$500 Tip

Author's Note: This story has been posted to Literotica. Com with the full knowledge of the original author, JimBob44. No part or whole of this story may be reprinted in any other format or on any other web site without the express written consent of the original author.

Any and all persons engaging in any sexual activity are at least eighteen years of age.

This story has been edited by myself, utilizing Microsoft Spell-Check. You have been forewarned; expect to find mistakes.

**..**

Lloyd Stitt shivered with pleasure as he completed his preparation for the evening's meeting. Before leaving the still quite steamy bathroom, he paused to look in the long mirror that hung over his vanity.

"That anti-fogging spray really does work," Lloyd mused, admiring his hairless body in the reflection.

Standing at five feet four inches and weighing one hundred and thirty pounds, he was a slight figure. His arms were sleek, his abdomen slightly concave. Staring at his hairless crotch, limp cock and heavy balls caused his flaccid cock to swell so Lloyd smiled but averted his eyes to his thick brown hair, meticulously shaped eyebrows, deep brown eyes, small nose and plump, pouting lips.

Entering his bedroom, Lloyd admired his cast iron bed. Finding the matching cast iron lamps with Tiffany style shades had been a stroke of good fortune. The antique white bedside tables perfectly matched the armoire, low dresser and tall dresser.

Lloyd's Their Private Saddle unicorn stood in the corner, just waiting to be 'saddled up' and taken for a ride. The black patent leather saddle looked perfect with the animal's antique white coloring.

From the low dresser, Lloyd pulled out a pair of white silk micro-briefs. He shivered happily as the silk travelled up his hairless legs. The laser hair removal had been a tad pricey but to Lloyd's thinking, had been oh so worth it. He then pulled a set of silk pajamas from another drawer. Again, the silk material caused shivers as he dressed in the long sleeved pajamas. Finding his pink bunny slippers, he put them on his feet, then hopped from his bedroom to the living room.

The grandfather clock told him it was only six forty three; he had seventeen minutes before his guest was due to arrive. Sweeping his glance around the living room, Lloyd smiled and raised an imaginary glass of champagne to toast his deceased father.

"Yes, Louis, I am sure the thought of leaving your money to your filthy disgusting degenerate son is causing you just that much more torment in Hell, isn't it?" Lloyd said, giggling.

Lloyd decided to pour himself some St. Elizabeth's Superior Whiskey. Even though he was twenty three, the sole package store in Swift Falls, Tennessee refused to sell him any liquor; they did not believe he was twenty three years of age. So, Lloyd ordered his spirits from the Internet. His storage unit in the basement of the high rise multi-use complex had a case of St. Elizabeth Superior Whiskey, a case of St. Elizabeth Superior Rum, a case of Guaddalupe Victoria Tequila, and a case of St. Elizabeth Superior Extra Dry Gin. That case, Lloyd was sure would still be there for decades to come. He'd taken one sip of the perfect martini made with the gin and had spat it out.

At eight minutes past seven, just when Lloyd was picking up his cell phone to make a call, the doorbell of his seventh floor condominium chimed, echoing throughout the spacious abode. Lloyd scurried to the door and peered through at the screen. He gasped; the Latino male was simply gorgeous even in grass stained football jersey.

"Yes?" Lloyd asked, pressing the touch screen intercom.

"Uh, Bitty Lopez," the football player said, voice somewhat high-pitched. "Uh, Lloyd uh, Lloyd Stitt?"

"Yes, yes, you're a tad late," Lloyd sniped, fumbling with the deadbolt and hasp locking mechanisms.

"Sorry; Coach wanted us run a couple more drills," Bitty said, standing in the lobby of the seventh floor. "Didn't even have time take a shower."

"Oh! Oh, so you, you're all sweaty?" Lloyd shivered, looking at the snug Norwill Cyclones jersey, the football pants and dirty cleats Bitty Lopez wore.

The jersey was in the school's new colors; the cap was a brand new NU Cyclones cap. The white cap had the navy blue NU on the left and right sides of the crown and the front of the cap sported the simple tornado in navy blue. The jersey was white with 'LOPEZ' and the numeral '1' in navy blue on the back. The grass stained white pants had navy blue stripes running up the outside of each leg.

Lloyd shivered again, seeing the large lump running down the inside of Bitty's left leg. Looking up again, Lloyd was struck by how beautiful Bitty Lopez was. The place kicker for the Norwill University football team had thick black hair, most of it hidden by a Cyclones baseball cap. Soulful chocolate brown eyes peered out from underneath two black eyebrows. Bitty's slim nose perched above pouting red lips and Bitty's chin sported some dirt, ostensibly from being tackled as Coach made them run scrimmages.

"Well, don't just stand there. Come on in; oh! But do take off those cleats. I don't need you tracking that dirt all through my home," Lloyd ordered.

