Olivia's Escort Service - Version Bravo
Copyright© 2026 by Lubrican
Chapter 6
Romance Sex Story: Chapter 6 - Bob found out his best friend's mom secretly worked for an escort service that all the high school boys thought was a front for prostitution. Bob couldn't believe she would do that. 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? And how would his best friend react if he found out?
Caution: This Romance Sex Story contains strong sexual content, including Ma/Fa Blackmail Consensual Heterosexual Fiction Incest Mother Son Masturbation Petting Pregnancy
Another two weeks went by. Bobby spent hours at their house, hanging out with Brad, while Brad tried to teach him what coding was all about. To Bobby, it was like a foreign language, with words he didn’t understand, except some of these words had dollar signs and brackets and pound signs in them, among other things. He listened patiently, but what he really wanted to do was go find Olivia and lick her pussy. He saw her, of course. He’d go to the bathroom or to get a glass of water. During their very brief interludes, their eyes met and both could see the passion in the other’s.
“This sucks,” Bobby said, at one point. She had been standing at the counter chopping lettuce to make a salad and he had told Brad he was going to get a snack.
“Bring me something,” said Brad, his attention fully on the app he was building. It was a game where a puppy with floppy ears had to negotiate going through a digital house while avoiding a snarling cat.
Bobby had walked up behind her and slid his hands around her, cupping her heavy breasts and bouncing them a little. She was wearing a bra, which gave them a completely different feel in his hands.
“Naughty, naughty,” she said, letting her head fall back to press against his shoulder. He was two and a half inches taller than she was and when they hugged, her nose was right at the top of his ribcage. “I love that, but it’s too dangerous.”
“He wouldn’t leave his chair even if there was an earthquake,” said Bobby.
“Still,” said Olivia.
He had just stopped molesting her and stepped back when Brad bounced into the kitchen.
“I changed my mind,” he said. “When I eat a PB and J it gets on my fingers, which gets on the keyboard, which makes a mess. What I need right now is a grilled cheese sandwich.”
“Well, I’m not going to make it for you,” said Bobby, whose heart was doing 125 beats per minute. He had almost gotten caught! “PB and J is one thing, but melting cheese is out of my wheelhouse.”
“Well, your wheelhouse must be pretty raggedy,” said Olivia, her voice calm. “Any man who can’t make a grilled cheese sandwich needs a minder.”
“I’ll make a grilled cheese sandwich!” said Brad, posing with his fists on his hips and his head looking up.
“Teach Bobby how to make one,” said Olivia. “I have enough to do without becoming his minder.”
“Oh, no, no, no, no,” said Brad. “You cannot be his minder because he is a pervert who would try to put a move on you.”
“What?!” yelped both Bobby and Olivia at the same time.
Brad opened the bread sack and, as he reached in, his voice was casual.
“You haven’t seen how he looks at you, Mom. He’s had a crush on you since he was, like, eleven or something.”
“I have not!” said Bobby, trying to make his voice sound heated.
“Yes you have. Admit it. You think my mom is hot.”
“Even if she was hot I wouldn’t say that out loud, right in front of her. Geeze, Brad, have some consideration. Your mother doesn’t want to have that kind of crap in her mind.”
“Actually, it’s not so bad,” said Olivia. Both young men looked at her. “Bobby is polite, and helpful, and intelligent. I’m sure he has girls crawling all over him, based on his looks and personality. I’d much rather he have a crush on me than some perverted old man who drools when he looks at me.”
“Drools?” Brad said. Then he laughed. He abandoned the bread, hunched over and dragged his right leg as he moved toward his mother.
“Me want sex with you, lady,” he growled. Then he wiped his mouth. “Me sorry for drooling.” He laughed again until Bobby thumped him on the arm.
“Don’t say things like that to your mother,” he said. “C’mon, man.”
Brad stood up, smiling. “I don’t want sex with her. I was just acting like you.”
“Bradley!” snapped Olivia.
Son went to hug mother.
“I’m sorry.”
“No, you’re not!” said Olivia as she slapped his ass as hard as she could. Her son was an inch taller than Bobby and she often felt like she was standing in a forest when she was with both of them.
Brad leaned back and when Olivia looked up at him, with a frown on her face, he kissed her forehead.
“That’s all the sex I want with you. Dad’s a fucking idiot for neglecting you, so I guess you’ll have to get your sex from Bobby.”
He leapt back, laughing, expecting Olivia to chase him, but she didn’t.
“Are you giving me permission to have sex with your best friend?” she asked. There was no mirth in her voice.
“Calm down, Mom,” said Brad, who could sense things had gone further than was wise. “All I meant was that if you divorce Dad then Bobby can console you.”
“Console me,” said Olivia.
