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Olivia's Escort Service - Version Alpha

Lubrican

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Olivia's Escort Service - Version Alpha

By Lubrican

Description: Bob found out his best friend's mom secretly worked for an escort service. 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?

Tags: milf,maydecember,yonger man with older woman,first time,pregnancy

Published: 2026-03-25

Size: ≈ 43,329 Words

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Version Alpha

Foreword

This foreword is to assist the reader in choosing which version of this book most appeals to the reader’s fictional interests. This plot idea was inspired by Kelly’s Secret Life Exposed by Max Swan. Max likes it when things are rough, but I wanted the idea to go in a softer direction. As I wrote it, it developed in two different directions. The primary difference is that Version Alpha has no taboo aspects in it, while Version Bravo does. The beginning of both stories is almost identical up to roughly chapter six but after that, as the story progresses, wide differences appear.

Chapter One

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.


The opera was all that either one of them could have hoped for. The music was beautiful. It was dark enough to be almost private. They were in a big city, so it was unlikely that anyone in the room knew who they were. The plot of The Magic Flute stroked them with the exact emotions they wanted. For Bobby, the monster chasing Prince Tamino in the very beginning were like the feelings he’d had for his best friend’s mother for years, but which were completely forbidden. Tamino, himself, represented what Bobby wanted to be. Papageno was like Brad, his best friend and sidekick. Bobby also felt like there was some kind of magic flute in his life, because he was out, on a date, with his dream woman. Princess Pamina was the innocent girl Olivia could remember having been. They both knew at least one evil person in their lives that the priest, Sarastro, initially and the queen of the night, represented. Everybody in the room had endured trials and tribulations, at one time or another in their lives, and who doesn’t want a happy ending?

All this emotional undercurrent was not lost on either of them. They stayed in their seats during the intermission and talked about the show. Bobby even mentioned the magic flute he didn’t even know he had, which had gotten Olivia to go on this date with him. He was at once the boy she had known so long, and the man she was surprised he had become while she wasn’t paying attention. Somewhere during act two, Olivia’s hand bumped into his, and her fingers interlaced with his. He’d already been at a low level of sexual stimulation for hours, and this simple touch closed the switch that instructed his penis to become as hard as rock. It slowly relaxed as the stimulation went no further but then returned at the end of the opera. By then, both of them felt a little weary just from the sustained emotional influence of the show.

When he didn’t stand with the rest of the congregation to leave, she looked at him with a tilted head.

“I can’t stand up right now,” he said, softly.

“Why?” she asked.

“I’d embarrass both myself and you.”

“Oh. I see,” she said. She didn’t laugh or jeer, which he had been afraid she’d do. “Well, there’s nothing that can be done about it here. Has your heart ever been broken?”

“I thought it was the end of the world when Regina Connors said she never wanted to see me again,” he replied.

“When was that?” she asked. That name didn’t ring a bell.

“That was in third grade,” he said.

Now she did laugh, and the tinkle of it didn’t destroy him. It made him leak.

“Where have you been all my life,” she joked. “Okay, how about this? Did you ever get hurt badly enough that they had to take you to the hospital?”

“No.”

“You’re not helping,” she chided, gently. “What is the most unpleasant, scary, terrifying thing you’ve ever worried about?”

“It was tonight, when I was afraid you’d laugh at me and tell my mother I asked you on a date. I was afraid you’d tell me I could never come see Brad again.”

“You can’t,” she said, calmly. “This has been fun, but you can never again even dream of taking me on a real date. I think it probably would be best if you never came over again.”

The look on his face made her feel awful, but then she asked, “Are you still hard?” and the look on his face changed instantly. Then it went back to worry.

“No,” he said.

“Good. Let’s get out of here before it comes back. I know what young men are like. Most young men have a boner sixty percent of the day.”

It was her use of the word “boner” that chased away the immediate fear that she had meant what she’d said. He’d never heard an adult woman use that word.

It was the fact that she kept his hand in hers that gave him hope until they got to the car. Once he had installed her he got in and turned to look at her. He had to know.

“Did you mean that ... about me never coming over again?”

“Don’t be ridiculous,” she said, calmly. “All I did was say what was needed to help you get out of the theater without the whole world knowing about your completely inappropriate feelings for me.”

“It wasn’t for you,” said Bobby. “It was because of the opera.”

“Of course,” she said, slapping her forehead softly. “How could I be so egotistical as to think a young man like you might find an old crone like me attractive?”

Now who’s ridiculous?” he said. “It was because of you.”

“I know,” she said, reaching to pat his thigh merely inches from his cock. “Does this date include anything to eat? I’m starved.”

