Encounter: Doin' the Boss, a Strange Love Story

by mattwatt

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa, Consensual, Brother, Sister, Light Bond, Interracial, Black Female, White Male, Oral Sex, .

Desc: Romantic Sex Story: Catherine Shaw, the boss, is the goal of one of her workers, Jess Sawyer; Jess goes to strange lengths to establish a relationship with her but wins in the end.


Catherine got to the garage later than she usually did. At this time of day there was no one there, as she went to the lower level where she habitually parked her car. There was a kind of eeriness to it for her. The only sound was her heels as they clacked on the pavement, while she walked toward her car.

She forced herself, her mind or I guess imagination, to stop trying to play tricks, tricks about lurkers and muggers and all. It even caused her to smile a bit and just barely suppress a giggle.

It was a matter of her 'game', as she thought of it but this empty garage was no place to initiate the game. That was her message to herself. She made an internal promise to think about it later, make this walk, this solitary walk mentally later and then she'd play with herself and enjoy the big bad men or muggers or rapers who'd inhabit the fantasy. She play it later. That was her promise, as she approached her car.

He stepped out from behind the pillar by her car, by the front fender, and it surprised her enough that she only barely suppressed a kind of shout in her throat.

"Ohhhhhh!" she said, and stepped back a few steps from the driver's door, by which he had been lurking.

Of course this had the effect of putting her out of the range of her best defense, getting into the car.

She tried to calm herself and prepare for a kind of defense, and with all the will that she could muster she said:


In a whispery voice he said: "Hi!"

"What?" she asked again and only got a low voiced chuckle from him. It sent chills up and down her spine.

"Name?" he asked softly.

"Catherine," she said, not knowing for sure why she complied so readily.

"Lovely Catherine!" he said.

He stood a little taller than Catherine's 5'10"; he wore an evil looking hood, kind of a ski mask thing, that made his unwanted presence even more sinister than it might have otherwise been.

"A real black beauty!" he said softly and watched her.

"Does that offend you, calling you that?" he asked.

She was surprised by the question.

"No, that doesn't offend me," she said, "You being here with that mask, and that knife, they offend me."

He chuckled.

"What are you going to do?" she asked. "I have a martial arts belt!"

"Good," he said, "Game changer; I'll use this."

He pulled an evil looking pistol out of the back of his pants waist band.

"Ohhh," she said.

"You're going to?" she asked, striving for some clarity, and not even knowing what it was important, since his intentions seemed obvious.

"I want a blow job," he said. "A black beauty blow job!"

"Bow job!?" she repeated. "Only?"

"Yes," he said. "Time and all. A blow job, only."

It was then that she decided. She realized right away that she was going to do this. She had mace in her purse; she hadn't been kidding about her martial arts training but she made her decision.

"Kneel," he said.

"Yes," was her response.

She knew that that was the way that it should happen, with her kneeling. As she went to her knees, her mind went into a kind of fugue of memory.

Blow job! Wasn't that the way that it always was? Her memory raced ahead of her, taking her back to those places. Where she'd been raised and lived.

It had all started with her brother Evan. She remembered the night itself. Her Mom was working, a night shift at the place where she cleaned to keep her three kids in what they needed.

"Evan, what you want?" she'd asked upset that her sleep had been disturbed.

"Just kind of restless, little Cathie," he said.

"Why you comin' in here with your restless?" she asked.

He smiled: "Because my lovely little Cathie sister can help."

"What you mean, help?" she asked then.

He smiled and began to run his finger over her lips.

"What you doin'?" she asked and giggled as she did.

"Cathie likes that," Evan said.

"Ticklin'," was her answer, though to herself she actually admitted that she did like the attention that he was giving her.

"Thought you was out with that Rita," she said.

"Was and she didn't treat Evan very nicely," he said, "Only teased and no sugar."

"Sugar?" she asked suspicious.

"You know, Pretty Cathie," he said, "Sugar with your mouth, nice things!"

"Evan!" she said and giggled again at the very thought.

There was certainly no lack of sex education among the group of them and they were 'grab assing' her all the time, since she passed her last birthday, getting older and all.

