and she was helpless to stop it. It was a wonderful feeling, one he hoped he could feel for the rest of his life.

Finally, Jack grew tired of spanking her, deciding he wanted some release now.

Ryan felt a pause in the spanks, and thanked whatever god may or may not exist for that. Her gratitude was short lived when she felt a hand tear her panties off and discard them on the floor. She could guess what was coming next. She attempted to push off the counter once more, but Jack's weight kept her in place, and all she managed was to move her ass closer to the cock. "Starting to get into it, are you?" Jack asked, laughing to himself. "Don't worry, I love how eager you are."

His cock began pressing into the entrance to her asshole. Her eyes widened. She wanted to fight, but was completely drained of energy. She knew she couldn't fight what was coming, so she just braced herself for what she knew to be inevitable. How bad could it be?

Worse than she could have ever imagined turned out to be the correct answer. She felt the cock begin to enter her hole, the head entering first. She felt the friction as the cock entered, knowing that there was a reason people normally used lube. He seemed to be taking his time, but as the shaft began to enter, she started to feel real pain. It hurt so badly, and started to burn as he shoved his cock inside her. And so it went, him slowly making his way further into her, and her crying as he did so. As the cock made it all the way in, she felt relief, knowing it wouldn't go any deeper. He spent a minute moving it around. It felt weird and uncomfortable, as well as, of course, incredibly painful. She tried to let out a stream of curses, but his flabby hand around her mouth prevented that from happening.

"Ugh, this feels so good sweetheart!" Jack groaned into her ear, sending shivers through her. "Now, I'm going to start moving in and out slowly, and I'll pick up the pace over time. It'll probably hurt you, but you'll get used to it eventually."

Ryan just sighed, as much as she was able to at least. She felt him move back, then forward, once again stretching out her asshole. It felt like he was tearing her apart, and she screamed into his hand again. This would not stop him as he would continue his assault, and it would only get worse for her as he picked up speed. He moved in and out, in and out, stretching her asshole as he pounded her relentlessly. God it hurt so much. She hoped this sick freak would burn in hell!

Jack thought that this was even better than yesterday. Her nice, warm, and most importantly, tight asshole hugged his cock so nicely. It provided some amazing stimulation, and he just wanted to bask in this feeling forever. He continued pounding the hole, hugging her waist tight to him while keeping a hand over her mouth. His cock eventually couldn't take it anymore, and he let loose, dumping what seemed like barrels of cum into her ass.

Ryan felt the second he got his release, feeling his muscles seize up as she felt the cum fill her up deep in her ass. It felt so uncomfortable, but she was thankful he was done using her ass for now. Jack, having finished emptying his balls into her, relaxed, pressing his weight against her and removing his hand from her mouth.

"That felt so good, sweety," Jack whispered into her ear.

"I fucking hate you," Ryan sobbed.

"I know, but I love you. You're so cute, and you make me feel so nice." He stroked her hair as he said that. "Now, how about we discuss your new tasks as my girlfriend?"

"Girlfriend! Haven't you gotten enough from me already?!"

"You've done so much for me sweety, and I really appreciate it. But I'm not just interested in sex, I want an actual relationship with you. So, here are the rules. You're going to dress to my liking, which means tight shirts, short skirts, yoga pants, skinny jeans, and high heels. I'll let you have some agency, as you'll be able to choose which of those options you want to wear on any given day. As for makeup, I'd appreciate a little bit of makeup to cover up any blemishes, and maybe some eyeliner and lipstick. That's really it though. I'll take you out on dates once a week at least. You'll obviously call me your boyfriend. I'll meet your parents whenever I feel like it. You'll kiss me in public whenever I ask. And, most importantly, I'll get to use you whenever I want. You got all that?"

"You're such a fucking creep," Ryan wheezed.

"I know you feel that way, but maybe I'll change your mind. And even if I don't, you're still going to do what I say." Jack moved his hands to her waist, hugging her from behind, then kissed her neck. "So I'll ask again, do you understand?"

Ryan nodded, not willing to speak.

"Perfect." Jack planted a kiss on her shoulder. "You're really such an amazing girl. I can't wait for our first date. Now, give me a kiss, then I'll leave you to get yourself cleaned up."

Ryan slowly turned to face him, cheeks streaked with tears. She slowly leaned in, and planted a kiss on Jack's lips. He used a hand to hold her head in place for a few seconds as he enjoyed the feeling of her lips on his. He let her pull back, then smiled. "Can't wait for our first real kiss, darling," he said. He proceeded to wipe his cock off on her leg, then pulled up his pants and went to leave.

Once he was gone, Ryan looked at herself in the mirror. What was happening to her? At least she only had to put up with this for high school. She wouldn't have to spend the rest of her life with this disgusting creep. Right?