What are Sisters For? Ch. 02

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Her family puts the 'dis' in dysfunctional.
5.1k words
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Part 2 of the 2 part series

Updated 06/08/2023
Created 09/26/2017
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Cyndi44
Cyndi44
71 Followers

Val slid her somewhat sore ass onto the driver's seat of her 7-year old Beemer. It had been the one extravagant purchase since her first big advance check rolled in from, "The Killer Smoked Camels," the first in a series of moderately successful Robert Preston mystery novels. Val, nee Robert Preston, was not an impetuous spender, nor was she impetuous on much of anything. Yet here she was, driving home after having sex with a man for the first time. Since deciding to dress as a woman full time, she had finally succumbed to a long repressed desire.

Though it was a warm summer night, she turned on the seat warmer to soothe her backside. Her ass was sore but it was a small price to pay for the night's activities. Brandon, a slacker of a shoe salesman, half her age, was the lucky guy.

She really had no idea of how her wife, Cindy, might react. After all, it was her idea for Robert to become Val full time. But that was a long way from being okay with Val on her knees sucking off a twenty something. Or hiking her dress up to take him in her ass.

She felt the need to clear the air on the matter of her infidelity as soon as possible regardless of the consequences. She drove to Cindy's yoga class.

Cindy had been going to the class once a week for just over two years. It had obviously been good for her. She was always happy and relaxed when she came home. Val, the mystery writer, failed to see that as a clue. At least not until she pulled into the parking lot. The empty parking lot. There was no yoga class!

She changed course to home, already knowing what lay ahead.

As she had deduced, Cindy was not at home. Val made her way through the empty house, stripping off her sexy black dress, her bra, panties and heels. She took a quick shower and put on one of Cindy's shorty robes and waited. She didn't have long to wait.

Cindy came floating into the house, obviously very happy. She almost didn't see Val sitting on the sofa as she entered the living room.

'Your class must have run a little late tonight. Learning some new positions?"

"Why the sudden interest in my class?"

"You mean the class at the community center on Redwood Drive?"

Cindy knew she had been caught. "Alright, you caught me. The class didn't have enough people to make it viable after a couple of months. The instructor, Ray offered me private lessons.."

"And you took his offer?"

"Yes. At first it was legitimate. But you know that our sex life has been less than ideal for a long time. You know I love you so much. But I need it more often. Ray is so much different. He is more...physical. When he fucks me, it is hard and deep. I love the way he pounds me into his bed. The way he slaps my ass when he does me from behind. He satisfies me like you never have. I'm sorry."

"I knew our sex had been infrequent, but this! Do you love him?"

"No. I told you that I love you. But I needed more. Now that you are becoming Val, you will certainly want sex even less with me. Who knows, you might carry this even farther."

"What do you mean by that?"

"Maggie told me about you at the shoe store. How you went to the back room with the salesman. And how you left him high and dry."

"Well, I made amends to him tonight."

"You did what?"

"I made a date with him tonight. I blew him before dinner and he fucked me after. And I enjoyed it!"

"Oh my. You let another man fuck you? You had another man's cock in your ass? That's taking this cross dressing thing a little far, don't you think?"

"I would look at it this way. We had sex tonight. Just not with each other. But the question is where do we go from here? I see no reason you can't keep seeing Ray. I'll continue being Val, and see where that takes me."

Cindy mulled the idea for a moment. She liked the idea of continuing to see Ray, maybe other men as well. If Val needed to be with men, then she could live with that, too.

"Come here and give me a kiss," said Val as she leaned in close to Cindy. "I hope you don't mind if my breath smells like another man's cum!"

"Not if you don't mind Ray's cum on my breath!"

###

Robert sat nervously in the strange living room, waiting for his date to emerge from her room. Her father sat across the room, glaring. Robert's attempt at making small talk had been met with terse 'yes' and 'nos.' Now the two sat silently

After an eternity his date, Annie, made her entrance. She wore a tie-dyed t-shirt and a denim mini-skirt and sandals. The mini was just long enough to cover her ass cheeks. Julie's dad gave a disapproving look but said nothing. Her mother hustled the pair out the door before dad could veto the outfit.

Robert had borrowed his dad's Oldsmobile for the night. The big and roomy car was a beast to drive. But the bench front seat was perfect for a date. Especially since the date was for a drive-in movie.