Bobby didn’t know of any places to go to dinner in that part of town, and when he asked Siri for a list of fine restaurants, Olivia reached to take the phone from him.

“I want a cheeseburger and fries,” she said.

“We’re not exactly dressed for McDonald’s,” said Bobby with a crooked grin.

“Drive through?” she asked, with that tone of voice that a mother uses with her clueless son.

“Right!” he said. He started the car and blended with other traffic leaving the parking lot.

“Not McDonald’s, though,” she said. “Find a Wendy’s.”

“Why Wendy’s?”

“Because I feel like a square peg in a round hole right now,” she said. “I’m having way too much fun, considering the circumstances. Their patties are square, you know.”

“Yes, I know,” he said.

“And my mouth is round.” Her casual comment was logical, but the image of her round mouth opening made his mind jump straight to images he knew would never happen, but got his dick prepared for it anyway.

“Plus I like their fries,” she added, “and I haven’t had a chocolate Frosty for probably five or six years and I’m craving one right now.”

Bobby asked Siri to direct them to the nearest Wendy’s. They used the drive through, but then parked in the parking lot to eat. Olivia ate a spoonful of her Frosty first, and then unpacked everything else. Her moan of enjoyment as she bit into the sandwich sounded theatrical and she gorged on fries before she spoke.

“You have no idea how good this tastes,” she moaned. “I haven’t had fast food in years.”

“Why not?”

She used her free hand to sweep from her head downwards, with her fingers straight.

“This cannot be maintained if it is fed fast food. I have to run five miles a day as it is.”

He knew she ran. She’d given him more erections dressed in her spandex, with her ponytail bobbing as she left the house to run, than at any other time. Brad had even noticed it and commented on it, one time when he said, “I know she’s a babe, Bobby, but she’s my mom. Cool that jet in your pants, dude.”

After that he tried to hide it, but the jet never got cooled.

“Thank you,” he said.

She looked at him, chewing, and raised both eyebrows.

“For maintaining,” he said.

She swallowed and then said, “At first it was to try to stimulate my husband to act more like a husband should act towards his mate. Then Marci got me on her staff and I had to stay in shape for the new men in my life.”

“Well, whatever made you do it, I was a beneficiary,” he said.

“Thank you!” she said.

“Isn’t it hard, going on dates with guys who want to have sex with you, except you never let them do that?”

“There are all kinds of men in the world, Bobby,” she said. “Some men feel the need to be punished. Why they feel that way is as varied as the men’s fingerprints. But one of those types wants to be tempted and toyed with, but not allowed to have sex. It is a form of self-torture and they get off on it hard. I have clients I’ve been out with on maybe ten or twelve dates. They ask for me by name because they know there will be no sex. They aren’t after sex, or at least not what you and I would call normal sex. And other men just want to be in the presence of a woman they feel is out of their class. That’s ridiculous, of course, but it fills a need.”

“I understand that one,” said Bobby. “Tonight has been the wildest night of my life because you’ve been on my arm. It made me feel ten feet tall.”

“Well, based on how I feel, you apparently have some kind of magic flute,” she said.

“Are you a wild animal?” he joked.

“No. I’d tell you I feel wild, but I don’t want to make you embarrassed again.”

“I’m pretty sure that would happen anyway,” he said.

“Like now?”

“No, but at some point I’ll help you out of the car and I’ll see all of you and then I’ll see you walk, and that’s all it will take.”

“You’re a dangerous man, Bobby Forester. In fact, I’m going to start calling you Bob. Bob is a man’s name and Bobby sounds a little juvenile. You, my friend, left juvenile behind while I wasn’t looking and now I find myself in the presence of an attractive man. If I were some callow girl I might be in trouble.”

“But you’re not a callow girl,” he said.

“No. I’m not. And while you are enthusiastically welcome to visit my son, as you have in the past, there can be no ... adult behavior ... during this date.”

“Oh, I know that,” he said. “I might dream about that, but if it actually happened I’d be petrified. I’d be helpless. I wouldn’t have any idea what to do or how to do it and I’m pretty sure there would be nothing adult about me.”

“Are you a virgin, Bobby ... Bob?” she asked.

“Oh, man!” he groaned. “You can’t ask a guy that.”

“Of course I can. I’m not a virgin and I don’t mind admitting that. Why would you be shy about admitting you’re a virgin?”

Boys are virgins,” he grunted.

“Not so, my not-boy friend,” she said.

He understood it as she meant it, separating “boy” from “friend.”

