Olivia's Escort Service - Version Alpha
Copyright© 2026 by Lubrican
Chapter 10
Romance Sex Story: Chapter 10 - Bob found out his best friend's mom secretly worked for an escort service that all the high school boys thought was a cover for prostitution. Bob couldn't believe she was a hooker. Nobody in her normal world would have even imagined that. He had lusted after her for years. Now he could blackmail her into escorting him to the opera. Would she agree? If she did, how would it go?
Caution: This Romance Sex Story contains strong sexual content, including Ma/Fa Blackmail Consensual Heterosexual Fiction First Masturbation Petting Pregnancy
Brad’s first exposure to the new status between his best friend and his mother happened when he woke up the next morning. His brain was fuzzy, but then it informed him something had awakened him. He lay there and heard a thump, coming from somewhere in the house. His mother was spending the night at Bobby’s house, which meant there should be no thumps. Carefully, he got out of bed. The baseball bat he had used as a child was in the back of his closet. He was naked, but didn’t want to take the time to put on clothes. If a burglar was stealing their stuff, he wanted to interrupt that ASAP.
He opened his door slowly and peeked into the hallway. He didn’t see or hear anything, so he stepped into the hallway on his tiptoes. He made it even with his mother’s bedroom door when he heard the thump again. It sounded like it had come from the right, which was his mom’s door. Gripping the bat in one hand, he carefully turned the handle of the door. When the latch was clear he threw the door open and jumped into the room. He yelled “Hey!” about the same time his eyes took in Bobby’s naked body, with a pair of arms and legs wrapped around him as his hips rose and slammed down more rapidly than Brad would have thought was possible. The “Fuck!” that came out of his mouth came from the same place the “Hey!” had come from, which was a subliminal part of his brain. The “Shit!” that burst from his lips next was more intentional, and was the result of Bobby’s head turning and looking at him.
“What?” growled Bobby, without slowing.
“Brad?” came his mother’s muffled voice from under Bobby.
“Sorry!” Brad gasped. “I didn’t know you were here!”
“You don’t need to keep checking her panties,” said Bob.
“I wasn’t doing that!” yipped Brad. “I heard something and you two aren’t supposed to be here!”
“Why are you naked, Brad?” came his mom’s voice.
Brad’s hands, still holding the bat, went to cover his penis and he turned to rush out of the room. When he tried to close the door the bat got in the way and he just dropped it. He ran for his room, trying to get the image of his best friend just fucking the crap out of his mom.
“Ohhh, man,” he whined as he covered both eyes with the heels of his hands.
He couldn’t go back to sleep, so he just got up and went to get breakfast. When he looked at the clock it was only eight. When had they come home? He’d stayed up until one in the morning. They had to have come home after that. And it obviously wasn’t to sleep.
A noise made his head turn so fast his neck muscles complained. His mom was standing there, wearing the fluffy, thick, white robe he’d seen her wear a hundred times. He’d never noticed how much cleavage it showed until now, but otherwise she just looked like his mom.
“Are you okay?” came her concerned voice.
“Nope. Uh-uh. Not okay. I think my brain broke,” he said.
“It’s not that bad,” she said, in that voice he’d heard a hundred times. It was the voice she used when he was making a fuss over something silly.
“I can’t unsee that,” he moaned.
“Then go find a girl and do it yourself,” she said. “It’s not my first time. I did that in order to get pregnant with you.”
“Knowing that and seeing that are two waaaay different things,” he said.
Bobby showed up. He was wearing jeans and a T shirt Brad had seen him in dozens of times.
“Dude!” said the man who had just been fucking the crap out of his mother. “You okay?”
“No, he’s not,” said Olivia. “He’s traumatized.”
“Come on, dude,” Bobby groaned. “It’s still just us. Nothing has changed. I’m still your best bud and she’s still just your mom.”
“That is not true at all,” said Brad. “Everything has changed.”
“Do you want us to stop?” Olivia’s voice was serious.
“I don’t know,” groaned the young man. “No. I mean I know I should say no. I love you and I want you to be happy.”
“Just not that happy?” she suggested.
“No,” he groaned. “That’s not fair to you, either. I just need time to get used to it.”
“I remember hearing you say you were happy about this,” said Bobby.
“I did say that and I meant it, but approving of the concept is waaasaay different than busting in on it being exercised,” said Brad.
