Olivia's Escort Service - Version Alpha - Cover

Olivia's Escort Service - Version Alpha

Copyright© 2026 by Lubrican

Chapter 5

Romance Sex Story: Chapter 5 - 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  

“You have to keep your clothes on,” said Olivia, as they stood in Bobby’s living room. “I know you’ll be stiff, and once I’m naked and lying open to you I’ll be helpless. So your beautiful stiff penis has to be confined, where it will not be able to be naughty.”

“Okay,” said Bobby. He was excited, and bouncing a little on his toes.

“I’ll sit on the couch when the time comes,” she said. “You wait here. I’ll be right back.”

She went through the open doorway to his bedroom. The only thing to see out of the window in the bedroom was the neighbor’s fence. It was both small and dirty, so it was perpetually dim and he could not see her. He sat on the couch, trying to imagine what was going to happen.

When she returned, the only thing she was wearing was a red, lace thong.

“This is like the one I found in Paul’s luggage,” she said, as she turned to show him everything. “I got it just for you.”

“Wow,” sighed Bobby.

“I got it for you to take off of me,” she said, her voice throaty. “Do you want to take my thong off of me, Bob?”

“Yes, ma’am, I do,” he said.

“Then get up and let me sit down.”

He jumped up and she sat, with her butt on the edge of the seat. She leaned back and spread her arms.

“Take it off, now,” she said, softly.

He was nervous. He’d never done anything like this, before. It looked simple, but what if he did it wrong? He had to straddle her legs, which were closed. He leaned over, staring at her breasts and the stiff nipples on them. Carefully he reached for the band that went from the gusset of the thong over her hips and behind her. He slipped his fingers under the band and tugged, gently. She lifted her hips and the thong suddenly moved six inches. Her bare pussy lips were exposed and he stopped.

“Don’t stop there,” she said. “I can’t spread my legs if you don’t take it all the way off.”

“Oh!” He woke up and pulled the thong down her legs and off of her feet. Her feet spread apart instantly, so wide that they almost touched the front of the couch.

“You’ll need to be on your knees,” she said.

He got down and put his face three inches from Nirvana. He caught an unfamiliar scent, that smelled good, like a steak smells good. Her hands came and her fingers spread her lips apart, exposing a dark tunnel and, above that, a protruding little thing that looked like a tiny, miniature penis head. She put one finger directly on that protrusion.

“This is my clitoris and it will need a lot of attention from your tongue and lips. Please don’t bite it. My labia are what cover it up when I let go of them.” She demonstrated and then pulled her lips apart, again. “The dark hole is my vagina. That’s where I wish your beautiful penis could go, but that would be a disaster.”

“Why?”

“I told you already. I’m not on birth control and I can already tell you I’d be helpless if you decided not to wear a condom. I was helpless when Paul did that and my feelings for you are even stronger than what I felt for him. And I already know that, if we did that once, I’d crave it over and over again, and I’d be weak, and you’d put enough sperm in me to impregnate me. My belly would swell up and Brad would go crazy, trying to figure out who made that baby in my belly. It would just be a disaster.”

“What if I promised to always wear a condom?”

“Do you have one right now?”

“Well, no ... but that’s because I didn’t think I’d ever get to use one.”

“And if your pants were off right now, and your long, strong cock was loose, I’d pull it to where I want it to go. I wouldn’t care about the condom. I’m what men would call hot-blooded and women would call a cock-hungry slut.”

“Please don’t say you’re a slut again. It hurts my heart, right here, when you use that word.” He thumped his chest.

“I’m sorry,” she said. “When I feel like I feel right now, it’s hard to believe I’m a decent woman.”

“You’re more than decent to me,” he said.

“Now, lick and suck and just have fun. I’ll help push your mouth where I want it.”

Tentatively his nose got closer and closer until, suddenly, her hands found his ears and pulled. His nose smashed into her pussy and he opened his mouth to complain. Then his tongue tasted, and he found a brand new most favorite thing to put in his mouth.

