Chapter 176 – Endeavor

Unfortunately, it didn't go that well for her. On the one hand, she was bothered by his size. She had trouble going up and down while being filled so much by him. Any movement she took ground his tool against her walls and she kept grunting in pleasure, losing her focus every time it happened. On the other hand, her motions were a mess. This was her first experience riding a guy and she had no idea what she was doing. She often moved erratically, sometimes stopping herself in the middle of going up or down, and globally didn't keep any clear rhythm at all.

What's worse is that she kept coming by herself from time to time, especially after doing a sudden motion. Benjamin was watching her efforts, comfortably lying on his bed, with a slight grin on his face. After a few more minutes, she realized things weren't going how she wanted and became frustrated once again. Looking at his relaxed expression, she frowned and increased her waist speed for a short while in retaliation but it only made things worse, as she came even more strongly a few thrusts later. After returning from her high, she looked at him still seeming relaxed and her eyes filled with tears of vexation. This was quite similar to when he teased her during his massage on her, even though it was for a different reason this time.

"What's wrong, little devil? Are giving up already?"

"Shut up! I'm not!"

"Are you sure? If you give up, I'll do the work and I'll make you come so hard you'll never be able to forget about it. What do you think?"

Her eyes opened wide and she swallowed her saliva, probably imagining what it would be like. However, she shook her head after a short moment.

"No! I'm the one in charge here! I'm going to make you come like crazy instead!"

"What about we make a bet, then? The winner can do whatever she or he wants with the loser."

"W-what bet?"

"If you can make me come within two minutes, you win. Otherwise, I win."

"Ugh... That's unfair!"

"What is?"

"Two minutes is too short. I want ten minutes."

"Three minutes."

"...Seven minutes."

"Four."

"Five."

"Deal."

They shook hands to signify their agreement and Chloe focused once again, her most serious expression on her face, which only looked cute to Benjamin. He took his phone in hand, realizing it was past 3 am, and started a timer. The little girl timed her attack well. It was right in the middle of the night and everyone was probably deep in sleep right now. He redirected his attention to his little sister and checked what she was doing. She took a few seconds to think about her strategy, not wanting to repeat the previous disaster.

She thought the safest solution would be to use her hands and mouth again and make him come like this. This would avoid her from being overly stimulated and allow her to focus on the task until completion. However, she immediately gave up on that option. She was no dick and didn't want to go with such a cowardly move. What's more, there was no doubt he would tease her about it even if she won. No, she had to do it the right way and use her tight pussy to make him climax. It was just a problem of how. He was a tough opponent and she now knew he wouldn't go down that easily.

In the end, without any great idea to flip the situation around and running out of time, she decided to try things until she found something that could defeat her smug brother. She first rotated herself and rode him in reverse cowgirl, thinking that a different angle might stimulate his penis enough. She moved her waist up and down again and felt him pulsating inside her. She thought that was the correct answer but, unfortunately, she was also greatly affected by the change. His dick was now grinding against her lower pussy and each stroke pushed her to let a big moan out. Darn, this was so good. Sex was the best. She was going to come again. One part of her wanted her to stop moving and take a break but her body didn't listen, as if it had a will on its own. It continued to bounce on the hard cock and she orgasmed soon after, feeling a mix of bliss and frustration to repeat the same errors again and again.

After recuperating for a few seconds, she thought it wouldn't do. She had come once more but he didn't seem to be anywhere close to his release. She rotated her hips to face him anew, thinking about what to try next. She soon got a new idea and immediately went for it. Right now, only his penis was being stimulated. What if she increased that to multiple stimulations? The most obvious choice would be to go for a kiss again but that would also make her feel it too. So, she went for his chest instead. Remembering the numerous porn videos she watched in the past, men often seemed to like it when their chests and nipples were touched.

She bent forward a little and put her palms on his chest. Then, she started caressing him, with a great focus on his nipples, using her fingers to make circles around them or flicker them. For some reason, he smiled when she did that, but didn't seem to be much more aroused than before. Now, she had no other choice but to use her final move. She continued to move her waist up and down and laid her upper body on his torso. Then, she put her mouth over his right nipple and started to lick it. After a small amount of time, she switched to sucking it.

There was no way he would stay indifferent to that! It worked all the time in porn!