The Big Boss – Part I (A Lyla Story)

Lyla glanced nervously at the time on her phone while pondering which clothes she should be taking off for Dustin in exactly one hour.

“Required reading is on the portal and I’ll expect everyone to submit their assignments before midnight on Friday. TA hours are from three to five today,” the professor boomed from the speakers at the lecture hall. Jumping from her seat, Lyla needed to be fast.

As she walked down the hall, Lyla saw every male attempt eye contact with her. It didn’t matter if they were an undergraduate, like herself, or an aging professor who could have been her grandfather. Every eye had the same look that screamed, “I want you!” But Lyla didn’t want them, she wanted to pay the construction crew demolishing a kitchen in her recently acquired apartment in SOHO a few blocks away. She currently had five apartments and the newest edition was screaming for cash.

As soon as she hit the curb on Washington Square Park, Lyla was able to hail a taxi and get on her way to financial. It was a ten minute ride and Lyla hoped Houston Street wouldn’t be a bottleneck. Luckily, the taxi was able to bend around dawdling drivers with New Jersey and Connecticut plates and drop her off in exactly eight minutes.

The girl raced past the doorman of the building, who gave her a pleasant wave, recognizing she was a tenant. As soon as she hit the elevator, Lyla began to calming herself knowing that she was not going to be late. As soon as her floor was reached, Lyla held her thumb on the plate to gain entrance then began stripping as soon as the door shut behind her. Lyla jumped in the shower and turned it on full blast. The freezing water hardened her nipples and the girl shuddered but the water quickly turned hot. She generously squeezed her special soap into her hand and thoroughly washed her bald pussy then liberally poured men’s body wash onto her loofah and attacked her armpits and ass. Rinsing off quickly, she wrapped a towel around her and walked, dripping everywhere, into one of the bedrooms.

From inside a hamper, Lyla found a matching black thong and bra and snapped them onto her body. She smeared men’s deodorant onto her armpits then put on a casual pantsuit and white button shirt that she matched with simple black shoes with a small heel. In the mirror, she put on a small amount of blush and eyeliner, nothing more. Grabbing her bag, Lyla was back in the elevator with twenty minutes remaining. The same doorman found a taxi for her immediately and within minutes, Lyla was at the Conrad Hotel, dressed as if she were attending a conference or business lunch. Looking the perfect mixture of bored yet confident, Lyla walked directly towards the concierge and upon reaching asked her question, ”Do you have a key for suite rented by Jones Silverman Administrate? Should be a card for Samantha?”

The concierge handed her the key without losing his poker face even the slightest. With the key in her hand, Lyla walked to the elevator and selected the fifty-second floor. As her ears popped during the incline, she checked her phone. She had made it with two minutes to space. Walking down the carpeted hallway to the room, she waved the key near the panel and the lock snapped open.

“You made it! And right on time!” Beamed Dustin.

Dustin was well into his sixties and was the managing director and CEO of the real estate firm Jones Administrate where Lyla was an intern. She was a paid intern, making two-thousand dollars per week; a deal she had concocted with Dustin a year prior at the Penthouse Executive Club where Lyla was working. Dustin was clever man, with a brilliant mind for business and creative deals and, once he found out she was at NYU, on the dean’s list, instead of propositioning Lyla with cash, he offered her a lucrative job. Lyla still had to fuck Dustin, but it was a very clean transaction.

“Of course!” Lyla returned and walked to Dustin and kissed him as if they were in a loving relationship.

“Can I offer you a drink?” Dustin asked.

“Just one,” she replied. “I have a lot of school work to do and I need to be at the office later on tonight to help Jason stage an apartment.”

Dustin poured Lyla a scotch from the minibar and the two chatted.

“Which unit is Jason showing?”

“Fifty-five Thompson.”
“Is he going to let you show the unit?”

“He is.”

“Fantastic,” Dustin said, swirling his drink and looking hungrily at Lyla.

She took this as her cue and placed her drink on the small table before sexily kneeling in front of Dustin and reaching for his belt. As Lyla undid the executive’s belt and yanked his suit pants down to his ankles, she heard the tell-tale rattle of a bottle of pills; Dustin’s ED medication. No wonder he was so pleased she was on time, he must have timed her arrival with when he took his blue pill.

