Chapter 9
by college town perv
What's next?
Mrs. Osterman
I spent the rest of the day thinking about my upcoming appointment. I slowly built it up in my mind during my classes, trying to figure out the best way to get my **** -- or at least the **** I could get on Mrs. Osterman. As soon as the final bell rang, I walked as quickly as I could to the office. I went double time, my heart beating hard in my chest. And, because I was feeling so very agitated, it was incongruous and strange when Sherry calmly greeted me with a smile and just waved me through to Mrs. Osterman's office. "Have fun, Jason," she said brightly.
I shut the door behind me and glared at Sarah Osterman, one of my enemies. It was finally time.
Once again I was taken by surprise by events. Sarah Osterman, the sternest and bitchiest principal in our school district, was relaxing on the couch in her office. And not just relaxing -- she was lounging. Her hair was down, and she had one arm along the back of the couch. Her legs were stretched out and crossed at the calf. I noticed she wasn't wearing shoes, and she'd unbuttoned her shirt halfway down. I got a glimpse down her shirt and saw the curve of her breast just inside -- which gave me a thrill, despite the fact that I was there to get far more from her.
She smiled up at me. She actually smiled! Sarah Osterman was famous for never cracking a smile. Then she said, "Jason, my dear boy. Why don't you come over and let me suck your beautiful cock? Sherry was telling me about it earlier and I'm just drooling for it."
I was confused, especially given her behavior earlier. "But earlier..." I started.
She kept her smile and said, "I have to keep up appearances to maintain staff discipline," she stated. "Rachel could have gotten us in a lot of trouble." Then she beckoned to me with her index finger. "Come here, let me treat you right, baby."
I had been planning to start by calling her a bitch and demanding she lick my balls until I came on her face. It seemed pretty degrading to me, which was why I'd chosen it -- she wouldn't even really be participating that much, but instead she'd just be a target for my cum. Instead, I stumbled unthinkingly toward her and sat on the couch. My high school principal, a married, middle-aged Black woman, slid to her knees on the ground in front of me. She reached up and unzipped my pants, looking me right in the eyes the entire time
She pulled my pants down and my cock, already hard, sprung out. It pointed straight up. She stared at it. "Oh, my..." she said, in a seductive whisper.
"Mrs Osterman..." I started to say.
She looked up at my face again. "Now, Mr. Kraus," she said in her best teacher's voice, as if she were explaining addition to a particularly dim student. "We must discuss how you should properly refer to me in here."
Before I could speak, she continued. "While of course the final decision is up to you, I was thinking perhaps 'bitch' is the best term. Would you like to try it out?" Then she leaned forward, slid just the tip of my cock into her mouth, and sucked hard.
That sounded pretty good to me! "Suck it, bitch," I said.
She pulled off briefly. "Anything you want, baby," she cooed, then she began to suck.
I quickly discovered that Mrs. Osterman was not a great cocksucker. She was clearly trying, but just as clearly hadn't sucked many cocks in her day. She couldn't take me very deep, and she didn't use a good rhythm. I was just happy to be there, watching her make the attempt, but after a while even she could tell something was wrong.
As my cock deflated in her mouth, she looked up at me. "I'm... I don't do this very much, Jason," she confessed quietly. "I'm really sorry!" She looked like she was about to cry.
"There, there," I said. I didn't really know what to do, so I reached out and stroked her hair. By now she was really crying, and I was confused as hell, not to mention completely limp and not turned on. "It's ok," I said, continuing to stroke. "It's no big deal."
She tried to look up at me and I saw her eyes were rimmed with tears. She looked genuinely distraught and was still crying.
"You don't even have to do this, Mrs. Osterman," I said.
"Call me bitch," she corrected me. Then, realizing the absurdity of the whole situation, she started to laugh. After a moment she wiped the tears from her eyes and looked up at me. My cock was still limp. She looked at it and said, "I'm truly sorry, Jason." -- here I noticed that she switched between Jason and Mr Kraus depending on how she was feeling -- "I will try to make it up to you."
"It's really ok, bitch," I said with a grin. Just saying the word made my cock harden a little, and, seeing as it was still very close to her face, she noticed.
She looked directly at my cock and said, "What should we do about this?"
"How about you lick my balls?" I asked. Sarah dove in immediately and enthusiastically, wrapping her arms around my waist and grabbing my ass, while applying her tongue to my sack. She looked back up into my eyes as she licked, and I started pulling on my cock, which was fully erect by now.
Sarah carefully licked my balls as I masturbated, lavishing attention on every part, while looking up into my eyes. She even moaned -- strategically, I think -- from time to time. Then as I was getting close, she pulled back briefly to urge, "Cum for me! Cum on your bitch's face!"
I love it when a woman talks dirty, and that was enough for me. I exploded on her face, covering her fine Black features with cum. She was smiling as she took a selfie and then asked me for my number so she could forward it to me.
So in the end, I did follow through with my original plan for Sarah -- just not quite in the way I expected.
What's next?
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A Blessing and a Curse
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Free oral sex, but at what cost
Updated on Nov 28, 2023
by college town perv
Created on Jan 1, 2023
by college town perv
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