The Closer: Ch. 01

"Mmmmmmmmmmmm," Hailey moaned. "Fuck!"

"You like that big dick, don't you?"

"Hell yes. Fuck me."

"Tell me you like it."

"I love it. I'm going to cum."

"Cum for me, baby. Cum for me."

"Oh shit. Oh shit, I'm gonna cum. Fuck!"

"Go ahead. Let it go."

"Unh! Yes! Mmmmmmmmmmm!"

"Come on, baby. Cum for me."

"Shit. I'm...cumming! Ahhhhhh!"

"You're a little screamer, aren't you?" Eldon asked as he withdrew from Hailey's pussy.

"I don't usually make that much noise. I've never cum so hard before."

Hailey pulled her skirt down from her waist.

"What are you doing, girl? We aren't done yet."

Hailey felt the juice running down her thighs.

"I thought...I thought you..."

"That was all you. I've still got a way to go."

Eldon stepped out of his shoes and placed them under the desk. He took off his slacks and hung them over his chair, then dropped his underwear to the floor. He walked over to the sofa in front of the window and laid back with his cock sticking straight up in the air.

"Come over here and ride me, honey. Make me cum."

Hailey paused to kick off her shoes, then joined Eldon on the sofa. She pulled up her skirt, squatted over his cock, placed the purple head against her juicy pussy, and lowered herself down the shaft.

"Mmmmmmmmm," she moaned. "It's stretching my pussy so good. It's even better the second time."

"Ride it, tiger," Eldon encouraged her.

Hailey leaned forward, burying her face in Eldon's shoulder. She wrapped her arms around his neck, raised her hips until only the head of his cock remained inside her pussy, and then lowered herself again until the shaft was buried inside her. She took a deep breath, rose again, and then lowered herself once more, increasing the speed of her descent. Each up and down motion increased the intensity of the sensations flowing from her pussy to her brain. She felt as though her entire body were on fire. Her clit was rubbing against the wiry pubic hairs surrounding the base of Eldon's magnificent manhood. Her pussy was filled with the biggest and hardest cock she had ever seen, and every motion brought ecstasy. She was not unfamiliar with riding a cock. She had done it many times. But never before had she enjoyed it like she was enjoying it now.

"Ungh! Fuck! I'm--I'm cumming again."

"Ride it, baby, ride it. Get it. Get all of it," Eldon urged her on.

Hailey's hips were now a blur. She rode his cock faster and faster, taking it all the way from tip to base with every motion of her hips. She lost all track of time and place as a fountain of colors exploded in her brain. She inhaled, filling her nose and lungs with the scent of sex and Eldon's cologne. It took her a moment to realize the pussy she smelled was her own.

"Fuck. Fuck. Yes, fuck yes. Fuck."

Her second orgasm was followed by a third. Out of breath and overcome by dopamine, Hailey collapsed on Eldon's chest.

"Oh, you're not done yet my dear. I still haven't cum."

Eldon peeled Hailey off his chest and flipped her over onto her back. He positioned himself between her thighs and entered her pussy with a single thrust.

"Ungh!" Hailey grunted.

Eldon placed Hailey's ankles on his shoulders, leaned into her, and pushed. He wasted no time establishing a vigorous pace, thrusting in and out of her with all his strength and weight behind each downward exertion.

"Ungh! Ungh! Ungh!," Hailey grunted with every thrust.

Eldon pushed faster and faster. The sofa creaked from the force of the bodies slapping together. Hailey felt another orgasm building in the back of her brain. Her pussy had never endured such exquisite punishment. Her brain was no longer processing thoughts beyond counting down the seconds to her next orgasm.

"Are you on birth control?" Eldon asked her between thrusts.

"What?" Hailey answered.

"Are you on birth control? Do you use the pill?"

"Yes, yes. You can cum inside me."

Eldon increased his speed. He pumped her harder than she thought was humanly possible. He's an animal--no, a god. A sex god.

Hailey screamed as Eldon buried his cock to the base. His pace increased. He pumped into her harder and faster. He squeezed her ass cheeks and pulled her closer to him as he drove his cock into her juicy pussy over and over. His grunts and groans matched the pace of his thrusting. After several thrusts increasingly forceful thrusts he buried his cock deep insider her. He exploded inside her already soaked pussy, spraying spurt after spurt of cum into her cunt. The semen filled her pussy, while the overflow ran out onto the sofa.