He deliberately found a remote spot near the back of the lot. Even though he was eighteen and about to graduate, he had little dating experience. He hoped this date would make up for all that he had missed. Annie, while not the prettiest girl in his class, was certainly his 'type.' She was smart, had a good sense of humor and liked to read. It didn't hurt that she had a tight body. Her breasts were on the small side, but her shapely hips, lovely ass and long smooth legs more than compensated.

As most teenagers do at a drive-in, Robert and Annie completely ignored the movie. They memorized the title in case they were asked by their parents. Little did they know, but their folks couldn't have cared less what movie the kids went to see. They were just glad they were out of the house so they could spend some time without kids around.

As soon as Robert had parked the car, Annie had scooted next to him. He had kissed girls before. None had kissed him with the pent up frustration Annie kissed with him now. He knew she had not dated much. Her urgency was very apparent. She undoubtedly wanted more than kissing. She urged him to move out from under the steering wheel so she could straddle his lap. She had to hike her mini-skirt up so she could get on him. As she did, he saw her panties. Dark pink and shiny, with a white bow on the waistband.

He took the opportunity to explore her chest by sliding his hands under her t-shirt. As he suspected she was braless. He pinched her nipples and she moaned in pleasure.

"Let's do this. Let's do what we have to do," Annie said as she pulled her shirt over her head of thick red hair.

"What do you mean 'what we have to do?'"

"Isn't it obvious? We need to have sex before we graduate. I know I'm a virgin. And I would bet anything that you are also. Once we do this we can go back to being what we are. What better cover could there be."

" Cover? Cover for what? "

"Come on! I'm gay, you're gay. If we have sex then we can get through school. After that who cares?"

"But, but..."

"Don't tell me you're not. I noticed all your mannerisms and how you're never with girls sexually. Besides, your sisters used to spread it around school that you were a little off shall we say."

"They did that? I can't believe it. Annie, I'm not gay. And if you are..."

"I am. I'm a certain I am."

"Well I am certainly not and I'll prove it to you now!" Robert felt an uncharacteristic surge in adrenaline as he shoved her off his lap and onto the wide seat. Her skirt rode up even farther. He grabbed the waist band of her pink panties and he jerked them down her legs. He briefly held them to his nose and inhaled deeply. He tossed them into the backseat. He now had his first close-up view of a real-life pussy. His surge of masculinity started to subside.

"Eat it or fuck it but do something Instead of gawking at it."

Robert unbuckled his belt, lowered his jeans and underwear and climbed on Annie's splayed body. He had envisioned his first time to be a little more romantic with a little more foreplay. But Annie's urgency to 'get it done' prompted him to simply line up his cock with her hairy hole and shove. She yelped as he plunged into her. After exactly three strokes he felt his orgasm coming. Annie was yelling not to cum, but it was too late.

Annie spent the entire ride home alternating between crying and cursing him. Thankfully her next period was on time. She was done with men for good.

Robert returned home to an uncharacteristically dark house. However, as he passed his parents room, he thought he heard a rhythmic squeaking of their mattress. He smiled until he heard his mom yell out, "yeah, fuck me harder, George!" His dad's name was Sam!

Before he could move away he heard his dad's voice, "Yes, fuck the bitch hard. Pound that worthless cunt! Give her that big cock."

Robert was having a hard time processing all this.

"His cock is bigger. A real man's cock. I wish George had knocked me up back then. Then maybe my son wouldn't wear his sister's clothes! You hear me? "

A voice he assumed to be George said,"My boy Henry is all man. I'm surprised Sam's little wiener could even get you pregnant. Your sissy will be sucking cock just like his Daddy. Sam get over here and finish me off." Robert heard gagging as he quietly went to his room.

So his mom had been fucking George Stevens, his classmate Henry's dad! And this had been going on for some time. Robert knew the definition of the word 'dysfunctional' but he was getting a real world lesson in it tonight. As he lay naked on his bed that night, he had a decision to make: jerk off to Annie's panties that she had forgotten to retrieve or the visual of his parents dominated by a huge cock. He decided on both. He was eighteen after all.

