Lucky Bastard

Story Info
Down on his luck, but his fortunes change...dramatically.
13.9k words
4.78
166.4k
172
20

Part 1 of the 2 part series

Updated 10/24/2022
Created 04/20/2012
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
creepyrj
creepyrj
504 Followers

SO one day I was bored and thought about things and said "Oh why the hell not?". I hope you kids enjoy this one because it could become a sequel, or two, or maybe even three. Need to thank freakynlovinit for tossing me a hand with this one. I also need to thank you the reader for taking time in reading this one. Read it, love it, vote on it, tell a guy how you feel even, and there could be more of it. Enjoy the show kids!

*

Before sleep overwhelmed Leo's eyes a thought resonated in his mind. It was a simple thought, but one that rang out many times.

"How could I be so lucky?" he mumbled into the night.

It was the barest of whispers as her didn't wish to disturb the two beauties that lay curled into his body. His bleary, very fulfilled eyes looked down into the content sleeping faces and he let out a relived sigh. How he came to this time in his life was something his mind was still wondering. Luck may have played a part in it, but something told him in his mind that fate was more likely the reason for his happiness.

It was only three years earlier that Leo had graduated from college and gotten a great job at a software company. For the first eighteen months of his time he was busier than he had ever been in his life. While he dated a bit, the women he dated were nothing major in his life. A few were nice, but lacked that it factor. The rest were simple one night stands that he had no intention of getting back with.

Leo was a simple man with a lot of ambition. At five ten and a hundred seventy five pounds he was an average looking man. His green eyes and brown hair didn't really make him stand in with the crowd. The only thing that really set him apart from the pack was he took care of himself and ran daily. His diet was a harsh one of tough exercise and simple foods. He was raised poor and had to fight for every thing he had in his household of three brothers and sisters. At the middle of them he was lucky for what he got and was grateful for a while. As he grew older he wanted to get out and go higher than his family could.

In college he pushed himself hard and stayed focused in class. He worked a side job to make ends meet and scrimped and saved to get to the top of his class and get a good job offer as soon as he took off his graduation clothes. From the back end of the Bronx to the highlights of Manhattan, Leo took his place in the big world and made his mark fast. He got a good loft apartment on Nassau St and his life took quick strides into the fast lane.

His second eighteen months since graduating had really beaten him up. He met a girl that nearly killed him. She was hot and fun loving, but a complete slut. Leo really had a feeling for her after a few months dating, but in the end she ripped his heart out by dumping him for a supposed 'friend' of his named Daryl.

Daryl's lame excuse was they were drunk and one thing led to another. It was an excuse that stood for about ten hours, then Leo got a clearer focus when he found her cell phone under his bed. He found a video on the phone that abruptly changed his mind as it was them fucking on it. Neither of them were as drunk as they claimed and that was all he needed to confront his "friend". A brief exchange of words and a sucker punch from Daryl unleashed the lion that Leo was named after.

Leo kept his job even though he was almost arrested for the fight. Daryl's jaw was broken and he tried to sue, unsuccessfully. Leo, again, dated and this time he nearly lost all faith in women. The newest girlfriend was what every man claimed to want.

Tall, blond, and beautiful Penny was a welcome relief for about three months. Things were fine and then Penny's switch flipped. She went from nice to very clingy and possessive. Leo would say hi to a girl at work and Penny would freak out on him for looking at other women. The arguments of Penny's insecurities went wildly out of control and Leo finally had enough. He snapped on her one day after she harangued him for helping an employee of his out with a loan. It was so the girl could keep her heat on and she promptly paid him back the next payday.

Penny would hear none of his reasoning and railed against Leo for helping his friend. Things were so heated between the two of them to the point that she slapped him and called him all manner of vile things. Leo took the slap without a word and walked to the bedroom. Penny was shocked when he suddenly emerged with three suitcases filled with her clothes. She shouted at him to put them down, but he opened the trash chute and dropped them down it. Penny's eyes bugged out and she began freaking out. Leo calmly took her arm and walked her to the door. Penny struggled and fought him the whole way, but Leo got her out the door and locked it. He sat against the wall next to the door and listened as she carried on for over half an hour before the police came to talk her down.

