Olivia's Escort Service - Version Alpha
Copyright© 2026 by Lubrican
Chapter 8
Romance Sex Story: Chapter 8 - 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
Olivia told him to lie still and she went to the bathroom. He heard the water running and, after a pause, she returned with a warm, damp washcloth. She cleaned his stomach, cock, and balls. She sucked his limp penis into her mouth and went, “Mmmmmm,” as if she was tasting good food. She pulled off, sucking so hard she stretched him out, before he snapped back. She crawled over him and lay beside him, ready for more kisses.
It was half an hour later that he asked her if she felt better.
“I’m okay,” she said. “I’m not deliriously happy, but I’m okay. I’m going to go talk to a lawyer, today if I can find one.”
“I’d offer to go with you, but that might look kind of weird.”
“Brad is just going to have to get used to it,” she said. “I have to have you. I can’t go on without you.”
“What brought all this on?” he asked, stroking her hip.
“That stupid woman at the Putt-Putt place,” she said.
“Really!”
“Yes. I know it sounds stupid, but I was able to resist you trying to get me to have more children, but when she said that I thought, ‘Well, I’ll show you, you bitch!’ and suddenly my maternal instinct kicked in. It was strange. I never felt that before.”
“Not even with Brad?”
“I didn’t intend to get pregnant with Brad. In fact, I kept telling myself I couldn’t get pregnant. And then, when I did, I was so scared and worried that there was nothing fun about it until he moved.”
“He moved?”
“He’d been growing in me for five months, and I was used to the idea. My parents had adapted and Paul was even making moves to show he was going to step up. I was used to my belly being distended, but it was just weight I was carrying around, you know? And then he turned over inside me. I felt him roll. I felt his elbows or knees or something press against me like he was trying to stretch things, to make more room. It was in that instant that I realized he was a tiny, little boy who was depending on me. I fell in love with him in that instant. That’s when I started taking my pregnancy seriously.”
“Wow,” he said, softly. “I didn’t know.”
“Why would you? That’s not the kind of thing I’d mention to a boy who comes to my house to visit my son.”
“Yeah,” he said.
“But what I’m saying is I never wanted to get pregnant with him, and when that woman made me want to get pregnant it was like something had taken me into its mouth and was shaking me, like a dog shakes a squirrel it’s caught.”
“You were a little wild,” he said.
“I’m better, now,” she sighed.
“What we did was dangerous, wasn’t it?” he commented.
“Yes, but I don’t care. I love your semen and I want it all over me and inside of me. I want to bathe in it.” Her voice was tense, demanding.
“I promise to make lots for you,” he said.
“You better. I have a feeling this desire inside me isn’t going to just go away. It’s like a big bear, hungry and growling.”
“What can I do to help?” he asked.
“Stop being so fucking loveable!” she said, and then kissed his chin. “Every time I see you I want to get us naked.”
“We’ll work on getting the bear into a cage before our next date,” he said.
“It’s going to take a very big cage, Bob.”
“We love each other,” he said. “That means we can work together to achieve our goals.”
“I’ll try,” she said.
“Huh,” he went.
“What?”
“I just said we love each other and it seemed normal to say. I’m lying here with the woman I’ve adored for years and was quite sure I’d never even get to kiss, much less be naked with. And yet, here I am. Dreams really can come true.”
“Well, if I keep getting your sperm all over my pussy lips my dream might come true, too,” she sighed.
He actually stayed away for almost a whole week. Paul came back during that week and Bobby didn’t want to have to control himself that harshly. It was easier to be without her, than with her and unable to touch her, or blow her a kiss.
He chose the plan for their next date carefully. He wanted them to be in a public place, like the miniature golf course, or bowling alley, but with more people. What came to his mind was the old-school arcade that had been built in one of the stores in the mall. An eccentric man named Seth had collected old pinball machines and video game consoles as a hobby, at first. It was when he got an old slot machine that he started learning how to repair things. He wanted them to work. He had a smallish warehouse full of machines when he got the idea to open an arcade like there had been dozens of when he was a kid. He had the machines. He had the spare parts to repair them if they broke. And he had the expertise needed to keep them working. Instead of coins, he used tokens that he sold for a dollar apiece, or thirty for twenty-five dollars. A whole new generation of young people found out what their parents had played when they were kids. And a lot of parents took their kids there just so they could beat them at a game that wasn’t on a computer screen and that required a handheld controller.
Bobby and Brad had gone to this arcade in the past. It was like a museum filled with flashing lights and ringing bells. Noises of all kinds filled the air, along with the shouts of people who had either won or lost a game. It was into this madness that Bobby took her.
She had seen both Brad and Bobby playing video games at home, of course, but standing at a big console, with a large display in front of you, was different. She loved Frogger, but Missile Command was beyond her ability, past the first few screens. She had trouble looking in three places at once. Digger was better. When they got to Qix she was in her element. She could anticipate the moving line better than Bobby could, and her moves were lightning fast as she built walls to capture the Qix. He spent twenty-five dollars alone on Qix and didn’t mind at all because she was radiant as she played the game.
He was explaining how Donkey Kong worked when a voice said, “Mom!”
They turned to find a discombobulated Brad staring at them.
“What are you doing here?” asked Bobby, loudly.
“The question is, what are you guys doing here?” Brad replied.
“I was telling her about old time games and she wanted to see some,” Bobby said. It sounded lame, even to him.
“And you didn’t bring me?”
“Let’s not stand here yelling,” said Bobby. “Let’s go to Cuppa Joe’s, at the end of the mall.”