“Not that way,” groaned Brad. “I know he’s like a son to you and if you ever need anything you know either he or I will help you with it. There is a closeness here,” he waved his hand in a circle, indicating the whole room, “that goes much deeper than casual friendship. There’s nothing wrong with that. I love you and Bobby loves you and I know you love both of us. So? It does not bother me that you love him like you love me.”
Olivia folded her arms under her breasts, which just made them look bigger.
“Whether your father is neglecting me or not is none of your business,” she said, coldly. “If you’d ever get out of that room and go on some dates and interact with some women, you’d have your own relationship to ponder. I can take care of myself, and if I decide to take a lover I’ll choose him, myself, too.” She stared right at her son. Brad held up both hands, palms out, clearly in a supplicating manner.
“I’m sorry. I didn’t mean to touch a nerve. Like I said, we love you and we’d both do anything for you. I was just kidding around.”
“I’ll thank you not to kid around when it comes to my sex life,” she said.
“He has brain damage,” said Bobby, carefully. He could tell she was upset, but not to what degree. “I’ve told him I had a crush on you since we both entered puberty. No boy wants to hear stuff like that about his mother. He’s damaged and it’s my fault.”
“So, I’m a MILF?” she asked, her voice calm again. “Is that what you’re saying”?
“Geeze, Mom!” groaned Brad.
“I know what that term means,” she said. “You just suggested he was acting like that’s what he called me.”
“You are a MILF,” said Bobby, “but that’s something you have no control over and I was stupid to say all those things to him. I have nothing but respect for you. I would never do anything I thought would make you uncomfortable or worried. I just went through a phase, like all boys go through. Brad agreed with me. It didn’t mean anything. It’s just boys, being boys.”
She looked at Brad.
“So you think I’m a MILF, too?”
“No!” gasped. “That was when we were in seventh grade, or something. Every woman was a MILF back then.” He realized what he’d said and covered his eyes. “I’m not hungry anymore. Can I be excused?” He had reverted, to some degree, to being that thirteen-year-old boy.
Olivia walked to him and hugged him.
“I’m not mad at you, Honey. It makes a woman feel good when the right kind of man thinks she’s attractive. I saw you go through that stage and it looked awkward and scary and like you were tiptoeing through a mine field. I wished I could help you, but you’re right. It’s just something a boy has to go through while he becomes a man.”
“I’m sorry,” said Brad.
“Don’t be. You’re right. The three of us do have a special relationship. You two are the only two men in the world who have permission to call me that without getting something thrown at them, okay?”
“Let me go, Mom,” said Brad, his voice cracking.
“Why, Honey? I like hugging you. What’s wrong, Baby?”
She had felt him get hard in his pants as she gave him permission to call her a MILF. She didn’t react like most mothers would. She had tons of experience with men and knew that men get erections whether it’s socially acceptable or not. Nature drives their erections. That he had naughty thoughts about her didn’t bother her. In fact...
She let him go but reached for the front of his jeans. Bobby watched, frozen, as Brad looked down to see his mother’s hand find and squeeze his boner.
“You really need to go on some dates, Brad. I’m sure there are women out there who would love to make you this way and I encourage you to find them. I would like some grandchildren some day.”
She let go and looked at Bobby.
“Do I need to check you, too, Bobby? Are you as normal as Brad, when it comes to women you think look pretty?”
Bobby crossed both of his hands over his zipper.
“No, Ma’am. You don’t have to check me. I’ve always been too shy to ask girls out, but I promise to work on that.”
“Good. Now, both of you shoo and let a poor, downtrodden MILF get dinner ready.”
She went back to the counter, picked up the knife she’d been using, and started in on the lettuce, again. Bobby and Brad looked at each other. Brad let both palms face up as he raised his arms sideways. It was body language for “WTF?” Bobby shrugged shoulders and pointed toward Brad’s room.
Back in that room Brad sank down in his desk chair.
“Man!” he gusted. “What the fuck was that all about?”
“I’m not sure,” said Bobby. “I remember something about Paul neglecting her and you telling her I thought she was a MILF. You’re a fucking idiot for that, by the way. And, somehow, the subject became her sex life for a minute or two, in there. And then she felt your basket and it looked like she thought you had a boner. Did you have a boner?”
Brad put the heels of his hands over his eyes and rubbed.
“When she said I could think of her as a MILF it just happened. It was like, light speed, man. I didn’t mean to.”
“Well,” said Bobby, as he sat in the other desk chair, which Brad had abandoned for a new gamer’s chair. “She is a MILF.”
Brad took his hands down and looked at Bobby.
“Look, dude, I know you’re shy around women, but you can’t fuck my mother.”
“I could if she got a divorce,” said Bobby.
“She’s not going to get a divorce,” said Brad. “Things are rough between them, but I don’t think divorce is in the future, so find some other guy’s mother to lust after, okay?”
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