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Lucky Alan Ch. 11

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“Why so down, Mr. Alan Rogan?” asked the high school guidance counselor Judith Becker.

“I feel like my luck has run out,” Alan solemnly replied.

“Care to elaborate? She asked.

Alan sighed as he sat across from his mildly attractive guidance counselor. She was a married 33-year-old mother of 2 with a full D sized rack that was housed beneath her red silk button-up blouse. Her breasts appeared much larger on her gangly 5’10 frame.

“Well, I was popular amongst my peers, especially the women but drastically out of nowhere it seems they have all turned their backs on me and replaced me with someone bigger and better,” Alan explained.

“Ah yes. I’ve heard stories that you were popular with the cheerleading squad.”

“You’ve heard stories?” Alan replied nervously. “How much have you heard?”

“Enough. You have to understand Alan. You were merely a play toy to those dumb sluts. They only wanted one thing and after they got that one thing, you were no longer good for them. They’re users. They saw you as an opportunity and took advantage of you, promised you a popular lifestyle but as soon as the next big thing came along, they kicked you to the curb like yesterday’s garbage. So don’t beat yourself up over them. You were too good for them anyways.”

“Yeah, perhaps you’re right,” Alan shyly agreed.

Judith stood up and walked over to Alan and sat down next to him.

“I know I’m right. You still have so much potential, Mr. Rogan and so much to give. Any women would be lucky to have such an incredible huge cock inside them,” Judith straightforwardly stated.

Alan was completely taken aback by her bold statement and it didn’t help that her hand was placed upon his inner thigh just an inch away from his limp cock when she said it.

“Besides hearing the stories, I saw the video of you and the Wilcox sisters that went viral and I must say you’re quite the performer.” Judith complimented, as her hand was fully rubbing his blossoming erection. “We have a free one hour period. Care to give me a personal performance? It’s my job to make sure you reach your full potential and leave you with a peace of mind.”

Alan smiled with glee as Judith blew into his ear as the length of his cock grew longer and thicker.

“OHHH shit! The video doesn’t do your cock justice,” she gasped, hungrily eyeing his enormous boner while her hand steadily stroked the full large length of his hard shaft. “After years and years of feeling my husband’s pinky size dick in me, it’ll be nice to enjoy a real cock for a change and be fucked properly.”

Judith unbuckled Alan’s belt and jeans and slide them down to his shins. Her chestnut brown eyes widen at the sight of his huge stiff dick jutting up inside his Teenage Mutant Ninja Turtle boxers. She reached into the slit of his boxers and gasped loudly as she seized his massive shaft. After a few strokes, she pulled out Alan’s naked hard hot flesh of pillar and baring it in its entire glorious splendor.

“Oh WOW!” Judith moaned, her eyes lighting up like a Christmas tree in Time Square. “So hard, so thick, so humongous. I’m so fucked but I need to feel this beautiful beast in me, Mr. Rogan.”

Judith leaned down and pressed her big soft lips against the fat bulbous head of his cock for a long kiss. She steadily planted kisses all over the swollen plump knob. Her warm hand kept a tight grip around the thick root of his huge throbbing cock as her moist mouth closed around the fat tip. She glided her lips down the bulk of his shaft, making moaning and gagging noises as she proceeded to take as much of his hard wood in her mouth as possible.

Alan’s toes curled in his shoes and socks as his guidance counselor bobbed her head up and down his manhood with loud sloppy wet noises.

“This… feels… good,” Alan moaned.

“That’s what guidance counselors are for. To make the students feel good in any way we possibly can,” Judith replied, pausing and taking his saliva-covered phallus out of her mouth and descended her lips upon his enormous testicles. She licked and sucked each giant orb in turns.

Alan watched, horny and in lust while his guidance counselor devoured his thick hairless balls. His sexual excitement was amplified by the obscene sight of his huge cock resting in the middle of Judith’s face as she nurtured feverishly on his enlarge scrotum.

“Hmmmm, I love balls. I especially love huge fat ones,” Judith moaned.

She sucked on his large fat balls for a few more minutes before returning her attention to his giant meat pole. Her eyes marveled at the sheer size and thickness of his vein popping cock and sealed her juicy lips around a good chunk.

Judith moaned lovingly on his shaft as it stretched her mouth and caused muscles she never knew existed in her cheeks and jaw to work overtime. The swollen head of his dick touched the back of her willowy throat each time her mouth descended. While she Alan a deep steadily blow job, one of his hands began roaming down her back pendik escort and groped her surprisingly plump firm ass hidden beneath her black business skirt.

