Facing Punishment

Sabel Green was surprised when the app told her to meet up with her match in the assistant principal’s office. She walked into the main room that was between the principal and assistant principal’s office and then walked to Mr. Herbert’s office. To play things off, when she walked into the door, she said, “You wanted to see me, Mr. Herbert.”

“Yes, Ms. Green. Please come in and shut the door behind you.” Mr. Herbert said.

Once Sabel walked into the room and shut the door behind her, she walked further into the office and sat down in one of the chairs. Mr. Herbert was smiling at her and she couldn’t help but smile back. Mr. Herbert was a nice looking man, so she could do a lot worse for her first time being used on the app.

“So, here is what I want to do. I want to play up on the idea that I am the assistant principal and you have been a bad girl and I am going to punish you. I am not much into punishment in the way of whipping or what not, but I have other ideas for that. Sure, I will be spanking your ass, but other than that, I am not going to be doing much else like that.” Mr. Herbert said.

“Sounds fun. Should we get started?” Sabel asked with a bright smile on her face and Mr. Herbert nodded.

“How about you get rid of those clothes for me.” Mr. Herbert said.

Sabel did waste any time getting her clothes off. First she took her shirt off and then she pulled down her leggings, which she had worn to school today, which hugged her ass so tight that it looked like it was a second skin. Next she unclasped her bra and let it fall to the floor showing off her nice, perky tits. Last was the thong that she was wearing, which once they moved past her hips fell straight to the floor.

“Very nice.” Mr. Herbert said as he walked out from behind his desk and approached her.

“Now, I want you on your knees to suck my dick. I am going to fuck your face though, as that will be part of your punishment.” Mr. Herbert said as he rested his hands on her shoulders and gave a little bit of pressure to push her down so that she went down to her knees.

“Yes, Mr. Herbert. I have been a very bad girl.” Sabel said.

She reached forward and undid his dress pants and pushed them down around his ankles and then did the same with his boxer briefs. Sabel was pleased with the half hard dick that was in front of her face, it was already seven inches long and was getting longer and thicker the harder it got. Sabel reached forward and started to stroke the cock until it was completely hard and then she moved her face toward the cock and when it was in her mouth, she dropped her hands so that Mr. Herbert could punish her.

Mr. Herbert started thrusting into her mouth slowly at first. Sabel wasn’t well versed in getting face fucked, but she had done it a few times before, so she didn’t think that she would have a problem with it and that proved to be true as Mr. Herbert continued to thrust into her mouth.

As time went on, Mr. Herbert started to thrust more and more of his cock into the brunette’s mouth until his balls were slapping against her chin. Sabel had been able to deep throat for a long time now, so this didn’t seem to bother her all that much either. She did make gagging noises every so often as she wasn’t the one in control and sometimes Mr. Herbert would hit a spot that would make her gag. The gagging sounds made it even hotter for Mr. Herbert, which made it even hotter for him.

“Such a nice mouth!” Mr. Herbert moaned as he continued to thrust into her mouth.

Mr. Herbert normally had good stamina, but having the lovely Sabel Green kneeling before him with his cock in her mouth was pushing him closer and closer to cumming a whole lot faster than he would normally want, but he had other things that he wanted to do too, so if he came, that was fine.

He sped up a bit and was now fucking her face as fast as he would her pussy. He didn’t go as deep now though. He didn’t want Sabel to feel any discomfort for what he was doing to her. After a bit longer, Mr. Herbert could really feel that he was ready to release his cum.

“I’m going to cum deep in your throat!” Mr. Herbert moaned right before he started to shoot stream after stream of cum deep into the brunette’s mouth.

After he was done cumming, he pulled out of Sabel’s mouth and looked down at her and smiled as Sabel brought up the back of her hand and whipped her mouth so that she got cum that escaped her mouth. “You are redeeming yourself. There are still other punishments for you today though.” Mr. Herbert said and Sabel nodded as she stood up.

Mr. Herbert removed his shirt and got his pants completely off so that he was now completely naked just like Sabel was. Sabel was impressed with the man’s build as he had a nice six pack and nice pecs as well. “Now you need to sit back in your chair.” Mr. Herbert said and Sabel nodded as she sat down and waited for the assistant principal to make the next move.

Mr. Herbert got down on his knees in front of the brunette and pushed her legs apart and dove into her pussy right away. “Oh Fuck!” Sabel moaned loudly as the man made contact with her clit. It seemed that the man was going in for the kill.

He soon added some fingers inside of her tight pussy and that made Sabel moan even louder. “Yes, Mr. Herbert. Punish me.” Sabel said as she didn’t know how this could be considered punishment as she was feeling so good right now.

Mr. Herbert continued to please the brunette, but she got closer and closer to her orgasm and soon Sabel found out how this was going to be punishment. She was so close to her orgasm and she could feel that she was about to cum and then Mr. Herbert stopped all movement and her orgasm died down. Sabel now knew that the man was edging her, which was hot, but also would get on her nerves soon enough as she was going to probably have to end up begging him to cum.

“Oh fuck!” Sabel moaned as Mr. Herbert started back to work on her.

