tagFirst TimeLucky Alan

Lucky Alan


"Aw, c'mon man, fuck that! I shot him point blank right in the freaking head and somehow he still knifed me in the gut. Fucking hackers man. Fucking ten-year-old hackers!"

Alan Rogan was glued to his TV, screaming through a fierce game of Call of Duty when he heard his family's doorbell ring. As always, he ignored it and hoped his mom would take care of it.

"Alan!" shouted his mom from upstairs in the kitchen. "Alan, sweetie! Get the door, please."

(Jesus Christ, leave me the fuck alone!) thought Alan. "Hold on a minute, mom! You know I can't just pause the game!" he yelled back upstairs. "I'm going to kill these little pricks even if it kills me," he muttered to himself. Instantly after saying that, an enemy soldier darted into the screen and knifed Alan's character in the gut, ending the game. "God fucking dammit! Those little motherfucking shits!" screamed Alan as he hurled his controller across the room.

"Alan, dear! You have some company," shouted his mom, as she walked down the stairs and leaned around the basement door to inform him. "And she's female and quite pretty."

"Mom, what did I say about coming down here, I...Holy shit! A girl!" Alan snapped at his mom, as suddenly he panicked.

Never once in all his 18 years of being on Earth had a girl who wasn't related to Alan or a friend of the family stopped by just to see him... for that matter, no one had. Most, if not all of his friends lived in other cities, states, and countries, and the only way he ever communicated with them was through playing online on his PlayStation 4. Suffice to say, Alan wasn't very popular amongst his high school senior peers. He had always been on the outside looking in and as such kept to himself. Short, scrawny, and socially awkward, Alan was the stereotypical nerd who spent all of his time playing video games, collecting rare minerals, and reading comic books. Yet, he still was a very bright and remarkable young man, as he had made the honor roll in every grade level.

"Alan, honey?! Are you coming upstairs to see your pretty friend, or should I send her downstairs to see you?" asked his mother.

Alan cleared his throat and dried his clammy hands off with a towel. He put his left hand up to his mouth to smell his breath, which smelled like the M&M's he was snacking on while playing his PlayStation. He worryingly looked down at his rather dorky wardrobe: a red- and green- striped shirt that gave off a Christmas vibe, denim overalls that stopped mid-thigh, tube socks that came up just below his boney knees, and a pair of black-and-white high-top Converses.

"What a way to impress a girl," Alan snarled sarcastically. He headed up the stairs from his basement bedroom and into the living room, joining his mom and the pretty young girl whom he instantly recognized.

"Cassie?!" Alan exclaimed, shocked.

"Hey Alan. Did you forget our tutoring session?" she asked.

"We had a session today??" he asked, confused.

"Well, today is Thursday," she replied.

Alan had had such a rough day at school earlier that killing players online in Call of Duty was a great way to release his stress and some tension. Unfortunately, he didn't play such a good game.

"Alan, I'm meeting up with the women of my book club, so I won't be back for a couple of hours," his mother informed him. She winked at him, catching Alan off-guard. "It was a pleasure meeting you, Cassie," she continued, turning to the guest. "Hope to see you come around here more often. Alan doesn't get many visitors, especially of the pretty female variety." Alan's mother winked at him again and headed out the door, grinning from ear to ear.

Alan felt totally embarrassed and rattled by his mother's behavior. He looked over at Cassie, who, as she too felt a bit awkward, let out a slight giggle under her breath.

"You have a very loving mother..." Cassie stated.

"Yeah, um, thanks..." Alan shyly replied.

Finally getting over the embarrassment, he couldn't believe that Cassie Banks was standing in his living room. She was a walking wet dream of his. He had jerked off like a mad man after their first meeting and hadn't stopped masturbating to her lovely image since, causing quite a mess in his bed two to three times a day. Just the thought of her made him constantly horny.

At 5'6, twenty years old, and a sophomore in college, Cassie Banks was beautiful, with long blond locks and crystal-clear blue eyes. Many had said she could pass as movie actress Jennifer Lawrence's twin sister. The only difference would be their bodies. Cassie was much fuller in all the right places, particularly her chest. Alan had always found it hard to maintain eye contact with Cassie when she wore tight shirts that outlined her huge, round tits, and her big nipples seemed to be permanently stiff.

