We groaned in unison, though I'm not sure who was louder. Mom's body couldn't stop from shaking, and my legs followed suit as I struggled to hold on for dear life without coming immediately. Her hands clung mercilessly to the sheets on either side of Caitlin's head, knuckles bright white with tension. Being stretched so quickly had taken Mom off guard, and she collapsed on top of Caitlin in a heap.
"Sounds like somebody just bottomed out." She ran her tongue over Mom's earlobe, not allowing a sliver of reprise from the sexual onslaught.
"He did, he's all the way inside!" Mom involuntarily clenched her body and strengthened her grip on me, pulling me hard against her cervix. "How is Mommy's pussy, baby?"
"You feel incredible, Mom." My eyes nearly rolled back in my head. "I already feel like I'm gonna come."
All the honey leaking from Mom was spreading over my balls and thighs, coating us in slippery juices that filled the air with the smell of insatiable lust. I hadn't the courage to move any more than a few inches back and forth, afraid that being overstimulated by her gooey hugs would send me over the edge if I didn't keep myself in control.
"Not yet, baby, don't come yet," my Mother urged, turning her head so she could look at me for the first time since I'd entered her, flashing a sassy grin that she could barely maintain. "You still have another hole to fuck, first."
"Mmmm, good answer." Caitlin purred, kissing Mom on the cheek, turning the taunting up a notch. "Tell your baby boy what you did for him."
Mom let out a deep, breathy groan as I withdrew my cock, waiting until I had almost pulled out before she spoke. "I got my...my bum, uh, ready...for you."
She tightened up like she was sealing the exit behind me, but her insides were so slippery she couldn't keep me out if she wanted to. With just the bulging head pulsing in her buttery grip, I bore down to drive it back into her swampy cock-pocket so I could feel her meaty tunnel swallow me up all over again.
"Really, Mom?" My heart just about burst through my chest. "You did that for me?"
Caitlin winked at me and slapped Mom's ass, leaving a light pink handprint. "I brought her an enema kit, so she'd be easy to get into, Bunny."
I couldn't slow my racing heartbeat after this revelation. The adrenaline was impossible to ignore, so I made it work for me. I focused on just moving, trying to downplay how insanely good my cock felt trudging through Mom's sweltering insides when I tried to pull out again. In, out, I told myself with calm breathing. I centered my mind on my hips, nothing else, as I sawed back and forth inside my Mother, feeling her fat ass cheeks slap against my thigh with every thrust.
Caitlin brushed Mom's hair out of the way and sought to make eye contact with me. "Flex, Bunny."
"What?" I was too mesmerized watching myself plunge back into my Mother. The sound of her juices sloshing around me, her sopping wet walls trying to keep hold of me, almost made me come before I could even reach the bottom again.
"Flex like you're trying to stop yourself from taking a leak!" she encouraged me, holding my Mother tightly. "Flex, and push right up against her cervix, okay?"
I nodded silently and closed my eyes to eliminate all distractions.
"Good boy!" she cooed happily. "Now, stay there until you feel your orgasm calm down."
It felt like I was going to burst, and not in a sexy way, from trying to keep myself together. All I could think about, all I could feel, were things that brought me closer to the edge.
Mom shuffled underneath me in a way that made her cervix smooch the tip of my cock, pressing the spongy ring against my inflated bulge. Her tunnel constricted me like a vice so tight that I could feel her rapid heartbeat thumping through her squishy walls. Every dull thud was like a python tightening its wet, slithery hold around my rigid length, like Mom was trying to coax my orgasm to the surface by flexing her strong vaginal muscles to milk it out of me.
We both knew we were one wrong move away from giving her a buttery creampie, and as enticing as that sounded, even more lay on the horizon that I longed to experience. I tried Caitlin's advice and bore down harder, causing my Mother to squirm around like she was trying to find more room in her pussy to give to me, wishing for a crack or corner she could give me to feel me fill her just a little bit more.
I held onto her hips, digging my fingers into her smooth, creamy skin as I clenched myself for all I was worth. My cock expanded inside of Mom, further pushing into her deepest regions where the head ballooned to the size of a large walnut against the door to her womb.
Her round, half-moon ass cheeks were pressed against my thighs and bulged out in a way similar like Caitlin's breasts. So much ass meat spilled over the sides that it would put most other asses to shame with the excess alone. The softness of her jello booty was even more remarkable, how it would spring back into shape no matter how desperately I pawed at it, forming those two perfect, breathtaking cheeks like her ass was made of memory foam. I gripped her thick, juicy cheeks and watched the skin effortlessly cave to my touch. Like dough being pulled and kneaded, it offered no fight to my incessant mauling.
I was so focused on Mom's ass, and trying not to come, that I didn't notice she had risen up onto her palms. Mom was getting impatient and she didn't care if I made it into her ass or not. She just wanted to come.
Without consent, from me or Caitlin, Mom lifted her ass towards the ceiling so I almost fell out of her, waiting to see if we would say anything. When we didn't, she threw her hips back into me so hard that her ass cheeks slapped against my stomach with a smack. It was the starter pistol I needed to ignite the animal instincts I had been suppressing, so against Caitlin's advice I lost my footing in reality to enter a dreamlike state where only Mom's pussy and I existed.
I grunted in a tone unbecoming of a gentleman and savagely gripped Mom's hips when she moved forward again, this time yanking her against me when she pushed back so that we met in the middle and began fucking as though I wasn't mere seconds from exploding inside of her.
Her pussy formed a vacuum seal around my bulge that made wet, squishy noises seep out of her just as gratuitously as her juices were. Try valiantly as she may, she was too creamy to do anything but ooze honey onto my cock every time I bottomed out, failing hopelessly in her attempt to cling to me.
The sounds of wet skin slapping together echoed around the room as I pounded my Mother into the mattress. Mom's tits swung below her like two heavy pendulums, adding another instrument to our sexual symphony, clapping like thunder every time her hanging udders collided with each other. The shifting weight was pulling my poor Mother all over the bed, making stability difficult when her heavy milk bags kept throwing her off balance.
Mom held her butt in place with her back arched so her ass stuck out seductively, giving me easy access to throw myself against her and embed myself in her gooey tomb. She was clutching Caitlin like a pearl necklace, pinning her Sister against the bed as she searched for anything to keep her stable amid my torrent of deep, powerful thrusts.
