Arrogant Annie Ch. 01

This is my first story. If you have any tips or suggestions that would help me improve in the future, I would like to hear them. Also, I tried to be as accurate as I can with my English. However, English is not my first language, so I'm sorry if I missed any mistakes.

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It was already late when I arrived at my best friend's house with Tom. We opened the door with the key that my best friend Adam had given me. We were close, so it was normal for me to stay over at his house. Even today, when he canceled plans for drinking with me and Tom to stick around at his dorm studying. He was in his fifth year of college, just like me, but his was far more challenging than mine, so he spent a lot of time studying. We were both 24 years old, with Tom being our underclassmen and 2 years younger than us. Entering the house, we put the booze aside and headed to the living room.

"Hello!" I said, just to be sure we were alone. To my surprise, someone answered. I turned to see a 5'11', maybe even 6 foot, blonde coming down the stairs. It was Adam's 19-year-old sister. She was one of those Thick-Fit girls, but more on the fit side as she was quite muscular. She was also a popular girl -- a polar opposite to her brother.

"Oh, hi Annie," I said surprised. She came in for a hug and I could smell the stench of alcohol. After we exchanged a couple of words, I introduced Tom to Annie, as they never met in person. I explained to Annie the situation and offered her to drink with us as we had drinks to spare. She accepted and brought her own bottle of wine from her room upstairs.

We put on some music and started drinking on the floor. She was quite pleasant to Tom and to me. We talked about sports, tv-shows, college and even politics. It was going well. But I felt uneasy, as I knew Annie's actual personality, and she wasn't showing it. On the contrary, she seemed like a wonderful person.

After we ran through a few bottles, I was starting to feel the effects. I thought about stopping, but Annie insisted we open the last bottle. It was 1 in the morning, but we were in no hurry to go to bed, so we agreed.

Annie noted how hot it was and pulled off her sweater. I knew she had an insane body, so I was spotting a half boner the whole time, but I could see it took Tom by surprise. She was now sitting in a tight shirt and loose sweatpants.

She threw her sweater on the sofa and, as she turned, she caught Tom staring at her. He blushed and looked at the floor. Annie didn't bring it up. Instead, she just continued talking about the book she was reading.

I started thinking about how it was incredible what alcohol can do. It turned this horrible girl who hates men into a real sweetheart. I had never seen her like this before. Still, I didn't want to ruin the mood by bringing up the fact that she was acting weird. Maybe she could make a good impression on Tom and actually form a friendship with him. It would have definitely been only a friendship as she was way out of his league. I felt like shit thinking that, but she was a 9 or a 10. On the other hand, he could pass as a 6 on his good days, and his shyness didn't help.

At that moment, my phone rang. It was Adam. He told me to find a book he needed and take pictures of a dozen pages.

"I need to go send Adam some pictures for his studies. Will you be alright on your own?"

"Oh god! We are not twelve." Annie said and started shooing me away.

I looked at Tom and he gave me a smile and a shy nod. I left the room thinking about how this went way better than it should have. When I saw Annie, I thought she will be in her regular foul hypersexual mood, and that she would tease the hell out of Tom. He might not have been a virgin, but he was still only 5'6' and scrawny. A perfect victim for Annie to bully.

As I was taking pictures, my mind started wandering to the last time I saw Annie. We were in this same house and we were left alone in her room for 15 minutes.

Her brother left for the shop, and that was usually the signal for her to tease me. She was in shorts and a sports bra as she had just come back from her wrestling training. She put her arm on my leg and started talking about the guys she fucked. That was always something she would brag to me about. It's almost like she knew how hard it made me.

I would stare into her blue eyes just so I didn't look at her toned and muscular body. I never knew if she was lying or telling the truth. The stories were always crazy and hot. That time, she told me about this big guy she had in her room. She told me she persuaded him to be the first guy she pegged. I thought about how few men could refuse that girl. Even when she wanted something insane.

I started thinking about how sadistic she sounded when she talked about pegging the shit out of that poor guy. Again, I wondered how could it be the same girl that I had such a lovely time with today. I went through all the pages and sent them to Adam. Then I waited for a minute till my boner went away and started making my way down to our little party.