Lyla pulled down his briefs and his spotted cock jumped at attention. Smiling at Dustin, she took the head in her mouth and lovingly sucked while gently stroking his veiny shaft. Lyla had to be careful when she fondled the older gentleman’s balls as they hung exceptionally low and she felt they were far more delicate than a younger man’s. She scooped them up and held them while she skilfully used her mouth, tongue, and other hand simultaneously.

“Oh you’re amazing,” Dustin moaned.

Lyla continued to suck while she unbuttoned her blouse and unclasped her bra. She then unbuttoned her slacks and was able to almost completely undress herself with the man’s cock still in her mouth.

Dustin ran his hands over her flawless skin and through her silky blonde hair while trying desperately not to ejaculate. After a few moments, the pressure began to build, so Dustin coaxed Lyla to detach from his throbbing cock. Lyla smiled at him, stood up and began sexily undressing the remainder of her clothes. Dustin watched the scene with pleasure before standing up himself. He took his time undressing as well, he need it to calm down so he could last longer, knowing he’d soon be inside of Lyla. His heart was already pounding in his chest from the spectacular blowjob the young girl had given him.

Dustin came from a wealthy New York family and had married fairly early. He was a father of three before he was thirty years old. He divorced in his mid-forties and, after a brief second bachelorhood, married a woman fifteen years younger than himself. She was a lovely girl who, much like his first wife, came from a prominent New York family. With his second wife, he had another child, a girl. Dustin lived with his family at eleven Great Jones in NOHO. The daughter he had with his second wife was only one year younger than Lyla. His first born son was himself in his forties and had a teenage daughter who had her heart set on attending NYU. And, if she were to be accepted, would be a freshman during Lyla’s senior year.

Having struggled with his socks, mostly due to his erection, Dustin was now ready to join Lyla who was posing for him on the bed. For Lyla, sex with Dustin was always very functional. He never put her in many positions or took advantage of the girl’s athleticism. He was just from a different time, Lyla assumed.

“Condom?” Lyla reminded him, teasingly.

“Let me pull out,” Dustin suggested.

“No, it’s not a great time for that,” Lyla rejected.

“A thousand…,” Dustin proposed.

“If I have to take the morning after pill, I’ll be fucked up for days and it will cost me way more than that,” she reasoned.

“Ok, then, five,” Dustin said, negotiating strongly.


“Five,” he confirmed, reaching in his suit jacket on the back of the chair and pulled out an envelope. The tossed the envelope to the girl and she knew it was all there by the weight and the feel.

Dustin hated withdrawing cash in that quantity because it was always something that stood out on a bank statement. The entire reason he put Lyla on the payroll was so he could fuck her and not have these discrepancies that a divorce lawyer would be keen to investigate. In this case, Dustin had not withdrawn the funds from his account at all. He had punted some business to one of the agents working for him and the agent, in return, gave Dustin the finder’s fee in cash. Dustin could think of nothing better to do with some of the windfall than spend it on Lyla’s pussy.

“Alright,” Lyla agreed.

Crawling up on top of her, Lyla adjusted her body to remain in the perfect position for intercourse despite Dustin’s unathletic mounting. He wasn’t an overweight man, but his body was rather lumpy and his stomach quite distended. He breathed heavily, even when he was just walking. With Dustin completely on top of the girl, Lyla reached underneath her ass to find his cock and then pointed the head at the correct angle to penetrate her. She was always wet enough for Dustin as she found his station in life to be very attractive. He was a man who turned a decent family fortune into a multibillion dollar net worth. He was an institution in New York real estate and, when Lyla was working at the office, her colleagues talked about him like he was God.

Dustin, feeling Lyla’s wet lips with the tip of his cock, arched his back to penetrate and Lyla guided his cock inside. Dustin never penetrated gently, it was always balls deep in one thrust for Dustin. The first time they fucked, he was wearing a condom and the sudden jab was rather uncomfortable. After their first session, Lyla began the practice of excusing herself to the restroom just before sex in order to carefully lubricate her pussy to ensure a more comfortable session with the man. Since she started working for Dustin, she no longer needed artificial lube to fuck one of the most powerful men in New York.

