Executive Coaching: Sophie

Author's note: Stories in this series are standalone unless I indicate otherwise. This is part one of a two part standalone story. I know there was a lot of interest to see more of Jenna and her subordinate, and I appreciate the passion, but for now you'll have to wait. I do hope to bring Jenna back in a later story, though.

Here's a quick blurb covering Michelle, our executive coach, for new readers.

Michelle Headley is a tall woman, thirty-four years old, shoulder length blonde-hair, about five foot ten, with chiseled features. She had considerable success in her youth after launching and selling a startup that helped women manage their professional goals and careers. Now she works alone, coaching the elite businesswomen of the world. However, her coaching methods are a little unorthodox, and she goes the extra mile to provide a personal touch to her clients.

It had been a while since she'd been called in on a consulting operation, let alone one so unusual, but Michelle went where the money was paid and Appleton Preparatory was paying handsomely. They had even set her up in a beautiful office studio just off campus, which overlooked a beautiful stretch of rural Carolina hills and forest.

She looked up from her laptop as the door opened. "Mrs. Southam is here for her appointment," Michelle's assistant Dani announced.

"Let her in," Michelle said, rising and walking across the room. Michelle was wearing stylish black slacks and a white blouse today, with little dolphin earrings.

Mrs. Southam walked inside and Dani closed the door behind her. Mrs. Southam was a woman of medium height, maybe five foot five inches, with short, curly brown hair and light green eyes. Her thick full lips neatly highlighted her slightly rounded face. Wrapped in an unflattering pantsuit, it was hard to tell but Michelle estimated the woman had a curvy figure with a larger than average posterior. She was in her late forties or early thirties, but her skin looked good for her age, and she was in decent shape from what Michelle could determine.

"Nice to meet you," Michelle said, extending a hand to her. "I'm Michelle."

"Sophie," the woman replied, a hint of nervousness in her eyes and her hand shake. She had a strong Southern accent. "I have to admit, Ms. Headley, I am a tick unsettled by all this. It hardly feels necessary."

"Just call me Michelle, please. And have a seat," Michelle said, gesturing at the sofas. She took a seat on one herself and waited as Sophie sat down. "Dani's going to bring us some wine. White or red?"

"Oh, I don't know if I should drink, I might have to go back to work," Sophie said.

Michelle smiled firmly. "No, your schedule has been cleared for the next four hours. You'll stay here, and you'll have a glass of wine with me."

Sophie's shoulders slumped as she sunk into the sofa. "If you insist, white'll do fine, thank you."

Michelle pressed the button on the side desk, summoning Dani. "Now, I think you know why you're here, but I don't think you know who I am."

"You're an executive coach," Sophie said, frowning. "But that's all they told me."

"I'm a very special executive coach. Often I work with women in business, but as principal of one of the most elite preparatory schools in the country, you qualify as an executive. And it seems, unfortunately, that while your first five years of tenure here were quite successful, the last year has been a little troublesome."

Sophie's cheeks, pale and drawn out, flushed, and Michelle could see a trace of the former Southern beauty queen in here. She'd read Sophie's entire personnel file and done a background check, so she knew quite a bit about her client. "I suppose this is about the incident with Ms. Marsh."

"Allison Marsh, the equestrian instructor, yes?"

"Yes." Sophie shuffled her feet as the wine glasses were brought in. "Thank you, honey," she said to the young assistant, before taking a sip. "Well, I suppose you know I slapped her, but that ain't the whole story."

Michelle took a sip and set her glass down on the coffee table. She folded her hands together and leaned forward. "Do tell me the whole story."

"Well, she's been a right pain in the behind all year, tell you the truth. She's been posting all these skimpy bikini pictures on the socials and all, and the kids see them and it's disgusting. There's no respect. The boys are all telling dirty jokes about it and the girls want to dress that way." She shook her head. "Part of our message at this school is modesty and good, decent Christian values. We can't have a teacher do these things. Anyhow, I was telling her off in my office one day and she got in my face and called me..." Sophie paused, anger flashing in her green eyes. "Called me a fat prude. And I slapped her."

"I see," Michelle said. "It's interesting you feel that way. Weren't you a model, when you were her age?" She dropped a folder on the table, popped open to several pictures of a young Sophie in a stunning lacy purple and green lingerie set. "You don't feel hypocritical?"

Sophie grew redder. "Well, that just ain't fair. It was a long time ago, and I don't do that any more. It's not appropriate."

