Olivia's Escort Service - Version Alpha
Copyright© 2026 by Lubrican
Chapter 7
Romance Sex Story: Chapter 7 - 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 let go of her and backed away. He did it in the nick of time, because Brad stumbled into the room holding his head and groaning.
“Who tried to kill me by smashing my head?” he asked.
“You did,” said Olivia. “You drank a whole bottle of Rebel Yell.”
“I need to get a girlfriend so I can celebrate in a different way,” he groaned.
“I agree wholeheartedly. I would like to have grandchildren one day.”
“You’re way too young to be a grandma,” he said. “Do you have any aspirin? My bottle is empty.” He looked around. “Oh, hi, Bobby.”
“Hello. So what were you celebrating?”
Brad sank down into a kitchen chair.
“I sold the game I’ve been working on. They liked it so much they are giving me royalties, and they asked if I had anything else that was finished. You remember that little app I wrote that calculates what time it is anywhere in the world? They bought that, too. I just did that one for fun!”
“So how much will they give you in royalties?”
“We signed a deal for point oh-one-eight-five cents per sale.”
“That isn’t even a penny, Brad!” complained Olivia.
“If it sells a million times that’s eighteen grand,” said Brad. “Aspirin?”
Olivia went down the hall toward her bedroom and returned with a bottle of generic aspirin. She got him a glass of water and he took two.
“Will it sell a million copies?” she asked.
“They seem to think it will sell ten or twenty million. They are predicting it will go viral.”
“Why?”
“Because it is designed to be downloaded and played off line. That means no ads. Nothing interrupts play. People hate ads like they’re death, and it’s an action game, with infinite levels, and I designed it so that, if you die, you can either try that level again and again, until you beat it, or you can skip to the next level, if you want to. Most games make you start all over at the beginning if you die. People don’t like that, either.”
“How about the app?” asked Bobby.
“They bought that outright. No royalties.”
“How much did you get?”
“Eight grand.”
“They gave you eight thousand dollars for an app that just tells you what time it is in Timbuktu?” Bobby’s voice rose.
“Millions of people travel all over the world for business, or do business with foreign companies. Those people would like to know what time it is in Timbuktu so that they don’t call in the middle of the night. If they charge ninety-nine cents for the app, they stand to make millions.”
“Oh.”
“They want me to work on more apps geared towards business travelers, and said they’d like to look at any games I build in the future.”
“I see why you celebrated so much,” said Bob.
“Too much,” groaned Brad, resting his forehead in one hand.
“Eat something,” said Olivia. “It will help.”
“I’m just going back to bed. Sorry, Bobby. I’ll call you when Thor isn’t pounding my head with his hammer.”
“I was going to have you help me rearrange my bedroom, today,” Olivia complained.
“Bobby can do it,” Brad grunted. “He’s wished he could hang out in your bedroom for years.”
“I beg your pardon?” said Olivia.
Brad looked up and blinked. Then he looked at Bobby.
“I think I fucked up, man.”
“What are you talking about, Bradley?” snapped Olivia. Bobby was super impressed with her acting ability.
“Remember when I was six and wanted to marry you?” Brad asked.
“Yes.”
“Well, Bobby wanted to marry you, too.”
“I see,” she said. “Go back to bed. I’ll have something in the fridge you can heat up in the microwave when you rejoin humanity.”
“Okay. Thanks. I love you, Mom.”
“I know,” she said. “And so, apparently, does Bobby.”
“No, no, no,” groaned Brad. “We don’t want to marry you anymore. We just love you.”
“Go to bed,” said Olivia.
Brad got up and stumbled back toward his room. Bobby looked at Olivia and smiled.
“I wonder if, when he wakes up, he’ll remember what he said,” said Olivia.
“Probably not,” said Bobby.
“I also wonder if he’ll remember you two didn’t even meet until you were twelve.”
“I hope not. That could get awkward. I can’t imagine how he’d expect us to act,” said Bobby.
“Well, in the meantime, my son has told me you’ll help me out in my bedroom. Is that true?”
“Why, yes it is,” said Bobby.
“So ... you have time to help me rearrange my bedroom right now ... young man?”
“I do,” said Bobby.
“Then, let us repair to my boudoir and see if you can please me.”
They did, in fact, change her bed from being against the east wall to being against the north wall of the room. Her dresser got moved five feet, but stayed on the wall it had been on. In its previous position, Olivia was restricted by having to get out of only one side of the bed and then walk around it to get to the master bathroom. In its new position she could get out of either side and could go directly to the bathroom.
“Looks good,” said Bobby, as Olivia stood, hands on her hips as she surveyed the room.
“There’s something wrong,” she said.
“What?”
“There is no naked hunk of a man on my bed.”
“There could be, except if your son got up sooner than we wished, he might find out that my juvenile wish has come true.”