Lightning surged through my entire body like someone had flicked a switch on my nerve endings, firing up a machine that ran on autopilot in pursuit of its one instinctual goal: breeding my Mother. I wanted to take her ass still, but if it hadn't been for Caitlin's oversight, I never would have made it out of her without coming.
"Slow down!" Caitlin kicked at me with her legs, but it was tough while she was trapped underneath Mom, so she opted for a stern tone instead. "You'd better not come yet, young man. Your Mother worked very hard to get her bum prepared for you."
"He can come!" Mom's voice was shrill and desperate but muffled against Caitlin's neck. I understood her even before she whipped her head around to face me with a pleading look. "You can come, sweetheart. Come in Mommy's pussy, please, baby."
Caitlin saw right through her and rolled my Mother off to eject my dick from her just before I came.
"You little bitch!" Mom whined, frustrated that her impending creampie had been denied her.
"I know what you're doing!" Caitlin wagged a disapproving finger in Mom's face. "You think if you make him come quickly that you won't have to give him your ass, don't you?"
Mom stared into the corner of the room like a scolded puppy. "I don't know what you're talking about."
"Great!" Caitlin clapped her hands excitedly. "In that case, let's get you into position."
Mom's bluff was called, and the only card she had left to play was to cancel the whole thing, but I had a feeling she wouldn't take that route.
Caitlin crawled out from under Mom and kissed her on the forehead, hoping to calm her nerves. "Stay right where you are, Soff, and we'll get you ready."
"Wait," I urged. "Can we...I mean, do we have to do it like this?"
Mom craned her neck to face me. "What's wrong, baby?"
I blushed a deep maroon. "I want to see your face."
The mommies shared a look that said, "Isn't that sweet?" But based on the situation, I don't think "sweet" was what I had in mind. Mom wasn't afraid to use her facial expressions to let me know how she was feeling, and I didn't want to miss one bit of it.
"We need lube," Mom instructed. "Lots of it."
"Bedside table." I motioned to the small wooden end table by the headboard. Caitlin scurried across the bed and pulled the drawer open to find the small, blue bottle I hinted at. "That's it, perfect."
"You've been waiting on this for a while, I see." Caitlin twirled the bottle between her fingers.
"A Boy Scout always comes prepared" I said, parroting the motto I had learned as a kid.
"Ooooh, Boy Scout, hmm?" Caitlin uncapped the bottle and tipped it upside down. A thin stream of lube ran out and formed a pool in her palm. "Does that mean you're gonna tie us up?"
"If that's what I have to do to get in here." I grabbed a handful of Mom's plump bottom and patted it lovingly. "Then sure, I'll tie up whoever I have to."
That made Mom chuckle. "Let's just see how I handle it first, okay?"
"You'll be totally fine. I promise." Caitlin stroked her Sister's hair to distract her. Her fingers, slick with lube, slid through Mom's ass cheeks and brushed over her unsuspecting butthole.
"Hey!" Mom lurched forward and brought her tummy flat against the bed with her cheeks clenched together. The light peach fuzz on her bum stood on end as if her fight-or-flight reflex had just been triggered.
"Hey to you, too," Caitlin teased, slapping a wet handprint on Mom's ass with a thwack. That got her to spin onto her back to protect her ass. Now, apart from her eyes burning holes through me and Caitlin, she was exactly how we wanted her.
I looped my arms around Mom's legs and pulled her, so her ass hung off the bed, then lifted them high to the ceiling before easing them apart. Mom's pussy peeled open like it had been waiting for the invitation. Her lips, drenched with syrup, were sealed shut until her knees extended past her waist, but it couldn't stay that way once Mom was spread to her widest. Finally, the sticky curtains parted and exposed the magnificent jewel I was searching for, glistening with juice, and seizing for something to hug. Pink, plump, and puffy, Mom's pussy was calling to me like it knew my favorite song.
Nobody could resist such a display, most notably myself, and I gave in to the desire to be back inside my Mother as soon as possible. Her eyes fluttered momentarily as a gasp escaped her, taken aback to feel me unexpectedly push into her birth canal all in one thrust. "Oh, oooooh, that's so fucking good," she groaned.
"Bunny, we've got a job to do," Caitlin scolded me. She placed the bottle at the top of Mom's slit and gave it a steady squeeze so lube would flow over her labia and dribble between her tired lips. I was buried to the hilt, keeping her plugged so the lube went around my girth and began to puddle up between her asscheeks.
Caitlin hadn't told me to stop, and I sure as hell didn't want to, so I rolled the dice and prayed I wouldn't reach my limit before I was ready. Playing with fire isn't dangerous if you're playing with something warmer than fire, right?
Mom's legs rested on my shoulders, her small, cute feet overlapped behind me to keep me close to her. Her thighs were turning red where I was holding her but, like a seatbelt, it was a necessary evil to keep her in place.
Her tits were squashed against her body, flattened out like huge, fluffy, white pancakes dotted with two small, pink raspberries that looked ripe enough to eat. Even with my cock inside of her, I couldn't help thinking about getting her boobs soapy and wet enough to fuck. I knew she would absolutely dwarf my erection as soon as it pushed between them, as a buoy lost amid a sea of quivering breast meat, happily succumbing to the waves washing over me.
Daydreaming, again, would have been the end of me if not for my heroic Aunt to rescue me from my headspace. I felt a tingle rising from my balls like a starship through my body, rocketing my brain to the stars.
"W-what is that?" I asked between bated breaths.
"Just a little finger magic." Caitlin was standing beside me, clinging onto my shoulder with her tits squashed against my back. Her fingers, coated with lube, were gently roaming around my balls while I pounded her younger Sister. She employed the lightest of touches to trigger ignition in my nerves; a single finger being dragged along the surface was enough to get my legs shaking. I knew I was really in trouble when I felt all five of her nails meet in the middle, then spread outward like a starfish to slowly spread the violent tingles through my veins like heroin.
"You have to stop," I pleaded half-heartedly.
"No, you have to stop!" she shot back. "Take your dick out of your Mother! Right now! Come on, Bunny."
Mom sighed with disappointment, but I didn't have much choice. A sober mind would know I wasn't gonna be able to hold on much longer, but my brain was intoxicated by alcohol and the sweet, heavy aroma of two honey-soaked Mommy pussies.
Clearly, a sober mind I did not have.
