Chapter 9
by
FreeUse92
What Punishment Does She Dish Out
The Headmaster’s “Punishment”
“Please… you’re not going to expel me are you?” I asked.
“I have something much worse for you, Adam,” Mrs. Leigh said coldly.
Mrs. Leigh pulled her chair out from her desk and spread out legs and exposed her white cotton panties underneath. She placed two fingers to the knuckles in her mouth, wetting them and pulling them out. Her fingers soaked, she moved them towards her crotch and rubbed her clit and dug the two fingers inside of her cunt. I stared in amazement as she fingered herself and then withdrew and spread her cunt wide for me.
“Adam, for this violation of the student’s code of conduct, I’m afraid you will have to shove your cock into my cunt and keep shoving it in there until you satisfy me. I must insist I swallow all your cum when you are finished.”
YOU WHAT?
“Let’s get going, young man. Pull down your pants and shove your cock inside of me, so I know you’re sorry for turning this prestigious school into your own street corner,” She commanded and was now lifting her legs over the arms of her chair and pushing her hips forward and spreading her cunt for me to enter her.
Well… I wouldn’t want to make her any angrier. She was the boss. I unzipped my pants and pulled out my cock between fly. I came forward and positioned myself in front of her, my hips between her legs and moved my hips forward. Mrs. Leigh had an imperious look as I nervously prodded her. She looked down and back up at my face. My cock parted her moist cunt lips and disappeared into her, the shaft sliding in and out was now wetting with her moistness. She let out soft, barely inaudible pants as I rock in her.
“I didn’t want to do this to you Adam, but you left me ****,” She panted as she stared down at the sight of one of her student’s dick moving in and out of her cunt, “You are becoming quite the delinquent.” More pants, “Sure you have good grades, but this school is about more academics.”
I nodded and winced. My face was probably melting at this point. I felt hot and sick, and Mrs. Leigh’s cunt made it worse. Mrs. Leigh’s cunt was warm and tight despite her age, and she was using it well, the walls of her vagina closing in and out on me. The bodily squishing noises filling her silent office to the percussion of her chair creaking and our combined carnal breathing. I could stare down and see her juice and my pre-cum lining her wood floors as more dripped out between every stroke. I looked up and thanked God and let out a deep breath.
“Do you feel how warm and tight that my pussy is for you, Adam? That shows how disappointed I am in you,” Mrs. Leigh said gasping. “Adam, it’s important your dick feels the weight of your actions.”
I was feeling the weight of something that’s for sure. At that moment, I could hear the door open, and someone came in. The man who came in was old and balding in his 50s maybe and came over holding a lunch bag. He smiled as he entered, not appearing shocked at the scene of a student knee-deep in the headmaster’s cunt.
“Honey, I was at that taco place you love and thought of you. Have you had any lunch?” The man said. I paused my motions in shock, as I was maybe an inch inside of Mrs. Leigh. Mrs. Leigh was still spreading her cunt as the man walked in and I stopped. Mrs. Leigh looked a little annoyed at me.
“Adam, I didn’t say you could stop,” Mrs. Leigh said with annoyance. I looked at the man. Mrs. Leigh looked towards the man who just walked in and said, “Thank you, honey. Just leave it on my drawer over there. I’m busy disciplining this young man.”
The man bent over and kissed her cheek while she was on the chair with her legs spread out hanging over the arms and my dick connected to her, not commenting on the fact I was still an inch inside of her.
He left the lunch on the desk and said, “Well you look busy, I’ll let you go back to work. Don’t be too hard on the boy. You’re only young once.”
The man turned and left and closed the door behind him. As I stared at him, I could notice the picture frame on Mrs. Leigh’s desk with her and the same. That man was Mr. Leigh, her husband. Why didn’t he say anything?
“Adam, explain yourself,” Mrs. Leigh barked. “I didn’t say you could stop.”
“Oh… I was just wondering why your husband isn’t saying anything about me fucking you,” I said and turned back around and gave her my attention.
I started my motions again, my dick now moving back into her and out.
“He knows I run a tight ship around here,” Mrs. Leigh panted as we resumed fucking. “Sometimes only the stick will teach disobedient students like you. Adam, that’s not important, anyway. Pay attention to how your cock feels inside of me.”
I was. I clenched my jaw and looked down. Her hips were now quivering. I was coming close, and my body was shaking with anticipation. I grunted as I savagely jolted into Mrs. Leigh, my hands on her shoulders pulling us together, moving my hips with ferocity as I planted my seed deep inside of her womb. I withdrew and squeezed the last drops of my seed on her thighs and shook it clean.
Mrs. Leigh dug her fingers down again and spooned the semen dripping out of her cunt with her fingers and placed them in her mouths. She looked at me with irritation as she sucked on her fingers and repeated this over and over, cupping all the semen around her thighs and crotch.
“Adam, I wanted you to cum inside my mouth so I could swallow it all.” Mrs. Leigh said annoyed.
“I’m… sorry?” I said. My dick was softening, and Mrs. Leigh bent forward and took it in her mouth. I seized up with the tingly sensitivity in my crotch as she nursed on the softening flesh and sucked and lapped it clean. She squeezed the softening flesh like a tube of toothpaste, taking the last drops of cum on her tongue and lapping it up. She kissed it and sat back on her chair.
“Well, I hope you learned your lesson, young man. If I see you selling **** again, it won’t be just my cunt you penetrate you understand me? I promise you, you will have to spend the entire school day in this office filling every hole in my body with your semen. I’ll make you my own personal dildo,” Mrs. Leigh said contemptuously.
I nodded, and Mrs. Leigh went back to her administrative work. I left the office considering a future career in illicit **** dealing.
What Class is Next?
Disable your Ad Blocker! Thanks :)
Sexual Privilege
Freeuse for One
These branching stories are going to have 3 very simple premises: 1) You exist in a world where your character AND ONLY your character gets to have sex with whatever group or groups of people you choose wherever and whenever he or she desires. 2) The circumstances under which he or she can have sex with that group can be specified generally or specifically. 3) The response of the people you have sex with and/or the general public can be chosen.
Updated on Jun 11, 2026
by Cross C
Created on Aug 31, 2017
by SanctifiedVillified
You can customize this story. Simply enter the following details about the main characters.
With every decision at the end of a chapter your game state can change. Here are your current variables.
- 216,813 Likes
- 45,375,318 Views
- 8,561 Favorites
- 49,757 Bookmarks
- 4,253 Chapters
- 57 Chapters Deep
Comments moved below the chapter.
Jump to comments
Comments