Mommy's Challenge
Incest/taboo Story

Mommy's Challenge

by Derwolley76 17 min read 4.5 (56,000 views)
son mother brother sister try not to cum incest challenge punishment
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I was sweating bullets when my mother sat me down that night. She tapped her manicured fingers against the wooden table, her stone cold gaze fixed on me.

"Cole..." she began. "Where do I even begin?"

I couldn't even speak. She had discovered something no son wants their mother to see. But it was so much worse for me.

"Porn is one thing. I know how boys are. But this..." she shook her head. "Hundreds. I mean hundreds of videos in your search history. Every single one of them. Incest."

"Mom..." I try to plead.

She glared, slightly raising her voice. "Do you have any clue how this makes me feel? Sleeping in the same house as you? Let alone thinking about how often your sister is alone here with you."

"What!? With Lucy!?" I recoil. "Mom, I would never do that!"

"Uh huh..."

"I mean it!" I beg for her to listen. "I know. I know how this looks. I really do. But... it's all just fantasy. I swear on my life!"

"Just fantasy..." she repeated, seeming to mull over the words in her head. I shifted in my seat as she silently pondered. Her eyes suddenly opened again.

"Alright."

I sighed, just a little.

"We will discuss this again at a later time." She asserted, standing. But as she turned to leave the room, she glanced at me over her shoulder. "Oh. And no blowing your load for a week."

{-----------------------------------------------}

It was true, I had never seen them like that. Incest porn for me was just a little harmless fetish. Not something I'd ever want for real.

But I do have to admit. Maybe it was the result of being backed up for days on end, or maybe that little chat with Mom put the idea in my mind, but all week I feel like I've been seeing them both in a... different light.

I never noticed before how tiny Lucy's shorts were when she came home from college. Nor how often she'd casually walk the halls in nothing but a towel.

I never noticed how low cut my mother's blouses were. How much cleavage they showed off. How much cleavage she had to show.

It was an agonizing week for me, not being able to relieve myself. But by the 7th day, I was just glad that my humiliating fantasies were behind me.

As the final night came around, I didn't expect my mother to call my name.

"Cole." She sternly called from her bedroom. "Come here. It's about time we discussed your punishment."

My stomach dropped when I heard that. I swiftly stood from the couch, entering her domain. It was dark, lit only by a few scant candles atop her dresser. I shut the door behind me, and faced her.

"I... I thought..."

She let out a hearty chuckle. "What? That? Not touching yourself for a few days? Oh, dear. That was nothing."

My cheeks began to burn. Of course this wasn't over. She was right. I should've known that not masturbating was far too basic a punishment for something like this.

"Okay." I admit. "I'll... whatever it is, I'll take it."

"Good." She nodded. She cocked a hip, making her black nightgown sway just slightly. It hit me like a train when she said it. "Strip."

"Wh- wha-?"

She lifted a hand.

"Don't speak. Just obey."

The order made me feel light, shame washing over me. But I suppose I already felt so naked.

I complied, stripping off my shirt and dropping my pants. And with a quick glance of confirmation, slipped off my boxers. I stood nude, crotch covered. the cool air making me shudder in my vulnerability. She nodded toward a chair.

"Sit. Hands at your sides."

I did as she said, avoiding eye contact as my hands left my shame to be seen.

I expected a lecture. A scolding. Maybe even mockery. What I didn't expect was for Lucy to step into my line of sight. She was dressed in a silky bathrobe, giving me a bold look up and down..

"Hello, Cole."

I instantly covered myself back up.

"Lucy!? What's going on!?"

My mother grabbed my hands, slowly pulling them back to my sides. "Your dear sister Lucy is here to assist us." She explained. "You told me that... despite your disgusting little fetish... you would never actually want it for real."

"I don't! Mom, that's...!"

"Hush. If that is true, then this challenge should be easy for you."

My head reels as I hear her words. "Challenge?"

"If you fail, it means your perversions are too far gone. And I will have no choice but to have you out of my house."

That hit hard. I had no money, and plenty of college debt. I wouldn't last a day on the streets.

"I told you not to orgasm for exactly one week. Well... you've got about half an hour left."

On cue, Lucy pulled out a digital timer, setting it atop the dresser.

"All you have to do is keep due on your promise. Don't cum for 30 more minutes."

The pieces finally fell into place. Her order. The skimpy clothes all week. Me stripping. Lucy.

"Wait!" I try to plead.

"And the time starts... now!"

With the flick of her wrist, Lucy starts the timer, the seconds slowly counting down.

"Lucy, dear. Would you like to start us off?"