“For a man to eschew casual, meaningless sex happens for one of two reasons. One is that he has no self-confidence to try to put himself in that situation. The other is because he’s picky. He’s looking for the right woman and she has to be spectacular to snare him. That’s sexy. For a woman to reflect on whether she might be the one to harvest his cherry makes her horny - if she really likes the man. A virgin represents the unattainable, and women can’t resist the unobtainable.”

You’re resisting the unobtainable,” he said.

“This is different. No matter how attractive I find you, it is forbidden for me to do anything about it. I wouldn’t ruin your relationship with Brad for anything. And what future could we have, together? No, anything sexual between us would be so stained as to be unenjoyable.”

“So I’m both unobtainable and unenjoyable?”

“It’s complicated by who we are. I have enjoyed this date perhaps more than any other I can remember, but it’s still taboo. Think of it as incestuous. I think of you as my other son, sometimes. You wouldn’t want to have sex with your mother, would you?”

“Not my mother,” he said, “But you aren’t my mother.”

“I am for purposes of getting frisky,” she said. “It just has to be that way. It doesn’t matter how we feel.”

They finished their meal in silence. The emotional high they had been on had been diluted by her conviction that nothing else could happen between them.

When he dropped her off at the hotel, where her car was parked, he helped her out and kept her hand as they stood beside his car.

“Thank you,” he said. “I mean it. This was one of the best nights of my life.”

“You are a flatterer,” she said. “I almost wish I wasn’t your best friend’s mother.”

“Is it impossible for there to be a good night kiss?” he asked.

“Is that all you want?” she asked.

“Of course not, but I know how you feel about all this.”

“Would you like to know something, Bobby?”

“Sure.”

“You already know how I feel about Paul. You know I’ve dated a hundred men, or so. In all that time, however, you are one of the very few men to actually care about how I feel and listen to me as a human being, instead looking at me as something you think you bought. I’m not saying there haven’t been interesting men, or that I hated all the dates. Marci knows what kind of man to send me out with. But being out with you has been like hanging out with a handsome man you’ve admired for a long time. You’re a truly wonderful friend to Brad, and that means a lot to me. What I’m trying to say is that feelings can evolve, Bobby.”

“Evolve?”

“It means that how I feel right now might change, at some point in the future. We can’t control how we feel. All we can do is react to those feelings. Right now I’m reacting like I know I should react. But I won’t lie and say things can’t or won’t change. What I’m saying is that I’m going to need your help to keep things like they are right now. Okay?”

“Yes,” he said.

“In that case...”

Bobby watched as her face came near. He saw her eyes close and prepared to feel her lips on his.

He couldn’t have prepared for this kiss. Her lips were warm and insistent. Her head moved and there was a little hum in her throat. His penis sprang to an instant erection and he frantically pushed his butt out so it didn’t press against her. The kiss rattled him, but then she blew him away. When he pulled his hips back, one of her hands went and, as if it was completely normal, found and fondled his erection. She pulled her face back and there was a Mona Lisa smile on her face.

“Mmmm. It feels like you’ve got a nice one.”

“I don’t understand,” Bobby gasped, softly.

“This was a completely platonic date. I don’t get to do those very often. Are you going to ask Marci to send me out with you again?”

He thought about that. Her comments and actions in the last few moments had been illuminating.

“I want to?” He wasn’t sure how to respond. “I mean I thought that was forbidden.”

“We’ve already nailed down what’s forbidden. There’s a discount if the escort doesn’t have to get all fixed up,” she said. “If she’s going bowling or to miniature golf or something like that, where she can be casual, Marci charges less.”

“I like miniature golf,” said Bobby, hopefully.

“I haven’t done that in almost twenty years,” she said.

“So you wouldn’t want to go knock a golf ball around for a while?”

“I didn’t say that.”

“What are you saying?” he finally asked, with frustration in his voice.

“You know what I’m saying, Bobby. You’ve been delightfully mature tonight and I know you’re intelligent. Intelligent men are attractive, by the way. For us to continue in any kind of relationship we’ll need to be friends. Just think about it.”

“Okay.”

“And no funny business when you come see Brad.”

“Of course not. He can never find out about this.”

“Good.”

“Thank you,” he said, again. “You have no idea how much this meant to me, tonight.”

“Maybe I understand how you feel much better than you think,” she said. “Now, we kissed, but then we stood here talking instead of parting ways. That means that kiss was just for fun. I’m going to kiss you good night and then walk away. Do you understand?”

“Yes, Ma’am,” he sighed.

This kiss was different, in the sense that he could actually pay attention to it. It was also different because the tip of her tongue flitted against his lips. His reaction was automatic and she sucked his tongue. Her hands fell to land on his ass, and she kept him from pulling his boner away from her. He knew there was no world in which she did not feel it. A passing woman said, “Get a room!”