Mom shook her chest back and forth to keep my attention, biting her lip with giddy intrigue from watching how easily I could be lured into a hypnotic trance. "Stop staring, loverboy."
"I can't help it, Mom. You look fucking amazing!"
"Well, lucky for you, I'm also an amazing fuck!"
I looked down at Mom and knew the moment was near. She was practically leaking lube all over the bed, and I couldn't picture any of us being any hornier than we already were, so there was just one thing left to do.
Caitlin tapped her Sister's mons to tell her to pull her knees back, and though I'd seen her do so before, I noticed this time she was plagued with trepidation.
"Just...be gentle with me, remember?"
"We will be," I said, sharing an excited smile with Aunt Caitlin. "Right?"
"We have to start somewhere, let's see where it goes." Caitlin shrugged, eliciting a nervous grumble from my Mother.
Mom's wrinkled, pink asshole was poking out from between her globular ass cheeks, sparkling with the slippery lube Caitlin had already adorned her with. It clenched randomly, with no rhythm, more akin to impulsive spasm, like Mom was off her game. She had gone from a seductress to a submissive in just a few minutes, being ordered to wait patiently while her Sister and I took our time with her.
I extended a finger and poked it against the puckered ring, intentionally feeling out every small crease like I was reading braille. I circled the hole, though Mom was so tight it wasn't fair to call it that yet. Her pussy was an entrance, but her ass was a sealed box that required a delicate touch to unlock. She was quietly wailing like a banshee with low, drawn-out groans that seemed to go on forever. I had yet to put any pressure on her, and already my poor Mother was shaking like a leaf.
Caitlin slid up next to her and wrapped one arm under her head, laying her other across Mom's chest to rise and fall with every deep breath. I couldn't hear what she was saying, but her lips were pressed against Mom's neck and I could discern only the faintest of whispers. Mom said nothing, just stared down at me with wonder and fear battling for supremacy behind her eyes, but Caitlin was a chatterbox.
Whether she was giving helpful encouragement or enticing her to tough it out for my sake, I didn't care. Whatever she said translated to Mom unwinding enough that her bum, slowly but surely, began to relax. What had felt impenetrable now revealed a chink in her armor, and my eyes widened as I watched Mom's asshole dilate just a hair.
Progress is progress, I told myself.
I poked both of my thumbs against Mom's ring and pushed until I got traction, which I used to timidly spread her open while leaving her cheeks mostly in place. I managed to loosen her just enough that I felt the bumpy, gnarled texture give way to a core of soft, pink flesh that caved under my fingers.
I massaged my thumb around her slippery donut in small circles, occasionally applying a bit of pressure in the center in between Mom's deliberately tight clenching. Her best efforts weren't enough to dissuade me, and no matter how hard she squeezed I knew I was getting somewhere.
"Mom, you gotta work with me, okay?" I planted a kiss on her cheek and held my face against it. "Can you push when I push?"
Mom's face scrunched up. "Push?"
"Push for him, Soff, or he'll never get inside." Caitlin's voice was soothing, but not convincing.
"I-I don't know about that." Mom blushed up a storm but soldiered on. "Just...like, right now?"
"Push, Mommy," Caitlin encouraged, kneading one of Mom's doughy breasts with her fingers, dialing her perky, pink nipple.
Mom turned her face towards Caitlin and burrowed into her hair, grunting as she pushed out with her anal muscles to meet me. Bewilderment overtook me as I watched my Mother, in close-up, vivid detail, urging her body to accept me. Her asshole transformed from a small, wrinkled indent to a slightly raised bump, which smoothed out some of the smaller creases and made the edges of her ring puff up like rising bread.
I wiggled my thumb against the center of her asshole and applied some light pressure. Not enough to hurt her, but enough that she wasn't doing all the work. It took a few seconds of me twisting my thumb around the slippery pink halo for it to pop inside, and when it did, I couldn't get further than my fingernail before Mom recoiled in shock.
She didn't say anything, but her eyes were saucers as she took internal stock of what she was feeling. Her breathing was slow and deliberate, but shallow, relaying the message that she was doing her best to stay composed. Mom looked at me with anxiety spread across her face and, to my surprise, she encouraged me to continue with a brief, forceful nod.
The least I could do was make Mom feel as good as possible while she adjusted to this new feeling, so I ventured to give her a more familiar one. I knelt down, earning no reaction from Mom, though Caitlin knew instantly that I was aiming to have my tongue in her pussy.
"Can I keep going, Mom?" I did my best to stop my voice from wavering.
"Uh huuuuh," her voice droned, lost amid a torrid of new bodily sensations. "Just g-go...slooooow, baby."
My thumb pressed onward, wiggling back and forth to help Mom finally get comfortable with the feeling of being stretched somewhere so foreign. I managed to slide up to my knuckle but had to pause when Mom's instincts drove her to arch her back and try to eject me.
Caitlin placed a hand on her belly and gently returned her to the mattress before I was squeezed out, rubbing in gentle circles while she continued to whisper in Mom's ear. This time I could make out the odd word or phrase: "be strong" and "good girl" and "push." I thanked my lucky stars that Caitlin was acting as my personal assistant; I wouldn't have gotten this far without her.
I laid my cheek against Mom's silky inner thigh so she could feel my breath against her bald mound. Goosebumps popped up like polka dots across the smooth, bulging hill, and I took a second to admire the view before slithering my tongue between the delicate folds of my Mother's vagina. A lava flow of sweet honey spread across my tongue, and I followed it until my tongue reached Mom's molten center. I was suffocating in the heat rolling off her steamy pussy, but I didn't dare take a pause, not when I had seen Mom bringing her A-game for the past day.
I buckled down and held Mom's muff against my face, covering the length of her entire slit with my mouth so I could sate my hunger by devouring all of her at once. I dragged my tongue through her syrup-drench lips a few times, parting her curtains so I could pop them in my mouth for a short suckle on my way to her clit. The button was small but mighty, engorged like a small berry that took all my restraint to not brutalize with sloppy kisses. I traced a tiny circle around Mom's clit and tucked my tongue underneath it so I could turn a tiny bit of pressure into explosive results.
Mom's hips writhed with every advancement. What few defences remained began crumbling under my carefully directed exploration. It took a few minutes of patient maneuvering, but eventually I had my whole thumb inside Mom's bum, and she seemed to slowly come around to the sensations.