"With pleasure." She coos, parting her robe to reveal her tiny, green thong bikini.

My eyes nearly bug out of my head, a familiar stirring in my loins. Lucy eyes me up and down.

"Ooh. Someone likes what they see."

I grit my teeth, trying to keep my breaths steady. But as I watch Lucy slip fully out of her cloak, her long, pale legs, taut stomach, perky breasts, all barely hidden by thin strips of fabric, my erection was inevitable.

"Full mast. Just 30 seconds in." My mother tsks, running a finger across my bare thigh. "Not a good sign."

"Don't blame him, Mom. It's not his fault his sister's so sexy." Lucy giggles, running her hands up and down her bare skin. My dick twitches with every soft moan she mutters, every undulating thrust of her hips. And as she turns around, bending over to show how her thong disappears between her full, round ass, I am as mortified as I am entranced.

I instinctively shut my eyes, unable to bare the shame or arousal. But I spring my eyes open with a gasp as I feel my mother's hand wrap around my rigid length.

"Keep watching." She threatens, grasping my shoulder with her free hand. "Or I start stroking."

I whimper softly. But I obey. I watch as my sister continues her erotic motions. Swaying her hips, grasping at her breasts, tracing lines along the thin cloth covering her pussy. I can already feel myself more aroused than I've ever been.

"Alright Lucy. Enough teasing. Show him what he's been craving."

And with a devilish grin, Lucy slowly reaches behind her back. I suddenly feel my mother begin stroking me.

"M- mom!" I sputter. "I'm watching! I'm watching!"

"I know." She acknowledges. "Keep it up."

I swallow hard. The feeling of her soft hands squeezing my hardened dick, combined with the sight of Lucy untying her bra, it takes the fear of having my life upended to stop myself from thrusting into her now sticky palm.

Lucy's bra flutters to the floor, her perky breasts now on full display. She gently grabs at them. "So... what do you think? As nice as you imagined them to be?"

I sit silently for a moment, lost in my attempt to maintain control. But as I feel my mother's hand pick up the pace, I quickly choke out a response.

"They're lovely!"

"Aww." My mother coos. "How sweet of you."

It couldn't have been more than a few minutes by now. But I was already at the point where I'd normally get tired of foreplay and skip straight to the sex portion of my pornos. There's no way I could last the full 30, was there?

Suddenly, as if answering my prayers, my mother pulls her hand away. I let out a shaky breath, cock already beginning to ooze precum.

My mother licks the sticky residue from her fingers, making me throb.

"Enjoy your break while it lasts. You're gonna need it."

I nod, continuing to fight for control of my breathing as I lie my head back.

I had just watched my sister strip topless.

I had just gotten a handjob from my mother.

This can't be happening. This is insane. This is...

"Time's up." Lucy rings, sashaying closer to me. My gaze snaps to my mother.

"Wh- what!? But that was hardly-!"

"I called this a challenge for a reason. Be grateful you even get breaks at all."

"Yeah..." Lucy mocked, sliding her hands down my legs as she sunk to her knees. "Be grateful."

My jaw started to tremble as I watched her, her face now mere inches from my dripping, rock hard mast. I knew what was about to happen. Maybe I was still dazed with shock. Because I didn't register the full situation until I felt her soft lips wrap around me.

I gasped, eyes rolling to the back of my head as my sister began sweetly suckling. "Oh God... Lucy..." I whimpered.

She seemed to laugh, even with her mouth full of my cock. She steadied the base, beginning to bob her head with wet, fluid motions. What little amount of control I'd recovered now crumbled away, as my dick slickened with Lucy's licks and slurps. She pulled off, swirling her tongue around the tip, making my toes curl.

"Oh, Lucy. That's my girl." My mother encouraged from behind my ear. "She gets it from me, you know. I was the Blowjob Queen of my campus."

The mere thought of my young, sorority-aged mother sucking hard dicks at a college party made me want to cum right there. Right into Lucy's mouth. But what I heard next made my heart sink enough to deafen my arousal, if only slightly.

"Can you show me, Mom?" Lucy purred, taking a long lick up my member.

I felt like the world began to spin as my mother laughed, pulling off me.

"Why, Lucy. I would be honored."

And with that, she sank down beside her. My mother and sister together. Kneeling between my legs.

This couldn't be real. It had to be a dream. A nightmare. This couldn't actually be happening.

My mother gripped me. "Watch close, Lucy. You have the passion and skill, but you need to work on technique. For example..." I felt myself spiral as my mother swallowed me down to the base. She just held me there for a few moments, letting me twitch and spasm wildly in her tight, wet throat, before pulling away without so much as a gag.

