Chapter 1: The Beginning

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Status: In Progress  |  Genre: Humiliation Sex  |  House: Booksiesilk Classic Group

Featured Review on this writing by Spyguy

Reads: 239
Comments: 3



The Beginning

My name is Adam Stillwater. I'm your average white male computer geek from Flint, Michigan who attended Michigan State and spent five years getting my degree. I took a year off from school after my fiancé dumped me for a grad student and sent me into deep depression. I have limited social skills and a small dick. There, I said it. I've been told more than once, so I might as well get that out there. The social skills, I mean. Don't get me wrong. I'm all about self-help. Just being honest.

Trouble is, being honest doesn't help you on dating sites.

It doesn't help you anywhere with anything at all, as best I can tell. I should have learned to lie better. Life's all about getting your foot in the door and holding that crack open. It's all about what's behind the crack and finding a way in. Lie if you must. Play the game if you can.

Trouble is, I'm a bad liar - and I have slow and clumsy feet.

I met Blair Underwood on a Colorado ski slope after tumbling halfway down the mountain in the red zone. I landed on my ass at her very agile feet where I ironically spent the rest of my life. She told me I looked cute all bundled in the snow with my glasses strapped to my chin. When I told her I was a part time ski instructor, she nearly passed out with laughter.

"That's a lie," I groaned, looking down at my clumpy boots. "I'm a computer programmer who needs to go back to the amateur slope."

Blair helped me up, and I noticed she was strong. I noticed she was tall. "I like your sense of humor," she smiled. I immediately recognized she had the demeanor of a woman in charge. I also recognized that she was blonde and fit and beautiful.

"My company is having an executive meeting this weekend at the main lodge," she explained. "I'm always looking for computer experts. Why don't you join us for dinner this evening and we can discuss a possible job opportunity... that is if you can pull yourself away from your ski instructor position."

I agreed to come. It was the first time a lie had ever helped me, and only after I admitted it was a lie. I wasn't actually trying to be funny. It just turned out that way. Serendipity. The tide was turning for me. Turning into an avalanche.

"Let's say six o'clock, mister ....."

"Adam. My name's Adam Stillwater." We shook hands like men.

"Blair," she said. "Blair Underwood. It's nice to meet you, Adam. See you at six then?"

"Yes, ma'am."

Blair smiled at me like a postcard. "Good boy," she cackled. Then she walked off to the ski lift and joined two other gentlemen.


When I walked into the dinner meeting, Blair recognized me immediately. I was the most casually dressed person in the room. Well, I wasn't expecting an interview at a ski resort, so I wore what I had... jeans and a lumberjack button-down plaid shirt.

"I'm sorry," I apologized. "I didn't bring a suit and tie for the trip."

Blair walked over and graciously led me to her table where she introduced me to several middle-aged men who were as pressed and starched as a cotton Oxford.

"You planning to cut some timber this evening?" one of the men chuckled after introductions.

"Adam is a computer programmer. I thought I might invite him tonight to have a look at our little problem that nobody around here seems to know how to fix, that interface issue." Blair winked at me casually. It was sexy and reassuring. I was suddenly glowing with confidence.

"You should just hire a company to handle that stuff, just as we discussed in the last board meeting," the man grumbled.

Blair folded her arms impatiently at the gentleman. "I told you, Frank. I like to have my own people, keep my company autonomous, shovel my own shit." Frank shook his head. Blair was bold, crass, and deliberate. She glared at Frank's fretful expression like she'd just as soon dump a shovel of shit on his head as entertain his ridiculous opinions. She owned the company. That was clear enough. The majority stockholder.

"No timber tonight, sir." I interjected, shaking Frank's hand resiliently. "I just like this rugged look for tapping on the keys. It keeps the computers in line."

The table exploded in laughter. I must have looked like a clown making fun of myself. All was suddenly a winter wonderland of comradery and cocktails, a perfectly delectable dinner surrounded by crackling wood fireplaces and iron chandeliers... until Blair introduced the computer interface problem that had been so perplexing which I solved in less than ten seconds.

Then, everything went silent as a snow drift... everything except for Blair in her navy-blue sequins that accentuated her hazel eyes. She wore the perfect shade of eye shadow, a slight touch of rouge... a natural glow of authority.

"We will have our deserts, now." Blair nodded to one of the hotel hosts, and a sea of young men sporting black ties and crisp cotton headed out the side doors of the opulent dining hall. Blair motioned me to sit beside her as every eye in the room fell upon us.

"Only coffee for me." Blair held up her hand, waving off the strawberry cheesecake with chocolate sauce, then placed her dainty fingers on my thigh beneath the table. "No timber tonight?" she whispered. She massaged my leg softly.

"I'm sorry?" I was totally oblivious to her meaning and completely centered on her delicate digits digging into my denim.

"I like your outfit," she continued, her hand sliding closer to my crotch. Everyone in the room pretended not to notice. "I think you'd look even more rugged with stubble on your face. I bet you swing one hell of an axe handle."

"Huh? I don't grow a good beard, Ms. Underwood. My ex-girlfriend used to tell me..."

"I don't care about your girlfriend, Adam. I want to know about your hardwood. How long is it? How thick?"

Blair gave my junk a quick squeeze. I almost fell backwards in my chair and spit my cheesecake across the table. "I mean, it's okay, I guess." I should have lied. I'm a terrible liar. Actually, that WAS a lie.