Then it was over and she stepped back.

“Thank you, Bobby. Other than the blackmail, I had a wonderful time, tonight. You were a perfect gentleman and Linda would be proud of you.”

She turned, and her heels clicked on the sidewalk. Bobby stood, his arms slack. His erection made the front of his slacks protrude, embarrassingly. She turned a corner and disappeared and only then could he regain control of his body. He felt leakage through his cock and clenched to stop it.

Chapter Two

He almost got a ticket on the way home, but came to a complete stop at the stop sign just in time. A police car, stopped on his right at the four way stop sign, moved in front of him. He waved, almost giggling.

His little house felt ridiculous when he walked in. It had been built in the 1920s and consisted of four basic rooms. There was a living room, which was 10’ X 15’ and ran the width of the building. A door frame led to the bedroom and bathroom. There was no door mounted to the frame, and therefore no privacy if guests were in the living room. It got worse. You had to go through the bedroom to get to the kitchen, which shared a wall with the bathroom and the bedroom. It had been built to live in, and not to entertain in. He had wondered, occasionally, about the people who had lived some of their lives in this house. He would have bet his entire paycheck that no tuxedo had ever been in this house.

A European type wardrobe filled one corner of the bedroom and he hung the tux jacket on a hanger in it. The cummerbund and tux pants went on the back of the straight-backed chair between the wardrobe and the foot of his bed. His shirt went in the dirty clothes hamper. He stripped off his underwear, which had absorbed the leakage from his penis. Usually, he didn’t wear underwear, but tonight, wearing a tux, he felt like he should, for some reason.

He walked, naked, to the bathroom. He pissed, brushed his teeth, and then went ten feet to fall into bed.

He looked at the ceiling, which needed a coat of paint. It had been white at one point, but over the years a coat of ... whatever ... had gathered, making it look grimy and ancient. Maybe it was ancient.

He only thought about the date in generic terms, but his cock raced to get hard again. He squeezed it. She had felt it through his pants. What would it be like if her hand was on it now?

It took him not quite thirty seconds to ejaculate.


He managed to go hang with Brad twice without doing anything weird. Olivia smiled at him and called him Bobby, and then left them alone.

She hadn’t forbidden a second date, and the signals she had sent were so mixed that he was confused. So, based on their discussion, he went to see Marci again to arrange a second date. Again he asked for Olivia by name.

“I was thinking miniature golf,” he said. “That’s kind of fun on a date, isn’t it?”

Marci opened a lower drawer in the desk and extracted a folder. She opened it and shuffled a couple of pieces of paper. She stopped and put her finger on a page.

“You were rated as an eight out of ten, overall, and the things I really care about you got tens on.”

“I don’t understand,” he said.

“We have to be very careful of the men who use our service,” she said. “Not all men are nice and some are outright dangerous. Further, I firmly believe that no means no, and if a man doesn’t understand that, I will not put one of my girls in his hands. You were judged not dangerous, and you got tens in both ‘respect’ and ‘gentleman.’ So I’ll see if Olivia is free and wishes to go play a child’s game.”

“What else does it say about me?” he asked. “Did she say she was attracted to me?”

“That is private,” said Marci, firmly.

“But if she said she didn’t find me attractive, you wouldn’t send her on another date, right?”

“Young man, there is a box on our feedback forms that says ‘Never send me out with this man again.’ She did not check that box and that’s all I’m going to tell you.”

“Got it,” he said. “Thank you.”

“Just keep being a gentleman,” she said. “Now, go away. I have work to do.”


They had to go back to the city to find a miniature golf course. It was in an area of town that had a few old ‘50s motels that had been renovated into efficiency apartments. The course had that worn-but-spruced-up look to it, too, but the number of people patronizing the place was surprising. They had to wait ten minutes to start the course.

“I haven’t done this since I was a teenager,” she said, as she teed up the ball at the first hole. She whacked the ball so hard it bounced out of the confines of hole number one and Bobby had to chase it to hole twelve to retrieve it. Four people had played through by the time he got back and handed the ball to her.

“Maybe I should help you,” he said.

He got behind her, put his arms around her, and put his hands over hers. Her butt pressed into his zipper.

“You only brought me here so you could molest me,” she said.

“You’ll know if I start molesting you,” he said.

He helped her swing and the ball ended up three inches from the hole.

On the second hole he stood and watched as she took ten strokes to get the ball in the hole. A group of four teenagers was behind them and Bobby let them play through.

“Maybe you should help me some more,” she said.

“I’d love to,” he said.

He helped her on the next five holes, during which he felt her actually push her behind against him. He wondered if she was feeling to see if he was erect or not. He wasn’t, at that moment. He was just enjoying having his arms around his dream woman.