When I walked down the stairs, I saw an unexpected sight. Annie was sitting in Tom's lap, making out with him. She must have heard me because she turned around. However, all she did was give me a little smile and a wink before turning back around and continuing kissing.

"What the hell is this?" I yelled.

"It's called making out. Right Tom?"

"Y-Yess" he responded.

He seemed almost in a trance. I was gone for 5 minutes at most. How the hell did that slut charm Tom that quickly? Then another thought hit me. Tom had a girlfriend of 2 years.

I took a step towards them. "Tom! Stop! You have a girlfriend."

"What! He does? He didn't disclose that with me." Annie said theatrically. "I thought he wasn't taken as he is so short." she continued.

I saw Tom get embarrassed and turn red. It happened every time someone brought his height up in a conversation. This time was no different.

"It's... It's just kissing. We didn't plan on d-doing anything else" He was looking at the ground and stuttered, acting as if he didn't notice Annie's mocking of his height.

"Woah. Woah. Speak for yourself, little guy. I was planning on doing a lot more than kissing." she said, trying to catch his eyes.

"Ummm. I'm sorry, but I can't do that. I have a girlfriend."

"That is ok. All you have to do is break up with her after we are done."

"I-I can't do that," Tom said, still looking down.

"Sure you can." Annie lifted his chin up with her finger, so he had to look her in the eyes, and said. "I don't know who your girlfriend is. But what I do know is that she is not hotter than me. And I know that because I know a guy like you can't get girls like me. So forget about your 4-out-of-10-at-most girlfriend and let me do what I want. K?"

I just stood there, not knowing what to say. I was expecting Tom to start crying. And hell, could I blame him? But after a long uncomfortable pause, all Tom said was "Ok", his head now back looking at the floor.

Annie turned around. Evil look on her face. "Wanna join us?"

After I didn't respond, she just shrugged and turned back to look at Tom. He instantaneously lowered his gaze back to the floor so he doesn't lock eyes with her, which made Annie almost chuckle. She did this in a way that made it obvious she almost laughed at him, further humiliating him and angering me. She then grabbed his face and started kissing him. He didn't resist. Even after she started stripping him, he was as still as he could be. Next, she stripped his pants and grabbed his hard dick.

"I hoped you will at least be big down here. Well, at least it is proportional." Annie said and giggled.

She was no longer hiding her mocking attitude. Did she even want to have sex with Tom, or was she just enjoying humiliating him so much? I thought about doing something, but what could I do? Tell them to stop having sex? I mean, it WAS consensual sex. I couldn't tell them to stop. Therefore, I just continued watching. Angry, shocked, and ashamed.

Annie was stroking him. "I hope you can at least use this shrimp of yours. Hm?"

Tom didn't answer.

She got even closer to him and licked his lips. "What's wrong honey? Cat got your tongue?"

After Tom failed to answer once again. She turned to me. And eyes closed started laughing actressy. As if she was trying to make me realize how funny it was that Tom couldn't speak up. It made me wonder. Was this entire show for me? I mean, she was giving me more attention than the guy she was about to fuck.

Annie was holding his dick in between her middle and index finger. Her sharp, long, black nails were awfully close to his dick. Next, she centered her tight pussy over his dick while looking up in concentration. Then she started slowly lowering herself onto his dick. All the while looking at me playfully biting her tongue, eyes wide, head slightly tilted as to signal to me to listen for something. I didn't understand what she meant.

Then I heard Tom whimper as his legs quivered, "Oh G-God!"

Annie turned abruptly. Opening her mouth and gasping mockingly. "So you CAN still talk. That is good news. I like it when guys talk... or well scream when I fuck them. So don't worry too much about letting some sounds out. A lot of guys try to act mighty and not let out groans. But I made guys twice your size squirm with this tight pussy".

She raised her hips, making Tom's legs tense once more in anticipation of the next descent.

Just before lowering his pussy back onto his shaft, she added. "Oh, and I give you 2 minutes, tops. But I do hope you prove me wrong. You did the most today to cement yourself as a loser, but at least don't be a minute man."

She was no longer deciding to hide how evil she was. She was now openly degrading him. There was a pause as if Annie wanted to let what she said sink in. And maybe give Tom a chance to say something.

