Undercover Chairman - Cover

Undercover Chairman

Copyright© 2026 by CreepyUnclePete

Chapter 2

Erotica Sex Story: Chapter 2 - 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  

Colleen woke me in the morning, and I observed several disturbing things at the restaurant. One of the cashiers was telling the customers the price was a dollar higher than it really was and pocketed a dollar from most of them. For the few who noticed, she pretended it was a mistake and apologized. Nobody complained to the manager since it was only a dollar. She must have been stealing at least forty bucks a day. ‘Only a dollar’ adds up.

When the second cook started, I noticed that sometimes she would make an extra pizza that hadn’t been ordered. The extras were always for one certain delivery guy, her boyfriend. By the end of lunch, she had given him four extra pizzas, which he probably sold or gave to friends.

When the lunch rush was over and it was time for us to leave, Colleen put two uncooked pizzas in boxes and carried them to her car. She told me, “The company will never miss it. The ingredients only cost two bucks a pizza, and my kids will be hungry after school.”

I was torn emotionally. She was stealing! Stealing FROM ME! But it was only a small amount, and I knew her family really needed it. On the way home she gave the old excuse, “It’s no big deal. Everybody does it.”


It was Thursday night, Colleen’s night off from the diner. Most of her girls were home, but not in a rush to do anything. I was surprised the house was relatively quiet.

I asked, “Colleen, would you like to go for a drink? A glass of wine or something, to relax?”

She walked to the kitchen and took a box of cheap white wine from the fridge. “Let’s have a toast, to celebrate your first day making pizza.”

She poured the wine into two tall plastic cups, nearly filling them. She said, “Let’s go in the bedroom, it’s quieter in there.” The bedroom only held a king-sized mattress on the floor, nine or ten paper bags full of clothes, and an ashtray and alarm clock on the floor. Other than the air mattress I had slept on with Samantha, it was the only ‘bed’ in the house. I realized Colleen and four of her kids had slept on it the previous night.

We talked about the pizza business a long time, then she switched the topic to family. “I work so hard and barely make it. I love my girls, and want them to be happy, but it’s so difficult all the time. My second husband and I were happy until he got into drugs. He was stupid and ... and a cop shot him. I miss him a lot sometimes. Other times, I’m still PISSED OFF.”

We had each drunk three or four glasses worth of wine at that point. Colleen lit a cigarette and I watched her have a few puffs. She chuckled and asked, “So did Samantha get her claws in you yet? Do you want to marry her?” She took another big puff and giggled drunkenly.

“We made each other feel good, and I kind of like her.”

“That’s about what the other girls’ boyfriends think too. Why can’t any of us find somebody decent, who wants to marry us and stay with us? Is there something wrong with me? I give my boyfriends sex or at least a blowjob every day, and even let them in my butt sometimes. All the guys say I’m great at blowjobs, and I have huge tits!” She took her top off to prove her point and I found it difficult to move my gaze away from the massive mammaries held aloft by her overworked bra.

She said, “I need to know what’s wrong with me. Get your pants off and tell me if my blowjobs are great or not.”

I was more than happy to do as instructed. She licked and sucked me nearly to Heaven! She even deep throated me, swallowing the head of my dick! I watched her reach under her skirt and slide her panties down.

“WOW! SO GOOD!”

I was close to climax when she stopped the blowjob and rolled over. She put some petroleum jelly between her butt cheeks and commanded, “Try my ass, too. Tell me if it’s worth marrying me for my butt a couple times a week.”

I was more than happy to take her up on her offer, and slowly slid my cock into her little asshole. Her anal ring squeezed me tightly, as I slid in and out. I reached around her and played with her tremendous tits.

“Mmmmm! I like when you tickle my nipples. Oooh! That feels nice in my butt!”

Within a minute or so, I was close to orgasm again.

Colleen threw a sheet over us as the door suddenly opened. Little brunette Amy was only fourteen. She walked in quickly and saw what we were doing before the sheet blocked her view. She didn’t seem surprised, and her own body was only slightly covered by a few soap bubbles. “Mom, I’m taking a bath and there’s no more shampoo.”

Colleen told her, “Use bar soap. I’ll get more shampoo tomorrow. And I told you no more baths, they use too much hot water. Shower instead.”

“Sorry, Mom. Okay.”

The nude girl walked out and was closing the door as gorgeous blonde sixteen-year-olds Jeri and Carrie walked in.

“Mom, we’re out of cigarettes. Do you have any?”

There was a quiet “Pop” under the blanket as Colleen rolled over to reach her purse and my cock pulled out of her ass.

Jeri blushed and smiled. “Were you two fucking?”

I coughed in surprise and her twin said, “Yup, they were fucking!” Carrie blushed even more than her sister. “Mom lets guys do her butt sometimes too. You should try her ass. Her old boyfriend said it’s great.”

Colleen handed Jeri a few cigarettes and sharply said, “He was! Get out, so he can finish!”

I tried to put together some words as the twins left and shut the door.

“Ack! Uh ... you tell your kids what you do in bed?”

She shocked me even more with, “It’s not like we have five beds or anything. We only had this one, until you wanted to rent a room. We turn the lights off, but most the time they hear it from the other side of the bed while I’m doing it. Sam and Jessie help sometimes.”

I made up a minor fib to escape the awkwardness. “I should call and check on my Granddad. He was pretty sick last week. Back in a minute.”


I dressed and walked outside to make a call on my cell. I told my right-hand man, the CFO, that I would be out of town longer than I thought. He said he’d be fine taking care of things for a couple of weeks until I got back. When I walked back in the house, Carrie filled an old glass jar with wine, since there were no more clean glasses. She took a drink and handed it to her twin Jeri.

I got back to the bedroom, and Colleen had pajamas on and her hair in curlers. I asked, “So, what were we talking about again?”

 
There is more of this chapter...
The source of this story is Storiesonline

To read the complete story you need to be logged in:
Log In or
Register for a Free account (Why register?)

Get No-Registration Temporary Access*

* Allows you 3 stories to read in 24 hours.

 

WARNING! ADULT CONTENT...

Storiesonline is for adult entertainment only. By accessing this site you declare that you are of legal age and that you agree with our Terms of Service and Privacy Policy.


Log In