"Wow, Mom." Lucy marveled. "You're as good as a porn star."

My mother laughed. "No, dear. I'm better." She swallowed me again, this time bobbing her head as Lucy had done. But she was so much faster, so much rougher. I could feel myself tap the back of her throat with each pass.

I raced toward the edge as she sucked with vacuum force. She slurped that tingling feeling in my balls all the way up my shaft until it rang at my tip, begging, pleading for me to let my seed spill down this Blowjob Queen's throat.

"M- MOM!" I begged, hips thrusting in rhythm with her mouth. "I'M GONNA CUM! I'M GONNA CUM!"

She unsheathed me with a pop. "Do it. Then Lucy can help you pack." And without a moment's reprieve, she dove back down.

"Gah!" I shouted, grasping her head in a desperate attempt to somehow slow her down. My jaw tightened until it hurt, my fingers tangled in her hair, as I fought the screaming urge to unload into my mother's sloppy blowjob. I teetered on the edge, feeling her sucking the orgasm straight to my tip.

And then she pulled off.

I panted, teeth still clenched as I tried to stop myself from coating her face. She had barely broken a sweat.

She glanced up at me. "2nd break."

"Wow." Lucy began. "I didn't think he'd last this long."

"Yes. He's surprising me too. Maybe he was being honest."

I couldn't even bother fighting with her. I had nearly done the unthinkable. If I had actually blew my load... in my mother's mouth... with Lucy watching...

I couldn't let this happen. I had to fight this at all costs. Forget living on the streets, I couldn't live with myself if I failed.

"Someone's a bit... on edge." Lucy punned.

"I want to be fair to him. He is just a boy after all." My mother then stood. "I'm gonna get ready for our next game."

Even as I tried to focus on settling down my excitement, my gaze locked onto her as she moved to the front of the room. Lucy shuffled next to me, resting a hand on my thigh.

"I think you're gonna like this next part." She giggles. And she's not wrong. When my mother lifted her nightgown, revealing her cherry red bra and lingerie, my cock twitched to max hardness.

She had the curves of a Goddess. Wide hips with the powerful thighs to carry them. Gargantuan globes squeezed inside what was a spacious bra for the average woman. She could have been a porn star.

I was starting to wonder if she was one.

Lucy snickered at my gawking face, as my mother reached behind her back as she did. But this time, when the buckle came undone, the fabric didn't simply fall. It popped off. My mother's titanic titties bounced hypnotically before me, making me squirm in my seat.

"Ready for round 3?" She asked.

I could only shake my head.

"Yeah he is!" Lucy cheered.

My eyes followed as my mother's breasts swayed from side to side, fixing only when she once again kneeled before me. She lifted the hefty flesh, squeezing and playing with them just inches away from me. I had to squeeze my own thighs just to stop myself from reaching for them.

"Did you want to play too, Cole?"

"Mom..." I whimpered. "Please... can I just rest a bit longer?" Just staring at them made my twitching cock ready for liftoff. "I'm still way too sensitive."

"Oh, sweetie." She dismissed. "Don't worry. They're nice and soft."

I nearly leaped out of my seat as she wrapped those pillowy mounds around me. My hips bucked, my full 6 inches burrowing through the warm flesh, just barely breaching the other side.

"Aw, he loves them." Lucy giggled, as my mother began moving her breasts up and down my shaft.

Nothing could have possibly prepared me for the sensation. It was like fucking two warm clouds, made even worse as my leaking precum began lubing them up. My mother noticed this, and began bouncing them faster.

"Ooh, that's nice, isn't it? Nothing better than a lubed up titty fuck."

I threw my head back. I couldn't even look anymore. It took every fiber of my being, every ounce of shame in my brain to hold back from exploding all over her. And even as my orgasm creeped closer and closer, her pace never slowed. It somehow seemed to grow faster. Finally, I neared the tipping point. And I could do nothing else but beg for mercy.

"Mom, please stop!" I begged. "Please stop! Mom! Please! Oh God, please Mom just slow down!"

"Hmm." She pretended to ponder. "No."

My stomach flipped.

"Well... maybe. If you ask nicely."

"Mom please!"

"No. Not like that. Call me 'Mommy'."

"M- Mommy! Please slow down! Please slow down, Mommy!"

"I don't know." Lucy interjected. "You're not being very grateful for what Mommy's doing for you. Most guys would kill to fuck Mommy's titties."

My mother nodded. "She's right, you know. You should be thanking me."

"Thank you, Mommy!" I shout, lifting off my seat as I fight my rising orgasm.

