Olivia's Escort Service - Version Alpha
Copyright© 2026 by Lubrican
Chapter 6
Romance Sex Story: Chapter 6 - 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
For their next date, Bobby tried something bold. He found Brad working on something in his studio/bedroom, as usual.
“Hey,” he said. “Your mom said she wants to go bike riding at Lost Dutchman State Park. I have a bike rack on the back of my car and she asked if I’d take her over there and maybe go riding with her so she’s not alone. You want to go?”
Brad looked up.
“No. Thanks for making sure she’s safe.”
“No problem. Maybe she’ll wear something hot and I’ll get to dream some more.”
“Don’t make me think about things like that, you asshole. She’s too old for you. She’s had a fucking child, for Pete’s sake, and that child will be twenty-one years old in less than two months! It would be like Judy Garland dating Captain Kangaroo, except reversed. All you’re going to do is get frustrated, man.”
“I know how to deal with frustrated,” said Bobby.
“I don’t want to think about that, either,” said Brad. “Go. Be a gentleman and stay with her so nobody will hit on her.”
“You don’t want her to meet some nice guy and get something going with him?”
“The last thing I need is a step-father who will move in and demand I move out. Now, go away. I’m busy.”
He left and found Olivia dusting things in the living room. She had her hair up in a ponytail and was wearing terrycloth shorts and a tank top. He could see the bra strap under the tank top, but that was fine. She looked hot.
“Hey,” he said.
She turned and one eyebrow raised.
“I told Brad you wanted to go bike riding at Lost Dutchman State Park and had asked me to take you there with my bike rack and ride with you so you wouldn’t be alone. He said that was fine and told me to go away because he was busy.”
“I didn’t say I want to go biking at the Lost Dutchman State Park,” she said.
“Oh. I must have dreamed it. So. Do you want to go bike riding with me? There is a four mile mountain bike trail at Lost Dutchman that I hear is killer scenic.”
“You’re asking me for a date with my son only twenty feel away?”
“No. I’m accompanying you on a bike ride to make sure you’re safe from molestation. Brad thanked me for going to take care of you.”
“The only person who is likely to try to molest me is you,” she said.
“Nah. I’ll be busy pedaling my bike, trying to keep up with you. You’re in much better shape than I am.”
“You look perfectly healthy,” she said. She walked over to him. “Maybe even buff,” she whispered.
“It’s all upper body strength from carrying sacks of feed and mucking out stalls,” he said. “My legs get no exercise at all. You’re a runner. You’ll smoke me on a mountain bike.”
“Okay. I’ll go,” she said. “How often does an old lady get to smoke a twenty-one-year-old?”
“I’ll make sure to have something for you to smoke,” he said, patting his cock. “When do you want to go?”
“You told him I already want to go,” she said. “So, let’s go.”
“Now?”
“Yes, now,” she said. “I’ll have to change and check the air in the tires of my bike, but then I’ll be ready to go be ogled by my escort.”
“I thought you were the escort,” he said, with a grin.
“Not today,” she said. “Today I’m a poor, helpless, vulnerable woman who needs protection from all those nasty men out there who want to abuse me.”
“In some other universe, maybe,” said Bobby, with a smile. “I suspect you know how to take care of yourself.”
“Not today,” she said. “Go get your bike and come back. I’ll be ready to go.”
Olivia loved to run. She always felt free and all her problems were suspended as she loped along. She liked cross country running the most, because it required her to watch what was in front of her and engaged her mind. On pavement, her body went on auto pilot and her mind was free to wander wherever it wanted to. Most recently, it wandered to Bobby Forester.
At first it had bothered her that she kept thinking about the man who took her to her first opera, and wanted her like other men, but didn’t act like it. He was a true gentleman and those are rare. Any woman appreciates a true gentleman.
She went through her running outfits and found the one she’d bought by accident. She had liked the colors and lines in it and didn’t realize they were biking shorts until she got home. There were pads built into the part of it that would touch a bike seat. She had a mountain bike, but didn’t ride it often. On city streets it was stop and go and you had to be super alert all the time. It wasn’t much fun. There were bike trails all over the place, but they were outside of town, generally speaking.
She held up the shorts. They were red, white and blue spandex and she knew the material would cling to her like a second skin. She picked a top that was actually just a sports bra, except it was designed to be worn as an outer garment. It squashed her breasts and created deep cleavage. This would tease Bob.
She couldn’t wait.
When Bobby saw her, standing by her bike, wearing a bright blue racing helmet, he felt his cock start to react. She didn’t look like a woman in her late thirties. She looked like she was maybe twenty-seven or eight. As he got out, the basketball shorts he’d put on did nothing whatsoever to hide his growing erection. He pulled his tank top down, trying to stretch it, but it wouldn’t go that far.