Again Leo failed with the society standards of beautiful women. He had all but given up on them after Penny and for good reason. He swore that never again would he date a psychopath, but he laughed aloud when he thought of the varying degrees of psychosis in the world. It took him three weeks to be done with Penny for good, but he was free and clear. For that time and the months after Leo buried himself in work. It was on one of those fateful days he met probably the coolest dude he could have imagined. He met his friend Alan.

Alan was not the typical guy that Leo would normally had hung out with, far from it. He was a tall man whose Caribbean heritage showed in his skin and his hair. Alan wore his fashionable dreads long. They were long enough that they touched the middle of his back. More than once Leo had seen him without and the size of his Afro was one thing that made him laugh. Alan never let it out for long and kept his hair braided for sanity's sake. The two unlikely friends found each other when Alan was trying to hide from a disgruntled ex and it was only by Leo pointing the wrong directions to her at a bar that saved Alan a hard ear chewing. The whole misunderstanding was a slight one, but to the ex it was huge.

Leo and Alan's friendship grew quickly when they found out they were the same age. At twenty five they both had a love for music of most types. They played football in their spare time and both hit the gym regularly. It was after two months of hanging out that Alan began to see Leo's reservations to dating. While Alan was a ladies man of no small skill, he saw that Leo was quiet and reserved the whole time they would go out. Seeing his friend in a rut Alan began to devise a plan of action.

It was a month after they had last gone to a club that Alan decided to help his buddy out. Alan worked as a promoter in his spare time for various up and coming acts. Mainly of the rap and hip hop crowd he made a good living hosting events and parties for the rappers on the rise. Alan had a new act that was starting to blow up and decided to get his buddy to the scene. He got a good gig at a really down club that catered to an under twenty one crowd. He made sure the stock was packed and after he was sure he could do no more he called up his friend.

Leo was just on his lunch when his phone rang. He looked at the ID and saw it was Alan. Leo shook his head and answered the phone and was shocked at what he heard.

"Yo yo yo! OK Leo, I'm tired of you being boring! Your comin' out with me mon," Alan said and his Jamaican accent popped through.

"Oh yeah? Why's that?" Leo asked chuckling.

"Cuz you need to get out and see some life me brudda," Alan said laughing and his normally thin accent was gone replaced with his mother's pure tone.

"Uh huh....and when is it that you started using your Mom's accent to talk to people?" Leo asked chuckling.

"Well there's this girl I was trying to get with you see," Alan said suddenly in his normal voice.

Leo shook his head and laughed a bit as his friend explained his recent failure to pick up a girl from a Starbucks using his island charms. Leo was face down on the table when Alan explained how she 'politely' rebuffed his advances. "Politely" was a code word for she shot him down flat.

"But seriously man, I got a really big after party for a new crew that's goin' somewhere. Wanna come? I promise you'll have a good time," Alan offered.

"I got the McClellan account I gotta finish by this weekend Alan. Maybe if I can get it done I will," Leo replied.

"That's a bummer dude. Well get that shit done or I'm comin' to yours and draggin' you out!" Alan emphatically replied into the phone.

Leo chuckled at the threat and nodded his head, "Alright man. Then hang up and let me get back to work."

"Peace out my brother from another mother," Alan said in an overly upbeat tone.

"Later dude," Leo said and hung up.

Leo finished his small lunch and went back to work. What he didn't tell Alan was he was nearly done with the project, he just wasn't up to going out this weekend. Visions of lounging on his couch watching the Thunder game was a good idea to him. A few beers, maybe a pizza, and he was set for the weekend. Leo went back to his desk and began the process.

Alan heard the tone that Leo had and shook his head, he was lying. Leo was a horrible liar and that was part of the reason Alan dug him so much. No matter what at least he knew where he stood with him. As Alan pondered the future profits the party would net him he pondered Leo's fate. He knew full well the shitty relationships he had been forced to endure and wondered if anything would snap his friend out of it. Alan suddenly had an epiphany, he would drag Leo out anyways. The fun he was passing up was something Alan, as a true friend, couldn't let Leo miss out on.

Alan's devious mind began to spin thoughts and hatch plans as he pondered the fate of his friends new weekend plans. As he pondered them he happened to look up and saw a very fine specimen of woman walk by. He forgot about his friend for a brief moment as he ventured forth for the conquest.

