Lucky Alan Ch. 03

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Alan loses his virginity and meets Tiffany's sister, Charley.
3.2k words
4.51
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Part 3 of the 12 part series

Updated 06/07/2023
Created 03/26/2015
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TLMorgan
TLMorgan
955 Followers

Selma and Bessie played paper, rock, scissors to see who got a turn with Alan next.

"Oh yeah! Give me some of that big delicious cock," purred Selma.

Alan's huge cock was slowly hardening again after had had unloaded a massive fountain of cum on Tiffany's face and in her mouth.

"I got just the things to get your dick up a bit faster," mentioned Selma, and with that, she lifted up her hooded sweatshirt to reveal a skin-tight plain black tee-shirt that outlined her tremendous rack. "You seem like the kind of nerd who appreciates a pair of huge tits."

Alan nodded his head like a mindless zombie as he watched Selma hoist her tee-shirt over her head and tossed it to the van floor. Her massive mammaries were housed inside an enormous white sturdy bra. She gave her torso a little shake causing some major bouncing and jiggling inside her large bra cups. His big dick steadily increased it's growth.

"Get ready to feast your eyes on these F cup titties, baby."

Rather than taking off her bra the traditional way, Selma lifted up the large cups and both, enormously round knockers flopped out in all their natural hanging glory. The olive-colored mounds hung from her chest, full and round like bowling balls with visible bikini lines. Her areolas were a darker shade of brown and were as big as the bottom of a soda pop can with small nipples, thick and chunky that pointed right at Alan.

Alan was mesmerized by the enormity of the female flesh that hung from Selma's chest. His massive cock stood rock-hard in front of her.

"See! I knew my girls would do the trick," Selma rightfully gloated, as she squeezed her arms together, showing off her endless cleavage. "I bet you want to do all sorts of naughty things to my huge fucking titties? You want my big titties in your hands, in your mouth, and wrapped around your massive, hard cock? You want to unload tons of spunk all over them, don't you?"

Alan groaned and continued to watch Selma shake and wiggle her fat jugs.

"Enough with the foreplay already. I want a turn sometime this year," hissed Bessie.

Selma rolled her eyes as she leaned over and started crawling towards Alan with her giant pendulous breasts swinging moderately to and fro from her movements. Alan felt her heavy tits make contact with his pasty thighs and he moaned deeply and watched as Selma swooped her head down and took some of his meaty tool between her moist, sensual big lips.

Unlike Tiffany, Selma suckled his thick cock in a slow, calculating pace and each time she dipped her head down, she gorged more and more of his throbbing shaft down her throat. Alan fought back to urge to cum as he felt Selma attempting to deep-throat his cock. Her big nose grazed his abdomen a few times as she sucked. Alan laid motionless on the van floor as if he was in heaven with his toes curling. Selma managed to swallowed his entire, thick hard member down her throat. Her big lips pressed against the base of his fat cock that was lodged and distorted deep in the back of her throat. Her chin pushed against his huge balls as she savored his long penis in her warm mouth and throat and showed no signs of having a gag relax.

After several seconds of having his massive veiny cock down her throat, Selma slowly pulled up but kept her lips attached to his bulbous dickhead. She tasted his salty pre-cum as she sucked and licked the fat mushroom head of his cock. She moved her gigantic boobs up closer so that his hard shaft and fat balls were cushioned between them. Alan groaned loudly.

"Ohhh God! Ooohhhhhh!" he cried.

On instinct, Alan reached down and grabbed the head of Selma's head. He thrust his hips upwards between her spacious cleavage, pushing his extremely hard cock in and out of her mouth.

"Damn! He's face fucking and titty-fucking her with his beautiful, giant dick!" Tiffany observed, as she was enthralled by the action and started squeezing her big tits through her sweatshirt.

Bessie licked her lips as she tolerantly waited her turn with Alan. He steadily pistol his cock between her giant jugs and soft, juicy lips. Selma moaned as her throat graciously accepted the swallow head his seesawing torpedo. Copious amounts of saliva gushed from her mouth, down his already slick cock and between her boundless cleavage. The extra lubing allowed Alan to settle into a smooth thrusting rhythm as he fucked her heavy mounds. The inviting, soft cushions of her globes combined with her incredible mouth was proving to be unbearable for Alan to handle. He increased his speed, fucking her face and huge tits harder. They jostled and jiggled sensationally as he rammed his aching cock between the biggest, softest pair of tits he ever seen. Her chunky, hard nipples darted into his flabby abdomen with each thrust. Alan felt his balls ready to explode as they bounced around between her shifting, soaked jugs.

