Olivia's Escort Service - Version Alpha
Copyright© 2026 by Lubrican
Chapter 9
Romance Sex Story: Chapter 9 - 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
“I’m okay, now,” she panted. “Six orgasms is enough.”
“Are you sure?” he asked. “I can keep going.”
“I’m not a cheerleader, either,” she said, smiling. “Can I please suck your dick, now?”
“No,” he said.
“No?” She sounded both hurt and confused.
“I want to do something else.”
She stayed relaxed, laying back in the overstuffed chair with her legs spread wide. They were both naked and he was as hard as iron. He started masturbating with the tip of his penis only six inches from her swollen pussy lips. Her eyes glittered as she watched.
“Shoot it on my pussy,” she whispered.
“Where?” He asked, his hand making long, fast strokes.
“Right here,” she said, putting one fingertip on her clit.
“Okay. I’ll try,” he said. “You look so good. I want you to have twins.”
“Stop it,” she laughed. “I’m not trying to be sexy.”
“You couldn’t avoid being sexy if you rolled in mud and somebody shaved you bald.”
“Gee, don’t thrill me too much,” she teased. “Come on, Bob. Shoot on Mama’s pussy.”
“Here it comes,” he groaned. “Ohhhh, fuck me.”
He leaned forward and the tip of his prick split her greasy lips. He knew where her vaginal opening was, now, and he nosed the tip into that opening, just as the first jet rocketed out of the eye in the tip of his cock. He pressed harder, trying to make sure none of his spunk could escape, and sighed, “Ohhhhhh, yeaaaah.”
“That’s not right here, Bob,” she moaned. Her fingertip was still firmly on her clit.
“I missed,” he panted as the rest of his semen filled her vaginal channel. “Sorry. I’ve never been any good at darts.”
“It’s been so long since I felt that,” she groaned. “Push it in me. I need it in me, Bob.”
Instead he removed his wilting penis and pushed his long middle finger in her. He knew how to stimulate her clit while he did this, and he moved his face up to kiss her.
“I’ll do that when you’re sober,” he said. “Let’s wait just a little longer. I don’t want you to ever regret letting me put my cock in you.”
“You just put your sperm in me!” she objected. “You shot a lot in me, too, Bob. Stop that,” she said, pushing at his hand. “I don’t want to have an orgasm right now!”
He pulled his finger out and then stuck it in his mouth. He hummed as he pulled it out. ‘
“You taste so good,” he sighed. “I wonder if you’ll taste any different when you’re pregnant.”
She sat up, making it look like she had abs of steel. She grabbed his face and kissed him, but not a long or passionate kiss.
“Thank you,” she said.
“I try to know what you really want,” he said. “Who knew I could read a woman so well?”
“Not for that,” she said, reaching to scoop up some of the semen now leaking out of her pussy. She sucked her fingers like he had. “Thank you for helping me get motivated.”
“So, now you want to have my baby?”
“We’ll talk about that later,” she said. “Now, I know Bradley expects me to stay all night, but if I do that now I might regret it. I don’t want to regret anything at all. So I need to go home.”
“Okay,” said Bob. “As long as we get to do this again.”
“Ohhh, we’re going to do that again lots of times,” she said, “except it will squirt waaaay up inside me, so your happy and energetic sperms can find my poor, old, limping egg.”
“I bet your eggs are as beautiful as you are,” he said, as he stood. “I’ll bet my sperm cells absolutely go to war over which one will get to pierce your supermodel egg.”
“I’ve got to get out of here,” she muttered.
He just grinned.
When he dropped her off he didn’t go inside with her.
“I don’t know what the two of you will talk about, but I don’t need to be there to hear it,” he said.
She leaned across the console and kissed him briefly.
“I want to fuck you so much your balls will hurt for a week,” she said.
“You can try,” he said.
When Olivia walked into the kitchen it was empty and dark. The only light on in the house came from under the door to Brad’s studio. She thought about just sneaking past him and going to bed, but she knew that wouldn’t work. If he was going to be enthusiastic about ... things ... they needed to be transparent, to a degree. She tapped on his door and opened it.
“I’m home,” she said.
He was lying in bed and looked up from the book he was reading. He was dressed only in white briefs.
“Are things okay?” he asked.
“Yes. We have to take things at our own speed, though. If I would have stayed, things would have gone too far.”
“I thought that was the whole idea,” said Brad.
“It is, but it needs to happen at its own speed.”
“I hope the woman I fall in love with isn’t like this,” he said. “I really will have blue balls by the third date.”
