Miss Latimore
Chapter 4

Copyright© 2017 by Jessica James

Sex Story: Chapter 4 - The Snyder matriarchs - - Cyan, her daughter Ivory, her daughter Delft, and one day 8-year old Cinnamon - - handed Miss Latimore down, generation after generation. The 61-year old woman was brilliant, strong-willed, tough. She managed the business and personal lives of each household she was given to. Although when Cyan first bought Leticia, before she evolved into Miss Latimore, the little girl was just pussy. Far too talented to be merely a toy, she was elevated into family management.

Caution: This Sex Story contains strong sexual content, including Teenagers   BiSexual   Fiction   Mystery   Brother   Sister  

One morning at breakfast, Miss Latimore saw Sin looking at, frankly checking out, the penis of one of Delft’s newest lovers. The boy was oblivious to her attention as he was happily mixing three kinds of cereal into his bowl. Miss Latimore didn’t allow Sin and Rusty to eat cereal, certainly not that sugary crap, but had it stocked for Delft’s younger lovers. Delft occasionally fucked the sons and grandsons of her friends -- more of a novelty fuck than anything else when she was in the mood for a change of pace.

This boy, the one Sin was obviously curious about, didn’t yet have much in the way of a package. Perhaps he would someday.

Sin was trying to figure out why her mother would bother with such a shrimp. Sin thought back to what Miss Latimore had told her a couple of years ago, “What a man has between his ears is far more important in bed than what he has between his legs.”

Cinnamon said, “Even Uncle Big?”

Miss Latimore smiled, “Especially Uncle Big. Yes, honey, he has larger equipment than most men. But it’s his mind, his creativeness in bed. He knows what to do to a woman, what to say to her, when to push her limits. How to push her limits.”

Sin, as she did with most things, thought about it. “How far does he push?”

“As far as he likes. He does things to women, boys and girls too, that they didn’t realize they’d allow. Let alone enjoy.” She smiled again at the little girl, “Of course it doesn’t hurt that he...”

“Has a huge cock.”


No, that between the ears stuff wouldn’t apply to this kid who was happily pouring more sugar on his cereal. What was between his ears ... well, it would be cartoons and puppies and nonsense. Puzzling why Delft even bothered with the boy.

Later, Sin heard Miss Latimore say to Penny, one of her two assistants, “Clean him out.”

Another puzzlement. Sin knew that usually meant one of Delft’s lovers would be butt-fucking whichever little boy or girl happened to be handy. But this morning, Rusty was the only other male in the house.

And Sin wasn’t about to let him lose his cherry to some ... twerp.

Miss Latimore had always given Cinnamon the freedom to go anywhere in their apartment she wanted to. Miss Latimore considered it part of the educational process to listen to adult business conversations, to see her mother fucking and sucking, to go over household budgets ... to see life unfold. Unfiltered and in real time.

The doorbell rang and it was the boy’s mother. Sin hadn’t met her, she hadn’t met that many of her mother’s lovers. This woman, young and friendly, was polite to Rusty during the introductions. That moved her up a notch in Sin’s estimation.

Miss Latimore said, “Susan, Delft is about finished with Charlie. He’s had his breakfast and should be about ready to go home.”

Sin followed them back to Delft’s bathroom. Penny was drying the boy off and Delft was leafing through a Mega fashion magazine. Charlie grinned, “Hi Mama!”

“Hello there honey. Delft.”

Delft said, “Susan.”

“Enjoy him?”

“You bet. You can start farming him out in another year or so.”

“That soon?”


Sin moved around for a better angle and whispered to her little brother, “Pay attention.”

Penny lubricated Delft’s index and middle fingers, then did Charlie’s butt. The boy seemed to know what to expect as he grinned up at his mother.

Delft smoothly inserted one finger, then the second, and immediately found Charlie’s magic spot. His little hips were soon pumping as he reached his first dry-cum. Delft went faster, applying more pressure.

Charlie moaned, a sound that somehow combined innocence with sexual gratification as dry-cum after dry-cum coursed through his little body. His eyes rolled back and Penny held him to keep him from collapsing.

Delft intensified her efforts and Charlie’ jaw went slack. He wasn’t seeing anyone in the bathroom, his mind was completely given over to the waves of physical pleasure.