Bitty came in, kicking the offending shoes into the corner next to the door. The small navy blue NU Cyclones duffel bag was dropped nest to the cleats. Bitty's thick athletic socks muffled the sounds of their footsteps as Bitty followed Lloyd into the spacious living room.

"I, I'm having a whiskey; care for a drink?" Lloyd asked, indicating his liquor cabinet.

"Oh! I uh. We're not supposed to..." Bitty said, looking through the glass door of the well-stocked cabinet. "Oh! Gin! Could, maybe a gin and tonic?"

"Oh, absolutely, absolutely," Lloyd agreed and quickly prepared the perfect gin and tonic for his guest.

"Mm! Oh, oh this, God, that is good gin," Bitty praised after taking a cautious sip.

"St. Elizabeth," Lloyd bragged. "They're a distillery out of DeGarde, Louisiana. My friend was a bit of a whiskey snob."

They settled on the plush couch, close but not touching. Lloyd talked about domestic and imported whiskeys while Bitty contributed nothing. After a few moments of his mindless prattling, Lloyd chanced touching Bitty's muscular thigh, fingertips very close to Bitty's thick cock.

"So, you, you're the kicker?" Lloyd asked, gently squeezing Bitty's thigh. "You, my father, my father always said Pete Gogolak completely ruined the game of football."

"Who?" Bitty asked, placing the empty cocktail glass onto a crystal coaster on the coffee table.

Pete Gogolak, Gogolak; soccer-style? He was the first soccer-style kicker in the NFL," Lloyd explained. "Care for another drink?"

"Oh," was Bitty's disinterested response. "Hmm, no, no I better not; Coach don't like us drinking you know."

"Can, can I suck your cock?" Lloyd asked, braving a squeeze to the thick member the the snug pants.

"Yeah, sure," Bitty shrugged. "Here, or your bedroom?"

"Here," Lloyd said, sliding to the floor between Bitty's legs.

Bitty watched, dark eyes unreadable as Lloyd worked the football pants open. Lifting up slightly, Bitty allowed Lloyd to pull the pants down, revealing a well-used jock strap. Bitty's cock popped out of the left side of the jock strap, down' Bitty's left leg.

"Mm," Lloyd moaned, softly stroking the length of Bitty's cock.

He brought his face close to the jock strap and gave a deep sniff. The smell of Bitty's sweat filled his nostrils as he smelled the football player's jock strap. His fingers continued to lightly stroke the length of the fact cock.

"Mm, uncircumcised," Lloyd moaned, skinning the thick foreskin back, revealing Bitty's plum shaped cockhead.

Bitty said nothing as Lloyd eased the wide waistband of the jock strap down, freeing the fat cock. Bitty watched, eyes flickering slightly as Lloyd brought his cherubic face down, pursing his lips to kiss the tip of Bitty's cock.

"Uuumm!" Lloyd moaned, wrapping his lips around the tip of Bitty's cock.

"Mm!" Bitty grunted when Lloyd swallowed the entire length of Bitty's cock in one long, fluid movement.

Bitty watched Lloyd bob his head up and down the length of the cock. Bitty even thrust a few times, driving the fat cock down Lloyd's throat.

"I, I've never been able to deep throat..." Bitty grunted as Lloyd allowed Bitty's cock to slide out of his stretched mouth.

"Wasn't sure I could do it," Lloyd admitted. "You, your cock is, damn, how big around is this thing?"

"You should know," Bitty taunted.

"You, you fuck me?" Lloyd begged.

Bitty stood, pulling Lloyd to his feet. Lloyd bent his head and kissed Bitty. For a few moments, Bitty and Lloyd kissed, tongues dueling while Lloyd continued to stroke Bitty's cock. Finally, Bitty forcefully shoved Lloyd away and wiggled out of the stained football pants.

"Bedroom," Bitty ordered, leaving the pants crumpled on the long pile cream colored carpet.

Lloyd led the way as Bitty followed down the hallway. Lloyd entered the bedroom, followed by Bitty. Standing in the large room, Bitty glanced about with some interest at the expensive, tasteful furniture. Bitty's eyes lingered for a long moment on the large wooden unicorn in the far corner.

"I'm going fuck you through your pajamas?" Bitty snidely asked, finally focusing attention on the nervous young man.

Mm? I uh, oh Oh no, no, of course not," Lloyd said, shrugging out of his pajama top.

"Cute," Bitty sneered when Lloyd revealed his micro-briefs.

"Oh! I uh, any, any food allergies?" Lloyd asked, slipping his silk underwear off.

"No. Not that I know of. Why?" Bitty asked, looking at Lloyd's bobbling cock.