“This isn’t fair,” she groused. “I should be able to entertain you as a gentleman caller without my son being freaked out by it.”
“To be fair, I think he’d be freaked out by any gentleman caller you brought into your boudoir.”
“I suppose so, but it still isn’t fair.”
“I just had a flash scenario go through my mind,” said Bobby. “In it, I arrived with a gym bag with a change of clothes in it, and I announce that I’m there for a sleepover. Brad says his bed is too small and I’ll have to sleep with you.”
“Is there ever a time you don’t think about getting me in bed?”
“No,” said Bobby. “Should there be?”
“Stay there,” she said.
She left the room and was back within a minute.’
“He’s passed out on his bed. I want you naked.”
“Now? Here?”
She pulled her T shirt up and over her head, baring her braless breasts.
“Yes,” she said, her voice tight.
When they were naked his cock was so hard it pointed up, instead of out. They crawled onto the bed and embraced.
“I’m on my period, which restricts some things, but I want to try something I thought of.”
“Okay,” he said.
She rolled him onto his back and then straddled his hips. A white string exited her pussy lips, announcing there was a tampon in her vagina. She moved until she could carefully lower that string to the bottom of his penis. When she rested her weight, her pussy lips straddled his bone. She put her hands on his chest and then slid forward, experimentally. She bent her elbows and moved back.
“Oh yes,” she moaned. “There it is.”
“It’s always been there,” he said, with a smile.
“You don’t understand. In this position I can rub my clitty up and down your lovely hard penis. I know I can have an orgasm this way, and I really want an orgasm right now.”
“Then, by all means, rub one out,” he said with a grin.
He fondled her breasts and pulled at her nipples as she began moving faster and faster. She began to moan loudly enough that Bobby pulled her down for a kiss. She had been using her legs to move with, but in this position she transitioned to using her abs. She was able to jerk more rapidly and that was what she needed to get over the top. She made noises into his mouth and kept rubbing, though she slowed until eventually she was just sitting there. She pushed up off the kiss and stared down at him.
“We’re going to do that a lot,” she panted.
“I am happy to hear that,” he said.
“But you didn’t cum,” she said.
“I don’t need to. I’m deliriously happy just to be with you, like this.”
“It’s not fair if I cum and you go away frustrated,” she said.
“It’s fair if I’m happy with the way things are, at the moment. Don’t worry. I plan for you to get me off plenty of times in the future.”
They went bowling the next Saturday night. She did wear a pair of jeans that clung to her like skin, and a purple Kansas State University T shirt she pilfered from Paul’s dresser. She knew he never wore it. It had been gifted to him by someone after the KSU/Ohio State championship game in which Paul had bet a hundred dollars on Ohio. The KSU shirt was just to rub it in that KSU had won. Paul was a diehard OSU fan.
Bobby did, in fact, sit back in his chair, directly behind her as she danced forward and bent over as she delivered the ball. It was good that he enjoyed seeing her beautiful ass that way, because she destroyed him in the first line. She ended up with 198 pins and he got a whopping 56.
“It’s because you’re distracting me with your sexiness and allure,” he complained.
“You told me to dress this way,” she said. She leaned over. “Don’t get me excited. I’m not wearing panties and if you get me going I’ll get wet and stain the crotch of these jeans.”
“Damn, woman,” Bobby groaned, as his right hand drifted to “casually” lie on top of his cock. He was already stiff, but not uncomfortably so. During the second line she brought out the big guns. After each delivery she’d turn and curtsy, or do some other physical thing that drew attention her physical self. Then she’d blow a kiss, or say in his ear how horny she was.
He did better on their second line. He got 89 points to her 169.
After their third line she sat down beside him and said, “This has been fun, but I need you to get me naked and play with my pussy. Pleeease?”
They had taken the very last lane on one side of the bowling alley, and had started early, before people finished supper and went out to have fun. By the time they bowled three lines all the other lanes were full, most of them with four or more people, and the noise level in the place had gone up twenty decibels. A few people had glanced at them curiously. Her hair was in a high ponytail that bounced relentlessly as she moved. The T shirt was loose enough that it did not display her breasts, the way her jeans displayed her ass. She looked healthy and vibrant and she was with a man who was also healthy and vibrant. It was obvious she was older than he was, but most people only thought it was by five or six years. Her whirls and fist pumps, along with her grins of triumph, were stock and trade in that building. They just looked like a happy couple having fun.,
Granted, more than one man mused to himself that the bastard down on lane twenty was probably going to go home and get his dick wet in one of the best looking babes he’d seen in a long time, and more than one woman had looked longingly at Bobby and compared him to the man she was with, who was balding and had a beer belly, but by and large, nobody paid all that much attention to them.
To read the complete story you need to be logged in:
Log In or
Register for a Free account
(Why register?)
* Allows you 3 stories to read in 24 hours.