"How's she doing?" Caitlin asked me, forgoing an interrogation of my distraught Mother.
"She needs more lube." I held out my free hand to keep Mom plugged. "Can you pass me the bottle?"
Caitlin had other ideas. She put the bottle at the top of Mom's mound again and sent a torrent of lube cascading over her pudgy muffin. It trickled down over the round bulge and through her lips, which were now slightly parted, and pooled inside the opening to her pink tunnel. When the pool was too full, it ran down until it reached her asshole, where her thick cheeks acted like a dam to keep most of it from escaping any further.
"Bunny, can I play with your Mommy for a bit?" Caitlin didn't need to ask twice.
So much lube smothered Mom's pussy that Caitlin barely had to push at all. The maw clenched and relaxed like it was gasping for breath, so as soon as her fingers grazed the pink velvet, they were already starting to slip inside.
Mom greeted Caitlin's fingers like an old friend, spreading around them into an embrace that pulled them into a deep, fleshy hug. Showing her expertise, Caitlin flipped a switch and Mom's back arched on command. She needed leverage to grind deep on her Sister's fingers, and once she found it there was no stopping her.
Caitlin nudged against the roof of Mom's pussy and made a "come hither" motion, fingers caressing her g-spot as she began to move her hand up and down. As she plunged her digits into Mom's dripping peach, her pace increased.
Mom's honeypot was too saturated with our homemade mixture of slippery goo to silence the aggressive slushy of lube and pussy syrup that smothered her lower half. Caitlin was a conductor, enacting a symphony of soft whimpers and loud, gooey sloshing from Mom's core that cemented her, in my mind, as my new idol.
"Oh god, oh fuck, oh god," Mom chanted to herself. Her facial expression didn't stay the same for more than a moment, as the constant barrage of stretching, prodding, and kissing had momentarily reduced her faculties to that of a sex doll, but she played the part well.
I was awe-struck, absorbing every little detail I could to repeat Caitlin's moves in the future.
"Tell him when you're ready." Caitlin kissed Mom on the forehead, fingers still burrowed deep in her succulent sheath.
"I am." Intentional or not, I could barely make out Mom's tepid tone.
"Tell-, him." Caitlin demanded her to perform but did not slow her fingers for even a second to give Mom a breath. In fact, it seemed that her interest was in making speech as hard as possible. "Talk to your Son, Soff."
Mom snapped her eyes open and looked at me after a few disoriented blinks. She didn't say anything at first, she just stared at me with her head half-cocked to the side and a subtle smile creeping onto her face, like we were sharing a moment she didn't want Caitlin to see.
If I didn't know better, I'd say she was beaming with pride.
"Sean, honey," Mom's smile grew until it turned into one of those poorly hidden smirks people display when they don't want to appear overeager. "I'm ready, I think."
"For what, Mom?" My heart didn't just skip a beat, it skipped a whole bar. I knew the answer, but I wanted to hear her say it, and I think she knew that.
My Mother chewed on her lower lip, and even without much light, I could see sparks dazzling her irises. With conviction I hadn't expected Mom yanked her knees back so her plushy flower opened up to me, a sight I was beginning to fall in love with. She rolled back a little so her asshole pointed directly towards me in such a perfect position and coated in so much glistening lube, that if I had tripped, I imagined I would have slipped right inside.
"I'm ready." Mom's tone was adorable, juxtaposing the sultry scene of her presenting her body to me like a trophy as her anxiety vanished into an ocean of raging horniness. "For my Son, my big, strong, sexy stud, to fuck his Mommy-slut in the ass for the first time in ten years!"
"Laying it on a bit thick, dontcha think?" Caitlin chimed, cuing a giggle from both Mommies.
I considered making a pun about "laying" and "on thick" but I couldn't get there in time; Caitlin was already reaching for me with an obvious intention. Her fingers curled around the base of my manhood, insisting that I stop stalling as she pulled me towards my Mother, waiting with open arms.
Mom's bum was still dangling off the edge of the bed, so I didn't have to climb on top of her for Caitlin to guide my missile towards its target.
Caitlin used my dick like a mallet to give Mom's pussy a few playful taps. Mom's pudgy mound quaked with every strike, and our sweat gave rise to the sound of soft slapping each time I thwacked against the meaty hill. My bulging cockhead came to a rest at the top of her slit, her clit tickling my frenulum.
Caitlin patiently traced my cock up and down Mom's sloping crease, gathering the juice between her succulent folds. I nudged Mom's lips apart on the way down, but Caitlin was sure to avoid letting the natural magnetism between our bodies spoil the event. If she had let me back inside Mom's pussy, I would have finished there, and we were all better off waiting for the big finale.
Throbbing veins bulged up and down the length of my manhood, decorating the shaft with blue lightning bolts that lead to a purple, spongy bulb that pulsed like the bass at an EDM concert. Each heartbeat engorged the fat helmet like a fleshy balloon, pumping it bigger than I had ever seen as the moment of my dreams became a reality.
Mom's honey generously coated me like a warm blanket, glistening between her Sister's fingers as she guided me towards my Mother's timid butthole.
"Now remember...," she choked out.
"Gentle," Caitlin and I said in unison. She released my cock and brought her hand to cup one of Mom's heavy breasts, massaging the dough in her palm.
Mom was holding one leg while Caitlin pried back the other, each seeking to expose my Mother's holes as voraciously as they could. Their free hands were now linked atop Mom's chest, seeking to comfort her, rising, and falling in tune with her rapid breathing. Caitlin brushed her thumb over Mom's trembling fingers, which were white as a sheet from her unrelenting grip. Nothing could sway Caitlin, who stayed calm and continued to gingerly kiss her Sister's neck despite the vice threatening to sever her hand.
Caitlin gave Mom's hand a tight, reassuring squeeze and nodded at me, comfortable that she had subdued Mom's anxiety. The spell was working for now, but her trance could break at any moment.
My cockhead nuzzled between the globes of Mom's soft, round bottom. I couldn't help from slipping in the waterfall of lube that ran down the length of her slit as I tried to position myself. I knew I found it when I lodged inside of the gooey pocket of warm lube pooling between her cheeks, kissing the tightly puckered ring that we had worked so hard to loosen.
