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11/11/2020 

Welcome to Whoreland Pt. 2
Category: Roleplay Stories

"GOD DAMN!! DO IT, WHITEBOY! TAKE DAT SHIT! FUCK MEEEEEEEEEE!!" Baby Cakes smokes, smiles, and cums. She scratches up and down Spence's back as he sweats all over her, pounding her black twat harder and harder and harder! She cums two more times.

Spence pulls out and shoots his wad up towards her big bouncing tits. Baby Cakes holds 'em up for him, shaking 'em like crazy as all that thick white jizz paints her big black breasts white. It splatters every inch of those luscious jugs, hanging off her big black nips in long strands.

"Damn... that was good! You can fuck, whiteboy. You got a helluva nice dick too." Baby Cakes licks Spence's cum dripping piss slit, smiling as she gulps down the droplets of jizz that ooze out.

Spence just goofy grins and sweats, wiping his brow. It's been a helluva busy day for him... and he loves every fucking second of it.

...

While I spend all night trying to straighten out the crooked judge, the next morning Kim calls Tom and books him for the next episode of Sex Talk With Kathie Lee And Hoda. He very gladly agrees to come on the show.

Kathie Lee's dressing room before the filming of Sex Talk With Kathie Lee And Hoda...

"It's great to have you back on the show again, Tom. You did so well yesterday." Kim gives Tom a real sweet smile, touching his shoulder. He's sitting on my grandmother's plush, white leather couch in her dressing room.

Kim's wearing a sleeveless black pantsuit. The top is open down to her waist. Her awesome cleavage is on full display... and Tom's staring real hard at it. Kathie Lee comes out of the bathroom, a white towel wrapped around her head... and one around her very fit, over 60 body. Tom can't decide who to stare at. Kim giggles, noticing his hot dilemma

"Well... Tom... is your sweet little cock ready for us?" Kathie Lee gets right to the point, surprising Tom.

"Huh? I mean... yeah... I mean..." Kim giggles again, knowing how caught off guard Tom is.

"Kathie Lee... Tom is sweet. Don't be so forward." She playfully winks at my grandmother. Playing the hot good cop to my hot grandmother's hot bad cop perfectly.

Tom just sits there, grinning, his six inch cock rock hard in his brown pants. He's uncomfortable like that... and Kim and Kathie Lee notice very quickly.

"You look uncomfortable, To. Are you OK?" Kim sweetly smiles, lightly rubbing his right shoulder.

"Yeah... I mean... yeah..." Tom is at a loss for words. But he's happy. Grinning wide. He can't sit still, his cock wants to tear out of his pants.

"Well... (Kathie Lee pulls her towel from her gorgeous body, dropping it on the floor)... I say take those pants off and let's get this party started... again." Kathie Lee whips the towel off of her head and shakes her half dry hair, softly tossing the towel at Tom, a very horny grin on her very slutty face.

About two minutes later, Tom is ravenously eating Kim's pussy as she lays back on the table in the middle of the floor while Kathie Lee voraciously sucks his cock on her knees in front of him. Another awesome day for Tom already.

Tom surprises my grandmother, grunting into Kim's pussy, cumming in her mouth super quick. She gulps it down, sucking him clean in a jiffy.

"Oh... sorry. I got really excited. I'm sorry." Tom apologizes, ashamed of his premature release.

"Don't be sorry, Tom. It's a big compliment." Kim softly caresses his face, then pulls him back into her dripping wet snatch. Tom gets right back to devouring that awesomely delicious twat and that honey sweet pussy juice.

"Yes... Tom. It's a very tasty compliment." My grandmother licks all around Tom's still hard cock, making sure it's spotless. She moves behind him, taking off his pants and tightly whites, tossing them on the couch. Kathie Lee spreads his cheeks and dives in, licking his winking anus, pleasantly surprising Tom.

"Oh my God... that's awesome, Kathie Lee. Just like this delicious pussy, Kim." Tom is really excited. His cock bounces in Kathie Lee's right hand as she tongue fucks his ass, softly jerking his cock at the same time. Kim moans and writhes happily on the table, cumming into Tom's mouth. Her sweet cream shoots against the back of Tom's throat and he gladly drinks it all down, sucking Kim's soaked, spasming pussy til it's totally dry.