“Is that a pistol in your pocket or are you just happy to see me?” she teased.
“I don’t have any pockets,” he growled.
“Oh my!” she said in a manufactured squeal, putting three fingers over her mouth. “Whatever can that be?”
“That is my joy stick,” he said. “I use it to play games with. Maybe later I can teach you one of the games and you can play with it.”
“Brad has a jock strap, somewhere,” she said. “Do you want me to go find it?”
“Oh, I can just imagine it. You’re rooting around in his dresser and he catches you and asks what you’re doing. And you tell him you’re just looking for his jock strap, because Bobby needs it to try to control his boner. Yeah. He’d be happy to tell you where it is.”
“Let’s just go. When we get there I’ll suck the juice out of it and it will get soft. Then we can ride and have fun.”
“I think I will already have had fun,” he said.
The trail was not difficult and was well-worn into the desert landscape. They could see the Superstition Mountains in the distance and there were plants like towering saguaro cacti, prickly pear, cholla, and ocotillo all around them. Tree-like creosote bushes dotted the landscape and twice, a road runner crossed the trail in front of them, completely unafraid of humans. Bobby tried to stay behind her, to watch her hips move as she pedaled. They were both sweating heavily when they got back to the car.
“I need a shower,” she said as she belted in.
“I have a shower,” he said.
“Yes, but if I use your shower I’ll be naked and you might see me,” she said.
“I won’t look,” he said, covering his eyes with one hand with the fingers spread apart.
“Well, you certainly can’t take a shower at my house,” she said, “so I guess I’ll have to take my chances.”
They chatted about what they’d seen on the bike ride and then other inconsequential things as he drove to his house. Once inside, the temperature difference the swamp cooler had created made both of them get goose pimples on their arms.
She stood right in front of him as she pulled the sports bra over her head, freeing her heavy breasts. The cool air made her nipples pop.
“I could stare at you all day,” Bobby sighed.
“Aren’t you going to get undressed?” she asked.
“Am I supposed to?”
“How can you take a shower with me if you have clothes on?”
“I’m taking a shower with you?” he croaked.
“Of course. You know how valuable water is in this part of the country. Shower with a friend and save water.”
He stood, stark naked, by the time she had pushed the bike shorts to her ankles. She stepped out of them and ran her middle finger between the folds of her labia.
“I’m all sweaty,” she said.
“My shower is pretty small,” he said.
“I’m sure we’ll manage,” she said.
The shower they took involved very little soap. Most of the time they were plastered together, kissing. She reached to push his erection down and between her legs and then, ruthlessly, masturbated him with her thigh gap. He broke the five minute kiss to complain that she was going to make him cum.
“Then cum,” she said, brightly. “We’re in the shower and can clean you up easily.”
“I’m going to cum next to your pussy,” he panted.
“Try not to get any in me,” she said.
“Ohhhh, man,” he groaned, and leaned back as far as he could, looking up at the ceiling.
“Are you doing it?” she asked, stroking his chest. “Are you shooting right next to my pussy?”
“Ohhhhh, yeah,” he sighed, as his cock stopped squirting and only oozed.
She kissed him again, and let the water pound on them for another three minutes. Then she turned off the water and said, “Dry off. I need to show you something.”
When they were mostly dry, Olivia went out to the living room and got on the edge of the seat, on her knees, with her breasts lying on the back of the couch where a head usually went. This pointed her ass at Bobby. She looked over her shoulder and said, “I think I bruised my bottom on the seat of my bike. Can you look and see if I need to put something on it?”
As she was positioned, her fat, excited pussy lips formed a split peach that invited a cock to just slide in and have fun. Bobby went close enough to put his hands on her lower back, just where the swell of her hips started. He stroked her flanks while he bent over to “inspect” her gluteus maximus.
“It’s hard to see, so this might take a while,” he said.
“Take as long as you need,” she said.
He stroked her hips and butt cheeks, saying things like, “Nothing here.” Finally he had touched everything except her split peach.
“Just one more area to inspect,” he said. “It looks a little oily, or something, so I’m going to have to clean it off.”
“Okay,” she said, staring at him.
He leaned over and ran the tip of his stiffened tongue between her lips. Then he lapped at them like a dog.
“There might be some bruising here, but I can’t see everything I want to. Turn over and lie on your back so you can spread your legs and let me see better.”
“But you’ll see my ... pussy,” she complained.
“I know, but it has to be done. If you’ve bruised your pussy, then treatment will be required to make sure your pussy stays in good condition.”
“Well ... if you say I have to...”
She rolled into position and spread her legs as wide as she could.