Mom clenched up as soon as she felt my cock nudge her opening. I dragged the inflated head over the bumpy ring and tried to get her used to the feeling, applying just enough pressure to start stretching her without actually going inside. The slow, gentle prodding was calming her down, but didn't stop my own excitement from bubbling to the surface. I had to remind myself to be patient this time, or it may be the last time.
I watched Mom's breathing, stayed in time with it, and waited for her to take a deep breath before I began to push.
"Oh, oh, oooohhhhh oh fuck." Mom grunted as she accepted the first half of my cockhead inside her asshole, her brow furrowed in concentration. "W-w-wait."
I held still, trying to exude patience though I was anything but.
"Is that...the head?" she croaked meekly.
"Almost, Mom," I encouraged her.
"That's the hard part," Sophie said, lovingly stroking her Sister's chin. "Once he gets the head inside, you just gotta get used to the size."
Most of my cockhead had worked its way into Mom's bum, and though the flared bit was still waiting to push deeper, I could already feel the incredible warmth that awaited me inside. Looking at how tightly secured I was in Mom's bottom was curious; with such a tight squeeze on the balloon tip, the bottom was expanding more, and it looked as though Mom was going to have to take more than twice the size of what was already beginning to stretch her.
My dick throbbed with excitement, begging to go further, but was outshone by the intensity with which Mom's holes were spasming. Her pussy was gawking hungrily for something to fill it, to scratch that familiar urge she had just reveled in but knew it would have to wait until her ass, clenching with equal vigor, was fully explored.
I rested my hands on Mom's thighs to help keep the shaking limbs from collapsing. As I pushed them forward, Mom's body moved with me, and when she rocked back towards me, I held my cock in place. The momentum gave just enough force to surprise Mom by nudging the rest of the head inside, stretching her donut open as wide as it would need to go to fit the rest of me.
"Is that the head?" Mom squealed, ripping her eyes open to look down, for the first time, at her Son trying to get inside of her ass. "Ohhhh, god. Oh wow, oh god, okay Sean, please, baby, please go slow."
Mom clung to me like a wet bathing suit, leaving not a crack for air as she sealed her asshole around my cock in a grip that made her white knuckles look tame. Her heartbeat steadily thumped against me as her insides tried to constrict my entire width.
I slowly moved back and forth, but Mom was so tight I had to make an effort not to be forced out when I relinquished even a smidge of ground. As soon as the pressure relented, Mom's insides worked in tandem to try and push me out, succeeding only in smothering the head in a hot, gooey tomb of velvety soft ass meat. Her flesh strained as it failed to eject me from her ass, the edges of her ass rising like bread as the muscles did their best to push me out of her. I circled my thumb around the squishy ring to truly feel how hard Mom's tender asshole was working to stretch around me, amazed that she could be stretched so wide.
"Mom, can you push for me?" I wasn't above begging, but luckily, I didn't have to.
With a dull groan, Mom obliged and tried to push me out of her with real effort this time. Her wrinkled hole pushed outward like the outer ring was trying to climb my shaft, bringing more of her soft, tender walls to the surface to loosen up for me, puckering like a bright pink donut.
Without her constriction, I fed more of my dick into the buttery soft hole and was greeted by unparalleled warmth melting around me like lava. I watched in a daze as the ridge of my inflated cock emerged from Mom's asshole for a faint moment, glazed in condensed lube. I pressed against the softened entrance and felt it give way easier this time, accepting the whole head in one mighty gulp before halting an inch or so later. It felt like I hit a wall of soggy flesh and I didn't want to hurt her, so I ignored my instinct to start pounding now that I had a foothold.
My Mother couldn't stop from curling her toes each time the head crept out of her ass. Like clockwork her body would go through waves of relief when it was granted a pause from my slow thrusting. The wall of flesh slowly opened for me, each time greeting me with less resistance and a warmer hug as it became used to the sensation.
It was surreal, but somehow felt all too natural, to be pushing myself inside the ass of my Mother. After the last couple of days, I was seeing her as a new woman, but even so, I didn't expect I would ever get to feel what the inside of that new woman's asshole felt like. Most girls I had met were against anal, and knowing Mom was putting that aside just to see me happy was giving my heart all kinds of feelings.
Here she was, spread out before me, biting a hole in her lip just to keep it together, all to let me see what it feels like in another one of her holes. I loved this woman, and wanted to show it, but for now I couldn't do anything if it didn't involve her ass.
I was lost in the moment and lapsed for a second, letting those pesky instincts wander back into my head. I pushed too hard and felt Mom's whole body seize up, accompanied by her all-too-familiar groans. Reflexes pulled my cock out of her ass all at once, though that proved to be its own surprise.
Mom nearly bolted upright as I yanked myself out of her ass, but she quickly settled down once the shock had passed. I expected her to call it off--her one rule was to be gentle and I let myself get carried away.
"Wow," she said, letting go of Caitlin's hand for the first time to prod her puckered ring, tracing a circle around the bumpy, raised surface. "It feels weird."
"I know. I'm sorry, Mom." I kissed her leg as it dangled next to my head. "I went too fast; I didn't mean to--"
"No, like, this feels weird." Her face bore a smile that was mostly of curiosity as she explored her butthole. She took Caitlin's hand and thrust it between her legs so they could both gawk over how different her ass felt. "Sean, baby, how much did you fit into me?"
"Almost half, I think." I mindlessly stroked myself to the sight of my Mother and Aunt exploring her asshole, feeling how loose she was after only our first attempt.
Caitlin kissed her sister and slid a finger inside her bum, a feat easily achieved thanks to the abundance of lube. Mom gave a small jump before scolding her diabolical sister, but made no efforts to stop her from poking another finger against the slickened ring and pushing inside. Their tongues were a flurry as they bounced against each other, sloppily exchanging passion and saliva.
Caitlin pulled her fingers from Mom's bottom and gave her chubby pussy mound a few slaps, spreading the pink jewel for my eyes to soak in.
"He wants back in," Caitlin whimpered between kisses.
"I know." Mom briefly shot me a knowing look and, without abandoning her Sister, pulled her legs back with renewed confidence. Her hands rested on either side of her enormous ass cheeks and her nails dug into the pillowy soft mounds, pulling them apart so her asshole could be the center of attention.
Open, close, open, close.
My Mother's asshole was sparkling with lube, looking like a bright pink ruby in the sun as it winked for me. Thin strands of lube were strung like spiderwebs between her cheeks, and the very center of her butthole had tiny bubbles where the lube had started to be worked into a froth. I ran my thumb over her asshole and gently pushed, not enough to slip inside but enough to get her to start opening.