"God... That was so good, Tom. I think you deserve a reward for how sweet you've been to us." Kim wins at Tom. He groans with a very happy smile as Kathie Lee perfectly eats out his ass like only she can.

Another two minutes later...

Tom is balls deep up Kim's cunt, banging her doggy style as she leans over onto the table. He holds her extra curvy hips and slams into her cum as fast as he can. Dude is really, really excited to be fucking her.

"Tom... Oh my God... calm down. Your gonna blow you load too soonnnnnnnnnnnnnn..." Kim cums as Tom does. Their combined jizz floods her cunt. Kathie Lee leans in and licks up all the dripping cum oozing from Kim's pounded out cunt.

"Oh my God... I'm so sorry, again. I'm just so excited being with you two. I'm such a big fan of yours, Kim. I don't know what's wrong. I'm really sorry." Tom pulls out of Kim, head down, very frustrated by his total lack of stamina. He sits on the edge of the table beside Kim, looking at the floor.

"Don't get too down, Tom. I'm flattered actually. I mean... it's not everyday I come across a guy who's so excited to fuck me that he can't stop cumming as soon as he sticks it in. I'm not used to that. But it's fine. You're sweet. Don't be sad." Kim tries to cheer Tom up. Kathie Lee does too... her way. She crawls between his legs and starts sucking his balls. Tom perks up pretty quick. So does his cock. It bounces on Kathie Lee's forehead and hair as she sucks away on those hairy balls.

Tom can't stop grinning. He gets even happier when Kim bends over and starts sucking his cum dripping cock while Kathie Lee slobbers all over his nuts. They give Tom a double suck of a lifetime. He leans his head back and grins the biggest grin in the history of grins. Kim deepthroats his dick, quickly gulping down the drops of cum that ooze down her throat while Kathie Lee sucks hard on both balls, one at a time.

Tom actually doesn't cum again. He's lasting. He grins even bigger. He puts his hands on the back of Kim's head and enjoys the best blowjob he's ever gotten. Kathie Lee adds to it by sucking his balls as good as balls have ever been sucked. It's a truly awesome day for Tom... again. And it's just getting started.

He fucks Kathie Lee next, doggy style, bent over the table. Kim takes her place from earlier, spreading Tom's cheeks and licking out his ass. He pounds my gorgeous grandmother's cunt relentlessly for fifteen minutes.

"OH GOD, YESSSSSSSSSS!! FUCK ME TOM... FUCK MEEEEEEEEEEEE!!" She cums, squirting all over that average sized cock as it pummel her cunt. Tom grins happily, feeling so good about himself now.

Another fives minutes if pussy pounding and Tom cums again, this time up Kathie Lee's convulsing, neatly trimmed cunt. Her pussy grips and pumps Tom's cock perfectly, squeezing out every last drop of jizz in it.

"WHEW! THAT WAS FUCKING AWESOME, LADIES!" Tom takes a deep breath, pulling out of Kathie Lee, leaning back against the table. Kim gobbles up his cum oozing cock again, sucking it clean, happily drinking down the several drops of creamy jizz that pump out onto her quick licking tongue.

"I think we have a show to do." Kim smiles, softly sucking Tom's cock.

"Yes we do, sweetheart. Yes we do." Kathie Lee kisses Tom softly, then goes to her wardrobe to get dressed. Kim keeps sucking Tom as he leans back on the table, grinning his ass off, so freaking amazed at how great his life is right now.

...

"How did you date with Richard go, Nikki?" Stephanie asks her in her office. Our offices are in the same complex as the studios.

"Great. He has such a nice cock. Nice and thick. It felt so good in my ass. He couldn't get enough of my ass. He ate it for an hour, then fucked it for an hour and a half. I loved it." Nikki says smiling. She's sitting across from Stephanie who's sitting behind her big oak desk.

"Great. I'm glad to hear that. He's an important client so I'm glad you could please him." Stephanie smirks at Nikki, chewing on the end of her pen as she rocks back and forth in her massaging desk chair.

"Oh yeah... we had a great time. He wants another date later in the week. I told him I'd have to check my schedule. I told him I'd make time for him if I can." Nikki smirks back, very pleased with her date performance with Richard. Nikki's a very talented whore and she definitely knows it.

