Halloween in the Trailer Park! Chapter One (Agegap, Costumes, Raceplay)

Disclaimer: Fantasy. Not real. Fictional Characters Only!

Ryan, Andy, and Callan all looked around at eachother with nervous eyes. “We really doing this?” Callan said, swallowing hard. He was wearing a Spider-Man outfit and his mask was pulled up above his head. In the dim light sweat could be seen on his fore head alone with a few bright ginger hairs that had popped free.

“Ooooh yeah we’re doing it!” Said Andy, nodding so hard the Batman mask on his head flopped off. He squawked and grabbed it desperately. His dirty blonde hair was cut short but spiky and he pulled the band on the mask to get it around his head. His blue eyes were bright through the slits on the plastic mask.

“It’s do or die guy’s, its… its tradition! Right…?” Ryan grimaced and wished his costume had a mask, but he was a skeleton and had gone with black and white makeup on his face. It blended into his black hair though, even if he was so nervous he worried he’d sweat it all off! The other boy’s nodded to him and one after another they shoved their right hand’s forward. Each hand had its index, middle, and pinky finger extended. It was the secret sign… it meant they were hear for something better than any trick or treat!

They had one plastic pumkin, the cheap little bucket to hold candy. It was the tradition. Each of them had written on a piece of paper, an address, then tossed them in. The three boy’s reached in, took a piece each, then turned and took off into the darkness.

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They split up quickly, each getting some distance away from each other before they opened their piece of paper. Ryan looked at his, biting his lip not thinking about how it smudged the black and white paint on his lips. He looked at the address there, and his eyes widened as his breathing started to speed up rapidly. “Oh geeze…” He almost jumped into the air as he kicked off and took off running. He knew where to go now!

Getting to a small blue steel colored trailer, he skidded to a halt. He dropped the piece of paper to the ground, not caring in the least if he was littering. He got to the door, and gave it a shaky KNOCK KNOCK KNOCK, that made the wall around it shake a bit. It wasn’t a super sturdy trailer.

The door opened up and Ryan’s eyes went even wider. It was… a teenage girl?! Blonde hair stuck out from under a widebrimmed witch hat. The cone of which was shaped like a piece of candy corn! She had a choker around her neck, and her outfit was a candy corn themed witch outfit. The top was more like a beermaid, with a laced up front over a frilly white top that hung low over perky C cup breasts. Her skirt was candy corn colored, and didn’t make it even half way down her thighs. She wore platform pumps, and long black and orange striped socks that cut off just below the skirt. But as she rolled her eyes and chewed on a wad of gum, he got the feeling she did not want to be stuck here tonight. But she was holding a bowl of candy and held it out. “Yeah yeah, whatever.”

She said the words before he could say trick or treat, or anything else. Ryan swallowed hard, he had not expected her… but the tradition he’d only recently learned… He looked from side to side nervously, no other kids around. The blonde raised an eyebrow annoyed, her show was on and this annoying brat was taking too long. “You gonna take some or-huh?” The kid shoved his hand out towards her. Like was pointing at her, but his hand looked weird. Then she realized the hand sign he was making, and where he was pointing. The shocker, right between her legs.

A lot of things came together at once. “Holy…” The girl said eye blue eyes going wide for a second. She’d thought this was just some urban legend! But this kid was trying too… She bit her glossed up lip for a second, then looked around as well. “Fuck… Ok, why not?” Her face twisted into a intrigued grin and shed put the bowl inside, then reached out to grab Ryan’s skin tight black and white shirt. “Hehe, ok Skelly boy, lets see your funny bone.” And she pulled him inside.

Ryan’s facial makeup twisted a bit as his mouth curved into an amazed smile. It was happening, it was really happening! I mean, it was Andy’s big sister, not his mom… but who care’d!

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Andy followed the address, his breath loud in his ears. Mostly cause it kept bouncing back into his face from the inside of his plastic mask. The small slit in the mouth not quite enough for good air flow. The costume was old, based on super old fashioned batman. He loved it! Even if the cape only barely made it past his butt and it was blue instead of black.