Across town, Annie's parents were still awake when she was dumped out at the curb. Robert had wanted no part her parent's wrath. She stumbled into the living room, causing her dad to complain about kids today. Annie hugged each of them goodnight. When she leaned over to hug her mom, her skirt rode halfway up her bare ass. The implication of his daughter returning from a date without her panties is what he should have been concerned with. It was the 18-year-old pussy peeking out that had his undivided attention. He would never touch his daughter. But when she she paraded around the house in skimpy clothes it revved his motor.

Like Robert's mom, Annie's mother also got pounded that night.

###

After their mutual confessions of infidelities Val and Cindy's life settled into a routine. Val became adept at being a woman. She had accumulated a sufficient wardrobe and her real hair grew enough to be styled. She was glad to ditch the wig. She walked, talked, sat as a woman without thinking. She had no fear in leaving her house. Yet there was a very big loose end to deal with: her publisher.

She had begged off on doing a book tour to promote her last novel, citing fatigue. But she knew that would not work a second time. She would have to come clean. And it needed to be done in person. She booked a flight and convinced Cindy to take a few days off so she could tag along. She jumped at the chance to spend time in New York City. Especially since if things didn't go well it would be her last chance for a long time.

The two girls shopped the first day, trying not to break their budget and not succeeding. The second day Val had to tend to business or they would be making a lot of returns

She needed to talk with Jonathan Wulf, CEO of Bad Wolf Publishing, a major player in the mystery novel game. Jonathan was young for someone in his position. He had inherited the company when his dad passed away just days after he graduated from college. But he had managed to keep the company ship afloat. Part of the reason for that was the popular Robert Preston series of books. So he was willing to take a request from Robert. He had asked Jonathan meet with a Val Preston. Obviously a relative needing a job or internship. Any one else and he would not make the time.

His secretary announced Val as she entered his office. Obviously not here for an internship, he thought as he checked out the beautiful lady standing before him. He guessed her to be in her early forties. She was well dressed in a grey business suit, white blouse, and navy blue heels. If she was wanting a job, she was hired.

"Miss Preston, you have a very strong recommendation from Robert. I must ask if you are related?"

"Yes, very closely."

I would guess you were his sister, but if I recall he just has twin sisters and their names started with M's."

"Yes Maggie and Mollie. No, I am not Robert's sister. I am Robert!"

All the blood in his face seemed to disappear at once. He slumped into his chair. This could put his company in real jeopardy.

"Look, I'm as forward thinking as the next guy. But what the hell is this? It's not halloween so i'm going to ask again, what the hell is this?"

"With the help of my wife, I have decided to embrace life as a woman. I plan to legally change my name to Val. I know you are busy, so I will let you decide what course you want to take from here. Meet us at our hotel tonight and we can get dinner. You should have some ideas by then. Jonathan, I hated to spring this on you, but this is me from here out. If you decide to drop me, I understand." Val laid an envelope with information covering the name change and other facts needed to get a possible contract going.

Jonathan could only nod as he watched her shapely ass go out his door. He buzzed his secretary to clear the rest of the day. This would take some time.

Cindy was laying on the bed when Val returned.

"That was fast. He didn't drop you, did he?"

"I didn't give him a chance to. I left him to play with his focus groups, art directors and his lawyers. If he decides to keep me then he will be prepared with graphs and chart to show me at dinner. If not, I expect a handshake goodbye. But we are in the publishing capitol of the world, so I am sure we can line up someone else."

"I certainly hope so. Even if we do pick up another publisher money will be tight for a while."

"Yes, perhaps. Say you are missing your yoga class with Ray this week, aren't you?"

"Well yes. But what brought that up?"

"I'm thinking you might need a substitute."

"Oh Val, are you wanting to be my substitute?"

"Not that I would mind. But I've got something else planned. Jonathan will be wound up tighter than a rusty watch. Maybe, you know, you could help him relax."

"What exactly do you want me to do. Do you want me to fuck Jonathan?"

"I would not have put it so bluntly, but why not? I've seen the way he looks at you. Hell, he looked that way at me this morning before I told him who I was."

"Honey, he looks at all women like that. He is a serial womanizer. If it wears a skirt, he has hit on it. It's kind of a wonder he hasn't hit on you."

"Now I'm hurt that he hasn't"

"Don't worry, I'm sure he had a boner in the office this morning watching you leave. He's an ass man for sure."

"You picked all that up from the two times that you met him?"

