Little Sister Ch. 08

Story Info
Denise recruits Jean for Ralph's porn business.
1.7k words
4.46
35.3k
7

Part 8 of the 11 part series

Updated 10/01/2022
Created 03/10/2009
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Da_Vida
Da_Vida
172 Followers

When Jean joined Denise in the kitchen for lunch, Denise said, "I talked to Ralph this morning and he said that if your instruction went well this afternoon that I should make you an offer."

"Really, what kind of offer?"

"Based on your knock out looks, his experience with you at the party and what I've told him about you Ralph thinks you can be a real star in our business. He would like to have you do a debut film for him and if it turns out as good as he thinks it will, he'll pay you $50,000."

"That's a lot of money Denise. What do I have to do?"

"Nothing you haven't already done. Give some head and get butt fucked. But, before the explicit sex there is some verbal foreplay, which you either have a talent for or don't. Ralph likes the dialogue to be as natural as possible, not scripted so you have to improvise as you go."

"Tell him hell yes. I'd like to take a shot at $50K. That would go along way toward paying for school," replied Jean.

"If this works out $50K will just be the beginning," said Denise. "As you can see I've been doing pretty well working with Ralph and there is plenty in the bank that you can't see."

"What are you going to do with all the money you're saving," asked Jean.

"I know that I won't always have the looks or the freshness necessary to keep at this career long-term. I plan to find a good man who loves me, preferably with his own money, and have a fairly normal life. I think I'd like to teach biology in a college. I'd also like to have nice house and kids but with no financial pressures or worries."

"What do you mean when you say a good man that loves you," asked Jean.

"Well, part of it is what I described to you as the kind of man who is a prime choice. I also mean a man who consistently demonstrates that he is committed to me. A man who is emotionally attached and dependent on me to meet his needs is a man who is in love with me. This is how you monopolize the assets of a prime choice. When I have such a relationship with a man that will be the man that I will want to marry and settle down with," answered Denise in a voice that carried conviction.

Jean looked a bit sad and replied, "I think that you've been planning something like this since before you left home. I don't know what I will do when you get married and settle down. I'll be all alone again."

"Little Sister, you have a great opportunity here to become financially independent. As long as you don't do anything irreversible, you can always retire and take on the role of a man again. You can have a career, do whatever you like."

"What do you mean irreversible?"

"Well, just don't get into being a girlie boy to the point you have surgery and try to become a physical girl. There is no going back from that. On the other hand, you could have some modest tits implanted to help with your appearance, if you wanted. Breasts are reversible and if you decide to go that route, I can recommend a great plastic surgeon that is one of Ralph's clients. You just don't want to go overboard because you'll want to be able to conceal them when you need to pass as male, like when you're attending school," explained Denise.

"I haven't really thought much about it," said Jean. But, I do know you're the only family I really have and I don't want to lose you."

"You'll always be my little sister Jean. Even if I get married you can visit as long as you don't start fucking my husband. On second thought, we might be able to have a little fun even after I get married because anyone I marry will have to be a liberal minded person when it comes to sex. Don't worry about it. I'm not going to cast off my only sister."

Denise rose and walked around the table to where Jean sat and extended her arms. Jean rose and they hugged. Denise gave Jean a kiss on the cheek and said, "I love you Little Sister. I won't ever abandon you."

Jean took Denise's hands in his and stepped back gazing into Denise's eyes and said, I love you too Denise, since the first time I saw you."

"And, I knew from the first time I saw you that you were going to be the little sister that I never had," replied Denise. "It just took a bit of work but it was worth it."

Denise pulled her left hand from Jean's and said, "Ralph wants to shoot the debut film tonight, so we need to start getting ready. Let's go look through your clothes and see what kind of sexy outfit we can find to launch your film career." Holding on to Jean's left hand with her right hand Denise turned and led Jean out of the kitchen and toward his bedroom.

When Jean and Denise got to Jean's bedroom, Denise let go of Jean's hand and told him to go to the bathroom and prep up for his debut in the movies. When Jean returned he was completely nude but appeared to be at ease and gracefully moved across the room to the sitting area where Denise was waiting for him. Denise said, "Jean go put your "pocket" on so we can start picking out some clothes for you to wear tonight. You need to really look great for the cameras."