I replaced my thumb with the tip of my cock, and pushed. Now that she'd been loosened, it didn't take much force to get Mom's ass to stretch around me. I sank inside instantly, her asshole burying the head, sliding over the smooth crown like a glove. It clung tightly to me all the way down, encasing me in a vat of melted butter whose warmth rose to meet me.
With Mom holding her cheeks apart, it became almost too easy to gain ground. The tightness didn't change, but with the slippery pink insides now being spread and brought to the surface, it was easier to get the head inside with just a small push. I sawed back and forth, giving her greedy bottom inch after inch until I was sure she would soon be full.
To my surprise, Mom kept finding places to fit me. Every corner was being explored for the first time in a long time and needed to be stretched a few times before it began to loosen enough to be comfortably stretched.
At first, only the head could fit, and even that was a struggle to achieve. Simply trying to spread her bum, after it had been neglected for so long, was a challenge. Now, I could pull my dick all the way out and watch her wet, softened butthole wink at me, then slide the fat helmet back inside without even hurting her. It may have taken a few more minutes than I had planned, but the wait was worth it. The point where Mom began to squeeze was deeper inside every time I ventured in, and it was only a matter of time before she held all of me inside her asshole.
Caitlin plunged her fingers into Mom's sopping wet pussy and worked them in small circles around her clit, nudging the stiff button back and forth in tune with my gentle prodding. "I think you're done teasing him."
"W-what?" Mom needed time to come back to earth. "He's in my ass! I'm not teasing anybody!"
Caitlin clicked her tongue with disapproval. "But he wants to fuck you." My aunt looked to me. "Don't you, Bunny?"
"Uh-huh." The mere mention of picking up speed almost made me do so. "But...but I can go slowly, Mom."
Caitlin rubbed my arm reassuringly, though taunted as only she could, "Bunny, you wanna put your whole cock in your Mommy's warm, tight little bum, don't you?"
I grunted my approval, and both my Aunt and I looked to Mom for the same thing.
"Okay, sweetheart," Mom gulped nervously. "Go ahead--put it all inside Mommy."
Blood raged in my ears as tingles were born from the base of my spine, riding the adrenaline boost towards my brain like fireworks. My heart was a jackhammer that shook each bone in my ribcage like branches in a storm, pounding so mercilessly that I took to silently praying that it wouldn't up and quit before I was finished. Mom's words hung heavy in the air, glued to my ears. They played on repeat to create a background chant that built to a thundering crescendo when I committed to burying myself in my Mother's asshole.
I had been waiting to give Mom the last few inches slowly, and truthfully I would have been fine taking my time, but with courtesy removed, I couldn't stop my primal lust from taking over.
Velvet walls encased the final length of my throbbing cock, dragging me into Mom's hot, steamy anal depths. Her walls wrapped around me like a silk robe, lovingly marinating me in her buttery asshole with tender little squeezes that made me never want to leave her clutches. The root of my pole was being strangled by a tight, squishy noose that kissed my balls with its puckered ring each time it clenched. Each and every part of my cock was being tended to by my dotting Mother, and, whether it was gently kissing or ruthlessly smothering, she was doing an incredible job.
The noises my Mother was making would have stopped a normal person in their tracks, but for me, they were fuel to the fire. Being hilted to the base in her bum was a dream, but her desperate panting and stifled groans made it real. Mom knew that the feeling of my thighs touching hers meant that I, or rather "we," had done it. She opened her eyes and winced as she adjusted to the feeling of her insides being pushed around like a toy.
We stared at each other for an eternity, balancing in the serenity of the moment before it evaporated. I felt like a king, treated by his queen to the rarest delicacy our kingdom could offer. Mom was swooning over me, as I her, soaking in the last time she really felt like she could call herself a "virgin" from anal. Once I started moving, there was no going back. She had seen me in action and knew that if she could handle me pounding her backdoor, it would surely happen again in the future.
I tried to pull out of Mom to give her a short breather, but she resisted. "No, no! Just...stay with me." She let go of her grip on her ass and let the pudgy cheeks come together. Her hands firmly secured themselves to my bicep, caressing me with the kind of affection I had only ever found in her as she looked into my soul.
Mom's eyes fluttered as she started grinding her hips up and down, dragging my cockhead against the fleshy tunnel, and giving her momentum with which to time her powerful butt hugs. It took seconds for Mom to find her rhythm, but soon she was massaging my cock from root to tip like she had been doing it all her life. Her mouth was shaped in a small "o" as she worked her body like a weapon, deliberately assaulting my weaknesses but giving no pause as she felt the tell-tale signs of my orgasm building.
"Holy shit, I'm already gonna...Mom!" I gasped as my Mother's legs ensnared me, pulling me flush against her body. "I'm seriously gonna come soon, if you keep doing that."
"Doing what?" she cooed, flexing her asshole as she bore down with all her strength. "You mean this?"
I let out a very unsexy groan. "Yeeeessssss, that!"
Caitlin lay beside Mom, but turned her body so that her head was between Mom's legs. I hardly noticed her switch positions, so I was a bit taken aback when her hand wrapped around the base of my cock and gave it a hard tug. It didn't do much good to pull me out of Mom's ass, I barely budged, but her message was clear.
"Out, Bunny," she demanded with her tongue hanging out, "you can't come yet, so give your Mother a break."
I stepped back enough to give Caitlin room to slither my cock out of Mom's greedy asshole. It felt like I had spent an hour getting her warmed up enough to fit all of me, but it was a labor of love. Even though I knew it would push me over the edge, I wanted back inside more than I could believe. My cock flexed in despair, aching to sink back into Mom's creamy cocoon and bask in her warmth.
Mom's ass wasn't gaping, she was too tight for that, but it was shocking to see how relaxed and loose her butthole had become, without even being truly fucked yet. Just from holding me inside and working her magic, Mom had managed to turn her once tiny, wrinkled hole the size of a dime into a softened, bumpy ring that protruded like it was puckering for a sloppy kiss. Thick lube coated her asshole and gave it a remarkable shimmer, like a precious stone showing its value for all to see.
