My Freaky Life Ch. 2 Category: Roleplay Stories
This is my second chapter in my sex series about my freaky life... It mixes real life celebrities with TV show and movie characters... It's a wild ass sleazefest run amok... My family will be added gradually to the story... Enjoy my fellow freaks.
My Family: My Mom Patty (Patricia Heaton)
My Dad Dr Evil (Himself)
My Grandma Helen (Helen Mirren)
My Sister Kat (Kat Dennings)
My Sister Jessica (Jessica Simpson)
My Sister Nikki Dee (Meteorologist Nikki Dee Ray)
My Cousin Penny (Penny From The Big Bang Theory)
My Cousin Rachel (Rachel Maddow)
My Cousin Anne (Chef Anne Burrell)
My Cousin Jenni (Jwoww From Jersey Shore)
My Cousin Braun (WWE Superstar Braun Strowman)
My Cousin Bubba (Former WWE Superstar James Ellsworth)
My Aunt Kathie Lee (Kathie Lee Gifford)
My Aunt Dolly (Dolly Parton)
My Aunt Peggy (Peggy Bundy)
My Aunt Jane (Jane Marie Lynch)
My Half Brother Scott (Seth Green)
***
The Hamptons, New York
"So how's the sex biz, my gorgeous grandson?"
"It's rolling along nicely grandma. Sexiest grandma ever."
"Oh, you charmer. I guess that's how you get all the girls... That and this beautiful cock of yours."
I smoked the blunt my Grandma Helen and I were passing, while she sucked my cock slowly. She tickled my big balls and licked that talented tongue all over my rock hard cock. Her gorgeous, mature, cherry red lips wrapped tightly around my shaft, sucking it hard, up and down, slowly and precisely. It felt so good. I puffed and passed to grandma. She took a big toke on it and passed it back to me. She sucked my cock in, the warm smoke wrapping around my head. I passed the blunt to her again and she took a really big toke on it and passed the blunt back to me.
I watched happily as she slowly blew the smoke all over my cock and balls. My legs shook and my cock twitched. Helen smiled, admiring her work on her grandson. I smacked and squeezed her soft, mature ass, while she sucked me in and bobbed her head quickly on my happy cock. Her beautiful, full lips were so tightly wrapped around my cock. She sucked me faster and faster, tickling my big balls, laughing around my oh so fucking happy cock. I groaned and she sucked me faster, squeezing my balls softly rubbing them, her head flying up and down my cock. I came hard in her experienced mouth. Her red lipstick covering my cumming cock. I pumped my load in at max speed. Helen giggled and smiled around my cock, swallowing every drop I pumped into her mouth. I just smiled and smoked, loving it all. I squeezed her soft ass, smacking it again. Grandma sucked me dry, happily downing my jizz and licking my head clean.
Grandma Helen sat in my lap, facing me. She slid my still hard cock up ur well aged and well used pussy. I love my grandmother's pussy. I've fucked it so many times and it's always a pleasure. Helen put her arms around my neck, smiled so sexy and rode me like a mature sex goddess in heat. She bounced relentlessly on my throbbing manmeat. It thrust up her neatly trimmed, gray haired snatch, every inch tasting that delicious cunt, stretching it wide. I leaned in and sucked her magnificent, mature tits, nibbling on her thick, pink nipples, sucking those tits hard. "YESSSSSSSSS JAMESSSSSSSSSSSSSSSSSSSSS... FUCK ME MY BEAUTIFUL GRANDSON!! FUCK MEEEEEEEEEE!!"
She squirted all over my rampaging cock as it drilled up her cunt, every time she slammed down on it. That very skilled pussy worked my happy cock like only my grandmother can. The taboo aspect of pussy thumping my grandmother turned me on so fucking much. I blasted my load up her beautiful, gilf pussy, my cream filling that soaking wet granny cunt. I sucked her gorgeous, soft tits more as I happily pumped my load in her mature, soaking wet cunt.