He got to the trailer, it was a bigger one than where Ryan had ended up. Andy turned his head from one side to the other like he’d seen on tv. And when he actually got a pop from his skinny neck on the left flex he took it as a sign. “Yeah!” he said in a hushed whisper as he pumped a fist into the air. His hands were bare, the costume didn’t come with gloves, just blue nylon that went to his wrists. He charged up the stairs, hit the door bell, and jumped back. “You got this batman, you got this!” he said to himself, psyching himself up.

The door was opened and a tall black woman opened the door. “Oh! Hey there batman! Want some goody’s?!” She grinned and a gap in her front teeth was happily prominent. She was dressed like Cleopatra with a straight wig down to her shoulders, the golden tiara on it possibly built into the wig. He face had on heavy makeup with wingtip’d eyes and golden lipstick on her very full lips. And the rest of her white and gold outfit seemed to barely fit on her body which was incredibly curvy. *’Holy crap Ryan’s step-mom is SUCH a MILF!!’* Was Andy’s barely coherent thoughts.

The woman smiled warmly and held out her bowl, it had already seen some use by trick-r-treaters. And probably a few that had snuck back for seconds, but mostly to check out the dark skinned hotty. He started to reach out for some, but froze up remembering why he was here! His had was still and she raised an eyebrow. She could make out the young boy’s eyes staring up and down her body, and deep down she’d been loving those looks all evening… Then he turned his hand, straigtening fingers even as his wrist shook. And she raised an eyebrow. “Oh… oh hunny…” She leaned out a bit, looking around. Ryan whimpered a bit as he got a better look at her cleavage. Then she grinned at him like he’d just won jackpot. He totally had!

“Alright baby, you come on in. This Kween is gonna show you the, heh, royal treatment.” He nodded so hard he almost lost his mask.

_______

Callan was a bit slower on his walk. He coudn’t believe it. He couldn’t believe it! He got… He got-! His heart was beating so hard he thought he’d die. He had his mask down and the nylon wrapped around his head as he looked around through the wide slits in the plastic lenses. He approached a painfully familiar trailer and knocked on it with slow deadened thuds.

The door opened up and a lovely redheadded woman appeared. She was average height with long red hair. Longer than most thought since it was usually in a curly mass that seemed to defy gravity, but tonight she’d painstakingly straightened it out so that it hung down. Her face was in white makeup with lines around her mouth that went out to stretch her smile. Her outfit was made of rags and patches. She was a home made Sally from Nightmare Before Christmas.

“Huh? Baby, what are you doing back here so soon?” She asked in a confused tone, the candy put aside on a wide hip. She turned to set the bowl down just inside the door, then looked back. To see Callan holding out ‘The Shocker’ pointed her way. His skinny extended arm was shaking so hard it looked like it was about to collapse. She couldn’t see his face but his narrow shoulders were heaving up and down as his rapid breathing was heart. “Oh… oh my….” The woman swallowed hard, and despite herself she felt a surge of happiness. “Ok baby, don’t worry, ma-… Sally will take care of you tonight, no one else.” Her makeup made her smile seem freakishly wide, but no less warm and sincere.

______

Cherise had lived in Georgia her whole life, but most of that had been spent in Atlanta. She’d worked at a club in Southern Atlanta and made some damn good money shaking her big ass. But as she got a bit older and wanted to calm all that down, she’d finally found a nice out. Her friends and family had given her no end of grief for choosing to leave the hood to shack up with some cracka in a trailer park but she had her reasons. Marty was a nice guy, and he always tipped real well… And yes, she did love white boys, even if she gave half assed denial’s to her friends. But mostly, it was when one night Marty showed her a picture of his then little baby white boy, who he was raising along after his mother got sent up river. She swooned, she had to take care of that little boy!

Year’s later she still loved her white boy’s, if not more than ever. And Halloween? So many of them coming around! And she had edited her little outfit for their viewing pleasure… The outfit had a cloth that wrapped around her bosom, looping around her back. She’d trimmed it down so it more strangled her big tits than actually covered them. They bulged out above and below the white cloth. And the bottoms had hanging fabric on the front and back. She’d trimmed down the front to show off even more of her dark legs, her skin traced in multiple tattoo’s she’d gotten down the years.

