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Executive Coaching Jenna

Executive Coaching Jenna

by sordida
19 min read
4.63 (36000 views)
adultfiction

"And that is why," Michelle said, "the successful female executive must be in full command of both her personal and professional personas. She must achieve balance in both those spheres to be the best version of herself." She turned towards the crowd, who followed her with rapt attention. Her gray eyes surveyed their faces, identifying those she felt were of most interest. "That concludes the lecture on executive thinking. For those of you who wish to enroll in my personal coaching program, you can submit your forms to my assistant Samantha," she said, pointing towards the short gray-haired woman in the corner of the room. "Thank you so much for attending."

Smiling at the applause, she adjusted her shoulder-length blonde hair and stepped back to retrieve her shoulder bag. Michelle was a tall woman, thirty-four years old, about five foot ten, dressed in a sharp business skirt and blouse, with chiseled features. She'd had considerable success in her youth after launching and selling a startup that helped women manage their professional goals and careers. Now she worked alone, coaching the elite young businesswomen of the world.

Her process for choosing students was highly selective, because her coaching methods were... unorthodox, to say the least. And she preferred a certain type of student.

"Excuse me, Ms. Headley?" Michelle turned around to face a young woman with dark black hair and slender, Asiatic features. She was about five foot four, with a slim waist but large, perky breasts for her frame, barely concealed by the plunge of her blouse. She was probably in her mid twenties. "My name is Jenna Cho, I work as a publicist. I'm a huge fan - I've read all your books." She extended her hand.

Michelle's initial reaction was irritation, of course, as she had instructed people to speak to her assistant. But her cold, hawkish eyes noticed the woman had a wedding band on her hand. And she noticed further, the piercings of her nipples poking through the pale fabric of her blouse. "I see. Well, that's quite flattering, Jenna," Michelle said, shaking the girl's hand. "I'm afraid I'm not doing autographs right now, but if you want to find out about a signing, my assistant can help you with that."

"Oh, I'm not interested in a signing. I want to be in your coaching program." Her dark eyes sparkled, and her mouth crinkled around the mole on her left cheek. "I've applied many times, but I've always been rejected. So I wanted to make a personal appeal to you."

Michelle sighed. Of course she wanted to. "Look, the process is pretty complicated. I can't accept just anyone. And I really should be going..." She turned around, bending over to display the tight fit of her skirt around her arse as she picked up her computer. "Nice meeting you, though," she said, brushing the girl's arm slightly as she turned to walk away.

"Ms. Headley!" Jenna called out. Michelle stopped, sure not to turn around too early, before finally looking back. "Let me make a real push for it. I work in publicity for the restaurant Melodia. I know you've tried making reservations there many times." She smiled, and Michelle felt something flicker inside her core. "I can get you dinner there tonight. Bar seating, but it's still great."

Michelle pursed her lips. "A young woman like you with that kind of pull? How am I supposed to believe that?" The crowd was filtering out now, and she needed to confer with Samantha about her schedule for the next two days.

Jenna shrugged, a mischievous grin still plastered to her lips. "Meet me there at eight. You won't regret it." She turned and walked out the door before Michelle could respond, her wedding band flashing in a ray of sunlight that streamed through the window, black jeans fitting tightly around her tight ass.

Michelle smirked. This girl was an interesting prospect, without a doubt. "Samantha," she said, walking over to her assistant, who looked as harried as she always did, "cancel my dinner plans. I'm going to Melodia tonight."

#

Melodia was one of the many aggressively chic places that littered Manhattan. Michelle had been trying to get a reservation here for a few months now, but it was quite difficult, even though she was a famous author. To her great surprise, she was seated almost immediately. Dressed in a sleek blue dress that accentuated her ample bosom and slender hips, she ordered a glass of white wine while she waited for Jenna.

Jenna was definitely Michelle's type: married. Michelle's sexual appetite was restricted almost entirely to married women. She especially enjoyed women who were married to men. She considered it one of her favorite hobbies - seducing a supposedly straight married woman, the forbidden fruit, was much more delicious than any other sexual encounter.

Jenna appeared from the back of the restaurant. She was wearing a tight black dress with cutouts that revealed her hip bones and shoulders, and she looked positively delicious. Michelle quite wanted to see what lay under that dress, but she also knew how to be patient. She composed herself, comporting a professional demeanor. "You're a woman of your word, Jenna," she said, clicking her tongue. "I must say, I'm impressed. You must tell me how you swung this, and how you knew I wanted to come here."