"I love when you fuck me James. You're such a beautiful man with such a beautiful cock. My grandson has me hooked on his cock... you naughty boy." We laughed and kissed. Helen sat beside me. I lit a blunt and took a deep toke on it and passed it to her. We smoked and caught up on everything. I love talking to my grandmother. She's an actress and a worldly lady. She's a sweetheart too. We have always been close. "How's everything my love? I haven't seen you in awhile. Work has been keeping me busy. I miss my favorite grandchild."
"Just living my life, my gorgeous grandmother. Hottest gilf on planet earth."
"Always the charmer. Such a gorgeous man too."
We kissed. Helen put her legs in my lap. I massaged her feet as we smoked and chilled. I looked at her. That beautiful body... She's in her 70's,but still absolutely gorgeous. Her breasts are well aged perfection. I reached over with my left hand and groped them. Helen moaned, while she smoked.
I brought my assistants, Beth and Spence with me. Spence came in and filmed my grandmother's tits for my movie. "Look at those tits people. That's my grandmother Helen. A great actress and grandmother... a hottie too. Such a gorgeous woman." I pinched and pulled her nipples as Spence filmed. Beth walked over in her white bathrobe, those massive tits ready to bust out of the robe. She took it off and tossed it in a chair. Spence filmed her as well. Beth shook those massive tits and came over, kneeling in front of me, wrapping those awesome mammaries around my cock. I smoked and let Beth do all the work. My grandma groped Beth's tits as she fucked my big cock with her massive, natural melons. They slid up and down my oh so happy cock, wrapped tightly around it.
She quickened her pace, sucking my thick head, pumping my cock with those huge titties. Helen leaned over and spit on my cock, licking the head. Spence filmed it all. I smoked and smiled. Beth pumped my throbbing cock faster and harder. She chewed on my plump head, lapping up my precum, sucking my head with awesome power. Helen licked Beth's tits and my cock. I groaned and blasted Beth's sexy, mature face. Her long thick blonde hair flying wildly as she pumped my shaft, painting her face with my jizz. Helen sucked me dry, jerking my shaft super fast, sucking out every fucking drop of her grandson's cum. She then licked Beth's sexy, milf face clean. Slowly lapping up the cum. She and Beth, spit my cum back and forth into each other's mouths repeatedly, smiling at me. They finally kissed and swallowed my cream.
We all sat and drank and smoked. Ronda arrived. We made out. She looked fucking awesome. A very short and tight, pink mini dress, with pink pumps. Her long blonde hair in a braided ponytail. The rest of us were in white cotton bathrobes. "I missed you baby. I'm so fucking happy to see you James." Ronda kissed me repeatedly. I held her close, snuggling with my very beautiful wife. I pulled her tits out of her loose dress top... Spence filmed... We are in perfect filming sync with each other... I sucked her tits, pouring some margarita carefully on her tits... making sure not to spill it on her dress. Ronda moaned, biting her lip. My grandmother and Beth watched and smoked. I licked the drink off of her perfectly shaped B cups. I kissed them and sucked them hard, softly biting them, licking her erect, pink nipples. "Mmmmmmmm, my man is gonna make me cum... and we haven't even fucked yet." I smiled, softly grazing my teeth on her nipples, my warm breath blowing softly on them.
Ronda's nipples were so fucking hard. I pulled them and shook them with my mouth. I stuffed her whole tits in my mouth, sucking them hungrily. "FUCKKKKKKKKKKK!!" Ronda squirted. She wasn't wearing panties, so it shot out. I moved my mouth quickly to her pussy and sucked up her juices. She squirted hard into my thirsty mouth. I put my mouth right on her pussy and sucked out every drop of pussy nut. Ronda played with my hair, writhing on the sofa and my face. Beth came over and sucked my cock. I sat Ronda in my lap, reverse cowgirl.