“I’ll move a chair into the bedroom for you to sit in and watch,” said Bobby. “You’ll get used to it faster that way.”
Olivia turned and hit him on the shoulder. Brad covered his eyes with the heels of his hands again.
“She’s abusing me!” Bob complained. “And it’s all your fault!”
lt was the ludicrous nature of Bobby’s last statement that calmed Brad down. It sounded so much like Bobby – normal Bobby – that control came back into his grasp.
“I think it’s the other way around,” he said. “It looked like you were beating the hell out of her.”
“That was something different,” said Bobby. “We hadn’t done it like that so we wanted to know what it might be like.”
“You make it sound like a buffet dinner,” said Brad. “Try this, take a little of that.”
Bobby grinned.
“Actually, that’s not a bad way of describing it at all.”
“You can stop talking about my sex life,” said Olivia. “I’m exhausted. I’m going to bed.” She looked at Bobby. “Alone!” she said, firmly.
“Now see what you did?” Bobby complained to Brad. “Now I’m going to have blue balls.”
“I’m surprised you have any balls left at all!” snapped Olivia. She left the room rapidly.
Bobby looked at Brad.
“Sorry. She wanted to find out what it felt like on her own bed, so we came home a little early. We didn’t mean to wake you up.”
“My fault,” said Brad with a wave of his hand. “I thought it was burglars, which is stupid. The only things worth stealing in this house is all my gear.”
“Well, I hope you aren’t traumatized,” said Bobby.
“I didn’t see that much,” said Brad. “Mostly you, just doing pushups like there was a gun to your head and you had to make it to a hundred as fast as you possibly couold.”
“Okay,” said Bobby. “I’m probably going to spend the night here a lot from now on.”
“Is that really necessary?” groaned Brad.
“Yeah. She likes her bed a lot more than mine.”
She wasn’t asleep when he got to the bedroom.
“I told you I was going to bed alone,” she said, but there was no sharpness in it.
“I’m exhausted, too,” said Bobby. “All I want to do is take a nap beside you.”
“Just don’t touch me,” she muttered.
He crawled on the bed. She was on her side with her back to him, still wearing the robe. He scooted up behind her and spooned. He slid one hand over her hip and up to where there was a gap in the robe. Reaching in, he cupped one breast and then just lay there.
“I love you,” he whispered.
“You’d better,” she said, softly.
Then nothing more was said or done before they both fell asleep.
When Bobby woke up it was with that feeling that you know it’s time to get up, but you feel too tired and just want to go back to sleep. He was in the process of doing that when he realized there was no soft, warm woman next to him. His hand was just lying on the bedspread.
He lifted his head to find Olivia, standing next to the bed, still wearing the white, fluffy robe, just staring at him.
“Good morning?” he said.
“Good morning,” she said, her voice firm.
“What are we doing?” he asked.
“You’re lying there being difficult and I’m standing here trying to decide what to do about you.”
“Just love me,” he suggested. “How am I being difficult?”
“By being you,” she said.
“Oh. Well, that’s unlikely to change.”
“I don’t want it to ever change,” she said. “That’s the problem.”
“Okay. Do we need to talk about it?”
“No. I was doing fine before you woke up.”
“So I should go back to sleep?”
“No. You should take your clothes off. I don’t want you on my sheets in dirty clothes.”
“I’m somewhat confused,” he said.
“Don’t think about it. Just do it,” she said. “I’ll be right back.”
She turned and left the room. Bobby lay there a few seconds and, having no idea what was going on, sat up and pulled his shirt off. He was already barefoot and had nothing on under his jeans, so he was naked in no time. She had said “on her sheets”, so he pulled the covers back and slid under the top sheet and bedspread. He had never felt sheets that soft or slick. When she came back, she closed the door and said, “I told Bradley not to bother us until we come out.”
“Okay,” he said.
She dropped the robe and stood there, just letting him look.
“I can’t see your penis,” she said.
He threw back the covers to reveal he was already hard.
“Was it that way when I left?”
“No. It got that way about sixty seconds ago.”
She climbed into bed but stayed a foot away from him.
“Things are getting very serious,” she said.
“I agree.”
“I don’t know what to do about it.”
“I thought that was decided. I thought you were going to marry me,” he said.
“I want to marry you,” she moaned.
“That’s good.”
“But I’m afraid to marry you.”
He stared into her eyes.