Undercover Chairman
Copyright© 2023 by Creepy Uncle Pete
Chapter 2
Erotica Sex Story: Chapter 2 - 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
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 thirty 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 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 three 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 not a 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 Sam, 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. She 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 night, and even let them in my butt sometimes. All the guys say I’m great at oral, and I have huge boobs!” 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 butt too. Tell me if it’s worth marrying me for my ass a couple times a week.”
I was more than happy to take her up on her offer, and slowly pushed my cock into her little asshole. Her bottom hole 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 opened. Little 14-year-old brunette Amy 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.” With the ‘baby fat’ on several parts of her body, sparse but dark pubic bush, and promising almost-boobs, I couldn’t tell if Amy was mostly cute, or mostly sexy. I decided she was a dangerous mix of both.
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. You’re supposed to shower instead.”
“Sorry, Mom. Okay.” The nude pretty girl walked out and was closing the door, as gorgeous blonde twins 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 she said, “Yup, they were fucking!”
Carrie blushed even more than her twin. “Mom lets guys do her butt sometimes too. You should try it. 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 girls 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 ... None of them are virgins anymore, so it’s not a big deal.”
I was shocked that even her youngest had sex already, at only 14! 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 company 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 in the house, Carrie was filling an old glass jar with wine, since there were no more clean glasses. She took a drink and handed it to her twin. When I got back to the bedroom, Colleen had pajamas on and her hair in curlers.
I asked, “So, what were we talking about again?”
She started crying as she said, “We’re talking about how you’d rather call some old guy than screw me! What did I do wrong? Why don’t you like me?”
“No, I...”
“If you don’t want me or Sam, sleep with Jessie tonight. She broke up with her boyfriend.”
“No, but I...”
“Just go!”
She was angry at me ten minutes after sex, but wanted me to sleep with another of her daughters? I didn’t understand, not a bit. As I walked to the living room trying to figure it out, a mass of red hair blocked my view and something started crushing my chest. Jessie cried as she asked, “Just hug me please! Bwahahaa!”
After an enjoyable half-hour hugging and reassuring the wonderfully sexy teen, she told me, “I gave my ex-boyfriend Eric a blowjob in his car. He said he would buy the pregnancy vitamins for Sam, and offered a hundred bucks if I would have sex with another girl at his place. We let him watch. I don’t really like girls, but we need the money so bad. It was ... ugh! It was so gross! After all of that, he dropped me off at home and didn’t pay up!” I slowly stroked her back to calm her. She looked in her purse and took out a cigarette. “This is my last one, then I’m out again! Being broke all the time sucks!” Watching her lips and cheeks as she puffed was shrinking my pants.
“It’s ok, I have some money. My granddad passed away, and I inherited some money from him.”
“Oh, I’m sorry. That’s so sad. You must miss him a lot?”
I did miss him a lot when he died six years before. I made half a million a month, and still had most of the four million I got from granddad, but she didn’t need to know the details.
“It’s ok. Let’s go get you some cigarettes.”
“If you don’t mind, we need some other things too. Sandwich bags, shampoo, maybe food other than pizza and fried chicken?”
“Sure.”
“So, how much can we spend? I hope at least fifty? We need a lot of other things too.”
I smiled. “Don’t worry about the price, I have plenty. Let me call a taxi.”
“Taxis are expensive, let’s take Mom’s car. I’ll get her keys.” I wasn’t going to tell her that with some of the cards in my wallet I could buy a taxi COMPANY. She held my hand and led me to the big bedroom. “Mom, I need your keys. We’re gonna get groceries.”
“But I thought Eric didn’t give you any money?”
I said, “It’s okay. I inherited some when my granddad passed away. I’m buying.”
Colleen sadly said, “I’m sorry, I...”
She was interrupted by Carrie yelling from the bathroom, “Mom! We’re out of toilet paper!”
Coleen sighed, “I give up! Good night!” She pulled the blanket over her head. She had the now-empty box of wine near her on the floor.
Carrie yelled again, “Somebody? I need toilet paper in here!”
Jeri walked in with a half roll of paper towel and handed it to me. She smirked. “Go help her, Joe.”
“No, I...”
Jeri said, “I’ll give you a kiss if you do.”
“But...”
Carrie called again, “Hello? Toilet paper?”
Little Amy sounded annoyed as she grabbed the roll away from me. “I’ll do it. Grown-ups are SO WEIRD!”
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