Olivia's Escort Service - Version Bravo
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 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
“Boys, boys, boys,” said Olivia, as she sat back in her chair. Dinner was chicken and rice casserole and spinach, with hot rolls on a big plate in the middle of the table. When she had come and put her head inside Brad’s room, to say, “Supper is ready. Be sure to wash your hands,” the men had shuffled into the bathroom to wash hands and then shuffled to the kitchen table. It was a sort of zombie shuffle, as if some instinct was telling them to go somewhere and their brains (or lack thereof) weren’t involved. When they got to the table they sat, and didn’t move.
In Bobby’s case, he was metaphorically holding his breath, waiting to see what would happen. He wasn’t worried, or uncomfortable. He just didn’t want to derail anything anybody else might want to discuss.
In Brad’s case, he had no idea what to say. His mind was a big, empty cave with bats in it that kept flying nearby, whispering, “Fuck me. Fuck her. Fuck somebody!”
Olivia was probably in the best position. She had much more life experience and knew that, a few weeks down the line, things would have normalized and the awkwardness would be gone. The time between now and then might be rocky, but she knew the boys loved her and she knew she loved the boys, so she wasn’t worried about how things would turn out. To the contrary, she had a deep hunger for what Paul had withheld from her for years, and she wanted to get to feeling that, again.
When neither man reached for dishes of food, Olivia stood up, dished out portions and then sat back down. She ate a few bites while Bobby nibbled a bit and Brad just sat there.”
“This does not have to be this hard,” she said. “Bradley, do you love me?”
“Yes!” he blurted. It was the obvious thing to say and it was also true.
“Do you love Bobby?”
“Yes,” said Brad, with less excitement.
“Will you let me love you in a new way?”
Everybody at the table knew what this “new way” entailed.
“I don’t know,” moaned Brad.
“All right. Here is what I’d like to do. After dinner, I want us all to go to my bedroom and take our clothes off. Then we’re all going to lie on the bed, together. We’ll start with kisses. I’ll kiss one of you and then the other. Brad, you are your father’s blood and are going to take his role as the head of the family, so you should have the right to have me, first.” She stopped.
“Have you?” Chad’s voice sounded hollow.
“You have a handsome and quite big penis, and I want to feel that penis in my vagina. I feel like cobwebs might be in there. Can you do that for me, Baby? Can you give me what I’ve been missing for so long?”
“I don’t know,” gasped Brad. “This is too strange.”
“Okay, then, if you’re willing to give Bobby the first time, then you can watch us make love and see what I am going to want you to do from now on. I already know Bob is willing to make love to me. He won’t be shy.”
“Watch him?” Now Brad’s voice held something deeper.
“You are both going to be my lovers,” said Olivia. “I will not tolerate any fighting and fussing. Brad, you will always have first option, but when you can’t go on, I’m going to want Bob to take over. It can be the other way around but that’s up to you ... the head of this household.”
They sat there, their food forgotten.
“What do you want us to do, Brad?” asked Olivia. “You have the right to decide what is going to happen. You are the man of this house.”
“What happens when Dad gets back?” asked Brad.
“I will handle him. He will not interfere. He can go on fucking his intern on their little trips, or even at her house, or apartment, or dorm room, or whatever. He will not interfere with what I’m going to have with you two.”
“A week ago we were still saying this could never happen and that Paul could never find out,” Bobby commented.
“That was when we were trying to keep it from Brad. That is no longer the case. Brad has reacted well to the news that you and I are almost lovers, and that was all I really cared about. I did not want to hurt my little boy.”
“I’m not your little boy!” Brad snapped, automatically.
“I know, Sweetheart,” she said. “I got to feel how much you’ve grown up and I can’t wait to teach you how to treat a woman.”
“So this is really happening,” said Brad. His voice was stronger.
“Yes,” she said.
“And I’m going to make love to you and Bobby’s going to make love to you and we’re going to ... cum ... in you?”