Caitlin wasn't transfixed by the sight like I was, so she wasted no time in getting to work gobbling down my cock until the head brushed squarely against the back of her throat. She emitted a loud, hearty gag but didn't pull me out, instead content to let her saliva flow down over my length until little dribbles ran over my tightly pulled ball sack. She mimicked Mom's technique by holding me deep in her throat and working just the last inch or so back and forth against her windpipe, leaving not a crack for her to breathe. I was sure it was to impress me, to remind me she was just as talented as her Sister, but I convinced myself that she was savouring the taste of Mom's asshole, even if it sounded absurd.
"Is it good, sweetheart?" Mom's adorable voice penetrated my skull like a dose of heroin.
"Caitlin's throat?" I summoned all the intelligence I could and came up short, clearly missing the real question. I looked down to see Mom twirling her finger in a circle around her bulging ring, gingerly slipping inside just enough to make a nail disappear. "Oh my god, you mean that."
"Yes, honey. I mean this." Mom giggled, aware that she caught my attention with her finger. She lined up a second and slowly pushed inside, giving me a world-class seat to the show as her asshole swallowed up one knuckle, then another, then the entirety of her two fingers.
For a woman so cautious towards anal, she was certainly growing comfortable with it, boldly exploring her asshole to put me in a helpless state of hypnosis. Perhaps taking my time had convinced her that it was nothing to be afraid of, and now that her confidence was growing, she wanted to flaunt her ability to tickle a newfound fancy.
"You mean this, sweetheart?" Mom knew it would take some coaxing to get my gourd in gear, but she knew just how to do it. "Mommy wants to know how it feels having your whole cock deep in my bottom. Does it feel good in there, baby?"
I didn't produce an answer. Winter had overtaken my head and I couldn't defrost my brain. I just stared dumbfounded as I tried to absorb the striking imagery along with the overwhelming blowjob Caitlin was treating me to.
"Yurf muffer acked oou a queton," Caitlin gurgled in my lap, blowing bubbles as she withdrew my pole from her throat and took a much-needed breath of air. "Answer her, Bunny."
"How does my ass feel, honey?" Mom cocked her head and entranced me with a loving smile.
"It feels so fucking good, Mom." I sighed in exasperation. "I could fuck you for hours."
"Language, young man." I knew she was teasing; she wasn't in much of a position to scold me with her legs pulled up to her ears. Her Sister's loud, sloppy nursing of my cock didn't do much to drive the message home, either.
"You haven't fucked me yet, not here." Mom pulled her fingers out and resumed spreading herself, asking a question we both knew the answer to. "Would you like to fuck Mommy's bum, sweetheart?"
Caitlin pulled her lips off me in a smooth, slow motion. She kept her tongue flattened against the underside as she slid off, tickling my frenulum as she released me with a loud pop!
Drool still dripped from the head as she returned me to the entrance, taking the scenic route through Mom's gooey pink pussy petals as she did. From there, I only needed to give a small push to start driving my cock back through the sweltering warmth of Mom's buttery soft ass meat. We sighed in unison when I reached bottom, feeling like I was home again, with a little more endurance up my sleeve thanks to Caitlin's reprieve.
Once Mom had gotten used to being stretched open again, her ring gave me a couple of quick squeezes as if to say "go ahead." I tightened my balls and sent a rush of blood to the tip of my cock, expanding the spongy helmet so Mom would feel every inch of me being dragged out of her. She moaned like a banshee as her once tightly packed bottom was slowly emptied, trying in vain to keep me from slithering out.
I left the fat head nuzzled inside Mom's asshole, savoring the tight seal her circle formed under the flare of my bulging egg.
I placed one of Mom's legs on my shoulder so I had a hand free to travel up her tummy, coming to a rest with one of her enormous, white milkers overflowing my palm. My fingers traced Mom's rubbery areola, nudging her firm pink nipple until it was ready to cut glass. I lightly pinched and tugged on the nub, gradually increasing pressure until I surprised her with a sharp squeeze.
Not enough to hurt her, but enough to get her to tense up in a way that only reflexes can. It was with this reflexive bucking that I timed my thrust, delving into Mom's asshole until her pussy was creaming against my stomach. I did not pause this time but pulled out as soon as I hit bottom.
"Ooohhhh, oh fuck!" Mom yelped, layering her hand on mine, and squeezing down on her breast. "Fuck me, keep going, baby! Just like that! Oh, my fucking god!"
If it weren't for the situation, I would have laughed at hearing my Mother curse like this, but my mind had one thing to focus on right now. I drove my cock into my Mother's waiting asshole with enough force to smash the bedpost against the wall, banging the wooden frame in a loud, rhythmic pattern as I grew bolder in my efforts. I was wary of hurting her, but I had seen her face contorted in this particular type of bliss before and it told me not to stop.
Mom's asshole clung to me with every long, deliberate thrust. As I pulled myself out of the loosened tunnel, I was aware of how badly she wanted me to stay, warning me with a desperate whine whenever my cock came dangerously close to sliding out of her. Such a cry was something I couldn't ignore, and within seconds I found myself trudging again through the dense, gluey channel to end up in a tomb of pulsating flesh whose sultry hugs could melt glaciers.
Skin slapping against skin overwrote my Mother's primal, heated grunting, drowning out her wails amid a torrent of relentless pounding as I had my way with her. Though my pace had yet to reach a peak, as I wasn't sure I could hold back once I dropped the reins. Mom was still clutching my hand like she was on the ride of her life. This was the first time she had truly accepted someone in such a sacred, forbidden place, and every new direction we took only showed her how much more there was to explore.
The woman who had been so timid in having a single finger inside her bottom had taken to howling obscenities like a sailor to encourage me to give her more, and more, and more.
The well-lubed piston plunged into Mom's butthole like a machine was driving it, trying everything it could to rearrange its new home so it fit perfectly. The harder I went, the easier Mom seemed to take it, as if once I had enough speed, her slippery canal simply could not hold onto me, so it stopped trying. She was still unbelievably tight, but was no longer able to constrict and smother me the way she had before.
A surge of pleasure nearly took me off balance, but I wasn't ready to come yet. I tore my dick out of my Mother and let the rigid, glimmering length rest on her pussy mound, where it continued its strained throbbing.