Susan smiled and whispered to Miss Latimore, “Little slut.”

Sin glanced at her brother. Rusty was staring at Charlie, transfixed. His pajama bottoms were poking out. Sin hadn’t given him any Viagra since they returned from Sunny Shores. Sin thought: good.

Later, Sin asked Miss Latimore about the bathroom scene.

Miss Latimore, patient as always said, “Remember the G-spot?”

“Of course.”

“For little boys, men too, the prostate, which your mother was massaging, is the male equivalent.”

“Charlie looked like he was about to pass out.”

Miss Latimore smiled, “Last night he did. We let him sleep. Pleasant dreams, I imagine.”

“I want to do that to Rusty.”

Miss Latimore considered it. She didn’t like to set limits for Sin. Perhaps it was time. She said, “Penny.”

The assistant held Rusty’s hand and led him to the bathroom he shared with his older sister.

Miss Latimore opened a drawer and showed Sin some interesting looking equipment. She said, “Your fingers will be long enough to reach Rusty. For men, you’ll need to use a massager. With Rusty, start with your fingers, then use different massagers, see what works best. He’ll probably enjoy the vibrating ones.”

“I’m going to do him every day. For a while, anyway.”

Miss Latimore shrugged, “Up to you, honey.” Sin was simply in charge of her brother.

“What about Charlie, will he be coming back here?”

“Probably not.”

Sin was going over one of the Sunny Shores videos on her iPad with her mother. “Delft, look at Lukas. Look at that cock. You have to go see him. Have to!”

The video showed a smiling teenage boy, a truly beautiful boy, posing with Sin and Rusty’s arms looped around his thighs. Rusty, thanks to his daily Viagra, was erect.

Delft smiled and traced a finger along his little cock, “This young gentleman is looking good too.”

Rusty smiled up at his mother, pleased beyond measure at the rare attention. Usually it was Miss Latimore who interacted with the kids.

Sin smiled up at her mother, “Rusty loves being finger-fucked.”

Delft, her mind already racing ahead to her day’s schedule, said vaguely, “Oh?” and rose gracefully from the sofa to leave for the day. Sin watched her brother watch their mother stride away. He looked wistful.

Sin smiled at Penny, “Get Rusty ready for me please.”

Miss Latimore made a mental note to hire an assistant for Cinnamon. She was almost to the point where she could use one.

Rusty skipped, hand in hand, with Penny to the bathroom. He did love getting finger-fucked. He loved anything to do with his adored sister, but this new game ... awesome!

Miss Latimore had reviewed all of the Sunny Shores footage, that was just the way she was. Amused, she showed Delft how blatantly Cinnamon was humping against Uncle Big’s neck.

Delft smiled, “She’s a Snyder.”

But Delft was more interested in looking at Lukas as that magnificent creature strode through Sunny Shores with Sin, then Rusty, riding on his tanned shoulders. She smiled as her daughter openly thrust against the tendon in the teenager’s neck.

In the bathroom, Rusty eagerly accepted his sister’s one, two, three fingers. Penny wondered if the little boy would turn out to be gay. Then decided, no, Sin would never allow that.

For her part, Sin enjoyed the Uncle Big videos, but watched Lukas even more. She loved the tingly feeling she had with both of them. She rationalized her Lukas fixation was due to the fact that she saw Uncle Big pretty often, every time he stopped by to fuck her mother.

At Miss Latimore’s instruction, Cinnamon had started keeping a daily journal when she was four. Today, if Sin were Delft’s age and went back to read her diary years later, she would probably add Amy Schumer-like footnotes.

Dear Journal,

Sunny Shores was awesome .1

I wish I could fuck Lukas. But Miss Latimore will have Uncle Big be my first. I’m ready!2 She explained how it will happen. She decides when I’m ready. Uncle Big decides when he’s ready for me.