Michelle raised her eyebrows. "Why don't you do it anymore? I think many people would enjoy seeing you dressed that way."

Sophie spluttered wine. "I... I... I don't even own underwear like that anymore."

"Why not?"

"My husband..." She paused and scowled. "Seems you've done your research. You already know, I'm sure. We've been separated about a year. And he hasn't looked at me even longer. Even though I lost the baby weight after our third kid, he just..." She crossed her arms. "I don't need to tell you all this. It ain't your business."

"I believe it is. All of this is my business. You see, I don't think you slapped that young woman because she called you a fat prude." Michelle smiled and took a long sip of her wine. "I think you slapped her because she's wrong. You're not a prude. Inside of you, there's a slut."

Sophie's face twitched. She placed her wine glass down on the table. "Excuse me? Who do you think you are, to be talking to me this way? Some hoity toity consultant down from New York comes to my school, and calls me a slut? I'm out of here." She stood up and grabbed her bag.

Michelle sighed. "You know just as well as I do that if you don't complete your coaching to my satisfaction, the Appleton family will fire you. So please, don't play games with me." She gestured to the sofa opposite of her. "Sit down, please."

Sophie glared at Michelle for a moment, but eventually tossed her bag down and sat on the sofa. Michelle refilled their wine glasses. "I don't like that word, Ms. Headley."

"I'm afraid that I'm going to use it a bit more." Michelle sat up straighter. "You've never read any of my work, but SLUT is actually an acronym for one of my most important principles. Sexual Liberation Unlocks Talent. Do you know what that means?"

Sophie rolled her eyes. "I ain't interested in your fancy schmancy self helf bullcrap."

"It means," Michelle said, gritting her teeth, "that your potential as a professional woman can never be achieved unless you are sexually liberated and satisfied. You might be a good Christian woman, but you need to be sexually active, and sexually fulfilled. Otherwise, I'm afraid events such as this will continue to happen, and your career will peter out."

The principal stared at Michelle, agape. For a moment, there was silence. Then she took a long, hefty swig of wine and held her glass out for more. Michelle obliged her. She took a quick sip and wiped her mouth. Then she spoke.

"What makes you think I ain't... satisfied? You don't know me."

Michelle laughed and crossed her legs. "I know women, honey. When was the last time you had a fuck?"

Sophie winced. "Please, don't be so crass." But her legs shifted outwards.

"When was the last time you had a fuck?" Michelle said, harsher.

"Please--

"When... was... the... last... time... you had a fuck?" Michelle shouted the last word.

"Two years ago!" Sophie blurted out, tears sparking in her eyes.

"Do you masturbate?"

"I... it's sinful, but I've tried. I can't seem to get any traction."

Michelle nodded, satisfied with her answer. "Have you had a doctor check you for dryness?"

"No... it doesn't seem to be the issue. They reckon it's psychological." Sophie's face was red and she looked at the ground. "Truth is, I never masturbated before this year. I was a good Christian girl growing up, and I had a phase... I wasn't a slut, but..."

Michelle waved her hand impatiently. "Yes, yes, I understand. Continue." The sooner the woman came to terms with her inner SLUT, the sooner they would make progress on her career goals.

"Anyway, I turned back to Jesus and I met my husband. And we've been together thirty years. So I never really turned to self-pleasure. Besides, it's a sin."

Michelle leaned forward. She dropped her voice to a harsh whisper. "The fact of the matter is, you can't serve your Lord if you're unemployed. You have three kids. In my professional opinion, an executive woman like yourself needs to orgasm once a day, more if she can get it."

Sophie blanched. "Oh... oh my. Is that really true? I just don't know how I could find a man so quickly. Our divorce isn't settled yet. And I won't... I won't sleep with another man until then."

"You're not going to sleep with a man. In fact, I suspect you don't want to. Tell me, how often did your husband make you come?"

Sophie drained her wine. Michelle buzzed Dani to bring in more. This was going quite well. "I don't understand how that's relevant..."

"Answer the question."

She was pale. "I... he hasn't. In ten years. Barely ever, before then."

This poor, poor woman. Michelle was going to change her life. "Sophie, I cannot overstress the severity of your situation. You must learn how to masturbate to orgasm, or your career will be over."

Sophie's fingers trembled on the wine glass stem. "I wouldn't know where to begin. I just can't seem to feel... sexy... anymore."

