The Closer: Ch. 01

"You have beautiful breasts," Ian said.

"Thank you," she replied. "They're all natural."

"I can see that. No surgeon has ever been so skilled. They are works of art."

Hailey felt the heat rising inside herself once again. He has to smell my arousal by now. I'm so wet. He can probably see the wet spot on my panties.

Hailey kicked off her shoes, stood up and peeled her panties to the floor. She stepped out of them, using her bare toe to slide them toward the chair with her other clothes. She turned her ass toward Ian and bent at the waist.

"Do it, Ian. Worship my ass. Convince me to take your cock. Make me want it."

Ian's lips spread into a smile. He guided Hailey to the sofa and helped her to a kneeling position with her face pressed against the leather cushion and her ass sticking up in the air. He kissed each of her butt cheeks, and then planted a kiss on her anus. Her asshole winked at him involuntarily.

"You have a beautiful ass," he said. "But that comes as no surprise. You are a beautiful young woman. Michelangelo could not have created a more perfect body."

Ian spread her cheeks and lowered his lips to her anus. He planted light kisses on her asshole and on the sensitive flesh just above and below it. He pushed his nose between her round ass cheeks and kissed up and down her butt crack, pausing for a second before each kiss on her anus. He tapped her clit with his index finger. He stroked, flicked, poked and caressed it until he got the response he was seeking.

"Mmmm, that feels nice," Hailey cooed.

Ian licked up down the crack of her ass. He paused and swirled his tongue around her anus, then rolled and stiffened it and pushed against the tight ring.

"Oh," Hailey gasped. "That's different. I think...I think I like it."

Ian continued to stroke her clit with his finger while using his tongue to probe her anus. He felt the tension releasing from her butt cheeks. He saw the arch in her lower back increase by degrees as her hips rose higher into the air and she pushed her ass against his face.

When he felt that her physical need had reached the appropriate level, Ian placed his index finger against Hailey's anus and slid the first digit into her ass. Her sphincter opened for the fingertip, allowing access for a brief second before tightening against the invader.

Ian slipped two fingers into Hailey's juicy pussy. His fingers slid into her welcoming canal, producing a moan from deep inside the woman's throat. He slid the two fingers in and out of her slick canal. When her hungry body responded to the thrusting he pulled his finger from her asshole, leaving just the tip held in place by the gentle pressure of her sphincter. He pushed it back in, matching the rhythm of the two fingers sliding in and out of her pussy.

"That's feeling good," Hailey purred. "You're going to make me cum."

Ian maintained a gentle, leisurely pace, working Hailey's pussy and asshole with his fingers, while he rubbed her clit with his other hand. With measured patience he worked his finger a little bit deeper into her anus, pushing it past the fading resistance with each thrust. When he felt the ring of muscle attain maximum relaxation he removed his finger, spit into her asshole, and then resumed penetrating her anus with his index finger.

"I can't believe I'm saying this," Hailey cooed, "but that feels really, really, good."

"It's supposed to," Ian replied.

"Don't stop," she said. "I'm about to have my first anal orgasm."

Ian increased the speed of his thrusting fingers by just a little. Hailey reacted instantly, thrusting her ass backward to meet his probing fingers and drive them deeper into her cavities.

"Ugh! Mmmmmm," she moaned. "That's sooooo good."

Ian withdrew his fingers from her pussy but continued fingering her asshole and flicking her clit. Hailey bucked her hips and shook as the orgasm wracked her body.

"Ungh! Ooooo! I can't believe... mmmmm," she grunted. "I'm... cummmmming."

Ian pulled a bottle of lube from under the sofa. He applied a generous amount of the clear, slimy gel to his cock, and then poured some on the crack of Hailey's ass. He worked it into her anus, then pulled out his finger and replaced it with the tip of his cock.

"Now just relax," he told her. "This might feel some pain, at first. It will dissipate, I promise you."

"Do it," Hailey said. "Do it now, before I change my mind."

Ian pressed the tip of his cock against Hailey's asshole and pushed. Her sphincter--prepped and lubed from Ian's foreplay--stretched to accommodate the fleshy invader. Hailey felt her asshole expand. The pressure on her backside grew, but it was accompanied by a strange and unexpected feeling of pleasure that seemed to flow like an undercurrent to the painful stretching.

Ian's cock was not long, but it was thick, especially at the base. The smallish head penetrated Hailey's asshole easily, but as he plunged deeper into her bowels, he felt her body's resistance increasing. He pulled back a few inches, and then resumed pushing deeper inside her.