Jenna laughed as she sat down and called over the waiter. "My husband owns the restaurant." She wagged her finger at Michelle. "He's thirty years older than me, and I'm reaping the benefits."

Michelle almost licked her lips. Yes, she was the perfect quarry. "I see. I suppose I should have been able to figure that out. I did take a look at your applications, by the way." She took a sip of her wine as Jenna ordered a gin and tonic. "I think I know why you weren't called in for an interview."

"Oh?" Jenna said, raising her eyebrows. Bread and olive oil was delivered to their table, their scent tickling Michelle's nose pleasantly. "Why is that, Ms. Headley?"

Michelle leaned back, choosing her words carefully. "The truth is, my program is very demanding. Your resume is certainly impressive, but professional success is not enough, I'm afraid. You need to be open-minded. Willing to experiment."

Jenna frowned. "I don't understand. Is this some sort of political thing?"

Michelle folded her hands together, leaning forward. Jenna's perfume wafted across, rich and floral. "Not at all, actually. I am referring to your sexual inclinations." Michelle turned to the approaching waiter. "I'll have the oysters, thanks."

Jenna was staring at her, mouth slightly ajar. "What does my sex life have to do with executive coaching?"

The blonde laughed. "Why, everything, of course. My philosophy is the alignment of personal and professional lives. Your sex life is an integral part of who you are. A woman without a fully libertine, experimental and satisfactory sex life will never succeed as an executive."

"You're joking, right?" Jenna giggled awkwardly, though Michelle could see the fear in her eyes. This was what she enjoyed the most - the hunt. "You're an executive coach. You don't need to go over sex."

"Sex is everything for a professional woman." Michelle took a long sip of her wine, dragging her tongue across the rim of the glass. "I myself enjoy a picturesque sexual lifestyle. Regular sexual experimentation is an enormous part of my success as both a businesswoman and an author." She smiled faintly. "Does this frighten you, Jenna?"

"I... I don't know, it's just," she said, her cheeks flushed as she tried to find her words. "It's not what I expected. I just wanted to talk about professional coaching."

Michelle nodded understandingly. "I do know what you mean. That's why this isn't for everyone." The oysters arrived. "Do you want one?" Jenna shook her head and Michelle took an oyster. She slurped it out and licked her lips as deliberately and luxuriously as she could. "All I am asking of you is to keep an open mind and be willing to work with me on all parts of your life. Including your sex life."

Jenna's hands curled around the edge of the table, but her eyes were fixed on Michelle's mouth. "What would you need me to tell you?"

Michelle reached into her bag and pulled out a notebook. "This book is your sexual diary. Write in here all sexual experiences, from dreams to fellatio. Do this for two weeks. Then we can review it at our first coaching session."

"I don't know."

"That's quite all right." Michelle shrugged. "I am traveling the next two weeks, but when I get back, you should give me a call if you're still interested. If you've done what I asked, I will coach you."

Jenna's face darkened as she took the notebook. "This is... so weird. I'm going to go. The dinner's on me. Enjoy your meal." She got up and walked away briskly. And Michelle might have considered her a lost cause, but the girl did take the notebook. And Michelle's contact information was inside.

She continued slurping down oysters, wondering how Jenna's cunt tasted.

#

Jenna called Michelle exactly fifteen days later. They agreed to meet at Michelle's office for a coaching session. "And did you do your homework?" Michelle said, laying back on her bed in a nightgown, her fingers idly flipping her left nipple.

"I'll see you there," Jenna replied curtly.

"No, I need to hear and understand that you've done your homework beforehand, or else this will be a complete waste of time."

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There was a pause. "I took a record of my sexual activity over the last two weeks."

"Read it to me." Michelle's hand started to slide down her torso.

"Monday, July 12," Jenna said, her voice halting and fearful. "I was tired after work and my husband wanted oral sex. I resisted for a bit but I decided that I might as well give him a blow job and keep him satisfied."

"So you went down on him? Did he finish?"

"Yes. In my mouth." Jenna's voice grew strained. "I swallowed."

Michelle imagined a man thrusting his cock into Jenna's small mouth, her shapely lips, splattering his semen over her face and down his throat. Her finger teased out the hood of her clit between her legs. "And how did you feel after?"

"Tired. Unsatisfied. I washed up and went back to work after that. I didn't go to bed until late."

"Okay. Continue."