"I'm cumming," he cried out.

Selma kept her big mouth wrapped around his dickhead and swooped up her massive tits with her arm. His throbbing shaft was still lodged between their softness as cum began gushing from the head of his cock and flowing down her throat. He kept cumming and cumming until it started to spill from between Selma's lips and dibbled down her chin and onto the tops of her mountainous melons. She pulled her mouth of his cock, seized it with her free hand, and finished his massive load onto her tits. Alan begun panting heavy as his orgasm subsided and his load stop coming.

"His cum is so delicious Bessie. You need to try it," teased Selma, as she swallowed the remaining mouthful of Alan's white, hot jism.

"Oh, I shall and much more," Bessie alluded to. "So I hope you have enough stamina to go one last round."

To everyone's surprise, Bessie shed her jeans, socks, jacket, and shirt, standing only in a pair of matching pink bra and g-string. She got down on her hands and knees between Alan's legs, lifted up his huge flaccid cock and slurped on his hairless, fat balls. She sucked them, one after another causing Alan to moan and his cock to grow hard again. She licked and gobbled his huge ball sack as if she was trying to suck the skin off them. Bessie tasted his cum and Selma's sweat that soaked them. His cock was at full throbbing again in her little hand. She stroked it while massaging his hanging balls with her tongue.

Bessie slowly moved her tongue down off his scrotum and licked the area beneath them. Alan wheezed as she licked one of his most sensitive spots. His big wet balls dangled across her cute, petite pointy nose as she feverishly licked under them. This was a new sensation that urged through Alan's entire body and his cock was harder then it has ever been. She licked her way back up his balls to his steel-hard cock. Bessie licked his vein-popping shaft up and down on all sides like licking ice cream from an ice cream cone. She lapped up and swallowed bits of his hot cum residue from his last orgasm. She covered most of his cock with her mouth and started giving him a wet, sloppy blow-job. She seized his enormous, saliva-drenched balls and rolled them between her fingers as she wildly bobbed her head up and down his long tool. Her long brown hair flung everywhere with her bobbing movements and her substantially big boobs jiggled inside their respective bra cups.

After several minutes of the intense, wet sloppy blow-job by Bessie, Alan felt himself on the verge of busting his three load of the night and perhaps his biggest when she abruptly pulled her mouth away from his saliva-glistened shaft, stood up, and removed her pink g-string to reveal her hairless, pink wet pussy.

"I want you to fuck my brains out with that juicy cock of yours!" she exclaimed.

Tiffany turned to Selma whom put her black tee-shirt back on without her bra with a questionable look. Then the two of them turned towards Bessie.

"We were only suppose to blow him, not fuck him," said Tiffany.

"Besides, will that huge thing even fit in your tight, little ass pussy?" asked Selma.

"Will I'm about to find out," Bessie replied.

Alan was not expecting to lose his virginity ever, let alone have his dick be sucked on by three busty girls whom huge tits he had only seen on the Internet, all in the late hours on a school night. Bessie hovered over Alan's massive hard, standing penis. She briefly rubbed the bulbous head of his cock against the outside of her drenched pussy lips before lowing her wet cunt down on his shaft taking his virginity. His huge dick spread her pussy lips wide while her juices dripped down. Bessie emitted a low moan as she locked her bare feet under his thighs and rode him for a good long time in that position, slowly at first, savoring the inconceivable feeling and trying to get used to the size and thickness his girth.

Alan moaned loudly as he was experiencing the greatest pleasure he had ever felt. He was overwhelmed by the warm feel of Bessie's tight cunt as it moved up and down his throbbing cock.

"Oh fuck! You're so fucking big, Alan! OH, OH, OH! You're cock is so fucking big, you skinny ass nerd," Bessie moaned.

She began fucking Alan with more speed and gusto causing her huge natural E cups to lurch themselves out of their cups. Alan couldn't take his eyes off them as they bounced and rolled around on her chest now free from their captivity. They rose from her chest and plumped outwards, sexy, inviting, and pale. Her areolas were wide, dark pink, and bumpy with ruby-red gumdrop sized nipples in the center. They flopped about her chest in such a compelling way while riding his cock that Alan didn't want to reach up and play with them. He placed his hands on her petite yet round ass that wobbled each time she slammed herself down on his massive hard dick.

