38. Mom's Anal Development (1)
A week had passed since my new routine took hold—banging Suyeon after our morning workouts at her place, then tangling up with Mom every evening. With nonstop sex around the clock alongside two voluptuous bombshells overflowing with curves, a hunger for fresh thrills started bubbling up inside me bit by bit. Specifically, claiming Mom's anal virginity.
It was perfect timing too. Starting tomorrow, Chuseok plus the substitute holiday kicked off a full five-day break. Best of all, Dad was posted overseas this year, so no relatives crashing the party. Zero obstacles in the way of popping Mom's backdoor cherry. I'd already stocked up on everything needed for anal play. All that was left was getting her green light.
... [Drip... drip...]
"Mom's pussy really is the best. I lose my fucking mind every time I slide in here, hehe."
"Mom loves her son's cock stuffing her full too ❤️"
To kick things off in a good mood after that satisfying fuck, my white cum was already mixing with Mom's pussy juices, leaking out around my embedded cock. Time to lay the groundwork and convince her. Sure, Mom's cunt was my absolute favorite...
"Hey Mom, my birthday's coming up soon. Mind if I get my present early?"
"Of course, son. What do you want?"
"I want your first time."
I started by gently caressing her slick, glistening asshole, still shiny from pussy nectar and cum.
"There?... No way~ I've never done anal before, and it's dirty~"
"Nah, it's not dirty at all. You gave me all your firsts, so I wanna claim yours too. Please, Mom~?"
"Son, Mom'll make you feel amazing with her pussy instead. And anal takes a ton of prep."
"No worries there. I've got everything ready."
"..."
Mom stared at me silently, her face deep in thought. Just as I was debating whether to thrust my cock for a white-flag surrender, her lips parted.
"...Fine, son. Mom'll give you her anal virginity as a birthday gift."
"For real?"
"But no way you can shove that monster in from the start. It'd rip me apart. You know that, right?"
"Yeah, I know. That's why I prepped some helpers."
"Ugh~ You're such a straight-A student when it comes to this stuff..."
"This stuff? Come on, Mom, I'm acing school too, hehe."
With her permission finally secured, I bolted to my room like a shot and hauled back my prepped haul: enema solution first, then a lineup of dilators in escalating sizes to loosen Mom's ass, plus plenty of lube oil. Mom eyed the blatantly lewd toys clutched in my beaming, kid-on-Children's-Day face with utter disbelief.
"That excited, son?"
"Hell yeah~ Mom's last virgin hole is finally mine."
"Jeez~ Hand over the enema. I'll handle it in the bathroom."
"Want me to help, Mom?"
She snatched the enema from me, waving off my offer before heading solo to the bathroom. Even now, she still dodged showering together, so of course she'd never let me watch her enema. Guess it was par for the course. Someday I'd drag her into that shower with me...
Ever thorough—even masking the sounds of waste from her ass—she ran the shower for cover. About fifteen minutes later, she emerged, enema complete.
"All empty now, Mom?"
"Kid's got no filter... Yeah, all clear."
Blushing at the thought of offering her asshole to her son, she climbed onto the bed.
"Alright, Mom, knees up and ass down."
"Okay... This is so embarrassing..."
She'd clearly washed her lower half during the enema too—her fresh, fluffy ass cheeks parted to reveal a pristine pussy and an adorably pretty little pucker.
"Whoa~ How's even Mom's asshole this cute and sexy?"
[Slurp... slurrrp... smack]
I lavished praise while slathering her anal ring with thick saliva. Mom buried her face in the pillow, letting out faint moans as her cheeks quivered. Her once-dry ass crack now gleamed with my spit, and below her twitching hole, her pussy lips wept nectar. Clear proof she was feeling it up her ass.
"Mom's backdoor tastes delicious too. You like it?"
"..."
Still no words, just her face mashed into the pillow and ass shaking. Time to properly develop Mom's anal.
I picked the smallest dildo from my stash, slathered it in oil, then coated my index finger too. First, I slathered oil around and inside her virgin hole with my finger. Her sphincter clamped down hard on the intruder, tense as hell.
"Relax, Mom, let it go~ Tensing up makes it worse."
Even as I cooed and massaged gently, it took coaxing before the grip eased enough to move freely.
"That's it, Mom. Just feel it nice and easy like that."
I pulled my finger out of her loosened shithole and eased in the oiled-up dildo—about the girth of my thumb—into her rosy inner flesh.
[Squiiiish~]
"Ngh!"
A weird, leaking hiss escaped her lips from the alien invasion up her ass.
"You're doing great, Mom. Gonna go deeper now."
"...Guh! Hold on, son..."
As the slim, elongated toy sank deeper into her cheeks—reaching spots my finger couldn't—Mom's urgent voice rang out. I stroked her ass soothingly, inching the dildo with utmost care, but she clenched fiercely to block any more intrusion.
"It's normal to resist at first, Mom, but try relaxing."
"Can't... It's not pain, just feels so weird."
Her stronger-than-expected resistance sparked an idea: distract her nerves from her ass.
[Schlick... squelch!]
"Son, don't just ram my pussy like—"
"Ignore your ass, Mom. Just feel my cock in your cunt."
My raging hard-on filled her pussy to the brim, kissing her womb mouth. Her asshole instantly loosened its death grip on the dildo.
[Squelch squelch... schlick schlick~]
"Gonna fuck your pussy slow, so relax, got it?"
"Hnnng... Yeah, son, slower though..."
Watching her reactions closely, I pistoned gently while syncing the dildo's strokes. The pussy pleasure definitely scattered her focus—her ass smoothed out around the toy.
[Squelch squelch... schlick schlick]
"Better now, Mom?"
"Yeah... hng, it's okay, but still weird."
"That weirdness'll turn to pure bliss soon. Just enjoy it."
My cock's smooth scrape along her walls had her tunnel flooding with nectar in no time, signaling her arousal. I ramped up the thrusts gradually, working the ass-embedded dildo in tandem. Her pussy's ridges and folds writhed dynamically around my shaft.
[Plap plap plap... squish squish squish]
"Feels good getting both holes stuffed at once, right Mom?"
"Ngh! Not sure... haa~ But my pussy's twitching more."
After some steady pounding, her whole body quaked from double the pleasure slamming both holes. Even as she shook, she rocked her hips like a pro to take us deeper. Looked like she could handle a bigger dildo up the ass now.
I decided to flood her pussy with cum first, then swap toys. I shoved the current one balls-deep—handle out—grabbed her rippling firm cheeks, and hammered with fresh power and speed.
[Plap! Plap! Schlick schlick!]
"Ahh! Son, too rough all of a sudden ❤️"
"Gonna shoot one load in your cunt first."
Our slamming junction sprayed nectar everywhere, dripping down. My groin and her ass bubbled white foam, stretching in sticky strings. Each thrust, my lower belly nudged the dildo handle, double-teaming her shithole with her pussy.
[Plap! Gloop~ blorp~ blorp blorp!]
After relentlessly plowing her cunt, thick ropes finally erupted from my tip.
"Haaang~ Son's hot cum... filling my womb up ❤️"
She came with my load, and as I collapsed onto her back, her knees buckled, sprawling us both across the bed. Feeling her feverish skin—proof of our intense fuck—I nuzzled her nape with soft lip kisses.