The man continued to thrust his fingers inside of her drenched pussy and licking her clit. Sabel was loving every minute of this. She had never had anyone play with her like this before. All of the guys her age just went in for the kill. Of course, most of the time that she was with a guy her age, they needed to get done as soon as possible as they were either at school or at her house and she wasn’t about to let her dad know that she was having sex. That was just something that she didn’t want her father to know.

Here though, it didn’t matter as she and Mr. Herbert had all the privacy that they needed so they could take their time and have fun. Sabel knew what Mr. Herbert’s game was now and she wasn’t surprised when he stopped his movements again as she was about to cum. This time she was going to play into things a bit more though.

“Please, Mr. Herbert. I need to cum.” Sabel whined as she felt the man pull back for the second time.

“That’s right, Sabel. Beg me for it.” Mr. Herbert said.

“Please let me cum. Please, I need to cum.” Sabel said, playing into things even more.

“I’ll consider it.” Mr. Herbert said as he dove back into her pussy and started to push her toward her orgasm once again.

“Oh yes! Just like that!” Sabel moaned as she could feel herself getting close again.

Mr. Herbert continued to finger and lick the brunette’s pussy. He didn’t know whether he was going to edge her again or whether he was going to let her cum. He could tell that she was getting close, but he wanted to hear her beg some more, which she did.

“Oh, I am so close, Mr. Herbert! Please let me cum! Please!” Sabel begged.

That was enough for Mr. Herbert as he continued to lick and finger the beautiful brunette until she came all over his hand and face. “Oh yes! I am cumming!” Sabel moaned as she had a very powerful orgasm because of all the build up that she had.

Mr. Herbert caught all of the juices that he could in his mouth and as she gushed for him. Once he knew that she was done. He pulled back and whipped off his mouth and smiled down at the very dazed Sabel.

Once Sabel seemed to come out of her daze, Mr. Herbert helped her up from the chair that she was sitting in and led her over to his desk that had a side of it that was completely empty. “Lean down and rest your head and stomach on the desk. Now you get your spankings.” Mr. Herbert said.

“Yes, Mr. Herbert. I need to be disciplined.” Sabel said, still playing into the game that they were playing.

As she leaned over the desk, Mr. Herbert walked up behind her and gave her a hard slap to her right butt cheek and then he gave her one to her left butt cheek. He alternated like this for a while between each butt cheek until there were red hand prints on her darker tanned skin. After he had done this for about ten times on each cheek. He lined up his cock with her pussy and pushed in.

Sabel was so wet from her earlier orgasm and the fact that she was being spanked, that it didn’t take Mr. Herbert long to get balls deep inside of her, even though she was very tight. “Oh god!” Sabel moaned as he entered her.

“So tight!” Mr. Herbert moaned as he thrust his sizable cock in and out of the brunette.

He wasn’t wasting any time right now. He had been wanting to fuck Sabel Green for a while now. She was eighteen and willing now, as she was very willing to play the game that he wanted to play. He had been wanting to fuck her, so fuck her was what he was going to do. He wasn’t going to go slow like lots of other guys would probably do.

“Oh yes, Mr. Herbert! Fuck me hard! Teach me my lesson!” Sabel moaned as Mr. Herbert skin was slapping against her from behind.

Mr. Herbert was hitting all the right spots for Sabel as his cock was big enough to do that on every thrust. The more he fucked her, the closer she got to her next and probably last orgasm. She could tell that the man was getting close himself as he was really starting to pant with the speed he was going. She could also feel his cock starting to jump inside of her.

“I’m so close, Mr. Herbert! Please punish me further!” Sabel moaned.

“I’m close as well! I’m going to cum inside of you!” Mr. Herbert moaned and Sabel nodded over her shoulder which was the only time she had broke from their game the whole time she had been fucked by him and Mr. Herbert took that as confirmation that she was on some kind of birth control.

Not long later, Sabel was cumming again. “Oh shit! I’m cumming!” Sabel moaned and her pussy clamped down on Mr. Herbert and sent him over the edge as well.

“I’m cumming!” Mr. Herbert moaned as he shot his load deep into Sabel dripping wet pussy.

Mr. Herbert continued to thrust into Sabel until he knew that he had no cum left and then he pulled out of her and went to sit in his chair until he caught his breath. Sabel stayed in the position that she was in until she felt some of her energy return. She could feel Mr. Herbert’s cum dripping out of her pussy now and running down her thighs. She stood up and smiled at the man.

“You have redeemed yourself for now, Ms. Green. It was a pleasure helping you get back into good standing at the school.” Mr. Herbert said.

“It was a pleasure working with you as well. Do you mind if I get one of your tissues to clean myself up? Sabel asked and Mr. Herbert nodded that he was okay with it.

After Sabel was cleaned up, she got dressed and was about to leave the room when Mr. Herbert’s voice caught her attention. “Ms. Green. I hope you continue on this path of redemption you are on now. If not, I will be willing to punish you again.” Mr. Herbert said.

“You never know what might happen, Mr. Herbert.” Sabel said as she opened the door and winked at him as she left the office and made her way out to the parking lot to her car so that she could head home.