And then this boy, in his silly costume looking like the Batman from the 50’s showed up and gave her that symbol! The one from the tradition she’d heard rumors of years ago after moving here and hoped desperately for it to come true year after year! It had happened! A cute little white boy had picked her for halloween! And now she’d make this Batboy into a BatMAN! She had no idea that the houses were’t just picked by horny boys, but by a roulette game they played. That the only reason she had a visitor was that a boy in her house had partaken in the game as well…

She smiled and turned to lead Batman into her house, and he saw that there was no fabric hanging over her ass. It was bare, completely. Andy could just glimps a view of her pussy lips and his mouth went dry as he stepped up into the trailer. Cherise had a big fat ass, her pride and joy. It shook when she walked, wobbled like it had a mind of its own, and when she gave it a shake it jiggled like jello with a passion. And the whimper the boy gave behind her told her it was doing its job. “Close the door Batman, and follow this big booty…”

He couldn’t help but obey. She led him to her bedroom, and directed him to sit down. She stuck her ass in his face and jiggled it. “Welcome to my bedroom Batman… Looking for some time with an African Kween?” She twerked her ass in his face, and the boy’s ragged breathing was loud through his mask. “Uh-uh huh!!” She turned around to face him ,and her hands cupped at her full breasts struggling to get free from her top. Her finger nails were long and golden, matching her costume. “Tell me baby… what do you want first? What do you want to see? What do you want to touch…?” She bit her lip, her full lips in golden lipstick.

“I want… can I… Can I kiss you?” She froze, surprised by the request. In the club it would have gotten a laugh and a denial, against the rules. The few times she’d made money on the street it would have come down to a balance of hygiene and money… But here, in this moment, with this little white boy on her bed. Her heart melted. “Oooh baby… Oh of course honey!” She reached down to help push him back onto the bed. And with some more space, she straddled him. She grinned down as his face was pressed between her tits, reaching down she pulled the silly plastic mask off his face. Then reaching down, her long golden nails helped tip his chin up and she brought her mouth to his in a long wet kiss. “Mmm…MMMM!”

Her golden nails went into the boy’s hair as her thick lips pressed into his. The boy let out a moan as he gradually leaned into the kiss. She tilted her head one way, and directed his head another, then opened her mouth. The stripper’s tongue pushed out of her mouth into the boy’s and he moaned again with a sound of surprise and lust, and she ground her hips against him. She was so wet, and as she rubbed, she could feel his hardness and it was the happiest she’d ever been to feel a hard cock against her. Her hands left his head, confident he’d stay with the kiss, and he did. She reached down, felt along his shoulders, to his hands, then lifted them up. Cherise pressed Andy’s hands to her breasts. Her own eyes were half lidded and she saw his go wide as the boy was overwhelmed. He let out a moan, his hips bucked, and he broke the kiss with a cry and… a mess was made.

Andy fell back, flat on the bed and panting hard, and Charise just smiled at him. She loved how there were smears of gold on his mouth from her’s. Like she was marking him as her’s. Andy was embarrassed, he knew he’d just came into his costume and couldn’t believe it. “I… I’m sorry, I think I…” “Oh shh, shh, baby, its ok. It just mean’s you like me. Dontcha…?” Her wide grin showed she knew the truth, but the boy nodded, giving a weak return smile.

“Hey… Ain’t you one of Ryan’s friends?” She asked with a quirked head. Andy blinked and nodded. “Yeah, I’m-” “Uh uh!” She stopped him with a golden nailed finger to his lips. “No names baby… Or if you want a name I could call you Bruce Wayne.” She grinned widely, and this time his smile was easier. He almost forgot, yeah no names on this night. He also liked the idea that he was also Bruce Wayne too, that was just as good a costume as Batman! The geeky trivia helped him relax even more.