“Maybe we should get more comfortable on the floor and let me taste you,” Alan moaned. “Ever did a 69?”

Judith begrudgingly released his massive cock from her sloppy mouth and smiled. The two stood up and got undressed. Alan was first to be nude with the exception of his socks and shoes and lied on the ground with his enormous erection jutting towards the ceiling. He watched his guidance counselor get undressed to just stand before him in her tan stockings and admired her rather large saggy breasts once the white brassiere was off. With Judith’s body being long-limbed and slim, her big alabaster breasts were droopy and somewhat inequality on her frame in a very sexy mature way. She straddled herself above Alan’s face staring towards his throbbing manhood with her drippy pussy covered in layers of dark unkempt hair hovering over his mouth. For ten uninterrupted minutes, Alan and Judith oral pleasured each other. He used his mouth on every nook and cranny of her drenched pussy, licking and nibbling on her labia and clitoris causing her to explode in his mouth. Judith never felt such orgasmic sensation from having her pussy eaten with half of a giant hard cock lodged in her mouth. Her involuntarily loud moans were muffled by Alan’s thick member as she nursed on it through her orgasm. Judith’s cum had a tangy taste to it as Alan lapped up every last bit that flowed from her hot dark bush.

Foreplay was over and Alan was ready to fuck his guidance counselor’s brains out. He had Judith position herself on her side and he moved in behind her with his hard wet dick, rubbing the enlarge swollen head up and down the moist entrance of her pussy. Judith was moaning hysterically before the action and desperately wanted to grab onto something as the biggest dick she ever seen was slowly impaling its way inside her.

“Oh! Oh! Oooohhh! Ugggghhhhhhhhh!” Judith howled, as Alan pushed several hard inches of his throbbing cock inside her.

He started heatedly thrusting as much of his huge cock in and out his guidance counselor’s soaked cunt as it would take. Her gangly body became a ragdoll under his hard thrusting and made her big floppy alabaster tits surge up and down her chest. Alan seized one of her dangling hangers in his sweaty palm, lifted it up and sucked the bright pink nipple inside his mouth. Her pink areolas were quite big and Alan felt the bumpy surface against his sucking lips.

“OHHHHHHHH GOD ALAN! Not my nipple! OHHH GOD!” cried and moaned Judith, as Alan’s oral stimulation of her nipple was also a direct link to her hot dripping-wet pussy, further lubricating and making it easier for Alan’s cock to push in and out. A familiar smooth substance entered Alan’s mouth as he sucked on her eraser-sized nipple. “My milk. Dear GOD, you’re milking me.”

Alan sucked harder on her swollen fat nipple and squeezed the plentiful wobbling funbag to pump more of her milk into his mouth while he jackhammered his oversized phallus up inside her. His huge balls banged violently on the outside of her cunt which was stuffed to full captivity by his elongated boner. Alan lifted up one of her long legs with his short leg and increased his thrusting tempo. His mouth became a suction cup on her big pasty breast, sucking the huge bumpy areola and much of the droopy flesh between his lips and continued to drink her mildly sweet mother’s milk.

It was all Judith could withstand and her body became consumed and wracked with a blissful orgasm and she came. While going through the motions of her orgasm, she was astonished by this teenage nerd’s ability to fuck like a professional porno stud. The sex with her husband was never this good, intense and satisfying.

“Unh! Unh! Unnnhhh! OHHHHHHH! OHHHH ALAN! OHHHHHHHH!” she wailed. The slick walls of her pussy squeezed over his pounding member as it shuddered and continued to release a streams of cum. Alan continued to nurse on Judith’s big floppy tit, ingesting its divine mild milk while his monster cock steadily rammed in and out of her until her orgasm subsided.

After a couple more minutes, Alan pulled his massive cock from his guidance counselor’s drenched twat and turned her over on her hands and knees. He admired her round peach-shaped backside and once again teased her pussy entrance with the tip of his fat cockhead. He slowly slid himself back inside Judith and her hungry pussy quickly devoured him up.

“Ughhhhhhhhhhhhhh,” she grunted, feeling her hot pussy being stretched beyond its limitations to fit all over Alan’s humongous cock. She pushed her sizeable ass back towards him, allowing his cock to slide further and penetrate her dripping snatch as deep as possible. Alan soaked in the amazing view of smooth her pale ass and held onto her thin waist while plunging in and out of her.

“Fuck! Ohhhhhhhhhhhh fuck, you’re so fucking big!” cursed Judith, being maltepe escort fucked doggy-style in the middle of her office in the middle of the afternoon. Her big mom titties flopped forward and back and collided against each other with their hard leaky nipples spurting milk on her office carpet. “Unh! Unh! Unh! Unh! Unh! UNNNNNNHH!”