"It's okay?" she giggled, peering across the room, sipping her coffee as she carried on our conversation. She glanced at my face for the first time in forever, looking like a schoolgirl passing notes in the back of the classroom. "It feels better than 'okay' to me, Adam."

I was undeniably erect and needed to make an adjustment. Trouble is, Blair's hand was in the way. There's always some kind of trouble. Blair reached in her clutch and handed it to me... a magnetic key card that opened the door to trouble. She slipped it into my Timberjack shirt pocket while everyone pretended not to notice. She squeezed me again.

"Adam, I'd like to see you tonight if you don't mind, room 526 top floor. Let's say ten-thirty. We can talk about your contract."

"My contract?"

"Yes, Adam. You do want the job, don't you?" I nodded. "I thought so. Slide your card in the slot on the elevator, Adam. It will take you to my floor. You know how to slide things into a slot, right?"

"I... yes, I mean,,, I don't know about..."

"Yes, you do, Adam. You know all about it. You just slide it in and out... in and out, Adam." She squeezed me each time she repeated it. "Bring your comb and a toothbrush. I don't carry extras."

I felt a flush come over me like a fever. Sweat on my forehead and my upper lip. My breathing was quick and shallow. Shit. I should have lied. I should have lied. It's not really 'okay'. I'm not okay. I wasn't okay. I should have told her I had a headache, that I wasn't feeling well.


"Yes ma'am?"

"You don't have to call me that. You can call me Blair. Most people here do, even if they're dickless stock owners with stupid opinions."

Blair glanced over at Frank and gave him a knowing smile, then stood up to walk towards the exit, raking her fingernails lightly across the back of my neck. "See you tonight, Adam." Frank looked at me strangely.

"I'll leave the door cracked for you."


Blair is a self-made woman, although some have called her a graceless display of naked ambition.

Either way you slice it, she found success at twenty years of age, selling her private collection of rare stamps, giving her enough runway to finance a trip to the Soviet Union, where she traded privatization vouchers on the Russian commodities exchange. After graduating from Brown, she walloped the competition, laying the foundation for half a dozen startups before selling out for large profits.

She'd made her first fortune well before putting me to work in the IT division of her latest startup. She showed up at my cubicle one morning some months after I started work, taking off her glasses so I could better understand who I was dealing with. I already knew. She always saw through me in one flashing green glance, a greeting, and a warning that said, "Try me at your own risk."

"I've been hearing good things about you, Adam. Things are going well?"

"I try to do my part, ma'am."

"Ma'am is it still?" she said with a chuckle. "I go by Blair. I told you that before, remember? Or are you a slow learner?" I nodded, wordless.

"A few of us are having dinner at The Flagstaff House this evening. Care to join? I promise not to keep you past your bedtime."

"I'd love to." What else was I going to say?

"My car will pick you up. Shall we say at 7:00?" We shared an awkward moment of silence. I started to give my address. "We know where to find you, Adam."

"Seven it is, then. The Flagstaff House is great."

Blair studied my eyes for a moment. Had I done something wrong? She tapped a folder on my desk, saying, "See you around 7:15, then. She glanced at her watch, and her phone rang. "Just a minute, no, he won't. Yes, we'll see about that."

I reached into my desk drawer for a folder. By the time I looked up, Blair had turned the corner on her way to the escalator. A company car, an Escalade, picked me up at the prescribed time, and we started our drive up Flagstaff Mountain. The restaurant was in full swing as I arrived. I took my seat near the waiter station.

Our party was much larger and more formal than I had expected. I counted seventeen total. Blair was engaging her guests in a card trick, asking for their entire order, then dealing them a card from the top of the deck. When the waiter came, Blair called for each of the cards, and upon receiving them, recited each of the seventeen orders. She was smothered with applause. The beautiful magician.


Over the next six months, Blair and I developed a kind of comradery. She'd take me to her loft and fuck me silly. The first time it happened, she straddled my hips and humped me halfway through the mattress. I knew I wouldn't last long at the rate she was going. "Slow down," I panted, desperate to demonstrate my endurance.

All that got me was a sharp slap across the face. Then, she used the heel of her hand to push my face sideways on the bed. "What's wrong, Adam? Can't take a hard fucking from your boss? I'd hate to tell the guys in your division that you fuck like a sissy," she snarled. "Come on, pretty boy. Show me you know how to make a baby."

Three months later, she told me I'd knocked her up with twins.

A feather could have bowled me over. I asked her what she wanted to do. She said she would keep them. She was opposed to abortion, and she adored the idea of becoming a mother as long as it didn't interfere with the business.

I fell to one knee at her feet and asked her to marry me. She patted my head.

"I'll let you marry me, Adam. Do you know how many men would give their right nut to marry Blair Belmont Underwood, CEO of Underwood Enterprises? I'm not asking for your testicles, Adam. I'm asking for your loyalty. I want your love, care, respect, and heart. I want a prenuptial contract, too. I want your mouth and your tongue. I want your time and attention. Above all, I want your obedience. Can you give me your obedience, Adam?"

I was going to be a father. I couldn't wait for the delivery day. I almost got my wish. Blair delivered a girl and a boy ten days early, Anastasia Blair and Andrew Belmont.

They were both black.





Submitted: May 14, 2023

© Copyright 2023 Sammy D. All rights reserved.


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Add Your Comments:



Well written and with a statement at the end meant to be a shock, depending on the reader.

Mon, May 15th, 2023 1:35pm


I want more .... please write more...

Wed, May 17th, 2023 7:20pm


I'm starting to feel sorry for Adam already!

Wed, June 7th, 2023 10:33am

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