Arrogant Annie Ch. 02

This chapter picks up where the last ended. It's shorter and also different. An experimental chapter, to some extent.

All characters are 18 or older.

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I was lying on her bed, not knowing what to do. After that humiliating experience, Annie just took her panties off the floor and put them on. Deciding that this tiny red piece of cloth together with her choker was enough to classify her as "dressed".

I loosened up a bit the moment she left the room. Still, my body felt stiff and fatigued. I got up off her bed slowly and dressed. A corner with a bunch of random sex toys caught my attention. I didn't see it before because I was too focused on Annie, but now I went over to examine it.

First, I saw a couple of fleshlights, some simple, and one that looked like a complex machine. Next to the fleshlights, a few big dildos, vibrators, and weird butt plugs. There were 2 pairs of cuffs and even one of those ball gags you put around a person's mouth.

I could pick out one whip and a range of different colored blindfolds. I have never seen the rest of the stuff before. Realizing it would be awkward if she caught me snooping around, I got up and left the room to find her.

When I arrived downstairs, Tom was still sprawled out on the sofa where she left him, and Annie was pouring water in her water bottle. She took a few sips before turning off the tap. Then she put some in her hand and gave me the bottle. I didn't know if she was making me hold it for her, or if she was offering me a sip. With the small amount of liquid, she approached the bony body on the sofa and stood over it, legs apart.

"Wake up!" she said as she splashed water on his face.

He woke up, but was disoriented, still half-asleep. Tom probably couldn't comprehend why there was an amazon with big perky breasts in front of him. She nudged him with her foot, and he jerked away from her. He was stiff and with his hands halfway up to protect himself. Fear was in his eyes as he remembered what had happened.

"Well, good morning sunshine. How are you feeling?" She spoke with a fake smile.

"I'm OK." He responded with a voice crack, as he realized his dick was out.

He started pulling his pants up when she grabbed him by the arm and pulled him up. She was towering over him. He came up to her chin. He lowered his gaze, but as he was so close, his eyes were practically in front of her tits, so he just readjusted his gaze in front of him. Now I could once again clearly see why he couldn't rival her.

Her top-of-the-line physique of a goddess made his skinny body look laughable. Her legs were long and twice as thick as his. She must have weighed over 80 kilos, maybe close to 85. She was a head taller than him. He couldn't have been a lot over 50 kilos.

"If you are all right, then leave." She let go of his arm and let him pull his pants up.

Tom looked at me in confusion. I just couldn't bring myself to say anything. We were both intimidated by her. I might be a terrible friend, but there was nothing to be said. So I just stayed silent.

She wrapped her arm around him like he was her younger brother. Even humiliated like that, I could see that his pants were unnaturally raised. He was hard. Annie knew it too. And hell, he knew she knew. He just let her tug him to the door in shame. Holding him close to her mostly naked body. His head next to her naked tits. She opened the door and pushed him out.

"I'd say it was a pleasure, but for me, it really wasn't. If you know what I mean." She held up her little finger and gave him a wink as if it was some inside joke the 2 of them had.

He was standing with his back to her for a few seconds before turning around and taking a deep breath.

"C-Can I see you again?" he asked and finally looked her in the eyes.

Tom wasn't a dumb guy. He knew she only had sex with him to humiliate him, and that she probably didn't even like him. Still, she was too hot for him not to try asking. He was already humiliated, he thought that it couldn't get much worse. Once again, probably the loudest that night, Annie burst out laughing frantically. He took the cue to leave. He turned around and hurried down the path in shame.

"I got to say, hahaha, I like your courage Tom" Annie shouted after him before slamming the door shut.

She locked the exit. Walking past me, she took her bottle from my hand and took a few more sips. I was keeping calm, not showing my arousal and uneasiness. She went up the stairs once again. I tried following her, not knowing what to do, but she just told me to stay. Even though I wasn't fond of her commanding tone, I stayed down.

She was down quicker than I expected. I had hoped she would get dressed before coming down. However, she was still only in her thin red panties.

"Sit." she said, carrying a USB.

She plugged it into the TV and started playing around with the remote. Whatever she was doing, it was taking too long. The silence was getting unbearable. I also didn't like her not caring that she was half-naked in front of me doing God knows what, and I had to sit behind her and restrict myself from looking at her body.

Finally, a file opened with a bunch of videos. She clicked on one of them and a video started playing on the TV. I could see a muscular black-haired guy. Blindfolded, gagged, and tied to a bed. Her bed. This was a recording from her room. Then I saw Annie walk in the shot.

She was carrying the big device that I saw earlier in her room. She had a serious, almost uninterested, look on her face. As if she was cleaning her room, doing mundane tasks. She took a small flask from the nightstand and poured the liquid from the flask inside the tube of the machine.

When she grabbed the guy's penis, he let out a faint muffled sound. Then she raised the machine over his dick and slowly lowered it. It was hard to get it on the entire way on his dick, as it was enormous. The guy then tried to tell her something through the gag, but at that moment, she turned on the machine.