"Start fucking me! Harder, Alan! Fuck me HARDER! Fuck me like the animal I know you are! Bounce my big titties to my face! Knock me out with them! Ohhhh yeah!" she cried out. "You're huge cock is splitting my pussy! It's feels so amazing!"

Alan began doing his share of the work, hammering his hard cock up into his first pussy. Bessie leaned over letting her huge titties dangle down and smack his face over and over again. Alan released his vice-like grip on her ass and cupped both of her uncontrollably flopping hooters. He sucked on them greedily as her fucked her pussy intensely. Bessie squealed in delight as soon as Alan's mouth touched her hard sensitive nipples. He lightly nibbled on them as her big wobbly breasts overflowed his palms. He turned his attention to her bumpy areolas, licking and sucking on them. He then sucked for all he was worth a good portion of a fat boob in his mouth and repeated his actions on her other boob. This took Bessie through a series of awe-inspiring orgasms.

"OHHHH YES, Ohhhhhh YES! FUCK ME! FUCK ME! Fuck me harder, you big dick bastard! Oh god! Ohhh god! Ohhhh my FUCKING GOD!" she moaned.

The minivan was in rocking motion and the windows were steamed up from the fucking. Both Tiffany and Selma had bewildered looks on their faces yet were hugely turned on by this nerd with the biggest cock they had ever seen fucking their good friend right before their eyes.

Bessie climbed off of Alan and the two repositioned themselves sideways. Alan's cock was drenched adequately by Bessie's hot pussy that he could easily slide it right back in. He pounded her hard causing her beautiful, large breasts to pitch and roll up and down her chest. Alan peeked over her shoulder to watch her huge boobs surge. He groaned in pure ecstasy. Bessie reached down and rubbed her excited clitoris. She squealed, wept, and screamed in utter bless as she loss control.

"Oh god, I'M CUMMMMMMING!"

Alan continued to fuck her as she came. He felt her pussy tighten and spasm around his thrusting cock. Her juices trailed down his long, hard shaft and bathed his huge balls as they slammed into the outside of her cunt from his thrusting. Tiffany and Selma were amazed by how much juice flowed from their friend's fucked cunt.

"I gotta fuck him now," said Selma, as she removed her black shirt and tossed it aside, giving Alan another eyeful of her gigantic cum-on-me tits.

"Yeah, me too," Tiffany agreed, as she hoisted up her sweatshirt and the oversized purple tee-shirt she wore underneath it and tossed them down. Tiffany's ample triple D's were housed inside her black brassiere and Alan couldn't wait to feast his eyes on them.

She reached behind her back and unhooked her bra and flung it from her enormous, low-hung breasts. They were the size of grapefruits and fell across her soft, chubby belly with pink areolas the size of silver dollar coins and long, big eraser-sized pink nipples. Seeing their huge naked tits in addition to his swollen cock still moving deep inside Bessie's soaked pussy and her insatiable moaning, send Alan closer and closer on the verge to cum. He grunted and harden with impending release.

"Oh Alan! Shoot your big, fat load all over my face. I want to taste your sweet cum! Ohhhhhh god, Alan!" Bessie moaned.

The sensation of fucking his first pussy felt too incredible but Alan reluctantly pulled his throbbing dick out from her cunt and moved up towards her face. He let himself go into absolute pleasure as he unloaded a massive series of hot, white cum shots all over her Bessie's pretty face. He moaned and his body trembled upon releasing his filthy spunk. Bessie closed her eyes and had her mouth open wide to receive Alan's biggest load yet. He moved his cock around so not a speck of her skin was left untouched by his gooey semen. After his orgasm finally subsided, Alan, Tiffany, and Selma could hardly see Bessie's gorgeous face that was now completely covered in cum.

"Think I could squeeze another load out of his big, fat balls of yours to drench these giant tits?" Selma teased.

"Oh my god, you guys!" panicked Tiffany, as she jumped up into the driver's seat. The scene made her huge sloppy titties flail around wildly. "My dad is going to be getting up in like 5 minutes for work! We have to get out of here."

"Perhaps another time," sighed Selma. "Now get the fuck out of the van!"