With Dustin inside of her, free from wearing a condom, Lyla settled herself in to get pounded by the aging titan. She didn’t particularly like fucking him at this angle as Dustin made horrible faces while he fucked her. She could tell he was very much enjoying himself, but he looked quite terrifying with his face wrenched into a furious scowl, veins throbbing in his forehead, sweat pouring down his face.

“Ah! Ah! Ah!” Dustin’s guttural voice sounded like a shot-putter, stuck on a loop.

Lyla wished Dustin was fucking her from behind so she wouldn’t have to see the man she admired make those faces. Dustin disliked fucking her in any position other than prone as it was difficult for him. Doggystyle was the most difficult as Lyla was such a tall girl, he could only penetrate her if he was standing alongside the bed. Dustin would become physically exhausted doing this, and found that he wasn’t fully enjoying the sex when he was in such a state of fatigue. He knew that it was probably uncomfortable for Lyla to support his entire weight, but this was his time and Dustin was in heaven, especially when not wearing a condom with Lyla.

‘When I was twenty-five, after a night with me, you’d walk funny for a week!’ Dustin often said to her.

Lyla always giggled and smiled when he made this comment, but, what she really wanted to say was, ‘when you were twenty-five, my mother was in kindergarten….”

Coming back to reality, Lyla tried her best to look enthralled while Dustin grunted in-between thrusts. She wanted him to enjoy the sex, and not just because this particular session was costing him thousands of dollars, but because she did respect him and even cared for him a little. Lyla was quite wet and Dustin’s cock slid nicely inside of her. She always made a point not to touch Dustin’s stomach during sex, as she felt he didn’t like that, so Lyla busied herself making pleasurable noises and pulling on her hard, pink nipples. What she really wanted to do was rub her clitoris, but, due to Dustin’s bloated gut in the way, she found it impossible to reach her little love button.

“Ah! Ah! Ah!” Dustin continued thrusting inside of her as he sweated.

He was really giving his best performance, Lyla thought. His cock felt good inside of her and it was a treat for her as well; she hardly ever had unprotected sex. On the rare occasions she did, it was usually with people like Dustin; billionaires exclusively. She also knew he’d do a good job of pulling out. On the previous few times she’d allowed him inside of her without a condom, Dustin pulled out so early, he needed Lyla to suck him through his orgasm. The first time she allowed him was when he offered her a job and the price was negotiated very precisely.

“I’m going to get you an internship paying two-thousand per week. In return, you’ll be available to me every weekday, on my schedule,” Dustin proposed.

“So, I could end up fucking you for as little as four hundred dollars? I’m sorry, that’s just not enough,” Lyla negotiated back.

“I like to fuck most days but two-thousand is the most I can offer without accounting raising some concerns. What do you propose?”

“I don’t want more money, I want you to actually teach me real estate. I want a real role where I learn how to make money in this town in your business,” she stated.

Dustin pondered for a moment and then eyed the girl.

“Fine, but I want my five days.”

“Scheduling five every week will be tough. Unless we’re going to use your office and I don’t want to be so… obviously fucking the boss… Help me out here.”

“I’ll put you on a team and I’ll mentor you on days I see you. I keep a suite at the Conrad on the company books for discrete meetings and we can go there on days you work. No less than three days per week.”
“You won’t get sick of fucking me?” Lyla posed.

“You’re one of the most beautiful women I’ve ever had and I trust you. The trust is one of the most important things. I may need you to deny ever knowing me, if needed. I need to know you’d never testify at a divorce proceeding. And I need to know that you’ll keep your mouth shut unless it’s opening for me to shove my cock inside,” he ended with a lude joke.

“So… sex three times a week for the job and the mentoring? What about when I’m on my period, do you want then as well?”

“Those days, I’ll enjoy a nice leisurely blowjob,” he smirked. “Are you on your period now?”

“No,” Lyla shot back.

“Ok, but to seal the deal, I want a cherry on top. I want to fuck you without a condom today.”