The initial euphoria Hailey felt when Ian's cock penetrated her asshole--while she was still in the throes of orgasm--did not last long. She felt a sharp pain accompanied by an unexpected tinge of pleasure, but as the hard shaft in her ass penetrated deeper, the increasing thickness stretched her asshole beyond her expectations. She felt a moment of respite when Ian started to pull out, but it was mere moments later when his hard cock resumed probing her nether regions.

"Hold on," she panted, "let me catch my breath."

"No problem, my dear."

"You're bigger...your cock doesn't look that big, but it feels like a water bottle in my asshole."

"Believe it or not, you're fortunate that I volunteered for this assignment. The alternative would have been Eldon, and I'm told he is much bigger than I."

"Ah...you have a point. So, I suppose I should be thanking you for wrecking my asshole?"

"I promise you, my dear, I won't be wrecking anything and by the time we are finished, you will be grateful."

"That's what you say. I'm skeptical."

"Let's do this."

Ian put his hands on Hailey's hips and guided her toward him as he eased into the tub chair next to the sofa. Hailey was hovering over his lap with the tip of his cock nestled inside her sphincter.

"Now lower yourself at your own pace," he said.

Hailey braced herself on the sides of the chair and slowly settled onto the cock jabbing her from below. She eased two inches of cock into her ass before she once again felt the stretching that made her think she were being ripped in two. She pushed up, and then lowered herself another inch. Ian pinched one firm nipple between his fingers and rubbed her clit with his other hand. The sensations sent waves of electricity throughout her body.

Hailey lowered her torso one inch at a time, and then lifted herself until only the tip was remaining. She repeated this motion several times, with each successive repetition bringing her ass a fraction of an inch closer to Ian's lap. After several minutes she felt the strength in her arms giving out, and she knew where that was going to lead. After ten more repetitions her asshole was on fire, but so were her biceps. She raised her ass one more time, and then her arms gave out and she collapsed on Ian's lap with his cock impaling her asshole. She felt as though she were sitting on a tree.

Ian laid back in the chair and pulled Hailey's body against his. His cock was full embedded in her ass, which felt like a velvet vice squeezing his manhood. He cupped a full breast in each hand and sought out the stiff, rigid nipples. He rubbed them with his palms and then pressed them between his thumbs and forefingers.

"Oh, fuck," Hailey screamed.

Her body was at war with itself. Her ass was on fire, but at the same time waves of pleasure were sweeping over her body, from her nipples to her crotch and back to her brain, crossing and crisscrossing one another in a kaleidoscope of patterns. Ian thrust his thick cock upward into her asshole, and then retreated an inch. He thrust upward again, repeating a series of short strokes in and out of her butt. When Ian buried his face in her neck, Hailey's excitement rose a full notch. His teeth biting her earlobe raised it to another level. She felt as though her body were nothing but an exposed wire sizzling with electricity. She imagined sparks streaming from her orifices in a rising crescendo of pleasure.

She was not sure exactly when it happened, but after several minutes of Ian's upward thrusts the pain in her ass diminished. It never left, but it became so minimal that it was almost unnoticable. Or maybe the pleasure had increased by so many levels of magnitude that the pain was overshadowed. Either way, her body was overcome by waves of pleasure pulsating in all directions. Her asshole relaxed and accepted the cock stretching it wider than it had ever been opened before. She did not realize she was rubbing her clit, but that too sent even more waves of pleasure coursing through her flesh. She felt reduced to a network of nerve endings, all connected to her asshole and all vibrating at an insane frequency that was making her see every color on the spectrum at once.

"Fuck me!" Hailey screamed. "Fuck my ass!"

Ian lifted Hailey from his lap, stood up, and steered her to the couch. He guided her into position on her hands and knees and entered her ass from behind. There was no resistance. He asshole opened for his cock and hungrily swallowed the thick shaft. Ian buried himself balls deep in her ass and then thrust in and out of her tight anus.

"Yes! Fuck me!"

Ian placed a hand on each of her hips and squeezed. He leaned forward and pushed into her with smooth, steady strokes. He pushed until his crotch was pressed against her butt cheeks, then pulled out until only the small head remained inside her.

"Yes! Yes! Fuck me! Just like that!"

Ian increased his tempo, but he maintained a semblance of control. He was no longer gentle, but he held back just enough so as not to cross over to rough. He sublimated his own pleasure, concentrating instead on Hailey's welfare. His goal was to give her the experience of a lifetime--one that she would choose to repeat.

