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Chapter 86
by
MilfMaid
What's next?
The “Ace” In My Hole
As I got up and Chad lead me back to the couch a thousand different things began to run through my head. How different was this gonna be? Was it gonna hurt? Women always say anal hurts more… if it doesn’t, would I want this as a dude? I mean, dudes have butts… God I hope that doesn’t happen to me!
“Get on all fours, baby.” Chad says with a teasing smirk and a quick smack to my ass that made me squeal ever so slightly as my body jolted. With a very small, nervous nod I started to crawl onto the couch, my ass swaying and wobbling with every small movement I made as I crawled into position and took a deep breath as I prepared. I felt his hands start to softly grab and rub my cheeks, holding me close, as a deep, hearty chuckle echoed in my ear.
“Don’t worry baby, I can see you’re nervous.” As I heard the phrase don’t worry I could physically feel my body start to relax. All the strange thoughts in my brain started to go away, my breathing settled, and my body almost felt weightless. “Just bend over, arch that back, and enjoy yourself…” Chad continued as he lined up his cock with my tight unused hole. But as he commanded I arched my back ever so slightly, bit my lip and almost felt excited in anticipation right before he began to push himself in and-
“Oooooooh fuuuuuuck yeeeeesssssss~!” I squealed as my eyes rolled back in my head, my jaw dropped, and my mind emptied completely except for the pleasure that was filling my mind. It was a very different feeling for sure, almost foreign and unnatural… but at the same time… I did enjoy it! But, was it just because he told me to? Before I could really deep dive into my subconscious though my thoughts were quickly overrun by moans of pleasure as Chad begun to pump his hips.

“Holy~! Fuck~! Fuck~! Fuck~! Yes~! Fuck me~!” I moaned with every thrust, my eyes starting to roll back in my head as the foreign feeling of pleasure quickly began to envelop me, filling me with a feeling I had never felt before… yet another new experience that X-Change has given me.
“Fuck Jenny~!” Chad moaned from behind me as I felt his fingers dig deeper into my cheeks, threatening to leave permanent indentations in them. “I didn’t expect you to be such a fucking butt slut~! But you’re taking me so easy!” Chad growls as his hand smacks down on my ass again.
“Ugh~! I didn’t think I’d love it this much~!” I moaned as a huge goofy smile began to grow across my face. My voice sounded more and more like a bubbly schoolgirl by the second, losing her virginity and feeling her first cock! And, once again, it’s almost like that’s true. Sure, I’ve been fucked before, but never in the ass… and something about my first time being with my best friend felt… right? “Fuck that fucking ass~! Fuck it~! Fuck it~! Oh God FUCK yes~! Fuck me~!”
Chad growled again playfully as his hands smacked against my ass nice and hard before digging his fingers into me, forcing both of our movements to stop completely. At first I was confused, and then I started to whimper as he slowly pulled himself back and out of me, before sitting down on the couch. I looked back at him with a shocked and annoyed face, only to be met with a smirk.
“You want this dick? You gotta work for it, Jenny.” He grabbed the base of his cock and softly started to pump it, teasingly, as it stood at attention for me, making my mouth water. “Come over here and ride me. And I wanna feel that pussy of yours again.” He growled and gave me a daring look, that I quickly reciprocated.
“Yes. Sir.” I said teasingly with a quick giggle before pulling myself up and crawling over the couch until I am straddling him, knees on either side of his legs, cock aimed straight at my wet folds until, slowly, I pushed myself down again and- “Oooooooooh God~!” I groan as my eyes teasingly rolled back in my skull. “I forgot how fucking BIG you feel inside my tight little X-Change cunt~!” I giggled, before starting to bounce my hips up and down on top of him.