"When you didn't show up at the Help Center for our usual session, I got a bit worried and asked around where you lived. I had to ask a lot of people until a friend of your mother's gave me your address. You are one hard guy to track down, Alan," Cassie commented, chuckling.

"Oh... Sorry. I got a bit sidetracked," he explained. "I do apologize."

Several weeks ago, Alan's mom pulled some strings through a friend to get Alan a tutoring job at the Help Center, which required his services only on Monday, Wednesday, and Thursday. She figured it would be a nice way for him to meet people and make actual friends. On his first day, Cassie approached him and asked for help with her history. To his credit (and incredible fortune, as he thought later), Alan loved history and, being caught up with lust, he agreed to tutor Cassie until she passed her upcoming history exam.

"We can still have our session, if you'd like?" Alan asked. As always, his dark brown eyes drifted back and forth between her eyes and her melon-sized tits as they bulged beneath her thin button-up shirt.

"Well, I did go through a bit of trouble tracking you down, and since I'm already here, there's no point in wasting the trip, so...sure," Cassie agreed. "Plus, my history exam is on Monday, and after two weeks of studying, I still don't seem to have this stuff down. It's just hard for me to remember anything that I've read."

Suddenly, an idea popped into Alan's head. He knew the idea might be a long shot in hell, but he figured he had nothing to lose.

"Before we get started, I have to ask you an important question, and you have to trust me, okay?" he asked calmly.

"Oh-okay," Cassie replied, a little uneasy.

"Cassie, has a man ever gone down on you?" Alan asked bluntly.

Cassie was overwhelmed with shock hearing this shy, short nerd ask her such a personal question.

"WHAT!?" she finally responded. "What the hell kind of question is that?"

"Listen. Just trust me on this, okay? It's a little experiment. Now, just answer the question please."

Still in a bit of shock and confusion, Cassie hesitantly answered.


Alan was quite surprised, given how hot Cassie was and her popular reputation in college, at this response.

Cassie continued, "Alan... What does that have to do with studying? And what kind of experiment involves you asking me that?"

"It's quite simple. The reason why you don't remember any of this stuff is because you don't care about the information. It serves no value to you, so your brain doesn't see any reason to hang on to it," he replied in a smartly manner.

"I still don't get what that has to do with you asking me such a personal question," Cassie asked, still a bit confused, as her pale cheeks turned rosy red.

"We need to give you a reason to remember. Something that will make you care about this history stuff, and some good stimulation should do the trick," said Alan.

"So does that mean you want to..."

"Yes, so you have to trust me on this," Alan pleaded.

Cassie paused for a moment, but didn't see any other option. She really needed to pass her history exam. She had tried everything, and knowing how smart Alan was, she was going to give him the benefit of the doubt. Cassie softly nodded to him, and then slipped off her shoes and slowly unsnapped her jeans.

The sound of her zipper going down caused Alan's heart to beat rapidly. He couldn't believe Cassie Banks was really going to let him go down on her.

Cassie felt the butterflies in her stomach from the anticipation as she slid her jeans down her long, ivory legs and dropped them on top of her shoes. She stood in front of Alan in her too-tight shirt, cotton panties, and cute little black ankle socks.

"Panties too," he notified her. With that, Cassie took a deep breath and slipped off her cotton panties, revealing her dark brown pubic mound before Alan's bulging eyes. This was the first pussy Alan had ever seen in real life, and it was incredibly beautiful.

"Consider yourself lucky. The only other man who's seen my vagina is my ex-boyfriend."

Alan took in the sight of Cassie's hot cunt as if he had found the Holy Grail, and he began to drool.

"Are you going to stare at my vagina all day, or are we going to get on with this lesson...?" Cassie asked, right before she spied Alan's enormous hard-on bulging from beneath his overalls. "My god, he's huge!" she whispered under her breath.

"Oh, right. Please, have a seat on the couch," Alan said, finally snapping out of his lustful trance. Cassie sat down on a nearby couch but kept her eyes on his massive boner. Alan boldly moved down in front of Cassie's closed legs, swallowed deeply, and nervously placed his warm, clammy hands on her thick, creamy thighs.

"I take it you've never done this before?" she asked.

"This will be the first for the both of us," he said. "But trust me, it'll work. Just sit back and relax. I just want to give you a warm-up before we actually begin."

