Chapter 24
by
FreeUse92
What punishment does Leigh dole out?
Schoolgirls, Anal, , Milf, A2M
“It doesn’t make sense. Why would you do that? He likes that porn! If he likes certain porn, why do you think the best way to punish him is to act out his porn fetishes?” Aunt Lauren asked.
“I’ve been in education for 20 years. Are you trying to tell me how to do my job?” Headmaster Leigh asked.
“B-but…” Aunt Lauren cried.
“**** and milf and ass to mouth is it, Adam?” Headmaster Leigh said, ignoring my Aunt’s plea. “It’s fitting that your Aunt is here. She can help me administer this punishment.”
“I-I.. can what?!” Aunt Lauren said, her face crimson.
“Stick your dick in one of our asses and make us taste it, or better yet stick that hard cock of yours in both of asses and make us taste both, Adam.” Headmaster Leigh said nonchalantly.
I kept staring at Aunt Lauren. I really wanted to do what Leigh asked of me, but I felt sorry for my innocent Aunt. Aunt Lauren wasn’t tied to the logic of this world. She was restless and still staring in disbelief.
“You’ll do no such thing!” Aunt Lauren said. “Headmistress… please. Adam really won’t learn any lesson like that. Can you please think of something more conventional?”
Headmaster Leigh looked annoyed and said, “I’m a busy woman. Since you seem to be unwilling to administer his punishment, I do have a backup plan.”
She pressed a button on her speaker box on her desk. “Iris Grant, please come to the headmaster’s office.”
Iris, if you can recall was my cousin and Aunt Saige and Uncle Tony’s daughter. She was my age and one of the cheerleaders in this school. She and I barely spoke to each other. Truth to be told, I think she hated me and hated my living with her. She had light brown hair with blonde streaks in them and was stereotypically dating the school’s quarterback.
“You can’t be serious,” Aunt Lauren said. “Why does Iris have to be involved in this?”
“Because you won’t do your job disciplining your reckless nephew,” Headmaster Leigh said.
Iris was on her phone and chewing gum while she entered the headmaster room. Her green eyes stared up from the screen and then stared daggers at me, probably pissed that I dragged her into this. I mouthed sorry.
“Ugh, what now?” Iris said.
“Iris, I’m afraid your cousin Adam is in trouble again. I’ll need your help to discipline him since your Aunt isn’t willing to do so,” Headmaster Leigh explained.
“Geez, why is that my problem? Like everyone in class thinks I’m in trouble when I’m only here to punish this retard,” Iris said. “You know how this makes me look?”
“I promise you, Iris, I’ll escort you back to class as soon as Adam shoves his dick in both our asses and explain in front of class that you weren’t in trouble but only helping me out,” Headmaster Leigh said.
“Ugh like whatever. Let’s just like get it this over with quickly,” Iris said. Iris put her phone away and threw her gum in a garbage bin by the door and came over to the desk and jumped on it and spread her legs. She lifted her private school skirt and parted her pink panties and smiled and added, “knowing this idiot is getting punished almost makes up for it.”
“I can’t believe this,” Aunt Lauren said. “You guys are all insane!”
Headmaster Leigh also got up and sat next to Iris on the desk. She too pulled up her business skirt and took off her white panties.
“I got to get out of here and find one sane person in this world,” Aunt Lauren said and left.
I looked back towards the door and wanted to go after Aunt Lauren. “Adam, eyes here. Start fucking one of us in the ass.”
Pulling down my pants, I complied to the Headmaster's demands. I wanted to sample Iris first, of course. Iris had her hands on her ass, spreading them apart as I pulled in close. I probed her anus with the tip of the cock, and she stared intently at it. I slowly pushed the thing up in her sphincter, and she tensed up, making it tight and hard to push in. “Relax.”
“How am I suppose to relax when I know that huge thing is going to go in me,” Iris said.
“I take it your boyfriend hasn’t fucked you in the ass yet?” I asked.
“Like no. That's gross,” Iris panted as I pushed another inch into her with care. She winced and breathed hard through her nose, her chest heaving up and down.
“Fuck it’s tight,” I said. “Just relax.”
“Adam, bring it here,” Headmaster Leigh said. I withdrew from her Iris’s asshole and drew it near to Leigh, who bent down and enveloped the head of my dick with her mouth and lips. Her tongue swirling around it and wetting it with her saliva.
“How does it taste,” I asked, smiling.
Headmaster Leigh ignored this and bobbed on it, moving her head rhythmically up and down and lining the cock with her mouth lube. After being sure, the cock was well lubricated I positioned back towards Iris and pushed it in her asshole once again. She tried her best to spread it wider and gritted her teeth, still staring intently at my shaft disappearing between her asscheeks.
‘Oh my god,” Iris cried. “Adam, it’s too big.”
“Adam, you aren’t taking your punishment seriously. Fuck her harder,” Leigh said watching.
Iris looked uncomfortable, and I tried to shove it in with more **** and pace, slapping my thighs against her ass. The ring of muscles on her asshole gripping onto me and being stretched by my cock in return. I would pull out every so often to admire her little ass ring pucker together after my dick pulled out of it. Iris’s mouth was gaping, and she was soft, “aahs.” She had bent back on the desk and lay down on it with her eyes closed and her hands still on her ass trying to spread them as far as possible as I pushed my dick forward into her ass.
“Now put it in her mouth,” Leigh said.
I withdrew from Iris’ little ass flower and moved to the side where her face was lying. Iris bent her head over and took it in her mouth and shot me a glare as she tasted her ass juice, her head bobbing on the tip and mouth on the cock. Iris slurped it and lathered her tongue on it and gagged every so often. I gave Iris a break and positioned between Leigh’s body. Leigh stretched her asshole wide as well, but it was much easier entering her asshole, and I gave it a much rougher treatment as I slammed into her. She made a circle with her panting mouth and let out pants as I rammed into her, the slaps of our bodies filling the room while Iris lay on the desk still trying to recover. I pushed Leigh’s hips over the edge of the desk and had my hands around the back of her neck and beat my hips like a drum into her. Her huge tits were shaking and nearly poured out of the top of her shirt, and her meaty ass banged against my loins as I pummeled her hard and fast. I felt close, and Leigh instinctively went on her knees and took the load in her mouth. She spent a good deal on her knees there cleaning and lapping and having her tongue know the surface of my balls and shaft. Iris too got up and on her knees and shared the cock and Iris and Leigh both kissed each other and exchanged fluids and went back to the softening piece of meat between my legs.
When they had enough, Iris got back up and excused herself. As I watched her left, I could see a trail of my and her fluid drip on her thighs to the floor. Leigh reached for a wet-nap and cleaned herself off and sat on her chair and dismissed me with more sexual threats if I were to misbehave.
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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
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