“Yes.”
“So you’re on birth control.”
“No.”
“What do you mean, no?” Brad asked.
“I mean I am not taking anything that will prevent sperm from fertilizing one of my eggs and making me pregnant.”
“So Bobby and I will be wearing condoms,” he said.
“Only if you make me, will I accept that. I love my two men. I don’t want there to be latex between us when we kiss, and I don’t want it between us when we make love, either.”
“But you could get pregnant,” said Brad.
“Yes,” she said.
There was a stunned silence. Even Bobby was stunned. It was Brad, who broke the silence.
“So, let me get this straight. You’re going to sleep with both of us, and we’re going to have bareback sex, and you’re going to let us cum in you, and you might just have a baby?”
“I think that sums it up pretty much,” she said.
“You can’t have our baby!” he yipped.
“Why not?”
“You’re my mother!” he barked.
“So, I’ll have Bob’s baby,” she said.
“Why do you want to have anybody’s baby?” groaned Brad.
“I got married because you were inside me,” she said. “I didn’t choose that, but the first time you moved I knew I could never love anything more strongly than I loved you. By the time you were ready to come out, I had already decided I wanted two more. Paul wouldn’t let me do that. Paul isn’t calling the shots any longer. If you forbid me from getting pregnant again I will be very unhappy, but I will honor your wishes. You are my husband, now.”
“Fuck!” grunted Brad.
“Language,” said Olivia.
“When she said we could get her pregnant did you pop a boner, too?” asked Bobby.
“Yeah,” moaned Brad.
“We can warm up dinner later,” said Olivia. “I do not want to waste two perfectly good erections.” She stood and unbuttoned her blouse. She wasn’t wearing a bra under it and the naked skin between the edges of the blouse were inviting. “Is anybody going to make love to me, or do I have to use my vibrator, again?”
Bobby was ready to go. And, suddenly, so was Brad. It wasn’t that everything had resolved in his mind. Rather, the view of that creamy skin between obviously bare breasts caused Brad’s little brain to kick in and his normal mind was more than happy to take a back seat and rest a little bit.
That lasted only as long as it took him to tear his clothes off, all the while with his eyes locked on his mother, who was also disrobing. And he was very much ready to go, in the penis department. Olivia, though, knew how spastic his body was likely to be, this very first time they were intimate together – not counting the shower, when he’d been as limp as a noodle.
“Let’s not waste this again,” she said as she pushed her son hard and knocked him onto the bed. She swooped, but only with her mouth, and Brad gave an agonized, drawn out groan as he realized what was happening and ejaculated just about as prematurely as it was possible to, not counting when he blew a nut in his pants. Then she swallowed, licked her lips, and kissed her son.
“We’re going to do that many, many times in the future,” she said. “Now, could you move over a little bit? I need Bob to make me feel good.”
Brad would forever claim that he didn’t mind that it was Bobby who got to fuck Olivia first. He was gasping for air and his eyes were as big as saucers. There was the faint taste of something he identified as his own semen on his lips, and when he scooted over only for Bobby to fall down right beside him, the fact that both he and his friend were naked, lying next to each other, seemed to be more important than the rest of what was going on. Then his mother’s knee dug between them and he watched in awe as her hand came to grip his best friend’s prick and direct it between her legs, where it suddenly just disappeared up inside her. She let out a groan that made Brad’s cock ooze the last of his cum and the only reason Bobby didn’t go off was because she reached down, raised up just enough to pinch the base of his cock, and then it was Bobby who was groaning.
“I’m going to need you longer than ten seconds,” Olivia panted. She slowly let go of the base of his penis and the dry orgasm he had just gone through eased off the electrical flow that suffused his groin. She settled down, driving him deep and then put her hands on his chest. Her head drooped and her stomach sagged, as she raked her pussy toward his face. Since his penis was in her, she couldn’t move far, but the little distance she did go put intense pressure on her clit.
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