"Very nice. Try and clear your schedule. Like I said, he's a very important client. Now... come eat my pussy. Make me cum three times." Stephanie smirks even more confidently. She spread her luscious legs in her gray mini skirt as Nikki gets up and very naughtily walks over to her behind her desk. She smiles right at Stephanie.

"Yes ma'am. I'd love to." Nikki says with a sexy kiss. She kneels down and gets to work, slowly licking up and down Stephanie's glistening labia, sucking on them, then snaking her tongue deep up that beautifully pink pussy.

While Stephanie gets a very nice treat at the office, Sex Talk With Kathie Lee And Hoda gets going...

Filming Sex Talk With Kathie Lee And Hoda...

"Our special guest today is making her second appearance on our show. She's a world renown supermodel and the new host of Dancing With The Stars... Tyra Banks!!" Hoda brings out Tyra. The crowd goes nuts.

Tyra's wearing a black bikini top and skin tight black jeans with knee high, black leather boots. She looks fucking amazing.

The crowd chants for her, cheering and cat calling for two minutes straight. Tyra sits next to Hoda, smiles a gorgeous smile and pumps her fists up in the air in time with the, "TYRA TYRA TYRA" chants from the raucous crowd.

"Well... that was a great ovation." Hoda says smiling a huge, happy smile.

The crowd gets the, "Tyra" chants going again. Tyra keeps smiling, loving the attention.

"OK guys, calm down." Hoda tries to calm the very horny crowd. But no luck. Tyra decided to help her out, pulling her huge chocolate titties out of her bikini top and shaking them for the crowd. They actually cheer even louder. Shocking. But they also get an eyeful of one of the hottest pair of tits ever. Tyra puts her tits away, laughing as she does. The crowd lets out a disappointed groan, but finally settles down.

"Whew! Finally. Welcome, Tyra." Hoda hugs Tyra. Kathie Lee blows her a kiss. Tyra hugs them both, then sits back down, waving at the crowd as they cheer for her.

Tom stands in the corner with Kim as they watch the show progress. Hoda interviews Tyra about her new gig at Dancing With The Stars... and Kathie Lee asks her about her latest sexual conquests.

"You know, Tom... you can fuck Tyra. I'm sure she won't mind. I hear she loves white cock." Kim whispers into Tom's ear. She reaches around him and rubs his crotch as she watches his reaction. Tom turns to Kim and gives her a, oh fuck yeah look. Kim giggles, lightly squeezing his cock in his pants. She keeps rubbing as Kathie Lee looks over and sees her. She motions for Tom to come over.

"Good luck." Kim kisses his neck. Tom smiles back at her and happily walks over to Kathie Lee, standing between her and Hoda.

"Tyra, this is Tom. He's a sweet man. He was on our show yesterday and he did such a great job so we brought him back today." Kathie Lee tells Tyra. Tom shakes her hand. Tyra gives him a sexy smile and pulls her tits out of her top again so he can get a real good, close up look at 'em. Tom's eyes almost pop out of his head. Tyra's big, all natural chocolate cans are world famous, and Tom is a mere two feet away from them.

"What do you think of Tyra's gorgeous breasts, Tom?" Hoda asks him, grinning from ear to ear. Tom reaches over and squeezes Tyra's big jugs, staring hard at 'em as he manhandle 'em.

"I think he likes them." Tyra comments.

"Indeed he does." Kathie Lee agrees.

Tom then gets behind Hoda and roughly gropes her small caramel titties through her pink silk blouse. Hoda just smiles her patented smile and goes with the flow.

Tom then walks over to Kathie Lee and yanks her white tank top up and molests her gorgeous, mature cans through her white bra. He motions Kim over. She walks over and he roughly grabs her DD tits through her black top, then shoves his hands inside it and squeezes those firm, bare cans for a full minute. He gropes all four hotties. Tom is feeling real fucking good about himself. He can't stop grinning.

"Well... I think we should kick this up a notch." Kathie Lee suggests. She gives her patented Kathie Lee naughty smirk.

"Oh yeah..." Tyra adds.

"Absolutely." Hoda chimes in as Tom molests her pink bra covered breasts from behind again.