“No, I don’t take birth control.”

“Why not?”

“I feel like it makes me put on weight.”

“Then I’ll pull out.”

“No. Are you clean?”

“As a whistle.”

Lyla furrowed her brow thinking.

“Every other day I’ll wear the condom. Close the deal and let me fuck you raw today. I’m mentoring you right now… closed the deal and reap the reward.”

“You’d better pull out…,” Lyla implored.

“So we have a deal?”

“As long as you pull out.”

That wasn’t the last time Lyla had Dustin’s uncovered cock inside of her. On a few other occasions he was able to get her to say yes for various favours. A year ago, when she wanted to buy her first investment property, she needed Dustin to get Jones Silverman to underwrite the loan from the bank. Another time she needed a building permit to perform renovations. Another time still, she was dry on cash for the construction crew and Dustin was more than happy to fill in.

Today, Lyla didn’t particularly need the five thousand, but as soon as he mentioned that number she thought about wide board oak flooring on her latest renovation. Truthfully, she preferred sex without the condom and she was enjoying this latest coupling, even if she couldn’t reach her clitoris to attempt an orgasm while Dustin happily fucked her.

Suddenly, the sharp focus of Dustin’s eyes became wildly distracted. A look of panic washed across his face.

“Are you ok?” Lyla posed, with more than a hint of concern.

Suddenly, Dustin grabbed his left arm as he let out a painful shout.

“Dusty?!?!” Lyla begged, using the pet name she sometimes called him.

“Argh!” Dustin belted and then collapsed on the girl.

“Dustin!” Lyla screamed.

Crushing her with his weight, Dustin was breathing shallowly but remained  unresponsive to Lyla’s yelling. Wet gobs of drool fell from his lower lip and landed on Lyla’s face. Panic stuck the girl as her boss’s, boss’s, boss’s, boss had her pinned to the bed, naked, and inside of her. Struggling, Lyla tried to roll him off her, but he was firmly planted inside of her and immovable. Lyla’s hips were open with her legs splayed around his back, jutting out to the sides due to Dustin’s hefty love handles. The entirety of Dustin’s weight seemed to be right on Lyla’s hips and he easily outweighed her by double. Exerting herself, Lyla twisted her frame in an attempt to escape from the side. Each snap of her hips gained her an inch. After more than a few jolts, she made real headway pulling her hips away from Dustin and managed to dislodge his still erect cock from deep inside of her. As soon as it popped out of her, cum gushed out of Lyla’s pussy.

“Fuck!” She cursed, while continuing to pull her body out from underneath the man. Apparently, Dustin had ejaculated during what appeared to be either a heart attack or a stroke.

Eventually, Lyla broke free and hopped up on the bed. Still naked, with semen dripping from her labia, Lyla rolled Dustin onto his back and began screaming at him.

“Dustin! Wake up!”

She slapped him in the face, desperate to illicit a response. Dustin’s eyes opened and he stared blankly at the ceiling.

“Dustin! Answer me!” She yelled.

He blinked but made no verbal response before his eyes closed again.

Leaping off the bed, Lyla grabbed the hotel phone and called the front desk.

“My boss is having a heart attack! Send an ambulance! Room fifty-two-eighteen!”

“Right away, hold on,” the man on the line said, calmly but with urgency.

Lyla put the phone down and panicked for a few moments. Dustin was naked on the bed with his still erect penis coated in both of their fluids. The entire room smelled like sex.

“Fucking blue pills!” Lyla cursed, betting this entire debacle was the result of Dustin’s medication coupled with his age and poor health.

Bolting to the bathroom, Lyla sat on the toilet and used a finger to clean as much semen out of her vaginal canal as possible. It was almost no use, Dustin had exploded inside of her and ejaculated a tremendous amount. He would often comment he was ‘saving up for her’ which was a double entendre on how expensive she was and his intentionally not ejaculating for days prior so he would unleash great gobs of semen with the girl.

Lyla flushed the toilet and grabbed two small hand towels and threw them in the sink and ran the water on hot. Grabbing one, she roughly washed her vagina then threw the dirty towel into the tub before grabbing the other and running back into the bedroom. She attacked Dustin’s penis with the hotel towel and the man didn’t make a sound despite the girl scrubbing his genitals with the scalding cloth.

