Undercover Chairman
Copyright© 2026 by CreepyUnclePete
Chapter 3
Erotica Sex Story: Chapter 3 - 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
On the way to work, Colleen said, “You must have had a great time? Amy shouldn’t be watching sex at only fourteen, but she said three of them blew you last night? Thanks for the groceries.”
“Uh ... it was really great!”
“So, did you have a good time with Jessie after?”
“Yeah, she’s hot!”
“Do you love her? Do you think maybe you want to marry her?”
“I like her, and we had a lot of fun...”
“But you don’t want to marry her either?” She let out a deep sigh as she parked the car. “I guess you can try Jeri and Carrie tonight, then.”
I froze in shock. She was offering me her sexy sixteen-year-old twins?!?!?!
She tugged my sleeve. “Come on, dough doesn’t make itself.”
We would be the only people in the building until the others arrived to prep for the lunch rush at ten, so we talked freely.
I thought a night with Jeri or her twin would be amazing, but I was curious. “Why are you in such a hurry to get them married?”
“When my dad passed away, I got his house, but my no-good brother got half his money and everything IN the house. Dad’s will says that his first grandchild to get married gets the other half of his money, about fifty grand. We really need it, with Jessie and Sam both pregnant. My nephew is getting married when he turns eighteen in three months. He gets the money unless one of my girls is married by then.”
I was surprised a mother would try so hard to marry off one of her kids, for that little money. Thinking about their situation, I understood why. I was shocked to the core, when she casually joked, “She’s only fourteen, but if it was legal and the guy wouldn’t hurt her, I’d even let Amy get married for fifty grand!” She said it with a dreamy look in her eyes, as if it were a palace full of diamonds.
When the lunch rush was over and we walked to her car with two more stolen pizzas, I told her, “Call and tell the girls to stay home tonight, and tell the diner manager you’re sick. We need to have a family meeting.”
“But I need the money from both jobs, or...”
“No, you really don’t.” I held up five thousand in cash and showed her my dozen bank cards. “Just make the calls, please.”
After she did, I pulled off the fake moustache and glasses, then told her who I really was. I expected the car’s windows to shatter from the pitch and volume, as she screamed in surprise. She agreed not to tell the kids yet.
At home one of the kids cooked the pizzas, then we all ate as they wondered what the meeting was about. Several of them asked, but I just said, “After we eat. It’s something good.” We gathered in the living room, and I had to force myself to concentrate. I needed to try hard, to avoid being distracted by the sexy sight of several of them sucking on cigarettes, and Jessie flashing me a glimpse of her ass.
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