When he didn't, she said "good luck", and sat on his dick.

She just kept going at him. Up and down in silence. As she worked him, I could see her defined back with some Chinese tattoos running down her spine. I could also see Tom's face in anguish, and I knew he was trying to keep his voice down. Trying as hard as he could to not confirm what she said just moments ago. However, after the fifth or sixth thrust, he could no longer silence his whimpers. He started letting out groans and moans, which surely made her satisfied. She looked in complete control. I thought he was just going to sit there and take it.

But somehow, he got the strength to push her to the side and on her back, all the while keeping his dick deep inside her. He continued fucking her, and I was amazed at his confidence and strength that came out of nowhere. I mean, he was a head shorter than her, and with all that muscle, she was way heavier than him. It must have been the confidence, that he momentarily got back, that made him start thinking again. He stopped fucking her.

"I can't do this. Oh god. I have a girlfriend." Tom started pulling his penis out of her but stopped halfway.

He looked behind him and saw that she wrapped him in her legs. He tried to pry her legs apart, but they didn't budge a centimeter.

He turned to her slowly and finally looked into her eyes. She had a serious look. Then she put her hands around his head. His hands were on each side of her head, but he could only lift her up a bit. He couldn't get up. He was too weak, too feeble.

"Uh-uh. I don't think so. You can't change your mind halfway through."

"No! This stops now." He said seriously.

He mustered all his courage and said in a firm voice. "Let. Me. Go."

She waited for a second, looking him in the eyes almost as if they were having a staring contest, before responding.

"You are getting pretty arrogant for such a small boy." Her voice was filled with anger and hatred. "I'm not letting you get away from me. You are free to try to save your pride and your girlfriend's honor by not cumming in a teenage girl. But you are not getting away from my leg lock. But if you satisfy me and make me cum. I might just let you leave with your pride somewhat intact."

She brought him as close to her as possible and whispered something in his ear before biting it. I couldn't hear what she said, but the pale look on his face made me shudder.

"L-l-let me g-go." He started stuttering like crazy. His voice was once again scared and weak.

She paid no more attention to what he was saying. Only focusing on milking him with her cunt. He tried to push them both off the couch. He only hovered in the air for a bit. All the while, she was still fucking him like an animal. He then collapsed on the bed, back into her embrace.

He was not even trying to best her at sex. Which was a good idea, because if the stories were true, this girl could fuck for hours. But then again, he couldn't do anything else but lie on top of her, waiting for her to finish having her fun.

Once again, I thought about helping him. This time I didn't move because I was frozen. Probably from fear. I wondered if she could boss me around like that. She was tall. But was she taller than me? I was 5'11' and not an inch taller. I wasn't built badly, but I wasn't built built. Not like her.

Tom's voice interrupted my thoughts.

"Please. Please!" He pleaded with her, realizing he cannot beat her and that it was just a matter of time before she broke him and made him cum.

Hearing that, she started laughing hysterically. "Hahahahaha. Oh-oh, weakling just couldn't hang. Cunt wins. Pussy loses. Hahahahahaha" She was having so much fun hurling obscene jokes at him.

She knew how much stronger she was than him. And she enjoyed humiliating him. How evil do you have to be? To be born better than someone and then to take so much pride in that, knowing full well the less fortunate can't do anything to oppose you. She knew he couldn't fight her when it came to sex. And knew he couldn't run away. I'm sure that made her feel good. That thought of dominating a poor guy. Teaching him a lesson. Telling him she is better than him and way out of his league in almost everything.

I realized I got lost in my thoughts again. Looking up, I saw the boy trying to withdraw, run away from her powerful squeezing cunt, but her tree-trunk legs locked him in once again. I saw his face. Tears falling down. I felt nausea take over me, but I couldn't look away from the sad sight.

He began thrashing around like an animal caught in a trap. Fear making him panic. One final desperate attempt at escape. She didn't budge no matter how hard he tried to lift her off the couch.

At that instant, he lifted her the furthest he ever did. I got hopeful, thinking he could get away from her. He was almost upright, her big body still wrapped around his little frame. Sadly, he couldn't stand up.

He looked at me in that position and opened his mouth "Help".