Cassie leaned back and opened her legs. She couldn't see over her huge jutting jugs to her pussy but knew it was becoming extremely moist from the idea of someone eating her out. Alan's heart raced, as he positioned his head right between her beefy thighs and came face to face with her very wet, very hot snatch. He had never gotten this close to a pussy before but started to remember the way professional porn studs eat out their counterparts. He closed his eyes and allowed his tongue to begin giving Cassie's cunt an oral treatment it rightfully craved.

Alan heard Cassie beginning to moan substantially at his tongue work. He moved his tongue steadily up and down against the outside folds of her bushy mound. He darted his tongue between her pussy lips and teased her hole. Cassie had never felt such a peculiar yet incredible sensation before, having her hot pussy licked. Her toes curled in her socks as Alan quickened his pace. Alan latched onto her swollen clitoris and attacked it mercilessly. His tongue flicked the clitoris while he sucked on it, causing Cassie to squirm on the couch and intensify her moans.

"Oh my god, Alan!" she panted. "Whatever it is you're doing, please, don't stop! I'm so close, Alan! I'm so close!" But before Cassie could reach her absolute climax, Alan pulled away.

"Hey pipsqueak, why did you stop?" Cassie gasped. "I told you not to!"

"Well if you want me to continue, it's going to cost you some answers," he replied while looking over her enormous chest and elongated nipples, as it heaved up and down with her heavy breathing.

"All right, all right! Ask me a stupid question so I can cum soon."

Alan was quite pleased with himself that his experiment was working. He was just as eager to return to eating Cassie's wet pussy and sucking down her sweet juices as she was wanting to cum. He picked up her history book and chose a random question.

"When the US Constitution was written and signed by the delegates to the Constitutional Convention on September 17, 1787, in which order did the delegates sign it?"

Despite the burning rage between her legs, Cassie inhaled before answering.

"North to South."

"That's right," Alan said. He sat the book down on the coffee table and buried his face back into Cassie's pussy, where he immediately continued his merciless assault on her clitoris. She moaned loudly as the inexperienced nerd tried his best to suck down all the juices that leaked from her cunt as he licked within its depths. She raised her feet up and placed them on the coffee table. She involuntarily squeezed her meaty thighs around Alan's head and he immediately wrapped his skinny arms under and around them.

"OHHHHH FUCK! OHHH YEAH! Eat me, Alan! Lick my hot pussy!" Cassie cried out.

Everything she mouthed off was sweet music to Alan's ears, as he increased the intensity of sucking on her fat clitoris. Cassie's moans continued to get louder and louder until...

*Ding!* went a timer suddenly, and to Cassie's dismay, Alan lifted his head up from between her legs and grabbed the history book.

"A timer? Really?" she asked, trying to catch her breath.

"It's to keep track of how long I stay down on you. It's automatically set for thirty seconds, but for every question you get right, I move it back by ten seconds. For every one you get wrong, I won't go down. That's how this game works," he explained. "Shall we continue?"

Cassie nodded her head enthusiastically to hurry up with the question so she could get Alan's tongue back into her drenched vagina.

"Egyptian pharaohs claim to be descended from the Egyptian god of the sun, whose name is...?"

"RA?" she guessed.

"You're on quite a roll," Alan praised, as he moved the time back by ten seconds on the timer.

"Hey Alan, I hope you don't mind me taking off my shirt. It's getting quite hot in here," Cassie alluded. Alan made no qualm about that, as he had been wanting to get a look at her huge double-D cup tits ever since he'd first laid eyes on them. The mere mention of Cassie wanting to take off her shirt further hardened his cock. He dove his tongue back into her slick cunt as she unbuttoned her shirt and tossed it beside her on the couch. Alan peeked up to her huge, soft breasts jutting up and jiggling beneath a black, loosely-fitted tank top that failed spectacularly at staying on her upper torso. She lifted the black tank top up to reveal her peach-colored bra-encased jugs, topped off with a generous amount of flesh pouring from over the top of the cups. Her big nipples fiercely erected and poked brazenly through her sturdy brassiere as Alan hungrily devoured her hot cunt.

Alan's bulging eyes sunk in the deliciousness of her huge wobbly chest as he kept his tongue buried deep inside her pussy. Just as the writhing and moaning Cassie was about to unfasten her bra...