Alan stood up on his feet and pounded her harder and faster with the impact of his groin slapping against her smooth ass causing the fleshy globes to ripple. Her gangly body was helpless under the merciless assault of his enormous cock and surrendered itself to ecstasy once again.

“UNNNNNHHHH I’m CUMMING!” Judith cried out, her stretched cunt clamped tight around his thrusting hard manhood and bathing it with her cum.

Alan held a firm grasp on her slim waist while she was cumming, furiously hammering her mature pussy for all its worth and felt his big balls stiffing up. He was nearing his end and quickly pulled his huge cock from her piss soaked pussy.

“OH Christ!” Alan moaned, holding his dick in his hand and jerking it as massive thick wads of jism roped from out of his shaft and all over her back and ass. He aimed his dick at each plump ass cheek and made sure both got plenty of his hot gooey spunk.

After Alan finished unloading the last of his semen on the back and ass of his guidance counselor, the school bell rung for the next period.

“Thanks Mrs. Becker. I really needed your guidance today. I believe you unlocked my full potential,” Alan praised and gathered his clothes and left out of her office through a side door.

“The pleasure was all mines, Mr. Rogan” mumbled Judith, with her face down in the carpet and ass up covered in enormous globs of cum…

After that unexpected but much needed guidance, Alan was famished. He decided to take the rest of the school day off and headed to Subway. He heard ramblings of an extremely top-heavy college student employed there.

“Welcome to Subway. I’ll be right with you!” said a familiar voice from the back as Alan entered Subway.

Honeydew melon-sized boobs appeared from the back seconds before the beautiful face above them.

“Alan Rogan. Long time no see,” greeted Cassie Banks.

“So it’s true,” Alan confirmed.

“What’s true?”

“Oh, just looking at the new sandwich you guys have. I didn’t think it was true that you put Fritos on a sub,” Alan replied playing stupid.

“Yeah, I thought it was a little ridiculous,” Cassie agreed but a bit suspicious of Alan. “So, see anything you like? It doesn’t necessarily have to be on the menu you know.” Cassie leaned over the counter with her arms smothered beneath her huge boobs that were wrapped tight beneath a green and yellow striped subway employee shirt. His eyes were immediately locked on her bugling breasts.

“Those look very appetizing,” responded Alan, smiling with glee.

“I see some things never change… Oh damn,” said Cassie, eyeballing the enormous growing bulge in Alan’s pants. “Except maybe that thing. Did you get bigger?”

“No. It’s about the same thickness and length the last time you saw it. Don’t think I can say the same thing about your boobs. They look twice as huge!”

“I went up to an F,” Cassie giggled. “32F.”

“Wow, an F! Lucky boyfriend.”

“Not so lucky boyfriend, “Cassie let out. ” I caught the bastard cheating on me and kicked him to the curb. I’ve been single for a couple of months now.”

“Oh. Sorry to hear that,” replied Alan pretending to sympathize.

“Don’t be. He wasn’t very good in bed. I had to fake orgasms in order for him to finish up and cum,” Cassie informed. “It’s been two whole months of no sex and no orgasm and then my former study buddy just happen to show up. Strange.”

“A coincidence?” Alan playfully questioned.

“I don’t know, maybe. My shift ends in 15 minutes. I’ll make you any footlong you want on the house. Just as long as I get your footlong in return. We have a deal?”

“If that’s today’s special deal, I’ll take it!” smiled Alan.

He ate and enjoyed his Turkey and Swiss cheese footlong sandwich and shortly after Cassie’s shift ended, she was sucking and enjoying Alan’s footlong in the back of her mom’s Chrysler black minivan. Alan lied sprawled out in the back wearing just his tube socks. Cassie was sitting on her knees bend over in just her panties and enormous sports bra as she vehemently licked and sucked the enormous throbbing cock that jutted in front of her. Her hands were on either side of Alan’s thighs, rubbing them for extra stimulation as she glided her sealed lips up and down his immense pole.

It seemed like only yesterday to Alan when he tutored Cassie for her History exam where every answer she got right, he ate her pussy until she came and after she had passed her exam, she rewarded him with a blowjob and tit-fuck. She didn’t want to go any further that night with the fear of his huge cock hurting but she seemed more prepared and eager to fuck as kartal escort she rapidly bobbed her head up and down his throbbing tool. She moved her mouth down to his giant balls, thoroughly licking them before sucking on each plump smooth testicle in turns.

