Arrogant Annie Ch. 01

She turned around and went up the stairs. Her ass swinging. It turned me on like crazy. But after watching how she toyed with Tom, I couldn't help but feel scared. I just couldn't suppress it. Thinking of putting my dick in her made me afraid. Thinking of her tensing her ass pushing my dick to its boundaries. I tried to suppress those thoughts. It wouldn't do me any good. If I were to put up a fight, I had to be confident in my ability. So I followed her, leaving Tom's limp body downstairs.

I went into the room that didn't in any way indicate it belonged to a crazy nymphomaniac. It was quite clean, with some posters of female singers and actresses on the wall. A bed big enough for 3 or even 4 people. There was also a boxing bag that she must have used for training, and next to it some sports clothes.

She stopped in front of the bed, still in her bra and panties, as she didn't take them all the way off when fucking Tom. Well, she also had a black choker she wore almost all the time.

I was staring at her well-defined back when she did a heel turn and faced me with a pouting mouth. "Ok, we'll do it here".

Then she sat on her bed and removed her bra and panties. Throwing them aside.

She then took her phone, put the timer on for 3 minutes, and turned to me. "You have quite a dangerous task ahead. And as you are my brother's best friend, I will give you one last chance to walk away from this"

She was back to mocking me. In front of me, her legs opened wide in the air, and she angled her head to the right. Looking at me. Waiting for my answer.

Now I knew well what those legs were capable of. Not just from her stories. I had first row seats to one of her triumphs. I knew how vicious that pussy can be on reckless men. My mind was telling me not to do it, that I could just walk away in shame. It would be better than her showing our video to her brother. Now I was back to insecure thoughts. Once again, I stopped them and just walked over to her.

As soon as I got close enough, she pulled me to her with her legs. There was no going back now. Our weird little skirmish had officially begun. This was it. I had to last 3 minutes as she did her best to make me climax.

"Brave boy" was all she said as she started the 3-minute countdown on her phone.

I inserted my dick in her tight hole. And started thrusting. She let me be on top and I didn't want to waste that advantage. I was keeping the same rhythm, taking regular breaths, and for the first minute, it was going all right. Trying to keep my thoughts occupied, thinking about anything but this ruthless goddess under me.

Then I felt a tug in my balls and stopped thrusting. It was like a signal for her to take over. She didn't let me rest for a second. I had a great penis that I took pride in. But she was working all 7 inches without any issue.

I was getting tired. I put my hands on her tits and squeezed them. But this didn't seem to faze her, as she was still silent. I have kept my eyes closed from the moment I felt that tug, so I couldn't even see her face. Was she in pleasure? Was her back arching as she was taking my dick deep in her? I felt a need to open my eyes and see how she was doing. After all, she could be containing her laughter looking at my struggle.

I opened my eyes and first saw her perfect abdomen now covered in sweat that made her skin glisten. I traced my eyes over her lovely chest. Then I saw her face. She wasn't laughing, but she wasn't in ecstasy, either. She looked... bored. Looking at me with a serious expression. Her sea-blue eyes locked on mine.

"What... what is it?" I asked in confusion.

She sighed and formed a sad expression. "Oh, it's nothing. I kinda expected more from you. I mean, I thought you will at the very least put up more of a fight than your friend."

My balls were boiling, sure, but we were halfway done, she shouldn't be taking all that shit now. And I told her just that. She looked at her phone, all the while still squeezing me with her pussy.

"Oh we are? Ok. Well. Warmup done." In that instant, she increased the pressure in her pussy.

The walls clamped on me hard. And I had to brace myself and clench my ass just so she doesn't suck me dry in that instant. The fucking became more savage. Her moves seemed barbaric but still followed the same rhythm. I was back to keeping my eyes closed. My thrusts were shallow and without strength. She took it on herself to lead. I started clutching the smooth bed sheet that was under us. I forced my eyes open, just to look at the time, trying my best not to look at her. She noticed that and said.

"Come on boy! We got a long way to go. Don't break on me now. You know what the forfeit is. And I promise you, my brother seeing you conquered will be the least of your worries." She was back to being in a good mood. It was obvious how confident she was in her victory and that she didn't think of me as a challenge.

However, hope started building up inside me as I realized I only had 50 seconds to last. Could I really do this? I wondered. Could I really pass Annie's challenge? That would somewhat shut her up. She was cocky all this time, but now the time was running out.

I gathered myself, pushed through fear, and looked her straight in the eyes. And even if I knew I was close, and that it was not a good idea, I half-whispered. "Only 45 seconds left.... Time sure flies when you are having fun. "

As soon as I said it, her face grew dark. She stopped smiling, which I mistook for a good sign, and formed an angry face. I swallowed and got tingles throughout my body. She wrapped her muscular legs even tighter around me before I could react, leaving me in the same position as Tom.

Then she whispered. "You - fucking - idiot."

The pressure I felt was insane. Her toned abs turned to rock as her pussy trapped me in her firm grip. Her legs crushed me so hard I thought I would snap. At that moment, I realized it. All the furious fucking she had given me, she was going easy on me. Toying with a man she didn't see as a threat.

I looked at the times as it was nearing 2 minutes and 20 seconds. But I feared she wouldn't make a mistake. She knew I had no chance of lasting 40 seconds.

I still wanted to try. I felt like I was being squeezed out. I felt pain throughout my lower half more than pleasure. This teenage girl was a machine. This was no longer sex. It was just her doing what she wanted.

"What's wrong STUD? Having trouble?"

I tried to respond with something, but all I managed was a muffled cry that made her laugh. "Well, not so cocky now, are we?"

I just had to make it. I couldn't lose to her. I barely picked the phone up but couldn't see the exact time.

She took the phone from my hands and looked at it as she tossed her hair back. "35 seconds if you must know. But you don't have to worry about that anymore. This fight is over."

"Noo, Y-you still haven't made cum you -UGH- bitch!" Now I couldn't speak properly as my brain was being fried by pain and pleasure.

"Oh, it is. With the pathetic performance you put in, it was over when you accepted my challenge... You small fry." And with that, she kissed me with her soft lips.

I opened my eyes and started shaking. I started cumming ferociously in her gripping pussy that now felt like a man killing machine. She broke the kiss just as my body started cramping. I was gasping for air, groaning, drool coming out of my mouth.

Looking up at my face, which had a painful expression, she tensed her lips and covered her mouth "to stop" her laugh from building. Then she let out a loud chuckle through her nose. And continues laughing quietly as if I couldn't hear her.

She let me out of her legs and pushed me onto the bed. Now she was on top of me. Both hands right next to my head. I didn't want to move. Not that I had the energy to. I stared at her in shame, trying to, at least, not to look away.

"You-" she began but was interrupted by the sound of the alarm. She rolled her eyes and reached for her phone. Her tits fell on my head. She turned the alarm off and spoke. "You are so fucked."