"Wednesday, July 14. I initiated sex with my husband when he came to my office for lunch. He didn't seem that into it, but I sucked him until he was hard and then I rode him."

Michelle began to rub her clit with the heel of her hand as her fingers hooked their way inside of her labia. She tugged at her nipple with her other hand. "And how was it?"

"It was fine." Hesitation. "It was all right."

"Did you orgasm?"

"No." Jenna sounded tired. "I don't know if I want to keep doing this."

Michelle's body quivered as she spread her legs, the slickness between them dampening the sheets beneath her ass. "No, keep going. Do you usually top your husband?"

"Yes. He doesn't like riding me."

"Why's that?"

"I don't know."

Michelle's breath was shallow as she exhaled into the microphone. "Keep going."

Jenna's voice wavered. "My husband traveled that weekend. I didn't have any sex the whole weekend. I was busy with work and I had plans with one of my friends. On Monday, July 18, my husband had to extend his work trip and I was feeling sexually frustrated. So I self-pleasured."

"Good," Michelle whispered, almost moaning into the phone as she pumped her fingers in and out of her cunt. "The professional woman should self-pleasure frequently. Daily, ideally, though at the very least on every day she isn't having sex."

"Really?" Jenna said. "Are... you sure?"

"Of course," Michelle said breathily. "I schedule time for self pleasure during my work day. It's critical for performance."

"Are you... right now?"

Michelle grinned as she rolled over, going on all fours so that her thumb could reach around to massage her perineum. "Perhaps I am. Do continue, Jenna. We're making progress."

A long, pregnant pause. Then she spoke again, and this time, Jenna's breath hitched a bit. "I used my vibrator. Normally, I would read some smut but this time I watched pornography. Lesbian pornography."

"Do you watch that often?" Michelle grunted, pleasure seeping through her loins as she stroked her thumb across her perineum.

"No. I usually only watch straight pornography. But I watched lesbian pornography, and I enjoyed it. I masturbated myself to orgasm three times."

"Tell me about the women in the video."

Jenna's voice came in short bursts now. "Blonde and a redhead. My friend I went to dinner with... on the weekend... redhead. Later that week, my husband was too tired for sex. So on Friday, after dinner, I..." She moaned loudly. "I watched lesbian porn again. And masturbated.

"The girls this time?" Michelle's thumb probed her rosebud as her fingers pounded away at her pussy, dripping onto the bedsheets.

"Blonde... Asian... blonde on top... oh fuck," she said, her breath rising into a shriek.

Michelle, with all the control of an expert, squeezed her clit in between her fingers and rubbed it rapidly, driving herself to orgasm as well. It was a tight, fast one, shooting through her cunt and into the bottom of her belly, bringing her knees down and laying her flat on the bed. She exhaled into the phone sitting on her pillow, her cheeks flushed with release.

"I'm looking forward to our appointment tomorrow, Jenna," she said, smiling.

Silence. Then, Jenna spoke. "Likewise." The call ended.

Michelle rolled over on her back. She'd completely ruined her new nightgown.

#

Michelle's office was in a high rise, with views overlooking downtown Manhattan. Seated in a comfortable leather chair, hands folded upon the mahogany desk, the blonde surveyed the younger woman seated across from her. Jenna was dressed conservatively, in a dark blouse and gray slacks, and she affected a nervous air. Still, Michelle's nostrils flared a bit as she detected a whiff of arousal in the air.

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Hers or Jenna's, she wasn't quite sure.

"Thank you for coming in today, Jenna," Michelle said, a small smile forming across her lips. "How are you doing?"

"Quite well," Jenna said. Her dark eyes narrowed and she leaned forward. "I want to make it clear that I don't intend to do anything that would be considered infidelity for my husband. I am here to improve my skills as a professional executive."

Michelle laughed and leaned backward, her earrings clicking as she surveyed her buttoned up charge. Oh, this would be a fun exercise indeed. "Of course, of course. We're here to improve your skills. Now tell me, are you facing any challenges in your current work?"

Jenna's lips parted in apparent surprise. "Oh! Okay, yeah, so, um, there's this girl, Britney, she's one of my new reports. She keeps coming in late and doesn't respect me during meetings. She talks back and I don't know how to make her understand that I'm her boss and she needs to respect me."

Michelle examined her fingernails and then slowly raised her gaze back up to meet Jenna's. "Have you tried disciplining her? I don't let young women talk back to me. I enforce rules in my workplace."