Their chit-chat was typically competitive as he clearly crushed her. On the last hole he picked up her ball and examined it.

“What’s wrong?” she asked.

“I was just worried you might have worn out the cover on the ball and might need a new one,” he said.

“I was going to kiss you goodnight again, but now I’m not!” she pouted.

This time he had prepared and drove them to an Italian restaurant. She ordered Lasagna and he told the server he wanted Risotto.

“Lots of breadsticks, please,” said Olivia. She looked around after the server left. “Do you think people are staring at us?” she asked.

“Would it bother you if they were?”

“Well, no, but nobody wants to be stared at.”

Bobby looked around. He saw an older man seated across from a woman who couldn’t be older than twenty-five. He pointed them out and Olivia glanced at them.

“She’s much younger than he is. Does that make you want to stare at him?”

“No, but I go out with older men a lot.”

“Okay, so she could work for an escort service, like you do. Or, maybe she’s his daughter and they’d just sharing a meal together. He could be her uncle and she’s here to visit him for the weekend. In any case, nobody’s staring at them.”

“All right.”

“Can I ask you a personal question?” he inquired.

“You can ask, but that doesn’t mean I’ll answer,” she said with a smile.

“How did you find out Paul was ... wasn’t loyal to you?”

“He was in the shower one day when I unpacked his suitcase and found a pair of another woman’s panties tucked in a pocket of his slacks. They weren’t mine and they were ... recently worn, shall we say. I confronted him and he said they were a gift for me. I told him they were used and he said it was an unplanned accident; that he’d lost control because the woman looked like me, and that he’d never do it again. It’s difficult to get excited about having marital sex when one of the pair has cheated. Plus, I kept smelling things in his suitcase, like perfume I didn’t own. Our sex life ground to a halt. Then, one day his phone dinged while he was outside washing his car. I knew that meant he’d gotten a text and I thought if it was from his work and important he might need to know right away. So I looked at it and it was from someone named ‘Barb.’ That meant Barb was in his contacts and I didn’t know any Barb. When I read it, Barb was telling him how much she loved his cock. There were a dozen cheesy emojis. It was pretty clear what he and Barb had been doing, and that he’d never stop. It was over and we both knew it, but neither of us wanted to divorce because of Brad. By the time Brad became a man, himself, we were more like housemates than a married couple. We have separate bedrooms but told Brad that was because Paul snores so much I can’t sleep.”

“I’m sorry that happened,” he said.

“It hit me hard. I didn’t know what to do, so I just kept doing what I’d been doing. Eventually I got used to it. I was lonely, though, so when Marci recruited me, I took a chance to see how awful it would be. The first man I dated was a grandfather and the reason he wanted me to spend time with him was to help him understand his granddaughter because the generational gap had caused them to pull apart and he wanted to re-connect with her. I had a wonderful time and told Marci I’d keep doing platonic escorts.”

“I’m glad things got better for you,” said Bobby. “I was blown away when I found out you worked for Marci’s Maidens and didn’t know what to think. That helps me understand what you’re doing and I’m not freaked out about it anymore.”

“I’m glad. I don’t want you to be freaked out.”

“One other thing,” he said. Then he stayed silent.

“What?” she asked.

“No. I can’t ask about that. It would be rude and crude and socially unacceptable,” he said.

“Bobby, I doubt seriously you could come close to being rude, crude, or socially unacceptable.” She frowned. “Unless you were drunk.”

“I don’t drink,” he said.

“Then ask me.”

“It’s really personal, Olivia,” he said.

“So have been the good night kisses we shared,” she said.

“Oh. Yes. That was definitely personal.”

“So?”

He dithered, but finally squared his shoulders.

“I’ve never been in your situation, but I know that, once you become sexually active, you want to stay sexually active. And I believe your dates were platonic. So ... um ... what do you do about ... urges?” He took a sip of his Coke, expecting her to say it was none of his business.

“I masturbate a lot,” she said, calmly.

Soda spewed from Bobby’s mouth and nose and he started coughing. Olivia sat there and asked if he needed help. He waved her off. She let him wipe his nose and mouth with a napkin.

“I’m sorry. Did I go over a line?”

“No,” he panted. “I was just surprised.”

“Surprised that I masturbate?”

He looked around, but they were in a booth with high backs and no other patrons were at the tables within earshot.

“I’d have to say yes,” he said, softly. “I’ve never thought of you that way, though I have to tell you I’m going to think about that a lot in the future. That’s your fault, not mine.”