Beth bobbed on my cock. She slipped my wet cock up Ronda's perfectly toned ass. Ronda moaned loud, as my thick cock inched it's way up her ass. Beth snaked her tongue up Ronda's perfect, bald, juicy snatch. Beth massaged my big balls, while she ate Ronda's snatch. Ronda bounced on my cock hard, slamming those muscular thighs on mine. "YESSSSSSSSSSS!! I LOVE YOUR BIG COCK JAMES!! FUCK MY ASS BABY!!" I squeezed her perky tits, rubbing her hard nipples with my thumbs and fucked up into her gorgeous booty. Helen puffed hard on the blunt and kissed Ronda, sharing the smoke with her as they kissed. I drilled my wife's ass so ridiculously hard and fast. Beth massaged my balls so fucking good.
I groped Ronda and Helen's tits as they continued sharing the weed smoke. Ronda screamed into my grandmother's mouth and squirted into Beth's mouth. Spence was filming everything, staring and drooling. I groaned and blasted my load up Ronda's awesome ass. My cock just pumped my jizz, full force up my woman's perfectly shaped booty. I shook her tits and squeezed, as I finished cum blasting Ronda's ass. We all kissed. A three way kiss with me, Ronda and grandma.
Beth pulled my cock out of Ronda's ass. She sucked me in and I immediately pissed in her mouth. Beth loves my piss. She happily drank it all down, sucking me and drinking my piss at the same time. I smiled so big. Helen leaned down and sucked my cum out of Ronda's ass. Such a sexy sight. She played with my balls and sucked Ronda's perfect ass clean. Beth drank all of my warm piss. She and Helen kissed deeply, sharing the cum and piss.
The next morning I was at my aunt, Katie Lee's show, promoting my movie, which wasn't finished yet. Kathie Lee came into my dressing room and greeted me so nicely. "HEYYYYY THERE... My favorite nephew. Best looking man I've seen, since the last time I saw you." She grabbed my face in her hands and kissed me deeply, our tongues fucking in our mouths. I hugged her and we made out for a few minutes. I groped her perfect milf tits, through her dark blue blouse. I love my aunt's tits. They are so fucking gorgeous. So soft and squeezable. She's awesome and so are they. "Well... looks like someone missed his aunt's titties. They missed you too baby." I pulled her blouse up and pulled her bra down. I licked those awesome, mature cans and sucked them so fucking hard. Her delicious milk shot out into my mouth. I happily swallowed it all down, sucking each tit hard, stuffing the whole tit in my mouth. I swallowed a couple of mouthfuls of Kathie Lee's milk.
"Mmmmmmmmmmm ... Get that milk baby... it's all yours handsome." She held my head to her chest. She reached down and rubbed my cock, through my pants. Unfortunately though, it was time for her to go start her show. We kissed. She fixed her clothes and walked out wiggling her sexy ass at me, looking back and winking at me.
The show started. Spence and I watched from my dressing room. I got the signal that I was next. "Well... Our next guest is someone very special to Kathie Lee... It's her nephew James... he's the King Of Porn and also a pimp. He also gets paid to impregnate women... He's even knocked up his aunt Kathie Lee."
"Yes he did. Best sex ever."
Lets bring him out... Here's James..." Hoda introduced me. I walked out to a nice round of applause. I sat in between them. "Welcome James."
"Thanks. WHAT'S UP NYC?" That got a big cheer.
"Yes.. I forgot... you're a New Yorker living in California."
"Yep...it's good to be back home."
Kathie Lee hugged my neck and kissed my cheek, rubbing those gorgeous melons on my left arm. She reached down and unzipped my pants, pulling my cock out on national television. "Excuse me Hoda. I just wanna finish something my nephew and I started in the dressing room. Go ahead and interview him... I'll just be over here with his big, beautiful cock stuffed down my throat."
Kathie Lee deep throated me right there in front of the live crowd. I fucking loved it. I love public sex. I put my hand on her beautiful head and enjoyed her sloppy blowjob. Her saliva ran down my shaft, her red lipstick smeared all over my cock. She sucked every fucking thick inch down her throat and licked my balls with my whole cock crammed down her talented throat.
"Well... Ok... James... you're here to promote a celebrity tits movie you're making. How's it coming along?" Hoda asked, staring at my aunt Kathie Lee.
