Undercover Chairman - Cover

Undercover Chairman

Copyright© 2023 by Creepy Uncle Pete

Chapter 1

Erotica Sex Story: Chapter 1 - CEO wants to know how his company is actually running, and visits several locations in disguise. Along the way, he sleeps with a poor single mother and her many daughters. - - - CAUTION: Contains smoking, prostitution, underage sex, anal, pregnancy, drinking, and female twincest. If any of those would bother you, please read something else.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   ft/ft   Fa/ft   Mult   Consensual   Lesbian   BiSexual   Heterosexual   Fiction   Rags To Riches   Workplace   Sharing   Incest   Mother   Sister   Daughter   Group Sex   Polygamy/Polyamory   Anal Sex   Cream Pie   Exhibitionism   Lactation   Oral Sex   Petting   Pregnancy   Voyeurism   Big Breasts   Smoking   Prostitution  

CAUTION: Contains prostitution, underage sex, anal, pregnancy, drinking, smoking, and lesbian incest. If any of those would bother you, please read something else.


I had 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 had gone from the number three pizza chain in the country to number four. We might fall to five if I didn’t change something soon.

I was stuck at an airport during a thunderstorm, and against my will I started watching 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 ran the place well and had a good group of employees. I decided to give everybody there a small raise. The next three stores 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 to her old and run-down home. 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 14 years old answered the door wearing flip-flops 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 stared up at me quite a while.

My nose was pummeled by a surge of scents; 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 a few 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 I 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.”

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

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

We walked through the kitchen toward the living room. The large table only had three wooden chairs, one of them held together with wire. The large living room was close to empty. There was a big 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 lying on her side on the loveseat, watching TV. Her hair was bleach-blonde with long dark roots. She had a large red sweatshirt on, and a blanket over 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 a pinky in the corner of her mouth, and I noticed she was staring 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 here, slow please, nice and gentle.” I followed her instructions, feeling her warm baby-belly as I patted her belly and stared at her big tits. She looked deep into my eyes with her pretty blue ones. She smiled, then raised the shirt even more.

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 girl walked away, I bashfully apologized to Sam, “Sorry.”

She grinned. “I’m not.”

I sat on the sofa and 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 obviously over 30, 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 were nearly the size of my head! From her blue eyes and plump lips, I could tell she had been a beauty a decade ago, but producing five kids had done 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.

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

I reached in my back pocket. By the time I had my wallet out, a beautiful beyond gorgeous teen girl walked in. Jeri had golden blonde hair in tight curls, pretty eye makeup, bright red lips, and long fake lashes. She wore large gold hoop earrings and white high heels, along with a sheer pink and yellow dress. The fabric of the dress revealed the shape of her narrow waist, rounded butt, and the outlines of her black panties and bra underneath. I guessed her breasts were “C” cups, and her small nose and ears made her face look even younger than her 16 years. I froze and gazed at her beauty.

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