“Masturbation is normal and natural,” she said. “It burns almost as many calories as having sex does. Plus, it’s a lot more fun than adding a mile to your regimen every day. I’m sure you masturbate, too.”

“Uh, I guess so,” he replied.

“You guess so? You’re not sure? Oh, you poor boy. Do you need me to help you learn how to release your sexual tension?”

“Good grief, Olivia, you don’t play fair!” he gasped.

“Bob, I think our relationship has progressed beyond that of a young man and his best friend’s mother. Yes, we still enjoy that part of the relationship, but we are also two adults who can have a rational conversation about things like this. I know how you feel about me, and I’m going to assume that, after our last date, you were in need of some relief of some sexual tension. I left you high and dry, after all. So I assume that, when you got home, you masturbated. Did you think about me while you did that?”

She waited for the deer-in-the-headlights look to slowly melt away from his face. She saw him frown. Finally, he spoke.

“Yes. Did you think about me while you got rid of any tension?”

It was a watershed moment in the relationship and Bobby knew it, instinctively. He had been unable to keep that question inside, and not tensed, waiting for her to crush him and laugh.

“Oh, yes,” she said. “I’d like to thank you for an hour of exhilaration before I went to sleep.”

“An hour?” The situation was so bizarre that he could only respond as himself, rather than a construct, designed to impress her.

“It takes longer for a woman to get there. You men are so hasty.”

“I can get off twice in an hour,” he said.

“Hmmm. That’s a handy piece of information,” she said.

“Is it? Really? I am really confused about what’s going on,” he said.

“You worry too much. Just be out on a date with me. I’m having fun and I think you’re having fun. At least what pressed against my butt when you helped me hit the ball suggested you were having fun.”

“I do not believe this,” he muttered.

She reached to touch his hand.

“Why did you want to see me as an escort?” She didn’t wait for him to answer. “Because you had a fantasy, or fantasies about me. Okay, everybody has fantasies. You can’t even control some of them. They just pop into your head and yell ‘Look at me!’ and you can’t un-see them. So you contrived to live out one of your fantasies - going on a date with me. That could have been a disaster, but it wasn’t. I had a good time. You had a good time. We both got a little horny and had fun dealing with that. I think of it as five hours well spent. Along the way it was obvious that you developed an erection because of me. I’m used to that. Most of the men who I escort develop erections because of me. In one sense, that’s my job; to make men erect. I have to live with that, even though I don’t find it exciting. Except with you I do find it exciting. I think of your erections as genuine compliments. The difference in our ages is what is causing problems. I’ve been thinking of you as a man in my peer group, because I like being with you. But I must remember that you’re barely out of your teens. So if things get awkward, don’t fret about it. I like being with you. You like being with me. Any awkward moments are just speed bumps along the way.”

“Along the way to where?” he asked.

“I have no idea,” she said. “I plan on simply enjoying the ride. Can you do that?”

“I have no idea,” he said.

“Do you want to keep going, or is this relationship out of gas?”

He lifted his hand and put it on top of hers.

“I get it that the age difference is a hurdle. To be honest, my goal on our first date was just to get it to happen. I mean I just wanted to spend time with you ... to just be with you. I didn’t think about anything beyond that.”

“That makes me warm right ... here,” she said, pulling her hand from his and touching the area of her belly button. “It is a rare and exceedingly nice moment when a man you admire pays you that kind of compliment. You just wanted to spend time with me and you didn’t push me to supply anything I didn’t want to. You were a gentleman, Bob, and that was very attractive.”

“Marci said I got a good rating.”

She smiled.

“Marci is like a mother hen. When I turned in your rating she looked at it and wanted to know more about you. It was the most enthusiastic rating I had ever given. I didn’t tell her how we knew each other. She just wanted to be sure I wasn’t doing anything stupid.”

“Stupid?”

“There have been irate husbands come into the office after they found out what their wives were doing on the side. She knows Paul and I have issues, but not that we are virtually separated. She wants things to get better for me and doesn’t want me to torpedo what’s left of my marriage.”

“I’ve never been in a relationship like this one. It feels ... I don’t know ... adult?”

“I hope it’s adult,” she said.

“There! When you say something like that it makes my imagination get ... unruly.”

“So? Is your imagination hurting anybody?”

“If my imagination made you decide you never wanted to see me again I’d want to kill it,” he said.

“Well, don’t do that. Just because your imagination runs wild doesn’t mean it will translate into real life, and I know that. So if, in your imagination, I’m wearing most of a belly dancing outfit that exposes the good parts, that isn’t going to make me want to run out and get a belly dancing outfit. I’ll just smile.”

“Did you really ... masturbate ... after our date?”