He went to say something else but this time all that left his mouth was a shriek. "AHHHHH"

She straightened her legs, squashing him in between. Next, she jerked herself backward, and they were back at the starting position. At that depressing scene. Only now he had even less strength and was closer to cumming. And she hadn't gotten tired in the slightest. He even put up a good fight, but she was too much of a perfect predator for him to withstand.

All he could do was try to do it again, even if he knew his lanky body couldn't wrestle her off. He pushed with all his might, trying to free himself from the deadly legs that were holding him in place as her pussy did the primary job. The poor guy must have sensed he was close. That there was no going back. He struggled, tried to get away again and again, and failed every time.

Annie must have felt it too. She looked up at him, a cruel smile on her face. She knew he was defenseless, that he couldn't endure any longer, that he was unable to not cum hard in her hot pussy as she just holds him to her.

And then the inevitable happened. He made the last cry and started cumming. He was shaking like a damn leaf. His eyes rolled backward and veins popped on his neck as his head sprung up looking at the ceiling. I could see her leg muscles tense as she compressed his torso. She continued squeezing him out for the next 30 seconds, pumping cum out of his balls. Devouring her victim until he went still and quiet.

The awful but hot sight got still. I didn't know if he was still conscious. But I got my answer fairly quickly. Annie unwrapped her legs from him and somehow pulled them under him.

Then, foot on his face, she used her toned naked leg to push the limp body off herself. I saw just how inferior his body was to hers. His petite body was soaked in sweat, and it just laid there. Worn down and battered. She sat up and stretched.

Then she kissed the unconscious boy. "Goodnight baby," she said.

She looked at me and shifted her position. Rage filled me as this girl, 5 years younger than me, sat on my friend like he was her stool.

"Bitch" I said.

"Well, he doesn't seem to mind. DO you?" She asked Tom who didn't answer.

"Is he ok?" I asked.

"Well, he is alive. And probably not crippled. That's the best I can offer to guys that bang me."

"Why are you like this? You know he is a good guy."

"Oh, come ooon. It's fun. Harmless fun. Good guys should also learn what I can do."

"You will apologize, you fucking bitch!" I snapped at her.

"Ummm, no, I don't think I will. I never apologize to weaklings who are under me."

I took a sharp breath, trying to cool my anger.

"But," she spoke abruptly. "We can make a challenge."

"What kind of challenge?!" I yelled.

Her jaw tensed in anger. Making her beautiful face even sharper. She was getting tired of me screaming at her.

"First off all, who the hell do you think you are, huh? The big guy screaming at a younger girl. But don't worry, you will get your chance to scream later." she said with a grin. Which made my dick jump.

"Ok. I'm calm."

"Ok. So. If you want me to apologize, beat me at the game. It's fairly simple. We fuck for 3 minutes. IF you are still standing at the end of those 3 minutes, aka. If I can't make you bust. Then you win. I will fall on my knees and apologize to your wimp friend. However. The fucking will be filmed. I already have a great camera in place, as I usually film my conquests and use the videos to masturbate to the faces of guys when they cum."

She paused for a second as if to wait for me to get impressed by this fact that once again sounded like a crazy fictitious tale.

"Anyway," she continued. "If you fill me with your cum. I will show the video to my brother. Then he will know that even you are the same as all men. Unable to best me. Oh and also if you do lose, I will continue fucking you till the sun rises. No matter how much you beg for me to stop."

"Jesus, you are fucking crazy," I said, rubbing my face in my palms.

"It's hard to imagine you are Adam's younger sister."

"Yeah, it's hard for me to accept that fact sometimes. That ugly virgin didn't luck out in the genetic lottery. Hmmmm, maybe I have him to thank for this body of mine. But that's not the concern now."

When she finished, she stared at me. Waiting for my answer.

"OK," I replied. "I can last for 3 minutes. And I will make you apologize."

"Yey!" She yelled and jumped up from Tom, who still laid motionless on the couch.

Annie came only inches away from me and stared at my face with a serious look. I knew it. My soul got crushed a bit when I realized she was looking down on me. Not only figuratively but also literally. She was taller than me. Not by much, but it was definitely noticeable.

"I will have soooo much fun breaking you" And then she smiled. "That's the main reason I love arrogant guys. You can torture them and see their big egos breaking."