When Jean returned with his clit-prick tucked tightly between his legs in its satin "pocket", Denise was standing by the chest of drawers and had a couple of the drawers open. She pulled out a pair of high cut panties in a beautiful shade of pink mist with embroidered detailing. "Slip these on," Denise instructed Jean, "lets she if your clit-prick is tucked tightly enough away to make them fit properly." Jean did as instructed. Denise gave him a careful inspection that included signaling for him to do a 360-degree rotation. "Excellent!" she exclaimed. "The spandex straps on the "pocket" are covered by the panties." Next she pulled from one of the drawers a matching merrywidow in a mix of sheer and floral embroidery. She handed the piece to Jean who held it up to his chest and turned with his back to Denise so she could fasten the hooks and eyes that ran up the back of the merrywidow. Denise told Jean to get his silicon falsies and put them in the underwire bra cups. When Jean had the silicon tits in place, Denise looked on with approval and commented, "Nice, the nipples on the falsies push out on the bra enough to be visible. They'll clearly pass for real tits under the right clothing." Denise next selected a pair of buff, lace top stockings and told Jean to put the stockings on and attach them to the garters hanging down from the merrywidow.

Denise took Jean by the hand and led him to his closet where she selected a pair of black pumps with 3 and ½ inch stiletto heels and handed them to Jean to put on his feet. After Jean had the shoes on Denise told him, "Take them for a spin Little Sister. Let's see how they look?" Jean walked across the room with short steps, placing one foot in front on the other almost as if walking a line. Denise admired the way the shoes and Jean's command of them gave his hips a nice twist as he walked. He moved with a fluid grace that exuded confidence. When Jean returned to the closet, Denise said, "I think I have the perfect dress for you," as she handed him a black sheath dress in satin shantung. The dress had a boat neckline with slightly off shoulder straps. The big smile on Jean's face indicated that he agreed with the choice.

Jean took the sheath dress and stepped into it. He pulled the dress up and slipped his arms under the straps and pulled them up onto his shoulders. Denise came around behind Jean and zipped the dress up. Jean inspected himself in the full-length mirror on the closet door. He observed that the dress came down to just above his stocking clad knees and as he spun around to inspect the back he saw that there was a modest slit in the back to provide a bit more freedom of movement. The dress had a soft silky lining that caressed Jean's body as he turned to admire himself in the mirror. "Damn. You look gorgeous Little Sister. You'll be a knock out. Let's get you a small purse with a thin shoulder strap to go with that dress and do a little work on your make-up and you'll be good to go."

As Denise was finishing a bit of touch up work on Jean's eyebrows and lashes the doorbell rang. "That's probably Ralph," said Denise, "I'll go let him in and you get your ear rings in and come on out."

Denise went to the door and looked through the security window observing that the caller was indeed Ralph. She opened the door and greeted Ralph. Ralph came in and gave Denise a small hug and a peck on her right cheek. "Is our new star about ready?" asked Ralph.

"Jean is going to be true eye candy. I think you'll be pleased when you see him," replied Denise.

As if on cue, Jean glided into the room and Ralph's eyes' were immediately drawn to the beautiful and sexy woman entering the room. "Wow!" said Ralph with a smile of approval on his face. "A star is born!"

Jean blushed at Ralph's remarks as he came up and extended a hand toward Ralph. Ralph reached out and took Jean's hand by the fingers and brought the back of Jean's hand to his lips where he gently kissed the hand. Still holding Jean's hand, Ralph raised it high above Jean's head and used it to slowly spin Jean through a full rotation as he took in every detail of Jean's appearance. "You look like you're ready so let's be on our way," said Ralph. With that he leaned over and gave Denise a kiss on the forehead and said, "You've done a spectacular job babe. Thanks." Denise smiled with pleasure at the compliment and then opened the door for Ralph and Jean's exit.

To be continued...

Da_Vida
Da_Vida
172 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
AnonymousAnonymousabout 10 years ago

i know this from 09 but add more chapters

mreneetgmreneetgabout 15 years ago
live a life Jean

Go explore new areas and new pleasures Jean. Everyone should try just about anything once and then after that if it was fun........do it again. Not only with sex but with life, go caving, white-water rafting, etc.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

My Big Sister His older sister has a few surprises.in Transgender & Crossdressers
Lap Dance Joke Gone Wrong Stripper joke leads to straight guy being used as a girl.in Transgender & Crossdressers
Dressed To Please Kate Husband and wife both enjoy the femme side.in Transgender & Crossdressers
I'm My Sister's Husband's Wife He replaces his twin sister at her wedding.in Transgender & Crossdressers
My Sister's Boyfriend's Slut On my knees, my panties pulled down, for the first time in Transgender & Crossdressers
More Stories