But I get to decide when he fucks Rusty. I won’t make Rusty wait as long as I’m having to .3

After I get used to Uncle Big I’m going back to Lukas. I bet he has a lot of girlfriends. I loved getting him hard rubbing my pussy on his neck. Huge cock! It felt so warm in my hand. Partly from the sun. But I felt inside heat to .4

1 All those boners. 2 No, you’re not. 3 Better rethink that, kid. 4 Too.

Over time, Miss Latimore was pleased that Cinnamon’s journal gradually focused less on sex and moved on to more thoughtful interior dialogues. Rusty was still too young to write very much that interested anyone, but Sin had him plug away at it. Every day.

He had been confused that Sin referred to him as pussy until she explained it.

Rusty was a pretty sharp boy, but as Miss Latimore explained to Delft, “He’s just not quite in Cinnamon’s league.” Delft shrugged. Her kids were pleasant to be around and often amused her. But Delft had her own full life to lead. Sin was Miss Latimore’s responsibility. Rusty was Sin’s.

Delft knew communications well. From her early days as a MegaMax magazine summer intern, aged 10. Followed by full time employment for a number of years.

She understood the trade / consumer interaction and knew the value of savvy PR.

Delft was ready to launch her art-fraud / art-theft firm which she named TrueArt. She reconnected with with the most sought-after public relations guru in town -- Madge Hopkins.

Madge, at 72, was one of the few old-timers who had shifted seamlessly from analog to digital. She was an NYC pioneer in launching, and sometimes ending, careers, businesses, movements, on the Internet.

She was tart-tongued and hatchet-faced. Madge had been an unfiltered Camel smoker for over 60 years. And had the raspy voice to show for it.

Mr. Big was one among over a dozen lovers she retained over the decades. He had told Delft, “Madge has a pussy as tight as Cinnamon’s.”

“You don’t know how tight Sin is. Miss Latimore hasn’t given her to you yet.”

“No, but I can tell from looking it’s going to be a little vise.”


Madge Hopkins loved Delft’s opening gambit for TrueArt. Delft had uncovered a forgery in the Metropolitan. Not an acrylic on wood that was one of millions of pieces in storage. Nope, this one had been on public display for 16 years.

Madge had been introduced to Delft by Hattie, Mr. Big’s assistant. Hattie told her, “Keep an eye on the kid. Word is she’s a champ at sucking cock.”

“So what? All fucking interns suck cock. This is fucking New York, Hattie.”

“I know, I know. But this one has a head on her shoulders.”

Madge grinned, “A head who gives head.”

Madge and Delft never became friends, but the PR woman gradually began to see that Hattie had been right -- this kid was going places.

Madge and Delft met for a strategy session. To plan the launch of TrueArt. Delft had Sin sit in. With Rusty of course.

Madge told Delft, “Okay, this forgery. We want the biggest possible splash. So I’ll leak it to the “Times.” Now that they’re finally getting their head out of their ass, they have a decent online subscription base.”

“Are they still the paper of record?”

“Not so much, but this is a local, national, international story. When the “Times” breaks it, I’ll have it go viral. Then you’ll do followup interviews with the trades. That cunt at Christie’s will say what I tell her to when she’s interviewed.”


“I can get you on the Today Show, they’re still floundering. Do you have TrueArt graphics yet?”

“Of course. Connie did the whole deck for me.”

“She’s good. Expensive.”

“Can you sex me up for the coverage?”

“Don’t be stupid, of course I will. Leaked nudes. Then videos. Print first, then the next day, sex tapes. I assume you have some?”

“Yes.” Delft made a rueful face, “I went through a phase a few years ago. Don’t know why I saved them even.”

“Well, they’ll come in handy. Were you street legal?”

Delft laughed, “Hardly.”

Madge thought, “I can use kiddy porn, but only with individuals. Well, give me what you have, I’ll tell Renata to sort through everything, edit it for the short-attention jerk-offs.”

“Okay. Good.”

“But I need some current footage too.”

“No problem, what do you need?”

“Just the basics. DP with a couple of hung guys. You with another girl. The usual.”

“I’ll have Miss Latimore organize it.”

“You sure you won’t let her come to work for me? I’ll make it worth her while.”

“Sure, just as soon as you launch True Art.”

Madge laughed, “Lying cunt. You’re giving her to that little cock-tease, Cinnamon.”

Sin grinned.

“Guilty. Now how slutty do you want me for the tapes?”

There is more of this chapter...

For the rest of this story, you need to Log In or Register