Alan quickly gathered up his clothes and shoes and jumped out of the minivan just as it took over.

"Thanks for the good time, lover boy!" shouted Bessie with sticky cum still covering and dripping on her face as she closed the back of the minivan.

Alan stood in the alley naked and watched the minivan disappear out of his sight. He got dressed and headed to his mom's car. The clock on the dashboard read 3:35am as he started up the engine and drove home after the most unforgettable experience of his life.

Alan got home and slept through most of the day. His mother checked in on him to see if he was going to school. Alan told her he wasn't feeling good so she called him off. Alan got up around noon, showered and played some video games until he got hungry. He went to a nearby Wendy's where he unexpectedly bumped into Tiffany. She smiled and Alan immediately had a flashback to seeing her braces drenched in his thick spunk.

"Oh, hey Alan!" Tiffany exclaimed. "I was hoping to run into you again."

"Really?" he nervously replied. Coincidentally, Tiffany had on the same sweatshirt from last night and her enormous, fat sloppy jugs swelled nicely from beneath.

"Yeah. I wanted to apologize about throwing you out of the van like that. Things went on a little bit longer than we all anticipated," she said.

"Oh... No biggie. It was a school night," Alan said.

"Yeah. I didn't go because of our raunchy late night fun... Speaking of which, since tonight isn't a school night, my parents are going to be out of town until tomorrow night. My dad just stocked up the fridge with beer. Perhaps you would like to come over and hang out with me and my sister?"

Alan was totally befuddled by her request. He contemplated after last night that she probably wanted to get her turn. He didn't know exactly where her sister fit into her plans.

"S-s-sure. I'd like that," he replied. "What about Bessie and Selma? You're not inviting them?"

"I did but they already had plans for the entire weekend. But don't worry, if you liked them, you'll LOVE my younger sister Charley," she emphasis. "She just turned eighteen last weekend. In fact, I'm here to pick her up. She works here. I'll introduce the two of you and don't worry, she knows all about last night. The minute I got home, she questioned me and has been very excited to meet you ever since. That's why I'm so glad to had ran into you today."

"Hey Tiff. I'm ready to go," spoke a female voice behind Alan.

"Hey Charley. This is the guy I was telling you about last night, Alan"

The young girl walked from behind Alan and stood beside her older sister. Alan's eyes opened wide and he nearly came in his jeans. Barely contained by a straining red tee-shirt with the Wendy's name printed on the front were the largest pair of breasts Alan had ever seen! They hung faintly close her navel, but pushed out fiercely like a couple of oversized torpedoes. The rest of her body was almost petite in comparison; slim waist and shapely hips, long, athletically toned legs, and thin shoulders. Charley had Gothic-pale skin that was heavily freckled around her nose and cheeks. She stood 5'5, had a reddish-brown pixie hairdo with fringe bangs and luminous crystal-blue eyes seen behind her thick horn-rimmed glasses. She was every titman's dick-hard fantasy come true.

"Oh, wow sis. You weren't kidding," Charley chuckled softly.

"Think you can keep your beast tamed until tonight, say around eight 'O' clock?" said Tiffany.

Alan was a bit confused by what she meant until he looked down and saw the massive bulge in his jeans. He blushed with embarrassment and hoped no one else in Wendy's noticed.

"Of course I can and eight sounds perfect," he replied.

"Okay, see you then."

Both girls walked out of Wendy's and Alan's eyes followed. Tiffany had quite a large, plump ass that her jeans molded over perfectly while Charley had a small ass but it looked tight and firm from his vantage point. He was mind-boggled by the fact that Charley's mammoth sized hooters swelled out visibly from either side of her slender back. They bobbled from side to side as she walked. It was truly unreal. Alan couldn't believe how she managed to walk upright carrying what seemed to be 15 pounds each on her chest, but he was thrilled to find out tonight...

TLMorgan
TLMorgan
955 Followers
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  • COMMENTS
3 Comments
AnonymousAnonymousover 7 years ago

Kinda, dunno, boring. dude gets sex too easy. Its like women just dreamed about his dick even tho they met him first time. Its silly. No character development.

AnonymousAnonymousover 8 years ago
Meh…

Cumming 7 times in a single day ? That was really too much for my suspension of incredulity…

AnonymousAnonymousalmost 9 years ago
so far so good

keep them coming

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