The three days till the weekend took longer than either friend imagined, but it finally arrived. Leo scored a big commission on the project as it was a big hit. His skills at graphic designs weren't wasted as he made a beautiful layout and spreed sheet. The numbers danced across the displays and as the executives watched the show Leo had also tossed in music to make the presentation that much more interesting. After all was said and done all the people in the room were applauding his work and his own boss was euphoric at the new found fortune that rolled in.

Leo sat in his desk and looked out over the city as it started to get dark. He loved the sunsets and watching them from his thirty fourth floor was always pleasant. He looked up from his reverie after a few minutes and saw it was closing time. He turned off his computer and got his coat and briefcase. He signed out his pass codes to the computer and left the office. The elevator was crammed full of people from the building and none of them even paid him a mind as they went down. Leo inhaled a short breath to keep the cheap cologne and stale perfume from infesting his lungs. The long descent came to a close and the door dinged the bottom floor. Leo wisely waited at the back of the elevator for the mob to sprawl out and leave before he exited.

A slow walk from the elevator to the security desk saw the long day come to an end. Leo pulled out his phone to ponder his order for the night when a hand grabbed his shoulder and stopped him cold.

"Stick em up!" Alan said trying to sound hard.

Leo rolled his eyes and sent his briefcase behind him and it caught Alan in the crotch. Alan grunted sharply as the edge of the case caught him square on in the jewels making him rethink his idea of trying to scare Leo.

"Give up?" Leo said in a superior tone.

"Ow," was all Alan replied as he chuckled at the reversal of fortune.

"What are you doing here Alan?" Leo asked confused to see his friend at his office building.

"Well my gig fell out at the last minute and now I'm bored. Looks like I'm infesting your place this weekend!" Alan said coolly.

"That sucks, for both of us," Leo said back jokingly.

"Now that just hurts man," Alan replied grabbing his chest theatrically.

Leo rolled his eyes and began to walk to the escalator to the lower level. Alan stopped being over dramatic and walked after. It was a short jog to catch up to his friend and they went down the escalator.

"Well if I'm not welcome to your place at least give me a lift so I can go somewhere fun," Alan begged.

"I can do that," Leo replied.

It was a while before the game anyways so he figured he could dump Alan off at his favorite club and have at least a night to himself. They walked the length of the garage to his car and got in. Leo's Nisan Ultima was a simple car, but a nice one that did everything Leo needed it to do. They drove out of the garage and out into the nightmare of Manhattan traffic. Leo had a policy of music in his car, if he drove it was his, if he wasn't then whomever drove was in charge. He put in a mix CD and the first song that played was a mournful song from Sevendust called "Angel's Son". Alan could get down to any music and sat back as the acoustic melody played.

"So where we going tonight? 40/40 or Groove?" Leo asked knowing his friends favorite haunts.

"Neither, I got a new club I'm gonna scope out bro. It's on 23rd," Alan said.

"OK," Leo said and turned out of the nightmare and onto better streets. They drove the distance to the club and Alan smiled a bit.

The area they were forced to park in was not too far from the club and Alan looked at Leo and smiled darkly. The music playing was one of Alan's favorite rock songs called "4 Walls" by Black Light Burns. Seeing they were parked Alan shot his hand across and killed the engine. With a deft twist he turned the keys and pulled them from the ignition. Leo was wide eyed as his head went from back to front and then he was alone as Alan bolted from the car.

"What the fuck?" Leo asked in pure confusion.

Alan was already out and across the street leaving Leo alone in the car. Leo let out a bemused chuckle and got out of the car. As he did Alan hit the key lock locking the door and setting the alarm. There was no way Leo was missing out on this and that was final. Leo sighed as he trudged across the street in a determined walk to his friend. A plan of strangling him with his braids came to mind, but Leo knew that good friends were in very short supply in his life. He put his hands behind his back and stepped towards Alan's smirking face.

"This is for your own good Leo, now here you go," Alan said as he handed Leo a lanyard with a pass.

"Fine, I had a feeling you were pulling my leg when you gave me that over dramatic message on Wednesday," Leo said chuckling.

Alan nodded his head and led Leo to the front door. They were greeted at the door by the biggest Samoan man Leo had ever seen. He was easily over six four and had to be about three hundred pounds. The man looked at their lanyards and nodded his head to the moans of the people in line. When they entered the club the hard bass lines of the new groups song was blaring. Leo had to admit it was catchy, but he wasn't a big fan of how over played it sounded.