“The woman you fall in love with won’t be like me,” said his mother.
“I didn’t say I don’t want her to be like you,” he said. “You are what they call a MILF, which I acknowledge, except not to me. I mean you’re my mother and I get why men would go nuts over you, but I don’t have those kinds of feelings for you.”
“That’s ... good?” she said.
“I used to,” he said, candidly. “When Bobby and I talked about it I got excited, but I grew out of it.”
“Good. I’m having enough trouble dealing with one young man and I don’t need another one to mess things up.”
“I support you,” he said. “Are there really women who work at Matilda’s who don’t ... you know ... when they go out with men?”
“It’s Marci’s and you know it,” she said. “And yes. There are girls who are escorts only, and other girls who may go further than that if they really like the guy. Marci knows what kind of man to send me out with. I try to make sure they have a good time even though they know there won’t be any sex.”
“Wow,” he sighed. “I can’t imagine you doing that. I mean I can’t imagine you with some strange guy, walking along looking gorgeous, and not at all like you’re a mom.”
“Just imagine me with Bobby,” she said.
“I can’t do that, either,” he said. He put the book down on top of his lump. “When I think about that I get a little pervy.”
“I thought you didn’t think that way,” she said.
“I don’t. Not if it’s just me and you. But you and him? I love you both so much that the idea of you two making the two-backed beast kind of turns me on.”
“Are you a voyeur, Bradley?” asked his mother.
“No. At least I don’t think so. I just get excited at the idea of you and him doing that.”
“Well, one of these days I’m going to invite him to stay all night. Will you be able to survive that?”
“Yup,” said Brad. “I’ll wear headphones while I listen to hard rock while I probably perv out on a sock.”
He grimaced.
“I’m sorry about that. My mouth got away with me. There won’t be any socks.”
“Yes, there will,” she said, leaning against the door frame and crossing her arms under her breasts. “I’ve been washing your socks for years, remember? And I’ve noticed the condition of your socks ever since they started sticking together.”
He covered his face with his hands and groaned.
“It’s okay, Baby,” she said. “You’re normal and I’m happy about that. I never minded taking care of your socks.”
He spread his fingers so he could see her.
“And you two ... tonight ... you didn’t ... um ... do it?”
“It wasn’t time, yet,” she said. “When it feels right we will, though, and I am very, very thankful that the other man I love approves.”
“I approve. Now, let’s get back to Marci’s Maidens.”
“I’ll get you a date. There is a girl named Michelle who is your age and who isn’t having that much fun escorting men. She would be most happy to be a stay-at-home mother and I like her a lot. I think she’d like, you, too.”
“Okay. Yes,” he said. “I need to find me a woman.”
“Will it be okay if the woman finds you?”
“Absolutely, as long as she doesn’t do things on the same dating schedule as you do.”
“I’ll tell her not to make you wait that long.”
“Good. Good. Did you at least have a good time tonight?”
“I had a fabulous time tonight,” she said. “Do you want to hear the particulars?”
“Nope. No. Not at all. Thank you very much but I’ll pass. Go on to bed and get a good night’s rest. I just need to read a little longer.”
She walked over to him and leaned down to kiss him on his forehead.
“Mommy loves you,” she said, as she put her hand on top of the book and pressed downward. “Do you want me to get you a sock?”
“No,” he groaned. “I know where they are.”
“Good. Good night, man of the house. I love you.”
“I know,” he said.
She stood and left, closing the door behind her. She went to her room and stripped. She brushed her teeth and got into bed, naked. She let one fingertip find the slippery slot between her legs. Bobby had shot his stuff up inside her. It had made her orgasm, but it had been a very unique kind of orgasm that she’d never felt before. It was like someone rubbing your tight shoulders, and you relax and just luxuriate in the feeling. It had been that kind of orgasm.
As she drifted off to sleep she tried to imagine the kind of orgasm she’d have when he put his penis all the way inside her.
She went to sleep with a smile on her face.
The next day Olivia got a name from Marci, who knew all the divorce lawyers in town. She called and was invited to come in for a preliminary interview. The lawyer listened to her without blinking. She didn’t mention Marci’s Maidens. When she was finished, he said, “If he has hired a private investigator to watch you, will he have any evidence of infidelity on your part?”
She felt herself blush. Then she told him about Marci’s Maidens.
“I had to find a way to save up some money before the split,” she said.
“I understand. Would any of the men you’ve dated be willing to testify that you were only friends, who went out together to have fun but it didn’t go farther than that?”
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