“After that night, all I could think about was getting this big hard delicious dick inside,” Cassie moaned, spitting out one fat testicle then sucking the other in her mouth. She sucked on his plump heavy balls for a couple more minutes then returned her wonderful smackers to his throbbing man meat. She swirled her tongue around the thick knob of his cock, then lodged it deep in her mouth.

Alan ogled down at this pretty, 20 year old college woman who moments ago finished making sandwiches at her job, moaning upon his oversized dick stuffed in her mouth and multiple strands of saliva coming out as she sucked. His toes curled in his socks multiple times from Cassie attempting to deep-throat his mammoth prick.

“Oooooh fuck,” Alan grunted, putting both hands on the back of Cassie’s blonde head and lifted his ass off the minivan floor numerous times, face-fucking her, filling her mouth balls-deep with his dick. She coughed and gagged and threw up large quantities of saliva all over his cock and flopping balls.

After face-fucking Cassie a few more of minutes, Alan released her head and she surrendered his sloppy hard cock from her mouth. Her chest, the tops of her plump breasts and in between were glistening with saliva.

“Hmmmmm, your cock is sooooo good. It feels and taste just as delicious as I remembered. I want to feel your hardness inside me. I wasn’t ready then but I’m ready now,” a heavy panting Cassie admitted. She sat back and removed her damp panties, exposing her perfectly waxed womanhood with a v-shape strip of dark hair above. “The last time you saw this pussy, it was covered in hair. I decided to change it up a bit.” She straddled over Alan’s enormous wet phallus and seized it in hand.

“This big dick was always a two hander,” she teasingly commented, rubbing the thick swollen head of his penis against her moist cunt lips and slowly eased herself down upon his pulsing meat. “Holy fuck your cock is so thick and long… But I can do this. I want to get fucked by his huge dick.”

Crouching on Alan’s giant dick with her bare feet firmly placed on either side of his legs, Cassie flinched in pain and began sliding her tight slick pussy up and down his organ. Her creamy juices immediately flowed down his hard dick on contact. She cried out as his throbbing member was impaled completely inside her each time she glided her velvet-like pussy down upon it. Cassie’s hands were firmly pressed down on Alan’s scrawny chest as she fucked him. Her huge tits bobbing heavy underneath her sports bra was pure heaven in Alan’s eyes. He so badly wanted to reach up and play with them but finally having her pussy sliding up and down his monster cock was a stupendous sensation.

It took Cassie a few minutes to adjust to having the largest cock she ever seen wedged and penetrated deep inside her. She sat down on his dick with her bare feet locked under his legs and started riding him with immense eagerness.

“OHHHH DAMN! Your cock is soooo deep inside me!” she wailed. “My pussy is stretching, Ooooooh GOD!”

“Hmmmm. And your pussy feels so good on my cock, Cass,” Alan moaned confidently, squeezing the meaty cheeks of her ass and watching her enormous melons bounce up and down.

Cassie blushed and smiled down at Alan. She grabbed the hem of her large sports bra and lifted it up and over her wildly flopping melon-sized hooters. Alan deeply groaned with his eyes glued on her insanely engorged breasts and how much larger they’ve grown since their last encounter. Her huge pink areolas and large thick nipples stayed the same and looked divined on her bouncing boobs. Her heavy melons lurched forward in such an exotic lewd manner as she rode his big dick.

Alan reached up and dug his fingers in the soft doughy flesh of her massive tits. He pawed and groped her mammoth melons and tried his best to control their untamed bouncing as Cassie fucked him like a raging manic. He pinched and twisted her enlarge rock-hard nipples and the stimulation drove Cassie insane.

“Oooohhh FUCK! OH! OH! OH! FUCK! Ooooohhhh fuck! Oooohhh,” Cassie cried out in pain and agony with his giant dick completely wedged inside her tight cunt that felt like runny creamy of wheat around his hardness. Alan still held and fondled her huge bouncing breasts with his clammy palms and sat up and started working his lips and teeth on her large areolas and fat glass-cutting hard nipples. Cassie wrapped her arms around his head, smothering him in her pendulous flesh bags and cried out.

” Ooooohhhh I’m CUMMMING! Ooohhhhh Alan, I’m cumming, Ohhhhhh!”

Alan freed himself for some air and lied back down. He kept his eyes on her big lively titties as he firmly held onto her thin waist and started lifting her up and down his throbbing cock. Cassie was still deep in her orgasm and cum rapidly gushed from her pussy and bathed his cock. Her body felt like a helpless quivering ragdoll under his fucking. Alan started pounding her really hard making his massive cock mimic a jackhammer.

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