" OK, Tom... get that dick out. It's time for ass fuck musical chairs." Kathie Lee tells him. The crowd lets out a huge cheer for that idea.

A minute later music is playing and all four ladies are bent over the glass table. Tom is walking back and forth slowly behind them, waiting for the music to stop. It does. The crowd cheers. Tom pushes his six inches against Kathie Lee's anus and pops in. He butt fucks my stunningly beautiful grandmother fast and hard. "GOD YES! FUCK MY ASS! FUCK!!" Kathie Lee throws her head back as Tom rails up her tight clenching butt. The crowd cheers Tom on.

The music starts again so Tom pulls out of Kathie Lee and walks back and forth again, his precum dripping dick bouncing as he goes.

Music stops. Tom enters Kim's ass and butt fucks the world's most perfect ass, reaching under her, grabbing her firm jugs and squeezing 'em hard while he piledrives my wife's butt. "MMMMMMMMM!! God... Fuck my ass!" Kim's eyes roll back. She truly craves anal sex. Her pussy moistens as that six inch dick drills steadily up her tight ass. She clamps down hard on it, bouncing her awesomely curvy ass on it, driving Tom butt fucking crazy.

Music starts again. Tom reluctantly pulls out and does the walk again. His dick pouring precum. It hangs obscenely off of the end of his cock. Kim keeps shaking her ass, teasing Tom. Tom slaps it, making Kim moan happily.

Music stops again and Tom quickly enters Tyra's bootylicious chocolate ass. She shakes it for him as Tom grabs her tits and squeezes away, plowing up Tyra's super smooth, super tight butt. He tries desperately not to cum. He grits his teeth hard, still butt banging Tyra full speed. She moans and cums, loving the rough ass fucking. He slaps her ass and fucks her harder. "FUCKING HELL!! GOD, YOUR COCK FEELS GOOD IN MY BLACK ASS!! FUCK IT HARDER, WHITEBOY!!" Tyra shouts, wiggling her ass even more. Tom slams harder up it, rocking the table with the force of the butt banging. His white dick powers up Tyra's chocolate ass like a rocket shooting into space.

Music starts again. Tom slowly pulls out, not wanting to cum yet. He's sweating and breathing heavy. He takes a deep breath and walks very slowly back and forth behind the ladies. His rock hard, bouncing dick is shooting precum like a fountain. Tyra reaches back when he passes her and swipes at his dick, licking his hand clean. She smacks her lips and blows Tom a sexy kiss, making his grin so wide. He's tired and trying hard not to cum, but he's so fucking turned on he can't stand it.

Music stops again and Hoda gets the dick. Tom slowly enters her ass, fucking her for about thirty seconds before he grunts louder than he ever has, cumming so hard up that jiggly, caramel ass. "Oh God... So warm. Mmmmmmmmmm. Fill me up, baby." Hoda reaches back and softly rubs Tom's sweaty, half smiling, very tired face. He fills her butt with his thick, creamy load, almost passing out from the excited exhaustion he's experiencing.

Tom stumbles backwards, his softening dick slipping out of Hoda's winking ass. Tyra grabs it and leans over ravenously sucking it, chewing on it as she greedily devours every drop of sticky sperm that drips out.

"Give it up for Tom." Kathie Lee tells the crowd, clapping as the crowd goes wild, catcalling and cheering louder than ever.

Tom grins, waving at the crowd as Tyra sucks him clean. He's worn out, but so fucking happy he can't stand it. This has been the most amazing two days of his life... and who knows... it might not be over just yet.

...

I end up making a deal... for good... with the crooked ass judge in Santa Monica. It costs me $5,000,000 but it's worth it. He's gonna approve our new construction which should lead to about $100,000,000 in new revenue. Fucking sleazy ass judges. I guess we all are really whores after all.

...

"GOD!! YOUR HAND'S SO BIG IN MY BUTT, BABY! MMMMMMMM!" Jessica (Jessica Simpson) is my older sister. She's also got my fist up her ass behind the Burger King I had put in on my property. Hey... I dig Burger King so I built one. Best thing about having money so you can buy what the fuck you want.