"I think I can help with that. Follow me." She rose and started walking, pleased that Sophie didn't hesitate. They walked down a hallway and through a door, which Michelle held open for her. "Come inside."

Inside the room was a television, a desk and chairs, a large box, a small cot, and a sheet of glass dividing the cot from the rest of the room. "As you can see, the glass is frosted on this side," she said, waving her hand in that direction, "and there's a cot for you to lie on if you would like that."

"Uh, for what?" Sophie said, a bewildered look on her face.

"You're going to go behind that glass and masturbate, of course." Michelle smirked. "Unless you don't want the privacy. That would make it much easier for me to instruct you."

Sophie yelped. "No... I mean, no, I don't think I can... isn't there a book or something I could use instead? I ain't comfortable with this."

"I'm afraid I need to monitor and ensure you orgasm before I let you finish this session, Sophie," Michelle said, taking a seat at the desk. "Now, trust me when I say this, Sophie, you'll feel much better after you've had a proper orgasm."

Sophie clutched her bag, and looked between the TV and the door. "And if I refuse?"

"That's your right. I'll tell the Appletons I can't help you." Michelle shrugged. "And then it's up to them."

Sophie swallowed. She threw her bag down on the ground and walked behind the glass. She lay down on the cot. "What do you want me to do?"

Michelle grinned and leaned back in her chair. She unzipped her slacks and dropped them to the floor. She slipped a hand into her panties. "Show me how you masturbate, normally."

Sophie shifted her big ass onto the cot and unzipped her trousers, sliding them down to her knees. She shifted a hand in between her legs and began to rub, slowly, methodically. "I usually lie down like this," she said, grunting a bit as she pushed inward. The smell of her cunt filtered into the room, her silhouette struggling to get comfortable.

"What do you imagine?" Michelle said, rolling her clit around in her thumb.

"A man, entering me. Making love to me."

"Are you stimulating the clitoris?"

"Yeah, I think so. The little nub, I read about it online." The shadow grunted and began to rub harder. "Didn't learn about it in school."

Michelle rolled her eyes. The South was such a wasteland. She was already decently lubricated, and while she could smell vague hints of arousal, as Sophie continued, there didn't appear to be any progress.

So Michelle clicked the TV on.

"What the heck?" Sophie said, stopping her movement. The TV was displaying a slideshow of images Michelle had taken from Allison Marsh's Instagram. Very revealing photos, proper thirst traps, of Allison in various skimpy bikinis and lingerie, often in provocative poses. "Why are you showing me this?"

Michelle's nose twitched. "Don't lie to me. I can smell your cunny all the way from here." Sharp and untapped, as if broken from a new dam. "Keep rubbing and look at the girl. Think about your anger."

To her surprise, Sophie stood up, with her ass towards the screen. Michelle licked her lips and slid a finger inside of herself, increasing the pace of her own stimulation. Sophie was grunting, moaning, panting, the slickness of her pussy loud and squelching. Her cunt smell was overpowering, dominating Michelle's.

"That stupid, stupid, goshdarned brat. Wearing those slutty clothes. Indecent," she mumbled to herself. "Walking around like a tart. Whale tail thong. Just begging for me to pull them down." She paused momentarily, her ass cheeks pressed against the glass, as though she'd just heard what she'd said. "I don't know what this is, Michelle."

Michelle let out a little moan. "Just go with it, Sophie. Are you close?"

"I'm closer than I've ever been. But I can't seem to finish."

"Have you ever tried one of these?" Michelle said, sliding a curved vibrating dildo underneath the screen, pulled from her box of toys. "Some women are toy sluts. I think you might be in there."

Sophie's barriers seemed to be dropping, as she immediately grabbed the tool. Growling as she pushed it inside of her, Sophie squatted and let out a long, trembling cry. "Oh Lord, please forgive me. I can see the horizon." Her plain white panties were around her ankles, visible beneath the screen.

Michelle pulled her own dildo out and began to pump it inside of herself, her panties now down at her ankles to match Sophie's. "Go on, come slut. Tell us who you're coming for. We both know who it is."

"Fucking... goddamn... Allison Marsh!" Sophie bellowed, bent over. "Allison fucking Marsh! Fuck me! Lord no, I can't stop!" she shrieked, each word punctuated by a squirt of fluid from her cunt, splattering and staining the glass. Exhausted, she fell over onto the cot, leaving a massive smear in the shape of her curvaceous ass upon the glass.