She didn’t have to do as much as she had thought she would. He loved sucking on the right lip and then the left. He liked making his tongue stiff and then parting her lips with it, running it into and over her clit. He pushed his tongue as deeply into her vagina as he could. Her moans of joy guided him. Instinct told him to only tease her tiny penis until she was writhing and begging “Pleeease,” over and over again. When he finally latched onto her bud and sucked, she went off like a bomb.

Oh yes!” she shrieked as her hands left his head and pounded the seat of the couch beside her. “Yes, yes, yes, yes!”

He knew what his cock felt like after he’d cum, so he treated her clit just like that. He gave it a few more licks and sucks and then decided she needed her nipples sucked, so he kissed his way up to her heaving breasts and did that.

“Ohhhh, Baby,” she groaned. “Get your clothes off!”

In that moment Bobby Forester had an epiphany. His brain knew what she meant. She wanted sex. If he took his clothes off he would get to put his dick in his dream woman and cum in her. He was already painfully hard, in his pants, and a drip of precum eased through the tube he really wanted to slide deep into Olivia Applebee. But another part of his mind, sometimes called his heart, told him that, in the aftermath of that sexual coupling Olivia would not be happy it had happened.

And he wanted Olivia to stay happy with him.

He crawled up until his face hovered over hers. His face felt wet, still, so he kept it a foot and a half away from hers.

“No,” he said, softly. “I can’t take my clothes off right now.”

“Yes, you caaaan,” she whined. “I need you Bobby! I need your beautiful penis in me.”

“Not right now,” he said. “Maybe later. Now is the wrong time, okay?”

“I hate you!” she shouted. Her hands flashed to his shoulders. “No! I don’t! I just haven’t felt that for sooo long.”

“I’m glad I made you happy,” he said. “When you calm down I’d love it if you sucked my beautiful penis.”

“Kiss me!” she ordered.

“My face is kind of wet,” he said.

“I know what I taste like!” she barked. Her hands moved from his shoulders to his ears and she pulled hard. With a yelp he let his face rush towards hers and their lips almost slammed into each other. Her kiss was hot, and he could hear the passion in the noises that issued from her throat. The kiss lasted for a full minute until he was able to lift his head enough to talk to her. She talked to him, first.

“I love you, Bobby,” she said, softly. “I’m not supposed to. It will only bring us pain, but I can’t help it. I love you and I have to have you in my life.”

“I’m not going anywhere,” he said, staring down into eyes that were lighter than the dark jade statuettes he’d see in museums, but darker than emerald.

“Yes, you will,” she said. “You should already be in college.”

“I like my job,” he said. He lived frugally. The little house he lived in was dirt cheap because it was old and ugly, but it was well-insulated, which meant he was comfortable in in the winter. It had an ancient swamp cooler in the living room window, which made the room surprisingly livable when the heat was oppressive. His car was old, so the licensing fee was ridiculously cheap and his insurance was liability only, so that didn’t cost much, either. Brad kept trying to get him to go to the community college five miles away and study coding, so they could work together on the games and apps Brad dreamed up. “Maybe I’ll do what Brad keeps pestering me to do.”

“What’s that?” she asked, pulling him down to lie with her. She plucked at his shirt. “I wish I could feel you skin-to-skin. These clothes are scratchy.”

“He wants me to go get an associates degree in computers, and work with him.”

She blinked.

“You mean you’d work with him in his room?”

“No. He says we’d have to have something bigger. He suggested that this room might be big enough but he says it isn’t zoned for business. Neither is your house, but so far he hasn’t had to give anybody a business address. His cards just have his name and phone number on them.”

“Take your clothes off,” she said, softly.

“You want that now, but later you wouldn’t be happy,” he said. “Some day I’ll pin you to the bed and make you squeal, but not now.”

“You’re mean,” she moaned. “You’re a beast.”

“Do you want me to leave?”

“Of course not. Don’t be an idiot. I love you. I can say that, now, because I blurted it out before. It’s insane for me to love you, but I do.”

“If it’s any comfort, I love you, too,” he said. “I’ve loved you for so long it was just in my bones, but now I understand it was just a misty concept all those years. Now, it’s like the clouds have gone away and I can see what love means. I don’t think it’s insane at all, Olivia.”

 
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