Alan started to regret the whole timer idea and groaned with frustration. His mouth watered as he imagined sucking on her bullet nipples and burying his face and whole head in her soft tit flesh. Cassie was also disappointed, nearly reaching her climax yet again, only to be stopped once more.

"On June 15, 1215, King John of England did what and where?" asked Alan.

"Is that a trick question? He could have been doing a million things like eating his wife's cunt to an orgasm, something I am longing to do," she answered.

Alan continued on. "He signed the Magna Carta at Runnymede."

Cassie went on to miss the next four questions, which didn't sit well with Alan. He felt his huge cock ready to explode at the vision of a beautiful, top-heavy girl sitting on his couch with her pussy dripping wet. He was praying for her to answer correctly so that he could finally get his hands on her tits and his mouth back on her hairy mound.

"In 1774, Rhode Island was the first U.S. state to ban something which is now illegal in all states. What was it?"

Cassie began answering almost before Alan finished the question. "Oh my god, I know this one... Slavery." Joy overcame Alan, as he watched Cassie reach up and unclasp her brassiere. He watched her hugely swollen round breasts fall from their respective cups into freedom; his first look at a pair of big tits up close. Cassie's pink, bologna-sized areolas blushed while her thick, fat nipples stretched forward like bullets and begged to be sucked. After their spectacular release, Cassie thrust up her hips forward and offered her drenched snatch to Alan's waiting mouth. He engulfed her hot, engorged clitoris as soon as his mouth made contact with her pussy. With the joy of finally seeing her perfect tits and knowing that they were hanging beautifully above him, Alan feasted on her pussy vigorously.

"OHHHH BABY! OHHHHHH FUCK! Right there! OHHHH YEEEAAAH! Mmmmm!" Cassie cried out. She reached down with both hands and held Alan's head at her cunt. Her large tit-melons bulged obscenely, trapped between her arms, and it was a sight Alan couldn't pry his eyes off of. He slowly slid his warm hands up along her flat stomach towards the plump bottoms of her dangling tits.


Ignoring the timer, Alan, filled with lust and hornier than he had ever been, filled his hands for the first time with a pair of luscious, heavy breasts. They were quite more than a handful, but Alan palmed every inch of her soft, doughy globes. Cassie gasped as Alan kneaded her huge tits and flicked each big, hard nipple with his fingers as his tongue was doing the same to her juicy clitoris. The intense stimulation Cassie was retrieving from her nipples and pussy was immensely overwhelming and brought her closer and closer to her orgasm.

"OHHHH ALAN! I'm going to cum! OHHHH god, yessss!" Cassie moaned, feeling a monstrous orgasm beginning to sweep through her writhing body.

*Ding, ding, ding!*

The timer was continuously ringing and Alan finally realized it, but instead of pulling away from Cassie's sweet, hot pussy, he reached back turning the timer off. He continued his feverish oral assault on her pussy, amplifying it to unbearable heights. Cassie moaned loud, long, and deep as she covered Alan's face with her abundant fountain of cum, her entire body quivering upon release. Alan relished in her sweet cum, loving the taste of a woman's orgasm as he did his best to suck down all her womanly fluid. His happy hands stayed busy, pawing her pendulously bouncing breasts and taut nipples, as her mighty orgasm slowly began to subside.

After a few minutes Cassie was able to regain her composure. It was getting rather late, and she had to be home in time to fix supper for her little siblings. She cleaned off, got dressed, thanked Alan, and said her goodbyes with a long hug and peck on the cheek. She was very aware of his massive cock pressed up against her crotch during the hug. Her leaving obviously left Alan very disappointed and extremely horny, but at least now he had plenty of masturbation material from his first experience with the opposite sex.

The next Monday, Alan was just about to start up his nightly Call of Duty session when Cassie made an unexpected house call.

"I got an A-!!" she yelled with glee when Alan answered the door, bouncing her way up and down into the living room and causing a major shake inside her skin-tight t-shirt.

"Congratulations! I knew the little experiment would do the trick and give you a reason to care," Alan said. In actuality, he was in utter shock that it had worked.

"And, because your atypical yet pleasant technique helped me pass my history exam, I'm going to return the favor," announced Cassie. She then turned and gave Alan a very seductive look. "So drop those pants and let's see that big dick of yours."

Alan instantly hardened, in more ways than one. His random plan was leading to a reward that was just beginning...


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