“Yeah… Bruce Wayne, rich little white boy… and he likes black women huh? Do you like dark lady’s Mr Wayne?” She leaned down as she said it and he nodded. “Yeah, you liked big, unnng-” She pulled her top down and her massive breasts popped free. They were round and dark brown, but with extra dark extra large areola’s around them. “Big black titties like these?” And she bent over to hang them right into his face. His wide eyes stared entranced. She squeezed one big tit with her long nailed hand. “Go on baby, suck em, suck these big black tits!” He needed no more encouragement and latched on, sucking hard at her breast. “Mmmm… that’s it baby… oooh yeah, suck on momma’s black titties… Oh I love it…” She moaned. “The other one baby, share that love…” He pulled off with a wet pop, and swapped, and now he had both hands on her tits too, squeezing and needing the soft pillowy flesh. She was grinding on him again, and sure enough, he was answering. Randomly thrusting up, trying to return the favor, and he was hard again… “Oh… baby… you do love it… Ohhh… Oh yeah… Ok, baby I need more.”

With a wet pop she pulled back. Ryan frowned, an adorably hurt expression on his face. Though he noticed vaguely that her nipples had gold flecks on them, and he knew they were transplants, from her lips to his, to her dark nipples… “Ok Mr. Wayne, scooch back on the bed baby, get comfy.” He did, pushing back with his knees and elbows as till he was sprawled out entirely on the bed, and then watched as she pushed her bottoms down. Her costume slid around her round hips and thick thighs with a grunt then fell down to reveal her bare pussy. She was smooth, recently shaved, with a tattoo above it of a some kind of curling symbol. A womb tattoo, that seemed to emphasize her sex. The lips were slick with moisture that glistened on the insides of her thighs. And she crawled up the bed towards him. Stopping as she got to the bulge in his costume.

She carefully, if eagerly, slipped her long nails into his costume trousers and tugged them down. His young cock popped free and came into view, the black womans eyes wide with wonder and lust. “Ohhh…” She moaned, finally seeing her goal. It was perfect. It wasn’t a giant monster cock, just a cute perfect white boy pecker. Stiff as steel, completely smooth from hair, and glistening with his cum. She leaned in, puckered up, “Mmmmm….Mwah!” she gave a sweet kiss with her full golden lips, almost engulfing the head of the cock with her thick lips. She grinned at the golden lip marks on it, then opened her mouth and engulfed it. Easily taking it to the base, her own moan of lust was cut off by his much louder one. “Unnng, oh g-g-gawd!” Even after just cumming he could barely take it!

Her long and very experienced cock swirled around his shaft, licking up every bit of cum and loving it all. Her tongue worked out and even played with his balls while she sucked and he gasped thrusting into her mouth. Her lips came away wet, and she went lower, and started to lick and kiss and suck at his testicles, leaving golden smears all the while. One hand expertly stroked him, and Andy could just moan and gasp, and she knew her sweet batman was about to explode again! She wrapped her lips around him, sucking like mad in loud wet slurps. He looked down at her, the way her hair bobbed and her eyes locked on his. And the boy gasped out a effort to warn her but couldn’t speak over his own orgasm. She pulled back to just sucking the tip as he unloaded into her mouth.

Cherise moaned as that thick white cum filled her mouth, one hand was down between her legs rubbing her pussy as she took in every single drop. She waited till he relaxed, swallowing some out of habit. Then pulled back. She opened her mouth for the boy, his eyes wide, chest heaving. Then she closed her mouth, and swallowed in a loud wet noise. “MMmmmmm…” her mouth opened up again, just her thick red tongue and a wide smile. “Mmmm… thats some god white boy cream…” His cock… did not completely deflate, just too damn turned on.

But she couldn’t just jump on it now… but that was ok, she’d seen how he’d looked at her pussy before, she pushed herself up. Got a leg under her and stood up, walking forward, a foot on either side of his shoulder. “You like this pussy baby? Wanna taste your black mama’s pie?” He just nodded with jerky motion, and she grinned like the cheshire cat as she squatted, then dropped to her knees around his face, and shoved her pussy against Andy’s face. The boy had seen a little porn, he’d talked with other boy’s. He knew that eating pussy was a thing, like blowjobs. And he couldn’t wait to try. So even as intimidated as he was to see that slick opening coming at his face he pushed his face forward and dived in.

