Olivia's Escort Service - Version Alpha
Copyright© 2026 by Lubrican
Chapter 1
Romance Sex Story: Chapter 1 - 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
Bobby Forester stood, his palms sweaty, his knees trembling a bit. He was dressed in a rented tuxedo in an alcove of the lobby of the Kingston Hotel, one of the swankiest hotels in town. There were several upholstered chairs, placed so that people sitting in them could have a conversation, but he hadn’t sat down. He was too nervous. One of two things was about to happen.
The first was what he hoped would develop. The woman he had hired from an escort service would arrive and go with him to (hopefully) enjoy seeing The Magic Flute, an opera he had always wanted to see.
He was twenty-one and this was the first time he’d used an escort service to get a date. He’d always been shy around girls, and had never had a real girlfriend. What he was doing right now was something he’d felt driven to, but was terrified about. That’s because the second potential outcome upon meeting his escort might be a blowup of epic proportions.
The reason for that was plain. He had hired a particular escort from the bevy of pictures of beautiful women. She wasn’t any ordinary woman, though. He already knew this woman.
She was his best friend’s mother.
He had found out she worked for the escort service by accident and, since he’d already had sexual fantasies about her, he waited until he was old enough to hire an escort and then chose her. He had known he was going to do this for almost a year, during which he had seen her on dozens of occasions. Her son, Brad, still lived at home. He had learned computer coding and developed games and apps, which he then tried to sell to various platforms. His work was good, but he wasn’t well-known enough to live off of his income, so his parents had said he could keep living there. He had to pay rent, but it was symbolic, really.
For almost a year, as Bobby sat and ate with them, or visited his friend to hang out, he looked at her and dreamed of going on a date with her.
That she was married was what confused him. He knew Paul, Brad’s father, but not well. The man traveled almost constantly for his job, and had never seemed to pay much attention to his son’s friend. He had never seen any act of affection between Brad’s parents. Not publicly, anyway. There seemed to be an air of tension when Paul was home, but it wasn’t anything obvious.
He checked his watch for the tenth time. The alcove he was standing in had no logical reason to exist, as far as he could tell. It was called the “Parlor”, where people could have a private conversation, but if people were going to have a private conversation why would they stay at a hotel to do it? Or why wouldn’t they go up to their room, if they were staying there?
It had just occurred to him that this might be a common place for people to meet, when he saw her.
Her hair was down, brushing her shoulders. She was wearing a black dress that showed a lot of cleavage, but went to her ankles. The bodice cupped her breasts as if they were precious eggs. A simple string of pearls graced her neck, and lay almost in the cleavage. It was the first time he’d seen her in high heels, and the first time he’d seen her walk in anything other than two inch flats or tennis shoes. She looked completely different than his friend’s mother. She had a confident stride that made her breasts bob just enough to draw attention, but not so much as to look slutty. She was wearing lipstick, another thing he’d never seen on her lips. It made her lips stand out in her face, as if they wanted to be kissed.
She came in and went straight to the alcove. When she saw him she stopped, suddenly. The clutch purse in her hand suddenly looked like a weapon.
“Bobby!” she said.
“Hi,” was his reply.
“Why are you here?” she asked.
“I’m waiting for you. You’re my escort to the opera.”
“That’s ridiculous, Bobby,” she said. “You and I are not going on a date.”
He was prepared for this eventuality ... or hoped he was.
“If you don’t go to the opera with me I’ll tell everybody you work for the business in town everybody believes is a cover for prostitution.”
Her eyes flashed.
“I am an escort only! I am not a prostitute and I have never had sex with any of the men I escort. Is that clear?”
“Yes. I believe you and I’m very glad to hear that. But, if I tell people who you work for, you’ll probably have to tell all of them the same thing.”
“This is blackmail!” she barked.
“Yes, it is,” he admitted.
“You can’t blackmail me, Bobby!” Her voice was strident, but had less conviction in it than before.
“Just go on one date with me. That’s all I want. I’ve been half in love with you since I was fourteen, maybe even before that. I know that’s crazy and people would call it a crush, but it’s how I felt. I just want to spend some time with you as my date, instead of my best friend’s mother.” He let a long pause go by. “Please?”
“This is crazy,” she said, but in a conversational tone. “I should say no.”
“Please don’t,” he said.
“I can’t believe you’d blackmail me like this.”
“I admit I’m a little desperate,” he admitted.
“Desperate?”
If I tell you something will you promise not to hold it against me?”