Jenna sighed and tossed her dark hair back on her shoulder, revealing the flushed, pale skin of her neck. Michelle shifted her legs as she admired a small, dark mole that poked out on Jenna's clavicle. "I mean, I tried. I gave her a shitty task and tried to get her in for a disciplinary chat with my boss, but none of it's working. Her uncle is on the board, so no one wants to do anything to her."

Michelle's eyes flashed, ice cold, and she could see Jenna collapse in on herself, her body responding to the power exuding from the older blonde. Yes, this woman would collapse under her hand. "That's no way to discipline a mouthy little bitch like that. But I can show you how."

"How?" Jenna's voice was a squeak.

Michelle pulled out her chair, away from the desk, and smoothed down her skirt. "Stand up in front of me." Jenna stood up and walked over, her dark eyes wide and enthralled. "Now, take off your blouse."

"What?" A petulant whine.

"You heard me."

Jenna's fingers moved slowly but decisively to the buttons of her dark blouse. "I won't take off my underwear," she whispered.

"You won't need to. Strip." Michelle spread her legs under her skirt, feeling warmth spark in her loins. Jenna unbuttoned her blouse, revealing her pale torso and considerable breasts. Jenna's skin was flushed, with dark spots that stood out attractively. Her bra was pink and lacy, giving a silhouetted glimpse of her nipples, already puffy and aroused. "Take off your pants."

Jenna grimaced, but her eyes glanced down demurely, cheeks burning crimson as she unzipped her slacks and let them fall to her ankles. She stepped out of them and her flats, revealing delicate feet with red painted toenails. Her panties were lacy pink to match the bra, puffed up by a considerable mons. Dark hair peeked out from the edges of the cunt wrapper. Her legs were muscular and toned.

"You sloppy, unkempt slut," Michelle drawled, a hand snaking out to grab Jenna's wrist and dragged her over to the chair. Jenna yelped but offered no resistance as Michelle laid her over her lap, ass out. Jenna had a tight, firm ass, and Michelle enjoyed leisurely dragging her over its contours. "You come to the workplace with that nasty bush in your pants? Have you no shame?"

Her hand came down lightly on Jenna's left ass cheek.

"Ungh,"

Jenna said, squirming a bit. "I'm sorry! My husband doesn't care. He's barely interested in me."

"You don't serve your husband in this office, slut," Michelle said. "You serve me." Another hand, on the other cheek, harder this time. Jenna yelped. "Next time you shave it. Nothing more than a landing strip, at most." She dragged a fingernail down the globe of Jenna's ass, trailing through the thin, dark hairs that lined her valley. The musk of Jenna's arousal was rich now, the dampness soaking from her cunt through her panties.

"Now, you suffer. And learn the lesson of your disobedience."

Jenna bit her lip. "Yes... ma'am."

"Count." She brought her hand down on Jenna's ass with a loud smack.

"One!" Jenna counted.

Smack.

"Two!"

Smack.

"Three!" The spanking continued, each smack ringing through the office, mixed in with Jenna's shrieking and yelping. By the time they finished, with a final, pained cry of "Twenty!", Jenna's pale butt was a fiery red, little nail scratches right down the round globes, and her face was a tearstained mess.

"Get the fuck up, you worthless whore," Michelle ordered. Her fully broken girl stood to attention, wiping away her tears. "Hands behind your back. Turn around so I can admire my work."

Jenna whirled around and did as she obeyed. Michelle stood up behind her and laid her hands on her ass, then reached around to cup Jenna's cunt over the fabric of her underwear. Jenna moaned, shifting her body into the fully clothed, taller woman. "You sure you don't want to take off these filthy, stained, panties, and fuck your brains out, pet?" Michelle whispered, her teeth nipping lightly at Michelle's earlobe.

"I can't," Michelle whined. "Not... not now. Not yet."

Ah, she was weakening. "Very well," Michelle said, releasing the woman and going back to sit on her chair. Her own panties were soiled as well. "Get dressed, Jenna. Today's session is over."

Jenna began to dress, her cheeks and bosom still flushed. "I don't understand."

"Understand what?"

"All of this," she said, buttoning up her blouse. "What this lesson was. Why I... let you do that. Why I..."

"Enjoyed it?"

Her face was beet red. "I... I don't... yes, but..."

Michelle raised a dismissive hand. "Don't overthink it. Use what I taught you on that brat."

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