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by Tisch Author IconMail Icon
Rated: 18+ · Interactive · Adult · #2323921

Derek finds himself on the short end of the stick at his new job. How might things go?

This choice: Very well for Brittany, not so well for Derek  •  Go Back...
Chapter #8

Sleepover!

    by: Tisch Author IconMail Icon
Just in the time it took for Brittany to get to her match, Derek was suffering. Like she mentioned, her butt was already sweaty, the slick skin of her butt sliding Derek deep within its clutches. On top of the now firm hold each of Brittany's cheeks held over him the smell and heat of the environment was pushing Derek to the brink of his limits. Even so, he remained awake. On the contrary, Brittany was enjoying herself. She felt Derek fall deeper into her butt, to the point where he could fall no further. She made sure of that. Squeezing the little guy, Brittany giggled as she felt his body rubbing against her butt. "I can see why Bri enjoyed him so much," the black-haired student thought to herself. "I hope he can withstand my ass, though."

Eventually, the girl got to her tennis match. She prepared beforehand, stretching and making sure she was well hydrated. During stretches, Derek was again troubled.

*PULL*
*SQUEEZE*
*BOUNCE*

Inside of Brittany's skirt, Derek was contorted around by her sweaty cheeks. He slid up and down, right to left, and was utterly drenched by the girl's sweat before the match even started. The poor guy just wanted to pass out at this point, the smell of sweat overbearing and of course the treatment being subpar. For whatever reason, though, Derek just would not pass out. Then the match started. At first, things seemed to be okay, at least in comparison to what had gone on so far. Derek remained firmly wedged in the same spot, uncomfortable but at least reassured knowing that things could have been worse. However, as the match went on, things did get worse: for Derek.

Brittany was playing her lights out. She was on the brink of a landslide match victory. Barring an outrageous comeback by her opponent, the pudgy girl was going to win no problem. While she was nearly ready to celebrate, Derek was nearly ready to give up and submit. "No more," he thought. "Please, no more." At this point in the match, Derek was further inside of Brittany's crack. He could no longer see her panties. On all sides of him, Derek could only see, hear, feel, and smell Brittany's drenched ass. Thankfully, he hadn't gotten all the way into where the sun doesn't shine. However, where he was at that moment was nothing to rave about. Brittany got back to her match, serving and returning, running to one side of the court before heading over to the other. Her butt wiggled and jiggled as she did so, tossing and turning Derek deep within its depths.

*BOUNCE*
*SQUEEZE*

"Yes!" the girl squealed. At last, she had won. Though it wasn't as much of a blowout as it could have been, she nearly set the school's record for the widest margin of victory in a singles tennis match. Brittany ran over to her teammates and coach and celebrated. She could feel Derek squirming inside of her butt and laughed, the humor of it covered by her delight for victory. The team and Brittany left the courts a half an hour later after the last match concluded. As a group, Dellmore had cleaned house and won comfortably. Clearly, the highlight of the team victory was Brittany's winning. They all boarded the bus and went back to the school to gather their things and leave.

Back in the locker room, Brittany undressed. She had a change of clothes at the ready for getting into and leaving for home. When she took off her skirt, Brittany recalled Derek. She smirked as she reached into her panties and dug in to find Derek. When she pulled him out from within her backside, the girl laughed. Derek was covered in sweat and shaking. What he had seen and experienced was far worse than he anticipated, it was even worse than Bri's soccer practice. And now what was he to do? The poor guy was so exhausted and beat up that just standing would be a challenge. Brittany set him down next to her as she finished changing.

"You, my friend, are an absolute charm," the girl grinned. "I cannot believe just how good you felt and how well you helped me perform. No wonder Bri thought so highly of you. Yes, this could very well work out to be a good partnership." Derek couldn't even speak as Brittany finished changing. "Well, it's time for me to head home. I guess you're coming with, huh? You and I are going to get to spend the night together. I like it." Finally, Derek spoke up. "No! Stop! This is- no, just stop. I'm a staff member here, this isn't okay." Brittany rolled her eyes as she picked Derek up. "Whatever. Not like you have a say in it, pipsqueak," she laughed. Derek shrunk. He went down to two inches. "Oh? Little man got littler? Well, this should be even more fun than I expected," Brittany grinned. Derek knew right then that he was in trouble. The girl then stuffed him down her shirt. As quickly as he disappeared in her skirt, Derek disappeared into Brittany's chest.

Does anything happen that night with Brittany or does it all go all right?
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You have the following choices:

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1. Nothing significant happens, Brittany brings Derek back the next day

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2. Something happens that night

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