Bang! Bang! Bang!

“Hotel security!” A man yelled through the door.

Then Lyla heard a key card being read and two men in matching blazers stormed in the room followed by a woman in a moderately priced skirt suit. Lyla was still naked and the two men were taken aback seeing the gorgeous blonde making no effort to cover her incredible tits or her completely shaven pussy. After what seemed like a minute, the pair noticed the naked unconscious man on the bed, laying on his back, at full mast.

“You should dress, and quickly,” the woman in the skirt scolded Lyla.

Normally, Lyla would never let anyone speak to her in such a demeaning tone, but she could hear a ruckus in the hallway and she decided to take the woman’s advice.

Lyla quickly grabbed her discarded clothes and took them into the bathroom and closed the door behind her. She threaded her legs through her thong and pulled it up, attached her bra, and put on the pants. To her horror, Lyla had grabbed the blazer to the suit but not the blouse, which was evidently still on the floor outside, and the blazer was cut to be very open and, quite unintentionally, exposed Lyla’s sheer black bra where you could clearly see her nipples.

“Excuse me?” A female voice called through the door while rapping softly.

Lyla opened the door and saw the woman in the skirt holding her garment. She was making an almost apologetic face as she handed her the white blouse.

“Thank you!” Lyla squeaked, grabbing the item and closing the door. The blouse was Saint Laurent that she had purchased at Neiman Marcus and was incredibly expensive. Possibly, the hotel employee was now concerned she was rude to someone important, but, most certainly, wealthy, having recognized the famous brand. Lyla was not wealthy, in fact, she had nearly ten million dollars in mortgage debt through her various properties. She did have a few dazingly expensive outfits for those occasions she had meetings with powerful people, and, sometimes, fucking them.

With her outfit back on her skin, Lyla took a deep breath and entered the room to see two men were attempting to strap Dustin to a gurney with oxygen being fed into his nostrils. He was still completely naked and they had covered him by placing him in some sort of a bag. His still erect penis was the big-top attraction that was the circus going on in that room.

“When did he lose consciousness?” One of the EMT’s asked in Lyla’s direction.

“Five, ten minutes at most…” she speculated.

“And he was having sex when he collapsed?” He continued.

“Ummm… yes, yes he was,” she admitted.

The woman in the skirt suit squeezed Lyla’s hand and it meant the world to her.

Just as the men were completing the task of strapping Dustin into the gurney, being careful of his erection, two police officers strode into the room. The woman in the skirt suit and the two men in blazers immediately approached them and the group spoke and occasionally looked at Lyla. Then, to Lyla’s horror, sitting on the nightstand was the envelope with the five thousand dollars.

Calmly, Lyla scooped up her purse and placed it next to the envelope. She then reached into the purse and extracted her phone, pretended to type on it then placed it down, directly on top of the envelope.

“Is he going to be ok?” she asked the EMT, using her most desperate voice.

“We’re taking him to Presbyterian and the doctors will take care of him, miss,” the EMT responded, rather coldly.

After hearing his response, Lyla deftly picked up her phone and the envelope at the same time and placed them in her bag. The moment she snapped the clasp shut, the police had accosted her on either side.

“Can we have a few words, miss?” the first asked.

“We’re going to need a statement,” the second added.

“Ok,” Lyla responded, trying to sound meek.

“What’s your relation to this man?”

“He’s my boss.”

“Uhhh-huh… where does he work?”

“We… both work at Jones Silverman…,” Lyla responded a bit defensively.

“Do you have a work ID that I can see, proving you worked there?”

Not wanting to come off guilty, Lyla quickly opened her bag and, luckily, pulled out her ID without exposing the envelope. She had brought it with her in case someone had recognized Dustin or the concierge gave her a hard time.

She pulled out the ID and the pair looked at it, then back at her.

“You guys doing any drinking? Did you take any drugs?”
“Ummm… we had a glass of Scotch, Dustin likes Scotch… but I don’t do drugs. Dustin doesn’t do drugs…”

“Dustin, huh? Are you very close with your boss?”