“Mmm….! Mmmm! Oh!” Cherise moaned out, and looked down past her own breasts to the blonde haired boy eating her out. She had never had anyone so eager to just get in that coochie! “Oh god baby… Oh god! Oooh!” She gasped out the words, both of her hands coming up to grab and squeeze her nipples. She bit her lips and ground into him with so much force it was uncomfortable for Andy, but he was having so much fun he didn’t care! The young trick-r-treater shoved his tongue into the stripper-turned Cleopatra and explored every part of her he could.

“Unnng… Don’t stop baby, oh god don’t stop… Oh god dis white boy bout to make me… AAAAHHH!” She cried out so loud it was heard by a few people passing her trailer. She felt her pussy gush, and she gasped in breath… and he kept going! Andy had no idea how a lady came, he barely had a handle on his own orgasms intellectually. So when suddenly she cried out in obvious pleasure and her cunny got seemed to gush into his mouth, he figured he was just doing good! So he went for more! She gasped looking down. “Oh gawd… oh gawd… oh gaaawwdd….” She moaned the words. Looking down she saw his eyes going up. He looked at her big round tits, then locked eyes on her. The sweet little white boy had his mouth on her, his tongue in her. That mouth that just a little while ago was asking for a kiss…! “OOOhhhh-AAAHHHH!” She rolled into another massive orgasm, and had to reach down fingers in his hair and scratching at his scalp as she practically squirted on this boy’s face!

“Agh! Ok, Ok baby, Ok!” She pushed off the headboard and rocked back onto her haunches. Her pussy left his mouth, and she saw the boy breathing hard, and-god bless white boys-licking his lips! “Oh heavens baby… You just bout made me cum my brains out… Oh god baby… You just… you know how to eat a nigga out baby!” She was breathing hard, but looking at his face, she saw it. She saw his face go red an how he looked away at the words.

She grinned broadly. “Oh… I forgot. Thats a badddd word for you, ain’t it baby?” He looked back at her for a second, and seemed to somehow get redder. But he nodded. “Y-yeah…” She giggled, and her bouncing boobies drew his gaze back. “Oh honey its ok. Sometimes that word… it just fits. Its ok. I know you like me…” The boy was still red, and just shrugged uncomfortably. She smiled and reached down to stroke his face. “Here baby, I’ll show you want I mean…” She grunted and got to her feet.

Andy looked up, the woman loomed over him, a smile on her face. Her big breasts were in full view, and her pussy was extra wet and slick. Pussy juices and his saliva all over her slit, her thighs. Then she turned around, bending over she reached back with both hands and slapped her ass. “This, baby, is a big… fat… nigga booty.” He stared at her ass, entranced. She gripped both cheeks and spread them, showing a clear view of her puckered hole, and the slit past it. “This is the best kind of ass in the world baby!” She gave it another smack, then jiggled it. “This the kind of booty that men do anything for… They give they money, they give they time… hell some nigga’s die for a ass like this…” She bent over, squatting almost over his face, then twerked her ass. The wobbly jiggly cheeks clapping in hard loud smacks as it shook before his astonished face.

“But for you baby… All I want, is for you to smack this ass… and tell me how much you love it!” She shook it again, and it took Andy a second to realize he’d been told what to do! But wanted to already, and his hand reached out, and he smacked her right cheek. “I… I love it!” She laughed and jiggled her ass more, then dropped down, on all fours with her ass infront of the boy. “Hard baby! Tell me what you love!” I took quick breaths through his mouth and nose, and with a grunt of exertion he swung again, this time his hand hit so hard his palm stung. Her fat ass jiggled around and he yelled it out. “I love this fat nigga booty!” “Mmmm! Yes you do baby!” She cheered him on, and he brought his other hand around, smacking her ass on the other cheek.