Bobby’s reason for going to the coffee shop was to give himself a chance to think. He had to come up with something that would throw Brad off the scent. They all walked in a strained silence through the busy mall. Nobody spoke until after they had ordered and found a table to sit at.
“Are you guys on a date?” aske Brad. “Did you hire my mother for a freaking date?”
“What do you mean ... hire?” asked Olivia, somewhat desperately.
Brad made a disgusted face as he answered.
“Mom, give me a break. Nobody volunteers that much, and only when Dad is gone. I followed you one night and saw where you went. The only reason I didn’t say anything was because I was sure nothing really serous was going on.”
“I don’t understand,” said Olivia, her eyes wide. “You followed me?”
“Yes. I watched as some geezer took you to an art exhibition and to dinner. But you didn’t go anyplace with him that had a bed. I followed you to that Matilda’s Maidens place and realized you were working for them. But it didn’t look like what those women do. I even checked your panties, to see if there was any semen in them and there never was, so I stopped worrying about it. I know Dad’s treating you like he’s an asshole. I love him, but he’d a dick when it comes to being a husband.”
Olivia straightened up and she leaned forward. Suddenly her eyes shot fire and her face was tense.
“You checked my panties?” she hissed.
“I know Dad cheats on you. I just wanted to find out if it went both ways,” he said.
“Why, I should -!”
Bobby reached for her hand and covered it. She looked down and then relaxed, sitting back.
“That is completely unacceptable, Bradley,” she said, in a more controlled voice. “How could you intrude on my privacy like that? I feel violated!”
“All I did was look to see if there were semen stains,” said Brad. “I didn’t sniff them or anything.”
Bobby reached for Brad’s hand, too.
“Shut up, Brad. You’re digging yourself into a hole you’ll never be able to get out of. She only escorts men, nothing else.”
“Even you?” Brad’s voice was tense.
“It’s a little different with us,” said Bobby. “You know how I’ve felt about her all these years. I did the same thing you did. I followed her and found out she worked for Marci. So when I turned twenty-one I booked a date with her through Marci, to be escorted to an opera. When she found out who the date was with I had to blackmail her to make her finish the date.”
“Opera?” was what Brad seemed to center on.
“It was called The Magic Flute. You should go see it some time. It’s really quite good.”
“My best friend dates my mother and goes to operas,” said Brad, as if he was talking about something alien invaders might do.
“I have a right to be happy, Bradley,” said Olivia.
“Yes, you do!” said Brad. “I agree completely. So, this has been going on since your birthday?”
“We’ve been on seven or eight dates,” said Olivia.
“You can’t even remember exactly how many dates you’ve been on?”
“I wasn’t counting, okay?” Now she was the one with a disgusted look on her face.
“So, what happened on your third date?”
“What do you mean?”
“Well, everybody I know are making out hot and heavy on a third date and ... you know.”
“Bradley Eugene Applebee, I will not discuss my sex life with you and it hurts me that the son I’ve raised would pry like that!”
“You’re right. I was out of line,” said Brad.
“It’s getting serious,” said Bobby. Olivia’s head whipped around and she stared at Bobby. “He was going to find out sooner or later,” he said with a shrug. “Rip the Band-Aid off, you know?”
“Actually,” Brad said, in an almost offhand way, “I’m really glad you chose Bobby to cheat on Dad with.”
“We haven’t cheated, yet!” said Olivia, but her voice was strained.
“I know I’m supposed to stay out of your sex life, and I will, but eight dates and you haven’t sealed the deal, yet? You’re giving the boy blue balls for sure.”
“No she’s not and stop talking about that,” said Bobby. “Why did you say you were glad it’s me?”
“Are you kidding? I love my mother. And I love you. She could not do better and she does deserve some happiness. You do, too, for that matter. I know you’re too stupid and shy to ask women out. And to use blackmail to do it? This is groundbreaking!”
“You can’t tell your father,” said Olivia, tensely. Brad held up one hand.
“I said you deserve to be happy, not stressed out. Are you going to divorce him? If you do I want you to have custody of me.”
“You’re a grown man,” Olivia snorted.
“So is my best friend. I kind of hope you two fall in love.”
“We already have,” said Bobby.
“Now that’s more like it!” said Brad with a grin.
“I don’t believe this is happening,” moaned Olivia.
“I bet this isn’t the first time you’ve said that,” said Brad. “Oh! Wait! No! You can’t fall in love! If you do that and get married he’d be my step-father!” Brad made faces of horror.
“Well, you’d better get used to the idea,” said Olivia, “and while you’re at it, get used to the idea of being a big brother, too!”
Brad blinked.
“It’s that serious?”
“Yes,” said Olivia. “I still don’t know how it happened, but he got under my skin and I fell helplessly in love.”
“Well, he’s been in love with you since forever, so that works out,” said Brad. “But wait a minute. You’ve been on eight dates and you already want to have a baby? Can women get blue balls, too?”
“How did you know your father was cheating?” Olivia asked, ignoring his barb.
“We got drunk one night when you were actually volunteering someplace and I asked him to set me up with his intern. He said no way, because she was his. Then he put a finger to his lips and said I couldn’t tell anybody. After that I watched you two. It was obvious there was nothing left. I figured you knew, too, based on how you were acting.”
“I did,” she said.
“Why did you come to the arcade tonight?” asked Bobby. “Were you following us?”
“No. I figured Mom was on an escort job and you weren’t picking up. I needed a break so I came down here to work off some stress.”
“I’m sorry if I’ve added to the stress,” said Olivia.
“Perish the thought!” said Brad. “I haven’t felt this good in a long, long time.”
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