It began pumping on his dick. The guy started thrashing around and yelling something in the gag. The scene cut off and after a second of looking at a black screen, a new video appeared. It showed a black guy and a white guy laying on the bed. One on his stomach, the other on his back. They were still, and it seemed like they were sleeping. Annie was in the middle of the two reading the book.

"Hold on just a second," Annie said, switching to the next video. Annie was getting whipped by a guy that was clearly on edge.

"Harder!!" Annie howled at him. Her voice broke from ecstasy. The next recording had no bed. Annie was naked once more, this time throwing leg kicks at her boxing bag. The bag was swinging around after loud thud. In the corner, sitting on the floor, was a woman drenched in sweat, trembling. A huge 2-sided dildo still sticking out of her vagina.

I understood what this was. She wasn't lying about recording guys she fucked. Well, not just guys. But it couldn't be. There was an immense number of videos in the file. Could they all be recordings of different people? As I was absorbed in the thought, Annie came near me. I saw her and gave her a puzzled look. She didn't change her expression, so I looked behind her. My heart sank when I saw the video on the TV.

There I was. Walking towards Annie as she laid, legs spread on the bed. I was so confident that I could challenge her. In retrospect, I should have just gone back downstairs, or even gone home. I know people say, "After the battle, everybody is a general", but it just seemed so stupid of me.

In front of me, Annie took off her panties and used them to tie her hair. I didn't even know that was a real thing. When she made a ponytail, she dropped to her knees and started to take my pants off. I attempted to stop her hands from doing what they wanted. She just clicked her tongue twice dismissively. I withdrew my hands, not wanting to infuriate her.

My pants were around my feet. My dick already hard. I was already leaking pre cum. Annie put her lips around the head and slurped the liquid. Then she gave my dick 2 good firm squeezes, expelling the last drops of pre cum. Her black nails moved over my urethral opening. I just sat and took it. Then she started scratching my stomach seductively with the nails on her left hand, a bit too strong for my liking, but I could tolerate it. With her other hand, she started stroking my penis. When her hand was near the head of my penis, she paused longer.

"Do you like our video?" she asked.

"No. No, I don't," I answered.

"Why? There is nothing to be embarrassed about. You saw you were my 66th private video."

66. I knew there were a bunch of videos, but the number still astounded me. Still, I was embarrassed. Mostly because she was giving me a hand job while making me watch it again. It was worse than I thought. I thought I was doing all right when I was fucking her, but I looked like a scared kid while keeping my eyes shut. She was licking my dick from the side, keeping her head turned towards the TV.

"Oh cutie," Annie said when the video was on the part when I tried to make fun of her. When I was ignorant to the fact that she was going easy on me. It made my face go red. She chuckled with her mouth open and her tongue under my dick. It made me angry as well as embarrassed.

"Oh, come on. Don't get mad. It was cute."

I didn't respond to her. She rolled her eyes a bit in an "ok whatever" manner. I was getting close. Her blowjob didn't have the same ferocious feeling as her fucking. It was like she was just killing time while we were reviewing the video. She finally swallowed my entire shaft to its base. Took a glance at me with my whole dick in her mouth. Then she looked back at the TV and pulled her mouth off my shaft. She spat on it a bit and repeated the motion of swallowing me whole a few times. The video was done.

But I wasn't, even if I was close. Annie leaned back on her left arm, still holding my dick in her right. Then she left my dick for a second to click the next video. As she positioned herself back in front of me, the video started.

She was in black latex gloves, holding a see-through fleshlight. A guy once again tied up to her bed. Not laying on the bed this time, instead, he was sitting on the floor, with his hands upwards, attached to the bed frame. A different guy once again, but it seems like she fancied tying guys up. She put his penis in the fleshlight and made a few fast and precise pumps. Then she pulled off his dick. Leaving the guy squeezing his ass, thrusting into the air.

"Fuck. Fuck. Oh shit, that was so fucking close. Cmon. I'm begging you." The guy was saying. But she acted as if she couldn't hear him.

A few seconds passed, and the guy regained his composure. When he saw her nearing the fleshlight to his dick once again, he took in a loud deep breath, keeping his lips tightly squeezed together, putting them in between his teeth. It looked as if he was preparing to dive underwater.

She then put his penis back in and started pumping. His abs became visible as he squeezed them tightly. Flexing, he held his breath. His face grimacing. One eye was slightly more open, and cheeks puffed out. She stopped pumping when he was still holding his breath and moved her hands away.

However, she left the fleshlight on his shaft. I could see his reddish dick visible inside it. He finally exhaled and quickly started taking short, shallow breaths. He surely wanted to cum but was fighting it. I couldn't see why, but he must have known what Annie was up to. She then grabbed the toy and yanked it off his penis with a popping sound. Leaving him moving his feet left to right.

"You ffffucking..." he stopped himself from finishing the sentence.