“Yes, Bob, I did, and I really thought about you while I did it. And I have to tell you this. I have never come home from a date and masturbated, thinking about the man I just went on a date with.”

“Oh, man,” he groaned, covering the zipper of his jeans with one hand.

“Let’s finish eating,” she said. “You beat me by fifty strokes, and I expect you to do something to make me feel better.”

“What would that be?” he asked.

“I don’t know. That’s your job to figure out. What do you do when you crush Brad in some game?”

“Brad usually does the crushing,” said Bobby. “He doesn’t do anything to make me feel better. In fact he usually rubs it in.”

“Well I hope you aren’t cruel and rub it in like that,” she said. “I want you to make me feel better, not worse.”

“How am I supposed to know what will make you feel better?”

“Maybe we could dance ... something slow. I haven’t slow danced in as long as I can remember.”

“You know what will happen if we slow dance,” he said.

“Of course. But it’s necessary.”

“Necessary?”

“You bragged you can get it up twice in one hour.”

She wiped her lips with her napkin.

“I want to see you get it up twice in an hour.”

“What?”

That will make me feel better.”


In the car, when he finally believed she actually meant what she’d said, he said, “We can’t go to my house.”

“Why not?”

“I live in a dump.”

“Are you a slob? Does it smell like a locker room? Are there cockroaches everywhere?”

“No.”

“Then I don’t care if it’s a dump. I just want to watch you masturbate. I’ve heard of men jerking off all my life and I’ve seen a bunch of erections, but I never saw a man masturbate to completion. Call me curious.”

When they got there and went in, she turned in a circle. He had redone the walls of the front room, which had been covered in garish flowered wall paper. He’d used cheap faux walnut paneling to cover the lower four feet of the walls, and had unstitched and stretched burlap bags to cover the top four feet. Where the bags met he covered the seams with cedar slats stained to match the paneling. He had thought of it as rustic, and the “decorative items” on the walls were supposed to enhance that. There were several horseshoes, and a bridle he’d asked for when his boss told him it was no longer usable. There were a few pictures of running horses and one of a stallion rearing.

She walked around, just looking at everything.

“This isn’t a dump. This is a man cave,” she said. “This room is designed to weaken a girl’s resistance and get her naked.”

“What are you talking about?” he asked.

“The horses running are all mares. Have you ever looked at the stallion closely?”

“No. I just liked it so I bought it.”

“Look at what makes a stallion a stallion.”

He did and was amazed to see a very detailed, very NSFW depiction of the genitals.

“Wow,” he said.

“Where did you get it?”

“There was one of those pop up rug and art sales things on a corner and I found it there.”

“If a girl merely glances at the pictures I bet it affects her subliminally.”

“Did it do that to you?”

She approached him and put her hands on his shoulders, leaning back to jut her loins against his.

“Let’s just say I appreciate good art.”

“I’m glad you do,” he sighed.

“Now, I feel that you’re ready to do what we came here to do. Shall we start?”

“I don’t know what to do,” he said.

“Of course you do, silly. You’ve done it hundreds of times. This time I want you to take your clothes off.”

“All of them?”

“The image of a man stroking something protruding from his open zipper makes me think ‘molester’ and the image of you with your shirt on and your pants off makes me want to giggle. I’d like to see your body. So get undressed.”

He took his time. The house had come furnished and he hadn’t changed anything. They were in the living room, which only had three pieces of furniture in it. There was a worn hide-a-bed couch, an overstuffed chair, and the TV stand. He folded his shirt and laid it on one arm of the couch. She sat in the overstuffed chair and just watched him.

He worked out, but not at a gym, or anything. He normally did a hundred pushups and a hundred crunches before bed. He got a lot of exercise at the stables, lifting hay bales and shoveling dung etc. He didn’t consider himself as “buff” and he hoped she didn’t think he looked too young.

He was commando under his jeans this day, so when he bent over to push them down to his feet his cock was exposed. He got each foot out of the jeans and took his socks off before he stood. He felt very tentative and decided it was the fight or flight syndrome. Then he squared his shoulders and decided if she laughed, that was her problem.

“My, my, my, my. You have definitely left boyhood behind. You look ... delicious,” she said. Her voice was a throaty purr.

“Really?”

“Men look at women’s breasts and butt and imagine them naked, don’t they?”

“Yes.”

“Well, sometimes a woman wonders what’s behind a zipper would look like. Neither of us usually get to see what we wished we could see.”

“So I look okay?”

“You look dangerous,” she said.

“Dangerous, how?”

“We have fantasies about each other, remember?” she asked.

“Oh. Right.”

“Now, have a little fantasy about me and show me what it looks like when a man masturbates.”