“Excuse me?”

“You know what I mean, miss,” the cop pushed back.

Lyla desperately wanted to go home. She could feel the semen leaking out of her vagina onto her black thong. The thin material was not very absorbent and she knew it would be running down her leg soon if she couldn’t get to the ladies room quickly.

“I am a student at NYU and I have an internship at Jones Silverman. I was meeting my boss to discuss an important work development and I’m not at liberty to go into details,” Lyla retorted, summoning her courage.

“Intern, huh,” the cop remarked. “Thought you interns wore blue dresses?”

The other cop snickered.

Just then, the woman in the skirt suit approached Lyla and the police.

“Miss, if you could hand me your ID, not your work ID, I’ll take down your information for my report,” the cop said, drastically changing demeanour now that the female hotel manager was observing the conversation.  

Lyla handed the officer her New York state ID. She didn’t have a driver’s license because, Lyla had never driven a car having lived in the city her entire life.

While scrawling the information into a pad, the officer balked.

“Is your address correct?”

“Yes,” Lyla responded.

“You live at one-oh-one Warren?”


“Who pays for that?”

“I do. It’s mine,” Lyla replied, shrewdly. “Well, one of my families properties,” she added, lying about the family part. Lyla had five properties but she was in mortgage debt up to her chin. Lyla was attempting to run a gambit that would net her enough money to be set for life.

Lyla never knew her father and her single mother was mostly absent when she was young. They certainly didn’t have any money. Lyla knew that if she reframed herself as slutty heiress and not fuckable intern, or even worse; high class prostitute, she’d be on her way quickly.

Handing her identification back to her, the cop closed his notebook with a flop.

“We’ll contact you if we need anything,” the officer responded.

With that, Lyla nodded at the woman in the skirt and then confidently walked out the door. As she neared the elevator, she heard someone approaching her from behind. It was the woman in the skirt.

Lyla pressed the button and the pair got inside. A moment later, the woman pressed the ‘stop’ button and the elevator halted in-between floors.

“Get out at the next floor and go back to the room. Stay there and don’t leave until the checkout crowd tomorrow morning. I’ll bring you some clothes, don’t worry, they’ll be clean,” she explained.

“I really would rather just leave,” Lyla responded. Just then, she could feel a drop of semen running down her inner thigh.

“Someone at the hotel called the paparazzi. They’re outside and they know Dustin Silverman just left in an ambulance after checking in with a young, blonde girl.”

Lyla froze.

“They got a ton of shots of him leaving in an ambulance and now they’re waiting for a blonde girl, in her late teens to early twenties, wearing a black blazer and slacks with a white blouse.”

“Oh, fuck!” Lyla cursed. “How  did this happen?”

“Those scumbags have tipsters all over the city and, unfortunately, someone here is on their payroll. You don’t want to be the mistress on page six, especially if he doesn’t make it.”

“Any news on how he’s doing?”

“None that you don’t have… he’s probably at the hospital now.”

For a moment, Lyla thought about going to the pharmacy but she decided to put that off until tomorrow. She hopped out of the elevator at the next floor and went back to the room. It was in shambles. The sheets were off the bed and the entire room looked like a crime scene.

Lyla locked the door and engaged the chain. Then she put the plug in the bathtub began filling it with hot water. She walked back into the room and carefully hung her wrinkled suit in the closet and put on a robe. A moment later there was a knock at the door. Peering out of the keyhole, Lyla saw no one. She opened the door and, hanging on the knob in a bag was a pair of sweatpants and a t-shirt with the hotel’s logo.

“That woman is saving my life!” Lyla whispered to herself.  

The spout on the tub was very efficient and was filling the space rapidly with piping hot water. Lyla removed the robe and slid her body into the scalding water. Holding her lips open with two fingers, she inserted her middle finger into her vagina and started cleaning out as much cum as she could. The semen clouded the clear, hot water as she drew it out. She couldn’t believe it had only been about twenty minutes since Dustin had tossed her the envelope.

To Be Continued….

If you enjoyed this story, you would probably enjoy the book by the same author below.

%d bloggers like this: