Olivia's Escort Service - Version Alpha
Copyright© 2026 by Lubrican
Chapter 3
Romance Sex Story: Chapter 3 - 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
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.
He took off his jeans again. He was as hard as iron. As he started stroking his cock he spoke.
“It hasn’t been an hour yet, has it?”
“I won’t make you do it yourself, this time,” she said. Without putting her blouse back on, she pulled him toward her. He over-balanced and had to put his hands on the back of the couch. That brought his cock right to her open mouth and he stared in almost consternation as she pushed his foreskin back and closed her mouth over the glans of his penis. She gave it a not-so-tentative suck and her cheeks caved in.
It was incredible. Not only was he not prepared for it, he hadn’t even thought of it as a viable fantasy. But the outrageousness of it didn’t make him spurt instantly. Instead, it gave him a kind of feeling of power. It wasn’t power over her. It was more like what a king might have felt back in the middle ages.
“You have no idea how good that feels,” he panted.
She pulled her mouth off of him, sucking all the time, and looked up.
“It’s going to feel even better when you cum in my mouth.”
She sucked just the tip while she tickled his balls and he warned her. She stayed on and she was right. He didn’t think he’d ever had a stronger, better feeling orgasm.
He looked down as he heard her swallow. As she pulled off again, she was still sucking and a string of white hung from her lips to the tip of his cock. Her index finger came up and captured that string. She looked up at him as she sucked that finger clean.
“You taste healthy, Bob. I liked that. I suspect I’m going to want to do that again, some day.”
“You’re going to want it?” he laughed, panting.
“There you go again, being dangerous. I think it’s time you took me home.”
So he did, and he got another fantastic good night kiss.
The third date she accepted with him included the instructions for her: Dress in a loose top and jeans. If you have boots, wear them. Have your hair in a ponytail.
Where are we going?” she asked, when he picked her up.
“Where I work,” he said.
“The riding stables?”
“Yes. I want to go on a trail ride with you.”
“I’ve never ridden a horse, Bob.”
“It’s easy. You’ll have a good time. I promise.”
When they got there she took a deep breath through her nose.
“That’s the scent of horses and the place they live in,” he said.
“I don’t know why, but I love the smell of horses,” she replied.
First, he just walked her down the line of stalls on one side. Some of the horses came to see what was going on and she petted their muzzles, mentioning how soft they felt. He took her down the other side, too. One horse shook its head and whinnied when she approached.
“It’s okay,” he said. “That just means she likes you.”
Olivia spent some time petting that horse and even talked to it. She learned its name was Sugar.
“That’s because you’re so sweet,” she cooed. Then she kissed the soft muzzle.
Sugar lifted her head and shook it again.
“Want to ride Sugar?” asked Bob. “She’s a good walker but she tends to want to stop and grab bites to eat along the way.”
“Can I?” she asked. She turned to him. “This is making my nipples hard, Bob.”
“Good,” he grinned.
He showed her how to saddle a horse and adjust the straps and choose a bridle. He saddled his own horse and they walked the animals out of the barn before mounting. He put his hands all over her ass, helping her mount.
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