Michelle's orgasm was quick, fast and satisfactory, marked by a rising chill cutting through her body and a short yelp. "Good," she said, as she wiped down with a napkin and zipped up her pants. "How do you feel, Sophie?"

"I... I feel amazing. Lighter than I been in years. Can I keep this thing?" Her shadow waved the dildo. "I am confused. I don't understand... my desires."

"Your desires are natural, and will become clear to you in time. Continue masturbating daily, whenever you get the chance. And of course you can keep the toy." Michelle stood up and smoothed her hair. "There's a washroom in the back here, so feel free to clean up before you leave. I think," she said, leaning at the door, "I can sexually liberate you in just two more sessions. But only if you do exactly as I say."

A moment of silence. Then a sigh. "I'll do what you say."

"Masturbate daily and email me a log of your experience before our next session. Location, fantasy, method and time to orgasm. And get me Ms. Allison Marsh's complete schedule. I already get yours sent to me." This was a boarding school, so Michelle was fairly certain she could find out where Marsh was at all possible times. "And I'll let you know what to wear ahead of next week's meeting." She laughed. "Have a nice rest of your week!"

She closed the door, affording her client some privacy. But it would not be a long break.

#

Sophie's Log: Day 1

I put the kids to bed around 9PM and retired to my bedroom. I tried masturbating for about an hour but while I was able to get wet and aroused, I was not able to climax. I used the dildo to penetrate myself while thinking of sexual encounters I had with men in the past, not my husband. Lord knows, I feel so much shame for this self-pleasure but I have to admit the orgasm I had in your office the other day has had me in the best mood I've been in years. I'm more focused at work and more effective. I think I will continue attempting masturbation as you've directed.

Sophie's Log: Day 2

Frustration continues. Today I wasn't even able to find time alone. A full schedule at school got extended because two kids got into a fight. Since this is boarding school I had to sit in a web conference with their parents and arrange separate housing for one boy to spend his suspension. Then I came home in the evening, sat down for dinner with the kids and spent some time afterward doing paperwork. My youngest, who's three, keeps leaving her toys out and the housekeeper doesn't work after dinner. So I had to clean up her toys instead of using mine. I did try to rub myself a bit when I got in bed, and even tugged at my nipples, but I didn't feel sexy in my sweatpants.

Sophie's Log: Day 3

I masturbated twice today. I haven't been this horny since I was nineteen. I woke up this morning at six AM ready to ride the walls, so I took the dildo into the shower and abused myself like a shameful pervert. I orgasmed in three minutes, and I must shamefully admit I thought of Ms. March again. I don't know what it is about her, but she drives me nuts. Infuriates me and gets me acting like a teenager.

I was so horny that I took the dildo to school and I masturbated for fifteen minutes during my lunch break. I locked the door of my office, pulled down my panties, laid my legs on the desk and diddled myself. My climax was approaching but I was interrupted by my secretary after some girl got caught cheating on a test. These gosh darn kids! I feel like I'm mommy to everyone, and they all get to play and enjoy themselves, but I don't.

Sophie's Log: Day 4

I poured myself a glass of wine after the kids went to bed and I scrolled through Ms. Marsh's Instagram. I imagined her slapping me back and the two of us naked and putting toys in each other. I am afraid. I feel you may have turned me into a degenerate animal. I have to go to church tomorrow and I felt so guilty I stopped using the dildo before I came.

Sophie's Log: Day 5

Today was pure torture. I was wet throughout the entire service and Sunday lunch with the church ladies after. I kept picturing all of them naked and doing all sorts of lewd and unspeakable things to each other. After I got the kids from Sunday school I had my oldest watch the younger two for a few hours while I went to do groceries.

In reality, I spent one hour doing groceries and two hours parked in the woods, masturbating furiously to pictures of the church ladies. I even poked my dildo a little too low one time and almost went into my behind. But I might be so depraved now that I only felt curiosity about it. My shame got the better of me, though, and I wasn't able to orgasm.

Sophie's Log: Day 6

Today I was looking through some of my old modeling pictures and found the ones of me in that lacy green and purple number. Somehow, that made me horny and I ended up masturbating for a half an hour while the housekeeper prepared lunch. As I orgasmed, I thought I could hear a woman's voice whispering in my ears, saying "Be a good baby girl, let it out for Mommy." I felt so ashamed but this was the best orgasm yet. I masturbated on all fours on the floor of my walk-in closet. I find that I cannot orgasm or feel sexy lying on my back in bed.