She was loving it, this was her fantasy. Her big fat ass being played with by a perfect white boy. His cock hard for her, and wanting her in the worst way, the best way… He smacked her ass again and again. She jiggled and twerked her ass and encouraged him. Teaching him dirtier words, things to say. She loved it… she got off on it so bad, and was living her fantasy. Finally she had to have more. “Ok baby… now I’m gonna give it to you…” She moved down a bit, her hips hovering over his crotch. Andy let his arms fall limp, they’d actually been worked pretty hard making that big booty jiggle right.

She reached down between her legs, and gripped his cock. She felt it, so hard, so ready… All for her. She was a pro, and felt the angle it was on, and lined up her snatch with it. And with a grunt she lowered down onto it, letting it push between her wet swollen pussy lips and enter her. “Oooh, gaaa… ” “Oh fuck yes, gimme that dick baby…!” they both moaned out in pure shared lust. She looked back at him, and began to bounce her ass, to grind it up and down on his cock. “Thats it baby, you a man now… mmmm but I like you more as a cute white boy, hehe…” He just grinned at her, and took her encouragement to smack her bottom again. “That’s right! Use that black ass baby! Show me how much you love your mama’s big black ass! This tight nigga pussy… Ung!” She cried out and pushed down, and felt it when he thrust up.

Andy couldn’t just lay back, he had to take more. He thrust up into her, trying to work with her. They both moaned out and worked to fuck faster and harder. His young cock pushing into her again and again. And as he got faster and faster, working into a wild fervor she just held still over him, and let the boy go to town as she moaned out. One hand pushed between her legs and rubbed her clit wildly. “Oooh god… Oh god yes baby… gimme that dick, give this nigga that white boy DIIICK!!” She cried out and her eyes rolled up as she came again, her pussy gushing onto him and Andy reached his third orgasm of the night.

His back and hips working, shoving his hips up into her again and again. “Agh, agh, aghhh! Oh god… Oh goddda I love it… I love this nigga pussy… I love this black asssssss!!!” He was developing a life long fetish being drilled into him by a horny woman with a deep seated kink to match. And as his eyes rolled back and he came hard he thrust up, pushing his hips into her as firmly as he could. His left hand grabbed her ass and his fingers sunk in. Gripping so roughly that his nails cut into her ass a bit, not that it could felt in the spot where he’d slapped her black ass into a shade of red. His right hand just kept smacking and smacking, weaker now but relentlessly clapping into her ass till his orgasm finally calmed down.

Andy went limp, lying back gasping. His chest heaving up and down rapidly as he sucked in breath. Cherise moaned… she’d almost came again just as he was fucking her, and even now the rapid orgasm’s she’d had before it had her pussy feeling like it was vibrating. “Oh damn baby… you did it… filled this nigga up… mmmm oh fuck yeah…” She reached down and rubbed her pussy, feeling the slimy white boy cream inside of her. Then working quickly, she moved aside, swung her hips a bit, and let herself fall into the bed next to him. She smiled down at the boy.

“Oh… You did so good baby… gave me the best Treat ever… a big one too.” She rubbed her stomach with her slick fingers, just a bit above her pussy, on the womb tattoo there. Cherise was always on birth control, had been for years. But ever since finding out about this so called tradition.. she took a break from her pills every October. And finally it had paid off. She smiled with a far away look in her eyes. “I… I did? For reals?” She looked down at Andy, his questioning hopeful young face. And she smiled at him broadly. “You did sooo good baby. The best I ever had…” It had been the hottest sex she’d ever had, but that was more to the taboo nature, and her own twisted kinks coming true… but he had done damn good, so why not give him an ego boost. Besides. he just needed some practice.

“Woah…” He looked away for a moment, then grinned broadly. She smiled down at him and her hand moved across his chest. “Um… I know its supposed to just be for, uh, tonight… But uh, can we do this again…?” She smiled at him, and that smile said everything… And if it didn’t then her moving down to press her lips to his, while her hand moved down to start stroking his young cock said it for sure. She was gonna get every treat she could out of this white boy.

Source: reddit.com/r/sexystories/comments/jhi7ko/halloween_in_the_trailer_park_chapter_one_agegap