“How can I say yes to something like that when you’re extorting a date from me?”
“I feel bad about this. Honest. I do. But I’ve dreamed about doing something like this, going to an opera together, with you as my date, and holding your hand during the opera. I know Paul would kill me for this, but it’s driven me nuts for so long I had to do something about it.”
She stared at him and then bit one corner of her lower lip. It was obvious she didn’t do that on purpose, to show that face.
“Paul might not be as angry as you think,” she said, referring to her husband. “What opera?”
“It’s The Magic Flute,” he said, hopefully.
“Hmmm,” was her response. “Every girl wants a white knight to come save her, at some point in her life.”
“Yes, and every boy wants to be that white knight,” he said.
“You look good,” she said, eying him up, and down.
“You look gorgeous,” he sighed. “You always look gorgeous.”
“I’ve caught you looking at me before,” she said. “I always thought it was hormones and you’d grow out of it.”
“It probably was hormones, but I didn’t grow out of it.”
“You haven’t been over for a few weeks. Are you spending time with any girls?”
“You know how shy I am,” he groaned. “I can’t talk to a woman if I like her even a little bit.”
“But you can talk to Marci and ask for me, specifically, to escort you to the opera?”
“Like I said. I’m a little desperate.”
They stood there as she thought about things for what seemed like ten minutes, but was really only thirty seconds.
“You want to know something funny?” he asked.
“What?”
“I’m better, now. I mean I don’t feel as jumpy inside. I actually got to tell you how I feel and I kind of relaxed or something. You don’t have to worry. I’d never in a million years embarrass you or tell anybody anything you didn’t want them to know.”
“So you’ve changed your mind?”
“Yes. I’m sorry. I shouldn’t have made you do this. You don’t have to go.”
“Do you already have the tickets?” she asked.
“Yeah,” he said. “I can probably scalp them, though, especially if I discount them.”
“You look handsome, even more than usual. You should still go.”
“No. I don’t want to sit there, alone, surrounded by couples.”
“I see. Do you really mean it? You’re letting me off the hook?”
“Yes. I’m really sorry. I should never have threatened you. If you ban me from coming over to see Brad I’ll understand.”
“You really are a novice, when it comes to women,” she commented.
“I guess so,” he said, not understanding why she’d say that.
“What time does the opera begin?”
“Seven-thirty.”
She looked at an elegant, jeweled watch on her wrist.
“Well, we’d better be going, then, or we’ll be late.”
“What?”
“We’ll be late if we don’t get a move on,” she said, patiently.
“You mean you’re going?” He sounded incredulous.
“Yes, but I’m going as your friend’s mother, not a hired escort.”
“That would be weird,” he said.
“You can take me out as an escort, but not as a friend?”
“As an escort you’re not scary. As Brad’s mom, you’ve yelled at me plenty of times.”
She laughed and came to slide her hand through his elbow.
“Come on,” she said. “I want to feel like a princess, tonight.”
What Bobby couldn’t know, and probably wouldn’t have understood even if he was aware of it, was that Olivia’s life had been going through a rocky patch for a while. It wasn’t the first time. When she was seventeen she’d succumbed to the ploys of the quarterback of the football team and ended up pregnant. He had stepped up, and they had gotten married a week after they graduated.
Things had been fine for a while, much better than for most young people in their situation. His father worked for the government and he got Paul an entry level government job that didn’t require a degree and had good benefits. He had a fair salary to start and her prenatal care was taken care of by their insurance. She had the baby and fell in love with being a mother. Paul went up through the ranks, eventually getting a job that paid a lot because he was sent out on inspections. That meant he got a bump in pay because TDY, or temporary duty away from home, had per diem enhancements that were generous. He got over a hundred dollars a day just to cover meals. If he ate a Pop Tart in the morning, a sandwich at lunch, and a steak at night, he had at least half of that money left over. Likewise, his hotel was paid for by Uncle Sam. All he had to do was figure out what to do with all those long, lonely nights away from his bride.
He was relatively handsome, and women (some women) are always on the lookout for someone to buy them a meal and pay for their drinks. If all it costs them is a toss in the hay, well, then, what’s the harm in that?