"I, uh, there, there's these edible lubes; made with you know, food stuff," Lloyd said. "Here, here's my favorite. White chocolate."

"White chocolate's okay. What else you got?" Bitty demanded, stepping to where Lloyd stood.

Bitty peered into the nightstand drawer at the various bottles of lubrications. Bitty said nothing about the two butt plugs in the drawer.

"Hmm; cherry, blue raspberry, honey, white chocolate, tropical passion," Lloyd read aloud.

"Tropical Passion," Bitty demanded, holding out a small hand for the bottle.

Bitty seemed to approve of the scent of the lubricant. A taste brought on a nod of approval and Bitty crawled onto the bed. Lloyd followed the football player onto the bed and kissed Bitty's pouting lips hungrily.

After a moment of kissing, Bitty shoved Lloyd away. Lloyd was about to retort angrily but Bitty began to lubricate the thick cock. The smell of coconut and pineapple filled the air and Lloyd watched Bitty's hand sliding up and down the length of the beautiful cock.

"How you want it? On your knees or..." Bitty demanded, impatient with the somewhat besotted young man.

"Knees," Lloyd whispered, mouth dry. "On my knees."

"Well?" Bitty snapped when Lloyd was slow to respond.

Lloyd got onto his knees and put his scrawny shoulders to the bed. Reaching back, he pulled on his buttocks.

"Mmph!" he grunted as he felt Bitty thrust two greased fingers into his rectum.

He grunted again as Bitty used three fingers to smear lubricant to his anal cavity. He shivered in pleasure as Bitty rotated the three fingers in his rectum.

With one hand on his hip, Bitty guided the head of the thick cock to Lloyd's greased hole. Lloyd groaned out as Bitty pressed hard against his resisting anus.

"Fuck!" Bitty cursed as Lloyd's hole tried to deny entrance.

"Push, push a little harder," Lloyd gasped out.

They both groaned loudly as the head of Bitty's cock pushed past Lloyd's struggling sphincter. Lloyd gasped out and Bitty paused for a long moment. When Lloyd made no other sounds, Bitty pushed forward.

"I, oh, oh God, this, this is always so..." Lloyd moaned, not finishing his declaration.

Sheets of white hot pain coursed through his slight body as Bitty's cock pushed into his rectum. Through the pain, Lloyd could feel Bitty's foreskin curling back. Lloyd could feel Bitty's cock pushing into him, stretching him, filling him. He could feel the foreskin rasping along his rectal walls as his muscles attempted to force the intruder out.

"God, I, I feel so, augh, so fucking stuffed," Lloyd sobbed out as Bitty's pubic hair rasped against his stretched, raw anus.

With a swivel of the hips, Bitty began to pull out of Lloyd's stretched hole. Bitty's hand on his hips held him firm as the cock slowly withdrew from his quivering hole.

"Ung! I, oh, oh God!" Lloyd cried out as Bitty roughly thrust forward, once more filling him.

Soon, Bitty had a good rhythm going. Lloyd's sheets of pain ebbed away and a feeling of intense pleasure began to well up in his guts.

"Oh, oh God, oh God yes!" Lloyd gasped out, grasping his erection in his left hand, cupping his right hand underneath the tip of his cock.

""Mmng, I, oh, oh yes!" Lloyd hissed out, pumping a steady stream of semen into the palm of his hand.

Bitty continued with a steady rhythm, pushing in and out, in and out. Bitty's breathing became ragged as Bitty's own climax drew near.

"Fuck!" Bitty cried out, heralding a satisfying climax to their coupling.

"Oh, so, so good, so good," Lloyd sobbed out as Bitty's cock slowly slid from his sore anus.

"Yeah," Bitty agreed, slumping onto the bed.

After a few moments, Lloyd softly kissed Bitty's lips. Bitty returned the soft gesture, pulling Lloyd closer.

"I, I need to fuck you," Lloyd whispered, his need quite urgent.

"Okay," Bitty agreed, some light fading from the deep brown, almost black eyes.

The stained and sweaty lines of the jockstrap looked almost gleaming against Bitty's reddish brown buttocks. Lloyd took a moment to admire Bitty's sweetly rounded buttocks as he knelt on the bed behind Bitty's kneeling form. He grabbed the white chocolate lubricant; it was his favorite. Bitty let out a low grunt when Lloyd's greased finger entered the resisting anus.

"I, go, go slow; I don't I usually don't let anyone fuck me there," Bitty whispered, voice strangled.

Lloyd said nothing as he continued to lubricate Bitty's squirming bunghole. Starting with one finger, Lloyd soon worked a second finger into Bitty's sweet little ass hole. Adding a third finger, Lloyd watched Bitty's anus flower open, ready for a hard cock.

