Olivia's Escort Service - Version Alpha
Copyright© 2026 by Lubrican
Chapter 2
Romance Sex Story: Chapter 2 - 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
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.