The Rules of Detention by Cupcake21

He could see the bulge of his dick sliding down her neck with each thrust. He felt his orgasm rising, and pulled his cock out.

“I don’t believe you deserve my load just yet,” he said.

Felicia breathed deeply through her mouth, trying to compensate for the time she held her breath.

“I think you got my dick good and wet for this next part.”

Derek turned to the desk, and used his hands to shove most of the desk’s contents into the floor. He grabbed Felicia by her arms and lifted her over her desk. He bent her over on her stomach, and placed the phone on it’s side, held up by two books. and pulled down her skirt, revealing a black laced thong, which matched her bra. “You dirty little whore. Wearing a thong under a skirt? Just who were you planning on fucking today?” he asked. He pulled the thong down to her skirt just below her ass, spreading her tan cheeks until he saw her glistening moist pussy and tight little asshole. He took his index finger and slipped it into her pussy, while holding her down by her arms using his left hand.

Felicia blushed at the sight he was seeing. She never felt more embarrassed than how she felt at this moment.

Derek smacked her ass again, leaving a red hand print in it’s wake. He loved seeing her perfect round ass ripple with the smack.
“I think you’ve earned my cock in that filthy little pussy,” he said. He leaned into her on the desk, sliding his cock into her pussy. The warmth surrounded his cock, giving them both a sensational pleasure. He started moving his hips, thrusting his large cock deep into her.

Felicia began to moan in pleasure and stopped fighting him off. She knew she shouldn’t have been enjoying it, but she couldn’t help it. She wanted him to keep going. He put both his hands on her hips and pulled her with every thrust, filling her pussy up with his cock.

Derek knew he was breaking her down into the filthy slut that she was. Her pussy felt so good riding him. He had this girl right where he wanted her. He pulled out of her and pulled her skirt and thong completely off before flipping her over on the desk. He grabbed his phone and started filming the area where he would slam his cock in her. He nestled himself in between her and put one of his arms under her leg to pull her to the edge of the desk. He started slamming his cock roughly in her pussy, hearing the desk scrape against the floor and the thudding sound of their bodies pulsate. He started going rougher and faster, hearing her squeals of pain and pleasure mix.

Felicia was about to explode. She could feel him hitting her g-spot again and again. It was getting her closer and closer to an orgasm.
She could feel the pressure rising in the pit of her stomach, and her legs started to tingle. She felt an wave of pleasure wash through her, and she moaned out with a pleasurable sound. Her legs tightened around his hips, constricting him into her.
After her orgasm, her legs finally rested, and she felt her body was exerted.

Derek noticed her body almost limp. “Tsk tsk tsk,” he said, putting the camera down. He pulled back out of her and grabbed her arm, yanking her off the desk. “Did you ask for permission to cum?” he asked, holding his hand at the base of her throat. He didn’t squeeze, but felt she needed to be punished.

“N-no. I couldn’t help it,” she muttered. Felicia felt she had done something wrong, but had no control over her body.

Derek shook his head. “You should have asked me before you came. I might have let you,” he said. He turned her and pushed her into the wall chest first. He put his hand on top of her head, still pushing her down and into the wall. She ended up in a supported position with her ass up in the air.

He started stroking his cock again, feeling her sweet juices lubricate him. “You had such a wet pussy. I wonder if it was wet enough for what I want to do,” he said, placing his cock on the entrance of her little asshole.

“Not there!” she yelled, jolting backwards. He stood up straight and pulled her head back by her hair. He leaned his head down to her ear again, “Do you dare challenge my authority?” he asked, his smirk flashing on the right side of his cheek.

“Let me ask you this, and answer me honestly,” he said, putting a little pressure on her asshole using the head of his cock. “Have you ever had anal?” he asked.

Felicia shook her head in a state of panic. “N-no, Master Mason,” she replied, trying to keep him in a good mood.

“You’re about to experience it,” he said.

Felicia tensed up, wanting to squirm, but knew it would only hurt worse trying to fight him off. He pushed the tip of his dick slowly into her asshole.

“Damn, that’s tight,” he commented, feeling her asshole surround the tip of his dick. He put his hand around her throat and pulled her into him.

“To make this easier on the both of us, try to relax,” he said, trying to fit more of his dick into her asshole. She did as he suggested, and his dick slid the rest of the way with ease.

She felt mortified at what he was doing with her. She had never had anal sex before and was very inexperience. It almost felt as though she was going to spit in two. He started slowly pumping his cock against the inner walls of her ass, feeling it swallow his cock.

“Oh my god, this feels amazing. Fuck!” he exclaimed, pumping into her asshole with more speed.

Felicia was groaning in pain, her eyes were squeezed shut and bit her lip. It was agonizing and demeaning to feel such an unnatural thing. She groaned loudly as his speed increased.

“Don’t do it so hard,” she said.

Derek pulled her hair again and she squealed.
“Don’t, tell, me, what, to, do!” he said, pumping harder and faster with each individual word.

He had never felt the pleasures of anal sex before. The walls of her ass just swallowed him up, and made him want to cum even more. But he didn’t want to cum just yet, he wanted to enjoy the last bit of detention he had for the day.

He could feel Felicia tensing up again, and that made it harder not to cum inside her asshole. He had to pull out before he blew his load.

Derek quickly turned her around and pushed back into a kneeling position.
“Suck me clean,” he demanded.

Felicia almost gagged at the though, but knew it was almost over. She got close to him before he grabbed her hair again and forced his cock down her throat. She started gagging again as he started pumping into her mouth, harder and faster than he was with her ass. She felt like her throat was closing in.

Derek pumped away until he felt himself burst inside her mouth. He groaned as he slowed down with the thrusts into her, and felt his cock twitch with every squirt he unloaded in her.

The warm silky liquid filled her mouth, and she tried to breathe through her nose.

“Don’t swallow,” he commanded, pushing the camera up to her face. “Open up for me,” he said.

Felicia felt disgusting. She was covered in saliva, her face was plastered with leaking cum and her own fluids. She opened her mouth, showing a sea of cum.

“Push all that out with your tongue and let it run down your body,” he said.

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