"Ungh, I oh oh God damn!" Bitty cried out as Lloyd pushed the knob of his cock against the resisting rosebud.

Lloyd paused for a moment. Bitty continued to gasp and wheeze for a moment, then seemed to relax. Lloyd gripped Bitty's slim hips in his hands and slowly pressed forward.

"Oh!" was all Bitty said as Lloyd continued to press forward.

At the halfway point, Lloyd swiveled his hips. Bitty shivered at this maneuver, causing Lloyd to smile. He knew exactly how delicious that felt; a fat cock swiveling, rubbing against the tight hole. Then Lloyd pulled a few inches of his manhood out, before pushing forward again.

"Mmng!" Bitty grunted and Lloyd paused.

"I, come on. You going fuck me or what?" Bitty demanded, voice strangled and tight.

Lloyd again pulled a few inches from Bitty's struggling, squirming hole, then pushed forward again. He could feel Bitty's muscles squeezing, rippling, trying to evict him from the tight anal passage.

"Oh!" Bitty gasped out.

Bitty's hole, which had been quite snug, suddenly became excruciatingly snug. Lloyd realized that Bitty had just enjoyed an anal climax. Struggling, using his hands to push and pull, Lloyd began to fuck Bitty's hole with vigor, long, hard strokes in and out.

"I, oh, oh sweet Jesus," Lloyd cried out, pumping a torrent of semen into Bitty's ass.

"Oh!" Bitty once more cried out in climax.

A moment later, Lloyd pulled his cock from Bitty's sweet ass. Leaning forward, Lloyd began to lick and suck his own semen from Bitty's stretched, raw anus. Lloyd could taste the white chocolate as well as his own somewhat bitter semen.

This time, when he attempted a kiss, Bitty jerked away. Lloyd was disappointed but shrugged it off. He told Bitty the hall bathroom was the first door to the right after exiting the bedroom. He availed himself of his bidet, cleaning his anus and his cock of lubricant. Entering his bedroom once more, he dressed in his silk micro briefs and pajamas. He found his bunny slippers and hopped into the living room.

Bitty laughed, a happy, musical laugh when Lloyd hopped into view. Lloyd smiled and offered Bitty another drink.

"No; we, we're really not supposed to drink at a client's home," she said, still brushing her waist length black hair.

"Mm? Makes sense, makes sense," Lloyd agreed, now looking at Bitina's 30C breasts as they bobbled in her simple tee shirt.

Sitting on the couch, he could see the frayed ends of her denim cutoffs peeking out at him. She stood, smiling and dropped her brush into her purse. With a nod of her head, she indicated the brand new Norwill University tote bag against the end of the long couch.

"All your stuff's in there. Oh, I, I rolled that ace bandage up; damn! Made it hard to breathe, having my boobs wrapped flat like that. And where, where did you find a double headed dong with foreskin? I've never seen that before," Bitina said, sauntering to the door.

"Hmm? Biggs Toys; they're out of Aitchel; this shit hole in Ohio," Lloyd said, fumbling with his cell phone. "And... There. Just sent you a five hundred dollar tip."

"Five... Five Hundred? Thanks!" Bitina smiled widely.

"Here, take the hat," Lloyd offered. "This is the design for next year's uniforms. I, my company designed it; go Cyclones!"

"Go Cyclones!" Bitina agreed, catching the clumsily thrown baseball cap. "Wait, your company? What do you do?"

"Me? I'm an Architect," Lloyd said. "But my company does dabble a bit in graphic designs."

"Cool," Bitina said, adjusting the cap to fit her head now that she did not have all of her hair stuffed into it. "You uh, you ever want me again, just call and ask for Bitty, hear?"

"Sure, sure," Lloyd agreed, feeling another erection begin as he could just see the cheeks of her delectable rear end peeking out of the hem of her tee shirt.

"Go Cyclones," she said again and was gone.

"Go Cyclones," Lloyd agreed, locking the door.

The End

**..**

***Author's Note: I write these stories for my pleasure; I post them here for your enjoyment.

I thank you sincerely for reading my stories.

Likewise, I also thank those that take the time to leave comments, good and bad. I also thank those that take the time to rate my words, those that take the time to 'Favorite' my works.

This is an entry for the yay-team-sex-and-sports-story-challenge-2025-coming-soon organized by Voyeurkenneth. Please be sure to vote for this and the other fine stories in this challenge.

This is an anomaly; there are no characters from any other JimBob44 stories making an appearance in this tale. However, there is a reference to the St. Elizabeth Distillery whose origin is established in the '101 in the Shade' series in the Incest/Taboo category. Also, there is a reference to Biggs Toys; that company was introduced in 'Vodka: Pecan Pralines' in the Toys & Masturbation category.

Have a swell day. And some of you, have a swollen day.