PLOP~PLOP~PLOP~PLOP~!
“That’s it baby~! Ride that dick like you are fucking addicted to it~!” Chad growled from underneath me with a small twinkle in his eye. I couldn’t tell if he was just extremely lucky, or knew what type of pill I was on, but as soon as he said the word addicted I felt something change in my brain… and I lost it.
“Yes sir~! Yes sir~! Oh FUCK~! I love this fucking cock~!” I was screaming at the top of my lungs now. My bounces became much more harsh and hard to control, almost animalistic as I was rutting myself over and over again, slamming my hips down hard enough that my ass was actually starting to turn red from the impact.
His hands had reached back and started to grope and grab my ass at the same time as well, sending small shivers and waves of pleasure up my spine and into my brain, just making me more stupid for pleasure. I could feel something building up inside of me, ****, clawing for release.
“I’m gonna cum~!” I squealed at the top of my lungs as my ass started to bounce more wildly now. “I’m gonna fucking cum~! My best friend is gonna make me cum again~!” I squeal, but as soon as I do something terrible happens… Chad grabs my ass, pulls me down to his lap, and holds my hips still. I probably still could’ve cum in this position but-
“Not. Yet.” He growled, which my body responded to and halted itself, stopping my own orgasm from reaching its climax. It doesn’t dissipate though, more just holds steady, unmoving, teasing me with a forever edge. “If you’re gonna cum, it’s gonna be while I fuck your ass.” Chad continues with that same teasing smirk. “So, if you wanna cum, slut…” his hand cracks against my ass again harshly. “Then you better turn that pretty ass of yours around and ride me like a good girl.”
Curse those words… and curse this pill!
“Yes sir.” I whimpered again, letting out a very soft moan as I started to lift myself up, feeling every inch of his thick and veiny cock brushing against my folds until, finally, it pops out and smacks against his own stomach, my juices coating it and making it shine. Part of me wanted to suck it, get his taste in my mouth again, but that wasn’t my order. So I turned around, sighed, and repositioned myself.
This time I stayed on my feet in more of a squatting position, legs spread, and moaning ever so slightly as I felt him push his cock against my tight little hole again. I heard his chuckle, deep and menacing behind me, until he growls in my ear again:
“Fuck yourself to orgasm, you dirty little anal slut.”
At this point it was like a horse at the starting line hearing the gun shot: I was off to the races! I was bouncing my hips hard and fast now, my head, and tits, bouncing around like bobbleheads, as I squealed and moaned with every small movement I made, while the orgasm that was previously on hold continued to build from his previously heightened state.

Chad started to also thrust his hips up in perfect timing with my bounces, and I couldn’t help but start to rub my clit as well. My mind was going berserk in a mix of lust and pleasure, my eyes rolling back in my head, and my moans loud and high pitched with every thrust inside of me.
“Yes sir~! Yes sir~!” I squeal, feeling myself giving in to the depravity more by the second. “I’m a dirty anal slut~! I’m your dirty anal slut~!” As the words left my mouth it was like the obedience pill worked with my own words as well, because every single word that left my mouth I believed even more.
“Yes you are.” Chad chuckles as he watches my ass bounce lewdly, wobbling in his face as it claps against his pelvis. “And you are gonna cum from me fucking this fine ass of yours… ain’t ya?” He growls as he watches, up and down, up and down…
PLOP~PLOP~PLOP~PLOP~!
“Yes~! Yes~! Yes~! I… I…” I was finally given permission, and that steady incline felt like a rocket ship taking off into the stratosphere, filling my mind and body with pleasure as I started to shake and scream. “I’M CUMMING~!” I moan as my ass slams down onto Chad’s hips again, my body starts to shake and convulse on top of him… and I orgasmed, from getting my ass fucked.
My mind was blank, lost in a state of euphoria as I felt myself give in to the pleasure, and Chad’s demands. It felt incredible, but as my ass continued to gape on his cock the weirdness started to come back again. It wasn’t until I felt his hand smack against my ass nice and hard again was I pulled out of my trance.
“Why don’t we do some yoga together, Jenny?” He growled with a smile.
What's next?
Lying Under Oath~!
An X Change Story
A Lawyer gets slipped an X Change during a deal with a new client and is shown brand new ways to conduct business. Can he keep his girlfriend, rivals, and company from knowing? Or will he end up as a free-use slut for all of his legal dealings?
Updated on May 30, 2026
by MilfMaid
Created on Mar 10, 2025
by MilfMaid
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