Eldon stood up. His manhood glistened in the afternoon sun, their combined fluids dripping onto the floor. Hailey laid still and caught her breath while a river of cum flowed onto the sofa and her wrinkled skirt.

"Clean yourself up," Eldon said, handing Hailey a hand towel and box of tissues. "You have a meeting with Mr. Trant in fifteen minutes. I'm seeing you at eleven tomorrow. I'll have a full review ready for you when you get here."

"Another meeting? Now? My clothes are a mess. My suit is ruined."

"It's not that bad. There's a dry cleaner in the building, you know. That won't help you know, of course. You can use the ladies' room on this floor to get cleaned up, but please don't be late for Mr. Trant. He is obsessed with precision. And don't forget this."

Eldon handed Hailey her panties.

* * *

Hailey spent her entire fifteen minute break between meetings in the tenth floor ladies' room. She touched up her make up, fixed her hair, and attempted to clean the semen off her skirt and blouse. With one minute to go she left the restroom and approached Mr. Trant's secretary.

"Hello," she said. "I'm Hailey Andrews."

"Hello, Hailey Andrews, I'm Chloe Buckingham. How can I help you?"

"I have an appointment with Mr. Trant?" Hailey responded. A hint of doubt crept into her voice.

"Really?" Chloe asked, "Are you sure?"

"Mr. Jackson sent me."

"Well, let's look at the schedule."

Chloe pulled Mt. Trant's schedule up on her monitor.

"Look at that. There you are. You must have been added while I was on break. Let's see...yep, added twenty minutes ago by Yvonne. She was supposed to copy me on that calendar invite. I'll have to talk to her. Go on in, you're two minutes late."

Hailey walked past Chloe and stopped at the door. She paused to knock first, then turned the handle and pushed the door open. She walked in to find a short, balding man in a dark suit seated behind a large desk with five oversized monitors attached to the front and sides of the desk. Unlike the other partners' offices, Mr. Trant did not have guest chairs placed in front of his desk. He did, however, have a small circular coffee table with a tub chair and a low sofa tucked in the far corner, near the window. He also had a bar cart stocked with a few bottles of liquor, some glassware, and an ice bucket.

"Come in, come in," said the man in a slightly accented voice. British? "I'm Ian, Ian Trant. And you must be Hailey Andrews?"

"Yes," she said. "Call me Hailey."

"It's a pleasure to make your acquaintance, Hailey."

Ian held out his hand to greet Hailey. She took his hand, squeezed, and then dropped it. Ian put his other hand on her shoulder and guided her toward the seating area across the office.

"Let's sit over here," he said. "As you can see, I'm kind of a tech guy. My monitor set up makes it difficult to have conversations at my desk, so I prefer to greet guests over here. Have a seat."

Hailey sat on the sofa, taking the space closest to the tub chair. Ian sat in the chair, placed his hands on his lap, and smiled.

"You've had a busy day, haven't you?" he asked.

"Yes, to say the least. This was not how I expected this day to proceed."

"On behalf of all the partners, I would like to say, 'welcome to the team.' I know you are not a new employee, but you are now in the process of becoming upper management. You will most likely become an equity partner long before any of your contemporaries are even eligible to be considered. How are you feeling?"

"Overwhelmed, would be my first answer. Excited, too, but mostly overwhelmed. And confused, also, if I'm being completely honest."

"I totally understand the feeling of being overwhelmed. A lot has happed today. You have been presented with a treasure trove of information and given a life-changing opportunity. I am pleased that you are excited about that opportunity. But tell me, what do you find confusing?"

"Well, using sex to close a deal...is that even legal? Or ethical?"

"Good questions, both of them. Let me answer you this way. Does any money exchange hands when you meet with a potential business partner?"

"No, not exactly. But, eventually, yes. Millions of dollars are changing hands."

"Millions of dollars change hands every day. But your negotiating partner is not paying you for sex. There is nothing that prevents two consenting adults from enjoying the pleasure of each other's company."

"You sound like Mr. Roberts."

"We are of a like mind on this. We were both involved in the creation of this position twenty years ago."

"Well then, what about my second question?"

"Is it ethical?

"In a perfect world we might not have needed to employ someone in this capacity. That's not this world. Our competitors are engaged in similar tactics. Harris Williams does all their negotiations in Las Vegas. Why do you think they go there? Winston Cummings owns an escort agency. It's hidden under several shell corporations, but our investigators did some digging and after six months of work reached the bottom. Spencer Wallace is a fifty-one percent owner in the biggest strip club on South Beach. They all are engaged in questionable moral behavior.

"The undeniable truth is that sex sells. It always has and always will. We aren't selling sex, but we do use it as a business tool. We looked at the methods our competitors used and decided to turn the paradigm upside down. They hire uneducated prostitutes and strippers and expect them to secure business on their behalf. They have constant turnover using unreliable agents with questionable motivations and sketchy backgrounds. The risk is unfathomable.

"Our model is superior. We hire one businesswoman, make her a partner with a vested interest in our success, reward her generously, and allow her to use all of the tools at her disposal. I like our model better, and the results bear me out. We're winning."

"You have given me a lot to think about, Mr. Trant."

"Call me Ian."

"Ian."

"Do you have any other questions I can answer for you?"

"Ah, just one more. What's next? Should I be worried?"

"Nothing that you need to be worried about, but you may be apprehensive, at first. My job is to help you get past that apprehension."

"Now I am worried. What are we talking about?"

"Hailey, most of your cases will resolve with an expert blow job or a spirited fuck. Some cases, however, are more difficult. There will be situations where you have to go the extra mile. And by the extra mile, I'm talking about your derriere."

"Oh no. Unh-uh. Nope. I don't do butt stuff."

"Have you tried anal sex before?"

"Yes. It was horrible. Never again."

"I'm not completely surprised by your experience. A lot of younger men--I assume it was a younger man who tried to bugger you?"

"It was. My boyfriend. Former boyfriend, I mean. We were both nineteen at the time."

"Let me assure you, Hailey, your experience today will be nothing like what you endured with your former boyfriend."

"That's right. Because I'm not doing it."

"What would you say, Hailey, if I were to tell you that I could guarantee that your experiences with me will be painless, pleasurable, and highly satisfying."

"I would say you are either deluded or lying. Or both."

"Fair enough, given your prior experiences."

Ian reached into his jacket pocket and pulled out a bottle of pills.

"Take two of these," he said. "You will find them helpful."

"Oh, so you're going to Cosby me and hope I won't remember anything?"

"Nothing like that. These are muscle relaxers. I'm offering them to you so you can choose to take them or not. It's up to you. If you take them, they will help you relax a little and avoid the pain sometimes associated with the initial penetration. You will not lose consciousness or suffer any loss of memory, I assure you."

"I think I'll pass."

"No problem. Like I said, it's entirely up to you."

"Entirely? Then I'll pass on this lesson, thank you."

"The muscle relaxer is optional. The training is not."

"I'm not going to take it up the ass. I don't do anal. That's final."

"Hailey, let me remind you of the contract you signed earlier today. The checks we have given you are your money, no matter what, but that is all the money you will receive from us if you do not complete your training. Also, your contract contained a non-compete provision, meaning you cannot go to work for another firm for a minimum of two years. The checks in your purse are not going to cover your expenses forever.

"I...see. I was not aware of that."

"You were given an opportunity to read the contract before you signed."

"That's true, but with Mr. Roberts throwing all those checks at me, I kind of skimmed over some of the pages of the agreement."

"Let's do this, Hailey. Let's start over from scratch. I'm going to put on some music, take off my clothes, and fix myself a drink. When you're comfortable, you can take off your clothes and join me. Would you like me to fix you a drink also?"

"Uh, sure. What do you have?"

"I have some gin, I have an 18 year old single cask scotch that I have been saving for a special occasion, and I have a very nice bourbon, also. I might have some cognac left. What would you like?"

"Gin and tonic?"

"Coming right up."

Ian pulled out his phone, tapped it a few times, and music started playing from speakers hidden in the bookshelves. He took off his jacket and hung it up in the closet. He removed his shirt, shoes, belt and pants, and then took off his socks and underwear. He was perhaps an inch or two shorter than Hailey, a little pudgy around the waistline, and his skin was so white it almost glowed. His flaccid cock was almost lost in the tangle of dark pubic hair just below his waist.

That certainly doesn't look like anything to be afraid of. He's a teddy bear. How much damage could he really do? He is probably gentle, generous, and considerate.

Ian mixed a gin and tonic for Hailey. He handed it to her, and then placed a coaster on the coffee table. He poured two fingers of scotch into a glass, and then sat down next to Hailey on the sofa.

"To your success," he said, raising his glass.

"To our success," Hailey responded.

Ian lifted his glass to his lips and sipped. He swirled the amber liquid in his mouth for a few moments, and then swallowed.

