Tries to be smart about it

Rob looked at the 3 bowls. He knew his options. He resolved that he would definitely take a dare that allowed him to cum. It was really torturous at this point, he had been teased all night and he needed release. That left 6 dares. Option 1: 6 from bowl 1. Option 2: 1 from bowl 2 and 3 from bowl 1. Option 3: 2 from bowl 2.

Rob walked towards bowl 3 and quickly picked one of the pieces of red paper in it. "Place it to the side, you'll open all the dares after you pick, in whatever order we want." said Carol. Rob then walked over to bowl 2. He hadn't decided whether he would take 2 from this bowl and finish it off, or if he would take only 1 from it. Since he had to pick one from here anyway, he did it quickly and placed a piece of paper next to the red piece.

Rob hesitated for a second which prompted his eager audience to yell out suggestions. "Take the 3!" came the voice of Alice. Rob turned to the crowd and his eyes met Lucy's and she pointed at bowl 2. Rob wanted this done as soon as possible and Lucy could make him do anything. So, he turned around, grabbed another dare from bowl 2 and placed it down.

"So," Carol announced, "these dares are not in a particular order! I will leave it to you as to how you will open up the dares"

At least Rob had some control. He reached for the red one first, and he knew he would have to read it out loud. "The girls will stand in a circle with Rob in the middle. Each girl gets a minute with Rob to try to make him cum. If a girl makes Rob cum, then between now and the next girl's night (next month), Rob must listen to any orders given by all the girls, regardless of where he is (within reason). If Rob survives one go from every girl, he gets to cum on whoever he wants and only she gets to give him orders for the next month." Rob didn't read out the last bit. It said "PS: if you win, pick me. You know I would tease you in a way that you would enjoy! - Lucy :)"

The whole crowd cheered. "What a great dare! I'm glad you picked that one and not mine. You should be glad too, I had you ruining your orgasm" said Alice. There was a discussion as to whose dare it was. The only one not doing a whole lot of chattering was Lucy, who met Rob's eyes with a knowing and sexy smirk.

Rob was unhappy about the forfeit within the forfeit that lasted a whole month, but if it was Lucy giving the order then...... it might not be the worst thing in the world. However, the thought of every one of these six - including Alice and Carol, giving him orders at school and beyond, scared his greatly. He would have no dignity by the end of the month. Rob's dick twitched once again tonight.

He then reached for the two bowl 2 dares now. He opened the first one. He registered the words before he started reading it out loud. THIS WAS WORSE THAN THE CUM DARE. This should be worth more dares, he thought. Just as he was thinking about how to protest, he felt a hand smack his bare ass. He turned to see Carol looking at him with some level of anger. His defiance immediately simmered down and he read it out loud. "Pick one of the following to be invited for the next girl's night: 1. Rosa Gomez, 2. Samantha Grace, 3. Lauren Lindsey. Pick by the end of the night or we will invite all 3" Cheers all around. Rosa Gomez was the raven-haired, beautiful, Hispanic math teacher at the school. Samantha, or Sam, was the secretary in the dean's office. And Lauren Lindsey, or Dean Lauren, as Rob always called her was the Dean of the whole school. This was starting to get crazy. Rob stared at the paper.

As he stared, Lucy quietly walked up and stood next to him. She faced the crowd alongside him, wrapping one hand around his waist. The other went on his dick and began stroking. "Don't worry, all of them are fun. Just open the last dare now"

Rob put down this piece of paper and began to open the last one. The last dare. He read it out loud this time before the words registered

"Since us girls have been drinking tonight, there's no way they can drive home. Rob, would you be a gentleman and offer all these sexy ladies a ride home. Oh, and since you are a gentleman, could you also walk them to their door and open the door for us."