Mom's butthole was stretched even wider now, and though it still looked too tight to imagine sticking a finger in, I could see now that the forceful tightness had been all but eliminated. Her asshole hung open just a touch, enough so anyone would be able to discern that it had been through quite an ordeal. The copious layer of lube that she was painted in was evidence that she would have no trouble accepting me back inside with one strong push. But I couldn't tear myself away from watching the puckered tunnel, worn out and looser than ever before, fail to return itself to its dainty origins no matter how hard it tightened up.
Mom fought hard to turn her racing breath into words. "Wh-why did you stop?"
"Why do you think?" I teased, confidently covering the excited shaking that my limb could not avoid.
"Gonna c-come for Mommy?" Mom was trying to entrench herself back in the seductive, sexy role, but found no stable footing amid the rubble of her first genuine ass pounding.
I nodded in defeat. "I can't, Mom. I can't stop."
Caitlin shushed me with a finger on my lips, taking hold of my rod and fitting it back in the opening of Mom's asshole. I begged her with my eyes, insisting I couldn't hold back anymore, but by the firm grip she had on my steel member I knew she could already tell I was at my limit. Caitlin slapped my butt and I lurched forward, sinking into my Mother's inviting asshole.
My thick pipe bore down hard into Mom's butthole, greased up so mightily that even her most powerful flexing couldn't do anything to stop me from embedding my cock deep in her guts. I held it there for the briefest of seconds, trying to find even a moment's pause to calm my brewing orgasm, but Aunt Caitlin was having none of it.
"Come for her--she's ready." Caitlin nibbled my earlobe and delivered her message directly, to which I could no longer resist.
Summoning every last ounce of willpower in my possession, I began fucking Mom in the ass with no intention of stopping. It took only a minute of uninterrupted pounding for the alarm bells to start going off. There was no going back, so I fully committed. "Mom, Mom I'm gonna--"
"You...oh, fuck! You can come inside, sweetheart! Give it to Mommy, gimmie all that fucking baby butter, please baby, feed Mommy's asshole!" Mom's voice was high and shrill, and contained no trace of the doting matriarch that had cherished me from birth.
Her arms braced her against the backboard as I began pumping with one goal in mind--come inside my Mother.
I bottomed out in Mom's ass and slumped against her chest, allowing nirvana to wash over me as I emptied my balls into her bowels, my head resting on her fluffy, pillowy breasts. My toes curled so hard I feared they might snap off, but that was nothing compared to the perverse electricity that ripped through my body like a shockwave. All my muscles lost their will to function as power was rerouted from them directly towards my penis, ensuring every last ounce of energy was devoted to inseminating my Mother.
The first burst of cum felt like thick, heavy pudding when it blasted out of me. Such a forceful convulsion sent the viscous cream barreling out of me so fast I almost recoiled. Mom felt the ejection baste her guts and would have leaped off the bed if not for my weight pinning her down. She gasped in shock, unfamiliar with the feeling of such a potent dose of cum tickling such a deep, unexplored part of her.
Two more ropes came flying out, one after the other, adding to the collection of gooey baby butter flooding Mom's asshole. The outpouring of these two deposits was less startling, but still had Mom bucking uncontrollably each time a new wave of hot, salty liquid splashed inside her.
It splattered against Mom's velvety insides and painted them like a messy canvas with long, white gobs of semen clinging to the spongy walls that ran down to form one large, bubbly hot pool of frothy cum.
I continued to dump little bits of cum into her, but the explosion was over. Mom's asshole was tenderly squeezing and pulling on my cock, trying to elicit just one more dose to satisfy it, but my balls were completely drained. I happily allowed my cock to marinate in her gooey insides, stewing in hot cum and slimy lube until I felt my cock finally begin to soften.
The silence hung heavy in the air, nobody wanted to be the first to break up the serene moment, but we all knew Caitlin would grow impatient first. Her hand rubbed the small of my back as she whispered to us both. "You two look amazing together."
I lifted my head and met my Mother's gaze. Her hair was a sweaty, matted mess that obscured most of her face, and her cheeks flushed bright red. Her tits wore the marks of our conjoined mauling like a badge of honor, but she looked like the perfect woman to me. I felt an undeniable smile creep onto my face as reality roared in front of me, daring me to feel some semblance of shame for what we had done, but all I felt was pride. I had made Mom my woman, she made me her man, and we were never going back to our old life.
Our breathing began to return, but Mom could barely muster the strength to tell me how much she loved me, placing a kiss on my forehead with her arms securing me in a bear hug against her pudgy body. It felt safe, it felt right.
It felt like home.
******
Epilogue
"So, there is someone else, then?" Donald sighed in defeat.
"Yes, there is, Donald," Sophie said sternly. "You and I had problems long before him, so we can't blame anyone but each other for this."
"You're full of shit," Donald snapped, tossing the last of his ratty cardboard boxes in the back of his car. "Tell yourself whatever you have to, it's all a lie."
"Well, I'm going to tell myself I'm happy and not concern myself with what my ex-husband thinks of it," Sophie retorted; arms folded across her chest.
"We aren't divorced, yet." Pain entered Donald's voice that would have evoked sympathy had it not been followed by such rage. "Not like you care;you've already got his goddamn baby in you."
Sophie looked down and admired her pronounced baby bump. She rested a hand on her swollen belly and caressed the round bulge, sending love to the little girl she carried inside her.
It had been seven and a half months ago that Sophie told Donald she was seeking a divorce. It had been on her mind long before that, but the demands of life kept getting in the way. Sophie knew, but didn't really consider, that Sean would have gotten her pregnant by now. Their lovemaking had not slowed for a single day since spending that first weekend together, and as a result, it hadn't taken long for her to start missing periods and start showing the undeniable signs that a baby was growing inside of her.
She had been scared beyond belief, but found a strange comfort that she pursued until it led to solid ground, and a life she was excited by--a life with her Son and father-to-be, Sean. The pregnancy was the push Sophie needed to make a change, and she had not regretted it since. Donald had moved into a new place while they worked on selling the house, which was due to be finalized in the coming weeks.
With the last of his belongings now removed from the house, Sophie knew her new life was just around the corner.
"That's it, then?" Donald scowled, anxiously fidgeting with his keys. "You just get pregnant by the first guy you see and I leave your life forever?"
Sophie beamed with a brilliant illumination, feeling as though her euphoria could fuel the entire world, should its own fire burn out, and she turned to say her final words to her husband.
She glanced down at her belly again, mind racing with possibilities for the future. "Yes, that's it...for now."