"Very nice," he said.

Hailey looked down at her glass and raised it to her mouth. She took a long drink and then set the half-empty glass on the coaster in front of her.

"You're thirsty," Ian said.

"I'm getting myself into a more relaxed headspace," she answered.

Hailey raised her glass a second time and drained it.

"Can I have another?" she asked, handing the glass to Ian.

Ian stood up and mixed another drink. He returned to the sofa and handed the drink to Hailey.

"Can I ask you a question?" Hailey said.

"Of course," Ian replied. "Ask me anything?"

"Do you enjoy anal sex?"

"I do."

Hailey picked up her glass, took a long sip, and then returned it to the table.

"Do you like it better than pussy?"

Ian took a sip from his drink, swished the scotch in his mouth again, then opened his mouth to speak. No words came out. He looked out the window, and then answered.

"I wouldn't say better. It's different. They are both pleasurable, but in different ways."

"How so?"

"Penetrating a woman's vagina with my cock is the purest, most pleasurable sensation I have ever enjoyed in my life. The contact stimulates every nerve in my body. It is exquisite. And when the woman is someone with whom I share feelings, it is a joining of souls. It is two becoming one. My heart nearly explodes when I am inside the vagina of the woman I love.

"Penetrating a woman's anus satisfies a different need. It doesn't feel all that different--if she is sufficiently lubricated. Oh, it is a little tighter, at first, but the anus expands and relaxes after a few minutes of gentle thrusting. It accommodates the invader. But psychologically and emotionally, it feels much dirtier. Nastier. Raw. Depraved. Degenerate. Sinful. It is a two-fingered 'fuck you' aimed straight at societal norms. It is surrendering to pure pleasure. It is freedom."

Hailey's face flushed. She felt warmth spreading throughout her body and settling in her loins. I can't believe this short, balding, older guy is getting me aroused. Nothing about his physical appearance appeals to me. Yet, here I am getting hot and wet all over again. This could be fun. Hailey reached for her tumbler, took another long sip of the ice cold cocktail, and set it back on the table. She unbuttoned her blouse, removed it, and tossed it onto the empty chair next to her. She stood up, unzipped her skirt, and dropped it on top of the blouse. Only her sheer bra, thong panties, and high-heeled shoes remained. She sat down, crossed her legs, and took another sip of her drink. She set it down, and then grabbed a lock of long brown hair and kneaded it between her thumb and forefinger, and then twirled it with her finger.

Hailey recrossed her legs and then dangled her shoe off her tanned foot. She stared into Ian's eyes and dipped her finger into her tumbler. Hailey and then touched the tip of her finger to her lip. Ian shifted his weight on the sofa. Hailey glanced down at his lap. His cock twitched and swelled perceptibly. It straightened and stiffened under her watchful gaze. Got him.

"What I think I'm hearing, Ian, is that you're a filthy pervert," Hailey said. "Did I get that right?"

"That is partially correct," he answered, "but it's not the entire story."

"Tell me more," Hailey cooed. "Tell me what I'm missing."

Ian stared at Hailey's rigid nipples poking through the sheer fabric of her shelf bra. He inhaled deeply, taking in first the scent of Hailey's perfume, and then beneath that the aroma of her rapidly moistening crotch. It occurred to him that his words combined with the alcohol were having the desired effect.

"Engaging in sexual acts that society generally frowns upon is exciting, I won't deny that. Whether it is the partner, the place, the time, or the act itself, breaking the rules is a huge turn on. I don't consider anal sex a perversion, but most people do. Confounding their expectations is a stimulant that elevates the sex and makes it more pleasurable--for me, at least, and for my partner as well, I hope.

"But there's more. I am also obsessed with the female bottom. The shape of it, the feel of it, the smell of it, the taste of it--I can't get enough. Some men are breast men, some are leg men--I'm a butt man. Worshipping a woman's ass, penetrating a woman's ass, making love to a woman's ass--that is my ultimate pleasure. The fact that it is a taboo subject only makes it better."

Hailey stood up, reached behind her back, unclasped her bra, and tossed it on the pile with her skirt and blouse. She cupped her hands under both breasts, lifted them off her chest, and the let them fall back into place before returning to her seat on the sofa.

Ian whistled under his breath.

Hailey glanced at his cock and noted that it was fully erect. She felt a wave of warmth flow through her body. She squeezed her thighs together, creating pressure on her clit. Another warm wave cascaded from her loins to her brain.