"Oh shit, I'm going to cum!"

Hailey rubbed her clit furiously.

"Oh shit! Oh shit! Fuck! Fuck! Fuck me! Ahhhhhhhhhhhhhhhh!"

Hailey erupted in an explosion of color. The electricity that was coursing through her body felt amplified to an infinite degree. She closed her eyes as her body convulsed in a tsunami of white light and sound. She blacked out for a second, but when she regained consciousness, she was still cumming. The last waves of pleasure washed over her body, followed by a flood of emotions. For a second she felt everlasting love for Ian, followed a second later by love for all of humanity. That feeling dissolved into a general sense of warmth and gratitude. She could not think of a time when she had ever felt more grateful and content.

Hailey collapsed on the sofa. She felt a rivulet of semen leaking from her ass and pooling in the creases of the leather upholstery. She looked up and saw Ian wiping off his shrinking cock with a wet nap. He tossed a hand towel to Hailey.

"Well?" Ian asked

"Well, what?"

"How was it? Is that something you can do again when necessary?"

"Am I only allowed to do it when necessary? Anal might be my new thing."

"What you do in your own time is entirely up to you, Ms. Andrews."

"Oh, I see. You finished buggering me and now we're back to addressing one another in formal terms."

"I'm only trying to be respectful. No offense intended."

"Ian, you just gave me the biggest orgasm I've had in my entire life. You can address me any way you want--Hailey, Ms. Andrews, mommy, slut, bitch, whore--I don't care."

"Well thank you, Ms. Andrews. Unfortunately, that went a little long. We're going to have to cut our conversation short. You have an appointment with Dr. Ramos in ten minutes."

"Dr. Ramos? Why?"

"We don't have time to discuss. You need to get moving."

"Well, this should be interesting."

"Get dressed. You don't have much time. I will have a full evaluation and programming module for you tomorrow."

"Was I that bad?"

"Not at all. But there are things to work on. Don't take it personally."

"It's hard not to."

"We all want you to succeed. That's the reason for the training. Now hurry up, Dr. Ramos is waiting."

* * *

Hailey found Dr. Ramos's office in the southeast corner of the tenth floor. The secretary, Erika, was on the telephone and waived Hailey toward the door.

"She's expecting you," Erika whispered with her hand covering the receiver.

Hailey entered the room, closed the door behind herself, and approached the figure seated behind the glass and metal desk.

"Hello, Hailey, I'm Xiomara Ramos," the slender woman with black hair and wearing a tailored suit stood up and held out her hand. "You can call me Mara. That's how my friends refer to me."

"Hi, Dr. Ramos, I'm Hailey Andrews."

Hailey took Dr. Ramos's extended hand.

"Mara. Please call me Mara."

"I'm sorry. Mr. Trant referred to you as Dr. Ramos. You're not a doctor?"

"I am. I earned my Ph.D. in finance at University of Chicago. I also studied two semesters at London School of Economics and taught two semesters at Oxford. Sometimes they call me 'Dr. Ramos,' sometimes its 'La Profesora.' They do that to annoy me. They're like little boys, sometimes. Most of them are older than me, but I still have to be their mother."

"I understand. I encountered similar behavior on the ninth floor, also."

"Like I said--boys. Enough about them. Have a seat, Hailey. Let's chat."

Hailey sat in one of the leather chairs opposite Mara's desk.

"I'm sorry I'm such a mess," Hailey apologized. "You look so crisp and clean. I look like a dirty dishrag. I did my best to freshen up before coming in here, but I wasn't given much time."

"No worries. We have kept you busy this afternoon."

"Very busy."

"How has your day been so far?" Mara asked. She fixed her crystal blue eyes on Hailey's mouth.

"Exciting. Overwhelming. Unexpected. Shocking?"

"That's understandable. Nothing could have prepared you for the events that have unfolded since your arrival this morning."

"I'm pretty worn out, to be honest. I've never had this much sex in one day. Not even close."

"I hope you still have some energy left. You have one more lesson before you're finished for the day."

"One more lesson? When? With whom?"

"Right now. With me."

"Excuse me?"

"Hailey, have you considered the possibility that person on the other side of the table might be a woman?"

"Okaaaay."

"We need to know that you can close the deal in those situations."

"But...wouldn't it make more sense to send a man? I mean, if she's a lesbian, I get it, but what if she's not? How will you know? How will I know? Isn't it more likely that the woman will be straight?"