"It's coming along great... Yeah... suck that cock baby...you down mind if I get yours on camera do you? Spence... come out here." Spence came out with his camera. I squeezed Hoda's sexy, small tits and pulled her white top up and her white bra down, exposing those sweet, mature caramel titties. She was shocked, but quickly went along and smiled. I pulled her brown nipples and squeezed those tits. Hoda's milk squirted out. I leaned over and sucked it down. Spence filmed it all, zooming in on her gorgeous brown nipples. Kathie Lee bobbed fast on my cock, every inch flying in and out of her throat. She tickled my balls, softly scratching them, sucking hard on my shaft, her saliva oozing out of her mouth.
"So you fuck your aunt Kathie Lee and your other female family members? I've even heard you've gotten some of them pregnant... Is that right!?" Hoda asked, moaning as I played with her sweet, brown tits.
"Yep. I have the hottest family and the women love my cock... so I give it to 'em. We have a lot of fucking freaky fun Hoda... as you can see." I sucked Hoda's mature, caramel cans and put my hand on Kathie Lee's head.
I grunted and dumped my load in her mouth. Kathie Lee swallowed it all happily, moaning so sexy as she swallowed my jizz. She lifted her head and pulled her top up, pulling her awesome, mature melons out of her bra and showing them to the camera. She shook them and played with them. I pushed Hoda's head to my lap and she sucked my big, happy cock clean. I sucked my aunt's awesome atits some more, swallowing more of her milk, as Hoda sucked me clean.
I pulled my mouth off of Kathie Lee's natural melons and squeezed them, squirting her milk at Spence and the camera. She laughed. I shot her milk out all over the table and floor. I sucked those all star titties in my mouth again and drank even more of her sweet milk. Hoda kept sucking me, wanting her own mouthful of cream. After about 20 minutes of fast, relentless sucking, she got her wish. I blasted a big load of my tasty cream in Hoda's sexy, caramel mouth. She let it hang off of her tongue and lapped it up, licking it off of my head, sucking it all down. We finished the interview. I fucked Kathie Lee in the dressing room. She was bent over, looking into the vanity mirror while I doggy style slammed her mature, neatly trimmed cunt, her tits hanging down, shaking wildly. I squeezed them, her milk oozing between my fingers.
I blasted my load up her cunt, filling it. She sat on Hoda's face and squirted it out into her mouth. Hoda drank it all down. I pissed all over my aunt's gorgeous face and in her mouth. Kathie Lee pissed in Hoda's mouth and Hoda pissed in Spence's mouth, while he ate her pussy. It was chain pissing mania in the dressing room.
Kathie Lee came out to the Hamptons with me. We pulled in the driveway and she pulled her top off. I pulled out some yayo and put it on her tits. I made a couple lines and snorted it off of those beautiful, natural tits. I sucked them clean and sucked down some more of her milk. Fuck, that was hot. Snorting blow off of Kathie Lee's tits, then sucking her milk down. Fuck, I love my family. I gave her some X and she thanked me by tit fucking me there in the car. She's a slut and I love that about her. I pounded those soft, mature, perfect funbags, while she smiled so sexy at me, licking the precum from my pee slit. I creamed her mouth. Kathie Lee sucked it down happily I put a line of blow on her ass, leaned over and snorted it, then shoved my tongue up her ass, licking her out. She giggled, loving it. I smacked her ass and squeezed it hard, eating her ass, while Kathie Lee sucked me clean. We went inside and I saw my queen. Kim had flown out. She ran over to me and kissed me. I picked her up, kissing her passionately, my tongue molesting hers in our mouths.
"My handsome king... I've missed you baby."
"Missed you too sweetheart."