"Come on, Pretty Cathie," he said, "How 'bout some of Pretty Cathie's sugar?"

"Evan, ain't no way that I'll let you do me," she said.

"Know that, Pretty Cathie," he said, "Just want some lip sugar."

"Evan, if I agree to that, it's all that I do, ever," she said.

"Of course," he said, "I know that; you're my sister but there's no harm in a little lip sugar for Evan."

There was silence in the room but she finally said: "Okay."

She realized, as she said it, that she liked the idea. It had been rolling around in her head for such a while, doing such things and she often wondered, when she heard her girl friends talk about doin' 'lip sugar' for a boy, what it might be like.

"What you want then?" she asked next.

"Out of bed, Pretty Cathie," he said, and she slid out of bed.

"Look pretty in that night shirt, Cathie," he said.

"Not taking my clothes off, Evan," she said in her next protest.

"No, that's okay," he said, and told her to kneel.

That's how it started and it was always with her kneeling. The position had to be right, it seemed. But Cathie wasn't prepared for how much she liked giving the 'lip sugar'. She never could explain it, apart from the admission to only a few that she was 'very oral'.

She knelt for Evan and grabbed his erection, when he produced it. It surprised her to see how long it was.

She learned with Evan, for once she gave in and knelt to give him a blow job, it became a fairly regular thing.

But Evan told Jimmy, her other older brother, and one night Jimmy came to call, when she was in bed.

"Cathie," he called out, waking her.

"Jimmy, what you want?" she asked, sleepy.

"What you do for Evan," he said.

"Ohhh," she moaned, "He told you."

"He did," Jimmy said. "Why don't you just get out here and kneel and show me how it is."

It went that way, for a time. Evan and Jimmy were pleased to have a resident cock sucker, as they loved to call her. For her part, she was exploring and trying to find out why she liked the position of kneeling, the silky hardness of an erection in her hand or in her mouth, why it appealed. She didn't really know, she just knew that she liked doing it.

Of course, this was Evan and Jimmy that she was dealing with and that meant, almost naturally that it would get out of hand. She was wary about that.

It did. They brought two friends over one night and all of them cornered Cathie in the kitchen. The one friend, who was smarmy, as far as Cathie was concerned, announced to everyone that after getting blow jobs from the 'ho', they were all going to get laid.

That's when Cathie got the frying pan. In the end it was a concussion for the smarmy one and a broken wrist for the other one before the fray settled.

In that altercation, Cathie was able to see her future flash in front of her and there was no joy in it, only abuse and continued problems.

She announced to Evan and Jimmy shortly after that, in no uncertain terms, that her mouth was private and the rest of her was definitely out of bounds for them. They took it well, especially having witnessed the fray in the kitchen and how well she'd handled herself in that instance.

That was when she began to distance herself from her family. Academics became her main interest, almost a mania. She knew that was the key to any kind of future for her. She also began to take a martial arts class, progressing very nicely, as she continued to work on it.

The future wasn't good for her family. When she was a year out of high school, working hard at various jobs, waitressing, and nights in a convenience store, her momma died of 'the consumption'. Jimmy went shortly after that in a neighborhood drive by but by then she was just gone.

Once Cathie had gotten to college, she never looked back at all. She'd packed away her strange love of performing oral sex and concentrated on athletics and academics. She'd grown and loved playing basketball for the school.

There was, however, the interlude with Sherman, who seemed to be all cock and attitude, and for a time, a short time, but an intense time, she went back to being the 'oral girl'. Sherman, however, turned out to be an Evan or Jimmy only in disguise.

At that point Cathie, lovely though she was, with her long legs, hefty breasts, and flaring hips and rounded butt, left the men alone and went on a career track, that now left her, Catherine Shaw, at the top of her part of the corporate ladder at 33 years of age.

It was the last great sexual adventure, at least until now, she thought, going to her knees.

Cathie was surprised at how it actually felt, getting down on her knees again in front of a man. She hadn't expected to be so pleased by the possibility. It made her smile, which seemed to confuse him.

"What?" he asked, noticing her smile.

"Gimme the goods!" she said, pleased with herself, giving herself the message:

.... There is more of this story ...

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