"In some cases, yes, but our research informs us that the likelihood of a woman closing the deal is substantially higher. Women are curious, and they are just as persuadable as men when they encounter an intelligent, beautiful, and well-trained female adversary."

"I don't know."

"I'll go over the data with you tomorrow. It's getting late and we have a schedule to maintain."

Mara reached down and unbuckled her strappy black sandals. She kicked them off, stood up and removed her charcoal grey pencil skirt, followed by her pink silk blouse. She motioned Hailey to join her behind the desk.

Standing in just her matching thong panties and demi bra, Mara's face was inches from Hailey's.

"Take off my bra, please," Mara whispered to Hailey.

"No foreplay?" Hailey asked.

"I don't need any," Mara cooed. "I'm ready."

Hailey reached around Mara with both arms and unhooked the bra. Hailey inhaled Mara's perfume. The scent filled her nostrils and made her head feel light. She was hypnotized by the rhythm of Mara's breathing. She could feel Mara's breath in her face and see the rise and fall of her breasts with each inhale and exhale. She was also aware of her own heartbeat, which felt loud enough to break the windows behind them if it did not first explode out of her chest.

Hailey pulled Mara's bra off her soldiers and set it on the desk behind her. She snuck a quick glance at Mara's small breasts. They were a lighter tan than the bronzed tone of the rest of her body. The small dark areolae were tipped by thick nipples that looked like small dark pencil erasers.

"Touch them," Mara urged.

Hailey lifted her hands and touched the dark nipples with her fingertips. They felt hard as pebbles against her soft fingers.

Mara's body shook. Hailey brushed her fingers across the nipples a second time. Mara breathed audibly and tilted her head back, thrusting her small breasts up and out toward Hailey's trembling fingers.

"What do you want to do, Hailey?"

"I--I--I want to suck them."

"Then do it. I won't stop you."

Hailey bent over and kissed Mara's neck. She kissed her throat, and then kissed downward toward the smooth skin between her breasts. Mara's breasts were soft and they no longer sat high on her chest like they did in her youth, but Hailey was mesmerized. She kissed the textured skin around one nipple and then worked her way to the other. She closed her lips around the nipple and sucked.

Mara inhaled sharply, her breath an inward hiss that was music to Hailey's ears. Encouraged by Mara's reaction, Hailey sucked harder before releasing and resuming with the other nipple. She gave each nipple equal attention, alternating from left to right and back to left again.

Mara's breathing became more ragged. Her already stiff nipples were like rubbery buttons in Hailey's mouth. Hailey sucked and licked with increasing frenzy. Her senses were overwhelmed by the scent of Mara's florid perfume, the sound of Mara hissing with every breath, the softness of Mara's perfect bronze skin and the rigidity of her nipples. But most of all Hailey was enthralled by the fact that this beautiful, powerful, intelligent, sexy woman was responding to her--Hailey Andrews. Her excitement was spiraling out of control.

Encouraged by Mara's reactions and driven by her own lust, Hailey bit down on the firm nipple nestled between her teeth.

"Ouch," Mara whispered.

"I'm sorry," Hailey apologized.

"Don't be. I didn't say I didn't like it."

Hailey released the nipple and migrated to the other side. She closed her teeth around it and sucked it deeper into her mouth. Her teeth scraped against the top and bottom surfaces of the fleshy nub. Mara's body trembled.

"Well," she cooed. "It seems that my little kitten is hungry. I guess it's time to feed you."

Mara took Hailey by the hand and led her to the white leather sofa on the opposite side of the office.

"Take off my panties," Mara instructed.

Hailey placed her hands on Mara's slender hips and located the thin strips of elastic and satin connecting the front and rear triangles of fabric. She lowered herself to her knees and pulled the material down with her. She took a good look at Mara's smooth bronze belly, noting for the first time the silken pattern of stretch marks that did not seem to detract from her beauty in the slightest.

She found herself at eyelevel with Mara's shaved pussy. Her puffy outer lips were separated by the delicate gray inner lips that protruded from within. The fragrance wafting to her nose caused Hailey's mouth to water. She pulled the panties to Mara's knees and then let them drop to the floor.

Mara lowered herself to the sofa and sat back, crossing her legs almost as an afterthought.

"I was going to have you keep your clothes on," she teased, "but that wrinkled, cum-stained suit isn't as much of a turn-on as you might think it would be."