I took her upstairs, in my arms. We made it to my bedroom and fell on the bed. She was on top of me. She was wearing a gray, very tight, wraparound dress, gray heels and a thin gray wrap as a coat. She quickly took her clothes off. I took my clothes off. I got her to leave her beautiful heels on. I groped and licked Kim's big tits. She moaned, holding my head to her ample chest. I sucked so hard on those thick nipples, licking them in my mouth. Kim grabbed my rock hard cock and stroked it between us. She rubbed it on her juicy labia. I alternated tits, sucking each one hungrily. She slid my cock up her pussy, riding me. We kissed. I smacked the world's greatest ass and squeezed it, loving the feel of it in my hands. Kim rode me, bouncing happily on my throbbing cock. I laid back on the bed, looking up at her. She smiled so sexy, blowing me a big ass kiss.
Damn, I'm in love. I squeezed those big jugs, rolling her perky nipples between my fingers, loving her wet pussy wrapped so tightly around my manhood. She bounced harder on my cock. I smacked her perfectly shaped ass again and again. Kim leaned her head back and moaned. She looked so fucking beautiful. She rode me faster, her ass slamming on my thighs. My cock was so fucking happy. Beth and Helen came in. They both knelt down and sucked my balls while Kim rode me as fast as possible. "YESSSSSSSSSSSS!! I'M CUMMMINGGGGGGGG!!" Kim squirted. I picked her up off of my cock and brought her pussy to my mouth. She finished squirting in my mouth. I sucked it out, licking my queen's pussy clean. Beth deepthroated my wet cock, while my grandmother sucked my balls and fingered my ass.
I enjoyed that, as I sucked on Kim's magnificent, thin runway topped pussy. Beth bobbed her thick blonde haired head on my twitching cock. Helen sucked my balls perfectly. Her mouth is so fucking talented. I turned Kim around and moved her to my cock. She grabbed it and slid it up her awesome ass. OH MY GOD... I love her ass. Everything about it. I love fucking her ass. She was facing away from me, her long black, shiny hair hanging down into my face. I reached up and squeezed those beautiful tits while she moved her ass back and forth on my cock.
My grandma ate her pussy, wiggling her tongue up it, rubbing her clit. Beth came over to me and let her massive tits hang down so I could suck them. They tasted so good. Her huge nipples shooting her milk into my mouth. Kim worked her ass back and forth on my smiling cock faster. "MMMMMMMM... FUCK MY ASS JAMES... I LOVE YOUR COCK!!" She moaned out and squirted into Helen's mouth. My grandmother lapped up her cream. I fucked up into Kim's ass, while Helen licked her perfectly wet pussy clean. I drilled up into Kim's perfect booty, my cock stretching her anus wide, thrusting all the way up that pleasure hole. The bed was shaking.
My mouth was full of Beth's enormous tits. Her tasty milk shot into my thirsty mouth and I swallowed it all down. I sucked her tits so fucking hard. My ass flew off of the bed as I ass thumped Kim so insanely hard. "POUND MY ASS JAMESSSSSSS!!" Kim shouted. She squirted again in Helen's mouth. I finally pumped my creamy load up Kim's ass, groaning loud as my cock shot it hard, my cream exploding out of my, oh so happy, cock.
Helen pulled my cock out of Kim's ass and sucked it. Beth joined her at my cock and the two took turns sucking me clean. It felt so fucking good. I pulled Kim back to me and kissed her, softly rubbing her all over. My grandmother put her mouth to Kim's ass and sucked out my cum from it. Beth kept sucking my very pleased cock. Her wavy blonde haired head bobbed wildly on it, her mouth wrapped so tightly around my shaft. Her lips suctioned up on my shaft, her right hand jerking it fast. She wanted a mouthful and I wanted to give it to her.
Beth sucked me faster and jerked me even faster. I grunted and came hard, blasting her mouth. Beth sucked out my cream, swallowing it down fast. She pulled my still cumming cock out of her mouth and gave it to my grandma. Helen sucked out some and swallowed it down happily. They pulled my cock out and let it paint their sexy faces with my jizz. They pumped every drop out, then licked each other's face spotless. Beth and Helen took turns sucking me dry. I kissed and held Kim, so happy and relaxed.