Anyway, my sisters bent over, holding the face behind the fast food joint, moaning her sweet little ass off as I slowly twist my lotioned up fist wrist deep up her very smooth, very supple ass. I slap it. She moans. I slap it again. She moans louder. I twist my hand in and out, slowly, feeling Jessica's anal membrane clamping down so tight on my greasy hand. God, it's hot. Her ass is so warm too. A beautiful fucking sight to behold.

Jessica rips her white tank top off and let's her DD jugs hang free. All natural beauties, so jiggly and perfectly shaped. Milk dribbles out of her puffy pink nipples as I speed up, twisting my fist faster up her slightly looser butt. I slap her ass again.

"God, yes! Please fuck my ass, baby bro. Pleaseeeeee." Jessica looks back at me as I fuck her ass with my fist, smiling so sweet, blowing me even sweeter kisses. I blow her one back and stand up. I gently remove my fist from her ass and watch Jessica hold my fist and lick it totally clean... lotion, ass juices, and all. Fucking sexy broad.

A minute later, I'm butt fucking Jessica as she leans against the fence, making slutty fuck faces against it as I drill fourteen inches of dick up her gorgeous butt faster and faster... and definitely harder!

"YESSSSSSSSSSSSSSSSSS!! POUND MY ASS, BABY!! YESSSSSSSSSSSSS!! GOD, IT'S SO NASTY AND FUCKING AWESOME!! FUCK MEEEEEEEEEEEE!!" Jessica squirts three times in a row, drenching me and the ground behind me with an avalanche of sweet pussy jizz.

I slap and squeeze her gorgeous, jiggling jugs and pound the living fuck out of her warm, wet, thumping like a runaway train butt. In and out a thousand miles an hour. My fat dick destroys that delectable butt, pummeling up it, twitching wildly as Jessica keeps on cumming. She screams and creams for thirty minutes straight. There's so much pussy jizz everywhere it looks like we let the water out of a blowup pool. Fucking awesome!!

I yank Jessica's head back and kiss her violently, my tongue jamming deep down her fucking throat as my giant cock repeatedly violates her very accepting butt, slamming Jessica's jugs up against the chain link fence.

I cum so fucking hard, pumping a gallon of thick, sticky sperm up my perfect sisters perfect behind. Jessica screams in super charged animalistic ecstasy into my mouth as she sucks my tongue so fucking hard it feels like she's gonna suck it down her throat and swallow it whole. I keep cumming, my warm jizz making Jessica shudder with delight, her perfectly curvy, all natural body shaking in my arms as my jizz floods out of her ass, pooling beneath us.

"Holy fuck... that was amazing! God... you can fuck, baby bro. I love you so darn much. Mmmmmmmmm." Jessica makes me smile, sucking my tongue, licking every inch of my mouth, kissing me so soft, but so passionately. She's a dream cum true... my dream making me cum so fucking hard and that's so fucking true. We kiss for five minutes straight behind the Burger King.

A chick comes out and dumps some trash and takes some pics of us. We keep on kissing. Our intensely horny love for one another blocking out anyone else. My hands happily squeeze her jiggling jugs as we kiss, loving the soft feel and amazingly smooth shape of those absolutely perfect cans. I'm totally in love with my sister and it totally fucking rocks!

"God... that was so much fun today, Kathie Lee. Tom's turning into quite the stud." Kim tells my grandmother as they relax in our living room, drinking some red wine.

"Yes he definitely is. I think we should invite him out here for some more freaky fun. Maybe some naughty fun in the log cabin. Maybe film it and put it up on your private OnlyFans for everyone to enjoy. I have some really naughty ideas for us." Kathie Lee winks at Kim over the brim of her glass. She drinks the wine down, immediately refilling her glass.

"Yummy. That sound like so much fun. I want James to be involved too. I've missed his cock for the last couple of weeks. I blew him earlier, but I want him pounding my holes like only he can." Kim winks back, sipping her wine, smiling seductively.

"Oh my God, yes. I want my grandson's gorgeous cock in all of my holes as much as humanly possible. That sounds so delicious. Maybe I'll invite Hoda over. We could always use another slut." Kathie Lee and Kim laugh, sipping wine and chillin'. The fun never ends here at Whoreland. You'll definitely see how true that is for yourself.

To be continued...

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