Olivia’s suspicions were aroused by his laundry. Some of his shirts carried the scent of a perfume she didn’t own. She was more alert, after that, but there wasn’t a lot of evidence until one time she went through his suitcase, as usual, getting his things to wash and so on, and found a pair of red, lace panties. They were a G-string design and she didn’t own anything even close to that. He didn’t know that his paramour of the week had slipped them in his suitcase as a souvenir. He never wore his wedding ring on these trips, and never told the women he was married. If the woman sensed something he’d say, “We’ve been separated for a couple of years, now, and she already has another man she says she’d going to marry as soon as we get a divorce.”
She put the folded panties under his dinner plate that evening, and it was obvious something was there. When he lifted the plate to look, she just said, “I found them in your suitcase when I was getting your dirty clothes to wash.”
He stammered and stuttered and tried to come up with a reason he had them. When he said he bought them for her as a surprise present, she said, “Smell them, Paul. They’re not new. I believe they are what is politely called ‘pre-owned’.”
She didn’t want a divorce. Brad was fourteen when this happened. He needed two parents, even if one of them was gone most weekends. The fire cooled even more and she realized it had been cooling slowly and she hadn’t paid attention to it. Their lovemaking had settled into a ‘once every couple of weeks’ rhythm and, what with being a mother and volunteering at school and the local library, she was busy enough and tired enough that she didn’t notice the slow degradation of their relationship. Now, the “frequency of having sex” had dropped to zero. Basically, she had been living in a sexual desert for seven years.
He begged for her forgiveness and promised he wouldn’t do it again. What convinced her that was a lie, too, was when he said the woman reminded him of her and he got inflamed. He hadn’t been “inflamed” in their bedroom for years, yet suddenly some other doppelganger brought on uncontrollable passion? Plus, she still smelled things in his suitcase that shouldn’t be there.
She was starved for the kind of male companionship she needed and felt she deserved. There were men she knew who would be most happy to bed her, but that wasn’t what she wanted. What she wanted was for a man to honor her and treat her like she was Cinderella; or at least adore her. She needed the kind of intimacy with a man that rose above mere sex.
It was irony that led her to start working for Marci, in a perhaps unconscious attempt to find that intimacy. It didn’t happen until Brad was sixteen and had his own interests that didn’t involve his mother. In a nutshell, she was pissed at Paul, but not enough to have sex with other men. She met another mom named Marci at a volunteer event and the two became friends of a sort. What made it so ironic was that Marci convinced Olivia that escorting could be both fun and profitable, even if no sex was involved. On a disgruntled whim, she went on one date and it changed Olivia’s general outlook on life. Suddenly a dozen men wanted to be with her, even if no sex was involved. Marci taught Olivia how to use her natural beauty, and how to walk and talk and inflame men. This was what Bobby noticed as that carried into her home life. It worked in spades, both for the adult men she interacted with, and a sixteen-year-old boy who hung around all the time with his best friend.
There wasn’t much chit-chat as he drove them to the opera house in his older Toyota Celica, which had seen better days and had a bike rack on the back. Both of them would have looked perfectly normal stepping out of a Bentley, or a Mercedes, but the Toyota was all he had. The tickets had been expensive and while he was paid a living wage at the stables he worked at, it wasn’t the kind of living wage that would supply opera tickets more than maybe once a year.
He knew how to behave. He had opened the door for her as she got in and when they parked, he opened it and held out his hand to assist her out of the car. She swung both feet towards the door out of habit. She sometimes wore short skirts on a date and she never teased the men she was with, by showing an acre of leg (or panties) when she got out of a car. She took his arm again as they walked toward the building.
“We probably look ridiculous,” he said. “People will think you’re my mother.”
“And what if they do?” she asked. “If you were my son I’d be proud to be seen with you like this.”
“Even though I committed a felony half an hour ago?” He glanced at her.
She pulled his arm against her breast.
“That was merely a negotiation tactic,” she said. “Now. I want to have fun tonight and I’m starting right now. I’m your date. It doesn’t matter what other people think. I’m here with you because I want to be here with you. Are you embarrassed by me?”
“Oh, hell no,” he sighed. “I’m with the most beautiful woman who will enter the opera house tonight. I feel like I’m walking on clouds.”
For Olivia, what overcame the age difference, and the social distance, was the honesty in his admiration for her. She knew this young man very well and she knew, down deep, that when he said he was with the most beautiful woman at the opera, he believed it.
The difference between the compliments the men she dated gave her and Bobby’s tribute was that Bobby didn’t want anything from her. He hadn’t said that to “get somewhere with her.”
A compliment like that has a tendency to weaken the adductor muscles in a woman’s hips.
Those are the muscles that keep her legs closed.
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