Katie Couric came over that evening. I was scheduled to do an interview with her the next day, but she wanted to come out to the Hamptons and hang out. We are friends and I like hanging out with her so it was fine. We hung out on the patio, overlooking the ocean, had some drinks and smoked some weed. Katie looks so adorable smoking a blunt. I got her to try and smoke it with her pussy. Spence filmed it. She did good. It took her a little while, but my grandmother showed her how it's done. My aunt Kathie Lee wrapped her gorgeous tits around my cock as I watched my grandmother Helen show Katie Couric how to smoke weed with her pussy. I love my fucking life. Kathie Lee snorted a line of blow off of my cock as I fucked those mature, 36D titties. That bitch is wild. I have the coolest female family members. Kathie Lee sucked my head, while I drilled her gorgeous, natural funbags. I popped into her mouth. She sucked me totally clean.
My grandmother and I did a couple of lines off of Katie's beautiful, perky tits. I liked them clean and sucked those hard, pink nipples, pulling them hard, letting them snap back into place. "Yeahhhhhhh, please fuck me James. I need your big cock so fucking bad." Katie asked and she received. I put her legs on my shoulders and drilled her mature pussy, my hands squeezing her gorgeous, natural C cups. Her milk oozed through my fingers. My grandma licked the milk off of my fingers. Kim got behind me and spread my cheeks. She licked my anus. It felt so damn good. She squeezed my cheeks, then rubbed my balls when she licked my ass.
My cock thumped Katie's cunt. I squeezed her cans and her milk shot up to my grandmother's face. Beth licked her face clean as I pummeled Katie's neatly trimmed, milf twat. She screamed out in orgasmic bliss and squirted on my, hard as steel, cock. I pulled out and Kim sucked my cock from behind. Katie squirted on Kim's tits. Kim sucked my big cock so perfectly, pulling it back towards her and engulfing it. She put it back in Katie's pussy and I drilled it for another 15 minutes. Katie squirted two more times, then I pulled out and pointed my cock at her face. I shot my jizz at her open mouth. She caught it, smiling the whole time. She swallowed my load and licked her lips, blowing me a big, sexy kiss.
I pissed right towards her face. Katie stuck her tongue out with her mouth wide open. She caught my piss. Helen, Beth, Kim and Kathie Lee also stuck their tongues out catching my warm yellow cocktail. That's was the hottest sight. Five gorgeous women, all taking my piss into their mouths. I was so fucking turned on. They all swallowed my piss. Katie and Kathie Lee kissed each other. Kim put her mouth on my cock and sucked out the last drops of piss. I put my hand on her head and enjoyed every fucking second.
It was a fun evening for sure. Kim and I went upstairs and showered. I had a lot of fun soaping her perfect body up, spending extra time on that world famous ass. We cleaned up and got dressed. We all went out to dinner, taking a limo. I was gonna meet my old pal from New York, Drita Davanzo, from Mob Wives and talk about the porno. On the way to the restaurant, my aunt, Kathie Lee, wanted to make out sum more. I wanted to try something kinky so I pulled her tight, white Capri pants down and spread some blow on her labia. I lit a blunt and gave it to her. She puffed and blew the smoke into the air, her head leaning back, loving my work on her beautiful, mature body.
I played with her tits and fingered her ass. Right when she was ready to pop, I leaned down and snorted some of the blow, quickly puffed on the blunt, then quickly went to her pussy. I licked her out super fast, my tongue rolling and licking like a sex crazed maniac. She screamed out and squirted in my mouth. I quickly snorted the rest of the blow from her labia, getting a pussy cum shooter. It was the best high ever. Kathie Lee played with my hair, grinding her twat on my face. I licked her totally clean, kissing that gorgeous, mature cunt repeatedly.
I kissed my aunt, loving those luscious lips. It was a helluva evening and it was only getting started. Drita is always a blast to hang out with and my sexual freakiness was on full power. It's just the way I am. I'm a freak... A sleazy, kinky one... my family makes it even easier for me to be sleazy and I love them for it. It's... My Freaky Life.
To be continued...
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