Then Annie said her first words of the recording. "Good. Good. Be a man and fight it. I see you chose to go this route, but I can't see why. All I'm trying to do is give you an orgasm."

He didn't respond, but exhaled in a half chuckle, shaking his head in disapproval. Maybe disbelief. She sat up and I could see her whole body for the first time. Even though it looked like she was dressed because she had a denim shirt on, it was actually all she had on. She stood in front of him, undoing the last few lower buttons on her shirt. Then she got in a wide stance over him and started squatting down.

The guy closed his eyes for a second and blew air out of his mouth in relief. A satisfied and proud smirk appeared on his face. Suddenly, she stood still. Only inches from his dick. The guy's eyes widened.

"You know what, I think we should do another one, and then you get your reward. The last one. I promise, I promise. You just last one more time." Annie said.

Then the guy jerked out of nowhere. Pushing his hips up, he tried to insert his dick in her. Like he tried to stab her. She recoiled and started cracking up. Annie was laughing often. She no doubt seemed like a cheerful person. The only problem was--she laughed like this only when sexually humiliating people.

The guy looked discouraged. But I knew he would try to ride out the last... what was it even? Fleshlight attack? Well, the crucial question was, was it the last, or was she lying. Still, he must have hoped that she would keep her promise if he proved to be man enough. I was right because he soon looked up at her with determined eyes.

Annie must have liked it, as she added, "That's the spirit."

She spat on the entrance of the toy and pushed her saliva in with her middle finger, making it more moist. Then she licked the entrance twice and sat back to her starting position.

"Ok honey, squeeze your glutes and brace your core. Remember. You get through this; you get to shoot your load in my premium pussy." Annie said to him.

He nodded his head in understanding. His penis got some rest, but it was still reddish and looked on the edge of orgasm. Deciding not to give him any more time to recollect himself, she pushed the fleshlight on his dick. This time with both hands and her entire weight. She came eyes to eyes with him while still pushing the toy to the base of his penis. Then she pulled away a bit. She continued pushing it up and down his shaft. He was trying to keep as still as possible.

"Cmon. Cmon!" he said. She continued attacking his dick. "Cmooon!" he yelled again.

"Just a bit more, honey. You are doing great. And remember, if you can't do it, you can always imagine it's my pussy." He looked so focused, I don't even know if he heard her.

Then he yelled, "Oh fuck. FUUUUCK! I-I can't! Cumming! I'm cumming. I'm AAAGH. FUCK!"

At that moment, she pulled the toy off his penis. She quickly grabbed it and squeezed it hard, making his cock redder than before. She pressed it flat on his stomach.

"Oops," Annie said, raising her eyebrows and looking at him. You didn't think I would make you enjoy it. You could have enjoyed it if you held your load, but I can't reward failure" she said and sneered at him. One side of her lip curled upwards.

The guy was tensing and spewing out cum. When he gave out his fifth or sixth blast of cum, he went still.

"You... You fucking bitch," he finally said.

She instantly looked at him with bulging eyes. "What the hell did you just say to me?" she asked. Her words passed through her clenched teeth.

"I just meant... AGH!" His words were cut short. She presumably squeezed his penis even harder.

"A hot girl makes you cum and you have that to say to her. Ok fine, I can be evil too." She began stroking his dick.

"Hey, hey hold on now. I didn't mean that. At least untie me.... Please?" She paid him no attention. "Annie. Ouch. Ugh. Hey, come on girl. Untie me. Ah, fuck. STOP! That hurts. I just came." She still didn't answer.

She was stroking him with incredible speed and power. His dick becoming more and more unnaturally colored. He started jumping around. His voice getting louder and louder. When he started kicking with his legs, Annie jumped up a bit and sat on them. Now he was in place. Stuck. His hands tied. His legs under her.

I chose not to watch anymore. I got the shivers through my whole body. I looked at how Annie was rubbing me, and it was so calm, so friendly. But the knowledge that she could give out such harsh hand jobs was all I needed to be frightened. I was now insanely close to cumming. I was looking at the backside of her head as she was stroking me.

She was focused on the TV like she was watching a documentary. Or a movie that was at its climax. Now that I wasn't looking at the screen, I could only hear that guy screaming his head off. At that moment, I felt my cum rush from my balls.

"Annie. Hey," I blurted.

She looked at me. "What is it?"

"I'm cumming!" I said louder.

She reacted instantly and impaled her head on my penis. My toes started curling, and I burst into her mouth, spraying a few blasts of cum straight down her throat. She didn't move for the next half a minute. Then she withdrew her head. She swallowed it all. There was not a drop of cum left in her mouth or on my dick.

I closed my eyes and leaned back on the sofa. Annie must have turned the video off because the guy's loud wails stopped. I couldn't be alone with this girl. Who knows what she might do. I wasn't dumb. This blowjob that she gave me was just a calm before the storm, only a warmup for something. She wanted to get me nice and ready. I had to get out of this house.