“It would help if I had a little ... um ... visual stimulation,” he said. He had nothing to lose by asking.

“You want to see me naked,” she said.

“Um ... yes.”

“Well, naked would be a bad idea right now, but turn around and let me see what I can do.”

He turned and heard the rustle of cloth.

“Okay,” she said.

When he turned she was still lounging in the chair, except her blouse was completely unbuttoned, exposing her skin from neck to belt. Her breasts were still covered and her bra was lying across one arm of the chair.

“Will this do?” she asked.

“I imagine it will,” he rasped.

Chapter Three

It felt bizarre, but he just started stroking, staring at her cleavage, which was flat, now that her breasts weren’t pushed together by a bra. Her breasts pushed the cloth of her blouse outward.

“You’ve made my nipples tingle,” she said, calmly, as she slid one of her hands under the blouse to the tip of the hump. Her hand moved and he realized she was squeezing her nipple.

“Is this going to be quid pro quo?” he asked, as his hand sped up.

“You want to see me masturbate?” she asked, her voice sounding completely innocent, somehow.

“If we’re being honest, I want to do this while I watch you do that,” he said.

“You and I being naked together would be foolish,” she said. “What we have is fun and exciting. If we ever got naked together it would become serious.”

“Why?”

“Don’t be stupid, Bob. We have strong feelings about each other.”

“So if we were naked, together, and I did this, it would get you too excited?”

“Yes,” she said, softly.

He took a few steps toward her. She didn’t object, even when he got so close he moved between her spread knees.

“If I go off now, it would get all over you,” he panted.

“Is that what you want?” she asked.

“I want you to want that,” he gasped.

She pulled one half of her blouse off of the breast she’d been touching.

“Don’t get it on my hair,” she said.

“Ohhh, man,” he groaned. Her calm invitation was like a taser. A long rope of semen shot out of his cock, went a foot and a half, and landed on the back of her hand. She moved that hand and he leaned so that his second shot landed on the breast, itself. His third shot was too weak to go far and she tried to catch it in her hand. He gripped his cock hard and stopped the drips he knew would come. He stepped back, breathing hard.

She licked her palm and then used two fingers to scoop his semen off of her breast and sucked that off of them, too. Finally she licked the back of her other hand, like a cat licks its paws. He just stared.

She looked up at him and said, “That’s how out of control I can get,” she said. “I’ve never done that in front of another man.”

“Wow,” he sighed, still holding his cock.

“I thought you looked delicious, and you taste delicious, too. You also cum like I imagine a stallion cumming,” she said. “Do you have a towel, by chance?”

“Of course!” he barked, letting go of his penis and dashing to the bathroom. He returned with a towel and damp wash cloth. She calmly cleaned her breast, then the back of the hand that had covered her breast, and finally her hands in general. She looked up at him, standing there, with his cock drooping, but not completely flaccid, yet.

“I said you had a nice one and I wasn’t wrong.”

“I should get dressed,” he said.

“If you must.”

“I can’t run around naked unless you run around naked, too, and we both know how you feel about that.”

“You’re not as dangerous right now as you were,” she said.

He grinned and pulled his jeans on, first.

“Don’t put your shirt on,” she said. “I like looking at your chest.”

“I like looking at your chest, too,” he said.

“Can you put on any music to dance to?” she asked, looking around the room for audio equipment.

“I can play my iPod through the TV,” he said.

“Do you have anything slow?”

“I think so,” he said.

He picked up the iPod and turned it on. He watched as songs appeared and moved on and then stopped.

“I have some Barry White,” he said.

“Perfect,” she said.

He turned on the TV and enabled the blue tooth connection to the iPod. The song started and he turned to find her topless. She came to him and pressed her hot breasts against his chest.

“This is nice,” she said, as they swayed.

“This is incredible,” he replied.

Before the song was over they were kissing, making out like two teenagers in the back of a car at Lover’s Point. When his hand came to cup one heavy breast, she moved to give him more room. A kiss broke and his head was down with his lips fastened to one of her jutting nipples before she could react. Her groan carried crystal clear indications that she liked what he was doing.

“We can’t go all the way,” she panted.

He looked up at her, turning his head.

“I know,” he said.

Then he sucked the other nipple.

The music changed to “I Love Rock and Roll” by Joan Jett, but they ignored it. He brought his lips back to hers and these kisses were tender. There was passion in them, but it was controlled passion.

“I’ve never felt like this about a woman,” he said.

“I’ve never felt like this about a boy young enough to be my son,” she said with a smile.

“So ... what do we do, now?”

“I can think of a dozen things to do, now, but all of them are too dangerous.”

“Oh, that reminds me,” he said.

 

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