Undercover Chairman - Cover

Undercover Chairman

Copyright© 2026 by CreepyUnclePete

Chapter 1

Erotica Sex Story: Chapter 1 - CEO and Chairman of the Board goes undercover to see how the business is actually running. Along the way, he sleeps with a desperate single mom and her many daughters. - - - As a special warning for the special people who don't read story tags; this tale includes creampies, pregnant girls smoking, teen sex, lesbian incest, alcohol, prostitution, and other assorted naughtiness.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   ft/ft   Fa/ft   Mult   Consensual   Lesbian   Heterosexual   Fiction   Rags To Riches   Incest   Mother   Sister   Daughter   Group Sex   Anal Sex   Cream Pie   Oral Sex   Pregnancy   Safe Sex   Smoking   Prostitution  

I finished my business degree and impressed my father by doing a great job as a Vice President at his huge pizza chain. He retired the previous year, and things weren’t going as well as they had been. Being CEO and Chairman of the board was a huge challenge. We went from number three in the country to number four. We might fall to five if I didn’t make major changes soon.

I was stuck at an airport during a thunderstorm. Against my will I watched a show “Bossguy Incognito”, or something similar. The head of a company disguised himself to see how things were really going inside the business. I decided trying the same thing might help me understand my restaurant chain’s situation better.

I was proud of my long, stylish red locks, but decided I would take one for the team. I shaved my head and put on glasses and a fake moustache. Instead of “Jonathan”, I would use the name “Joe.”

The first location I checked was doing fine. The store manager was running the place well and had a good group of employees. I decided to give everybody there a small raise. The next three restaurants were doing about average, and no major changes were needed.

For the fifth location I chose a store that had lost money the last two years in a row, so that I could find out why. I wanted to know how the workers lived too. I’d never been poor, or even close, and wanted to see what it was like.

The regional manager got me in touch with one of the cooks, Colleen, who thought she was going to train me and rent me a room at her house for my first month on the job. Over the phone I told her I’d pay 200 a month for a room, and I could give her 100 up-front.

I had a taxi drop me off two blocks away at 4pm, and carried my backpack of clothes. Before ringing the doorbell, I heard a lot of commotion inside. When I pressed the button, a girl yelled, “Somebody get the door!”

A brunette about fourteen years old answered the door wearing sandals and a comically large man’s t-shirt. The hem of the shirt touched the bottom of her knees, and her hair was nearly as long. She was slightly under five feet tall, compared to my six and a half, and stared up at me quite a while.

My nose was pummeled by a surge of scents. I noticed cigarette smoke, multiple perfumes, hair spray, fried chicken, and pizza. The auditory assault on my senses at least matched the olfactory attack. I heard people running around and several girls speaking quickly at the same time. In what seemed like only seconds, I heard:

“Where’s the curling iron?” “Mom, I need sandwich bags for my lunch tomorrow.” “I shouldn’t have to use condoms if I’m already pregnant.” “Jessie’s using it.” “I need the pink high heels, where are they?” “Take an apple and an orange to school, I’ll get some bags tomorrow.” “I don’t know, wear the purple.” “You need to. If Eric finds out you’re knocked up, he’ll dump you. You should keep smoking too.” “But Brad hates purple!” “Mom! Jessie’s hogging the curling iron, and I need it!” “Wear the white ones then! They’re next to the bed.” “Use curlers and the blow dryer and ask your boyfriend to get you one.”

I’m an unusually bright guy, but couldn’t keep half of that in my head at the same time, or make much sense of it.

The small brunette in front of me said, “I’m Amy. Who are you?”

“Hi Amy, I’m Joe. Please tell your mother I’m here.”

Instead of walking, she screamed across the house, “MOM! JOE’S HERE!”

Her mother Colleen shouted back, “Take him to the living room!”

She led me through the kitchen, which had a large dining table but only three wooden chairs. One was held together with tape and wire. The living room was far less than half full. There was a large but quite old tube-style tv, a sofa, end table, and loveseat. There was easily space for another couple of couches and chairs. The end table had chipped gray paint which was peeling off in a few spots. Both the sofa and loveseat were torn and stained.

A cute and very pregnant young lady was laying on her side on the loveseat watching TV. Her hair was bleach-blonde with long dark roots. She wore a large red sweatshirt and a blanket covered her legs.

When she saw me come in, she smiled and said, “Hi! I’m Samantha. I watched you walking here. The way you walk is really cool.” She put the tip of a pinky finger in the corner of her mouth, and stared at my butt.

“Hi, Samantha. I see you’re watching a cooking show? Do you like to cook?”

“When I can. Most of the time we’re broke, and just eat pizza and stuff from mom’s work. Um, can you help me? Pat my belly please? I feel like I gotta burp. Being pregnant sucks.”

“Okay, I guess.”

She lifted the sweatshirt so high I could see the lower halves of her large breasts, and a big purple nipple. At the bottom of her abdomen, the blanket didn’t quite cover her dark pubic hair. “Pat slow please, nice and gentle.”

I followed her instructions, feeling her warm baby-belly as I patted, and looked at her boobs. She stared deep into my eyes with her pretty blue ones. She smiled, then raised the shirt even more.

Her little sister Amy surprised us, asking, “What cha’ doin’?”

I tried to move away quickly but got a handful of breast by accident. A drop of milk leaked out, and I pulled away in a different direction as she covered herself.

Samantha told her, “Nothing, squirt. Go do your homework or something.”

As the little brunette walked away, I bashfully apologized to Sam, “Sorry.”

She grinned. “I’m not.”

I watched a chef make a gourmet apple pie, as Samantha kept staring at me. I was shocked when Colleen strode in. She looked nothing like I had imagined from her voice on the phone. She was as tired as she had sounded and looked about 35, but far from ugly.

She was wearing only a long black skirt and a huge white bra she was in the middle of fastening. Each of her breasts was nearly the size of my head! From her blue eyes and plump lips, I could tell she had been a beauty a decade before, but producing five kids did unkind things to her body. There were a lot of stretch marks on her belly and deep crow’s feet at the corners of her eyes. She didn’t look obese, but had an extra twenty or so pounds on her hips and abdomen.

She called over her shoulder, “Jeri, bring me a cigarette. So, Joe, you said you had a hundred?”

 
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