"Thank you for what?"

"For... for letting me fuck your titties!"

"Now put it all together." Lucy sang.

"Thank you so much Mommy for letting me fuck your titties! I love fucking Mommy's titties so much! It makes me want to... want to..." I feel balls pull up. My orgasm is mere twitches away. Three twitches. Two twitches. One.

She suddenly stops her movement, leaving my imminent explosion completely in my control. My toes curl tight as I fight the urge to twitch lodged inside her bosom. Somehow, miraculously, I manage to swallow it back down. She then pulls away.

"Nice job, sweetie. You're making me so proud."

My breaths had grown shakier and shakier. My whole body was trembling. I couldn't take any more of this. This had to end soon. It had to. It...

It was then that I finally glanced at the timer.

"Five more minutes." I exclaimed to myself. "Oh my God! Oh God yes,

only five more minutes!"

My mother and sister exchanged a sly smirk, as she stood once more.

"Yeah, five more minutes." Lucy mocked. "It'll be easy, right?" I feel my heart sink. It couldn't get worse, could it? Her hand, her mouth, her breasts. Each more tantalizing than the last. What could possibly top...?

I then watched in abject horror as my mother shimmied out of her panties.

Lucy leaned into my ear. "That's right. You've gotta last 5 whole minutes balls deep inside Mom."

It was like a bomb had gone off in my head. I couldn't accept it. I couldn't. This wasn't happening. After all I'd been through. All the close calls.

"Get him on the floor." My mother ordered. Lucy then grabbed me, laying me down on my back with my knees up and parted. My jaw hang open as my mother stood over me.

"Mom! I c-!"

"Mommy." Lucy corrected.

"Mommy. Please. I... I'll cum the second I'm in you. Please, just think about this!"

"Oh, I have." She turned around, giving me an eyeful of her huge, round ass. "And so will you. For a long, long time." She fell to her knees, each hand gripping one of mine for support, as she lowered her entrance dangerously close to my radiating rod.

"Good luck, bro." Lucy teased, before slapping my mother's ass. "Give him the ride of his life."

Time stood still for what felt like an eternity. For what I wish was an eternity. Before reality came crashing back down all at once.

As I entered my mother's tight, slick heat, everything went white. I saw my life flash before my eyes, including every time I ever masturbated. Every stepsister trapped in a washing machine. Every MILF who accidentally dropped her towel. It all culminated with this. My fantasy had been brought to life.

And became a nightmare.

I regained awareness with a gasp, feeling my mother rise up my length, before slamming back down. "Mmmm, baby. Your cock is just what Mama needed." She began to ride me, the sound of her jiggling ass slapping against my legs was just about all I could hear. She fucked me with vigor. Not like a lover. Not like a pornstar. But like an animal. Her position allowed her to piston up and down like an engine. Her body became a machine, its only purpose to make my cock unload deep inside her.

And it was working.

I clawed breathlessly at her hips, torso instinctively springing up to get her off me. But Lucy held me down by the shoulders.

"Uh uh uh. Take it. Take all Mommy has to give."

My legs wobbled as she kept bouncing in my lap, moans seeming to grow louder with each of my protests. It's like she was taunting me. Daring me to cum inside her. But I had to hold on. I had to. I had to.

When I felt the familiar sensation of an approaching edge, my stunned silence finally broke.

"Mommy stop! It feels too good! I'm gonna explode!" I begged beneath her rocking hips.

She kept her pace, glancing seductively over her shoulder. "Aw, what's wrong? Is Mommy's pussy too much for you? Don't you love fucking Mommy? Don't you want to just release all your hot, sticky cum inside me?"

I tried to drown her out. But it was all too much. I caught one last glimpse of the timer.

10, 9, 8...

"Woo! Go Mom! Ride that cock!"

7, 6, 5...

"I can feel you twitching so much, baby. I think my little boy's ready to cum for his Mommy."

4, 3, 2...

"FUUUUUCK MOMMYYYYYY NOOOOOOOOO!"

My mind shattered as I erupted balls deep inside my mother, pumping bucket after bucket of hot, gooey semen into her womb.

"Fuck yeah, Cole!"

"Mmm, good boy."

They cheered along with my scream of ecstasy while I continued to paint her insides white.

Just one second on the clock.

I collapsed, sputtering, still twitching in her tight heat as the aftershocks quaked through me.

It was over.

I actually did it.

I failed.

{-----------------------------------------------}

She was never going to kick me out. She just wanted to make sure i lasted long enough to endure every horror she had in store for me.

That was the real punishment.

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