"These guys are gonna hit it huge!" Alan yelled to Leo.

"They sound like JayZ and Naz mixed," Leo said back.

"No!" Alan said back semi defensively.

"Yeah, listen to that hit, then the cross, the hit sounds like Jay and the cross like Naz," Leo laughed back.

Alan took a second to listen to the sound he was referring to and suddenly he was floored, they sounded exactly like them! Alan started to laugh aloud and shake his head. Alan was a realist however, they sold the clubs tickets out and he was a producer. So as long as it made him money they could sound like Mariah Carey and he wouldn't care. As he listened he saw the variety in the club and his eyes vectored in on a tall, leggy blond that was showing off all that was needed to get his attention.

"If you'll excuse me my brother. Your boy has some play to get," Alan said shaking his head to loosen the braids.

Leo saw his target and shook his head as he rolled his eyes. She looked almost exactly like Penny and that was a killer to him. Leo realized that Alan wasn't looking and snatched his keys from the pocket as Alan walked to the woman. Putting his keys back in his pocket Leo decided to try and enjoy himself. He walked to the bar and as he got there a sight that nearly made his eyes bulge was greeting him. Leaning against the bar was a very sexy woman.

Her black hair was wild and curly as it came from her head to her shoulders like a savage mane. Her dark cocoa skin was nearly glowing in the low lights and her full legs were prominently displayed. Her outfit was what one could call cute/sexy all at once. It was a midriff shirt that showed off a taught belly. A very short pleat skirt graced her hips and when his eyes caught sight of her legs he almost fell over. She was wearing thigh high socks with red and blue athletic stripes on the tops. Her lips were painted a wild blue and she looked like a cheerleader gone wild. Her left arm had a wild sunburst design on it and her right a long stemmed rose that was dripping blood. Leo sighed as he walked to the bar and tried not to look at her.

The woman noticed Leo trying not to stare and she got a wild grin on her face. She sauntered right up to Leo and in a very naughty school girl voice asked.

"So what do you think of my outfit?" she teased.

"It's ummm...wow," Leo said back taking in the full sight of her.

"Wow?" she asked back almost hurt.

"Great!" Leo blurted trying to pacify her.

"Only great? Then I guess I better go," She pouted and turned away.

"No! No...it's...umm...really hot," Leo tried for the last time.

"Third times a charm," the woman said back smiling.

"Lucky me," Leo said smiling nervously.

"Indeed, lucky you," the woman purred as she took the seat next to him. "Drink?" she asked.

"Yes, beer and a...?" he asked looking at her.

"Midori sour," she replied.

The bartender nodded his head and got him a beer and made her drink. He handed them their drinks and Leo paid for them. Leo took his beer and the woman her drink and she surprised him by clinking her drink on his.

"To an overdone act," she toasted.

"To the uninspired," Leo joked back.

The woman giggled as she sipped her drink. Leo tipped back his drink a bit and got a good swallow. He sighed as he set it down.

"And you're here why?" she asked.

"My friend drug me out here. He is producing this mess," he replied.

"Oh you know Alan?" she asked.

"Yes. Why?" Leo asked suddenly confused.

"Cause he keeps trying to hit on me and my friend. Can you tell him a message for us?" she asked politely.

"Sure. What do you need?" he responded politely.

"Tell him Myra and Tamika said to to go eat a dick and leave us the fuck alone," the woman said emphatically.

Leo almost choked on his next sip of his beer. He coughed up some foam from the laugh that erupted from his belly. The woman patted his back trying to keep him from choking to death on it and suddenly felt bad.

"Oh god! Are you OK?" she asked with genuine concern.

"Fine," Leo got out in a high pitched gasp that was punctuated by another cough.

The woman gave him a concerned look as he looked at her and wiped the tears away. She laughed sheepishly as she hadn't seen him drinking while she said that. Leo shook his head and cleared his throat.

"Well I suppose that is payback for not telling you how good you look the first time," he said jokingly.

The woman giggled sweetly and patted his cheek.

"See now your making me feel bad," she said back smiling cutely.

creepyrj
creepyrj
504 Followers