"It's a gift that all real women have. We develop it soon after puberty. We know when and how men are looking at us at all times."

"And yet you can't read a roadmap! Seriously there is so much to learn. I did know he was a womanizer. He will have two to choose from tonight."

You want to make it a contest? It would be no contest. You may look pretty good but you are missing a major piece of equipment."

"I'll put my 'man pussy' against your girly pussy any day. The only difference is it doesn't make babies. Even so it does make baby lawyers!"

The girls did more shopping before returning to the room to get ready for dinner. They both had picked up cute little cocktail dresses to wear tonight. Cindy wore a black dress with a beaded bodice, a black thong with matching beading, black stockings and six inch black stiletto heels. Val wore a simple sleeveless black dress. She picked out a bright red pair of thong panties, a black lacy bra and patterned stockings.

They looked fabulous.

Jonathan arrived early. He let out a soft whistle when he saw the women. To Val's relief he was carrying what appeared to be charts and graphs. The bottom line, according to Jonathan, was that they estimated no net loss in sales. If Val would strongly promote her books by going on Howard Stern and other shock jock shows that she normally wouldn't get invited on, she could boost sales. Hell, some might buy her books just to be part of the freak show. He even had a couple of mock book covers with a 'Valerie R. Preston' byline.

Val and Jonathan started to shake hands but hugged instead. Val thought she felt him squeeze her ass cheeks during their hug. Cindy was certain that he squeezed hers.

After the celebration dinner, the three returned to the room for a nightcap.

"Val," said Jonathan. "We are glad to keep you aboard!" This time when he hugged her his hands slowly slid down to her ass. There was no doubt as he massaged her thoroughly. Val took the hint and grabbed his ass and pulled him tight. She raised up and gave him a long, deep kiss. She thought he might pull away, but he pulled her even tighter.

"Ahem," said Cindy. " And here I was expecting to be the one getting hit on!"

Jonathan smiled at her. "I'm sorry but I am fascinated with the idea of having sex with my top selling author. And Val looks so tasty. I hope you don't mind if I fuck your hus, I mean wife."

Jonathan turned his full attention to Val. He moved his mouth next to her ear and whispered. "I hope you don't mind. I can't think of a better way to seal our new deal."

Val tried her best southern belle accent. "Why mister Wulf, I thought you would never ask."

They kissed deeply with more passion than Val ever remembered ever having. Jonathan worked his hands underneath the hem of her dress. He savored the smooth feel of Val's bottom. He slipped a finger under the red thong and suddenly jabbed it into her tight ass. Val was startled by the invasion but quickly adjusted. As he wiggled the finger up to the second knuckle, Val cooed softly into Jonathan's ear, "yes, Jon, I would very much like for you to fuck me." Jonathan pulled the invading finger from its warm haven.

Val winked at Cindy. "The nice man is going to fuck my ass. You are welcome to watch if you want. If not, give us a while." Cindy opted to go into the bathroom and draw a hot bath.

Now alone with Val, Jonathan slipped his pants down. His cock was partially hard. It was a good bit larger than he remembered Brandon's cock. Val slipped down to her knees to suck her second cock. Brandon, the young shoe salesman was a contrast to the older, self assured businessman who stood in front of her now. However the view was the same. Val did not hesitate to take Jon's cock deep in her mouth. He muttered indistinguishably. Her tongue swabbed the large head. She was not in a rush. Neither was Jonathan. He wanted to last long enough to stretch out Val's tight little asshole. But for now he was enjoying the feeling of her hot, married mouth on his cock.

Val settled into a rhythm of taking it deep down her throat and working just the head in her mouth. Like Brandon, Jonathan could not last long with this treatment.

"Easy there. I want to cum but not in your mouth this time. I want that ass. NOW! " Val jumped to her feet. Jonathan unzipped her dress and she stepped out of it. She tugged her red panties down her legs.. Cindy had placed the bottle of lube on the nightstand. She reached back and rubbed a generous dollop in and around her anus as well as on his prick. Jonathan's steel hard member soon explored the entrance to Val's asshole. The extra lube eased its passage. Jonathan was very eager to have another hot man's ass. He wasn't only a womanizer — he was an equal opportunity fucker. And he had always thought his star author went both ways. His fear of losing him/her kept him from trying earlier.

Cyndi44
Cyndi44
71 Followers
12