What are Sisters For?

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

"What the FUCK!" Maggie said as she took in the sight of her brother wearing her favorite dress. "Not again. I-I'm I'm...speechless "

Robert's initial terror had eased some.

"Speechless? That is a first. But what is it you plan to do to me. I wouldn't go to mom for sure. She will believe it's your fault."

"You are a sick little pervert. Take my stuff off now"

"Now, now let's not be too hasty. I would hate for mom to hear that her precious daughters are still corrupting her little boy."

'What do you want?"

"I want your silence. And you will allow me access to your clothing or buy some for me.

"I will have to talk to Mollie, but that seems reasonable. Just please don't get mom involved."

This arrangement lasted until the girls went off to college. When they left so did all their clothes. So did his source of temptation.

###

Maggie was intent on turning her new sister into a real woman, or at least as real as she could be without drugs or surgery. She had thought that she had gotten revenge out of her system — apparently there's was a little left. Her mother had passed, away as had her dad. So there is no one left to browbeat her about turning her brother "funny." Maybe revenge was too strong a word. More like karma. Whatever you wanted call it she vowed to do the best she could.

The routine was simple. Maggie would wake Val and supervise her wardrobe for the day, her make up and hair style. This was followed by 2 to 3 hours of practicing walking in heels, talking convincingly, applying her make-up. Val was then allowed to write for another 2 to 3 hours then it was back to the routine.

Val made good progress the first week but it wasn't until the middle of the second week that the game got stepped up another notch. At the end of one day Maggie stopped her lessons.

"You are ready for the midterm exam. Grab a purse and let's go."

Over time, Maggie had coaxed Val to venture out farther and farther from her front door until she had covered a couple of blocks. But what did a midterm exam consist of?

"We are headed to the mall to do so shopping for you! It's time to test your progress. You pass the test if you pass, so to speak. You're ready, little sister."

"O-okay. If you think so."

Val decided on the drive over that the world looked much the same as a woman as it did as a man.

"Okay we're here, this won't be too bad. We'll hit a handful of shops. It's not too busy."

Val gathered her courage. After all they weren't planning to rob the place.

"Let's do it."

Val was wearing light yellow blouse and a mid-thigh length green skirt. It was bright enough to get attention, but not glaringly so. As she walked to the building from the parking lot, no one seemed to notice her. She relaxed a bit. She fit in as just another shopper looking for bargains.

"So far, so good, eh," whispered Maggie.

"So far!"

They stayed with the smaller, more intimate shops. The shop girls, if they suspected Val, hid their suspicions well. Maggie and Val tried on several outfits during the afternoon. Trying on shoes was a pleasure for Val, as she found a few pairs that fit her large feet. The sisters each had as many bags as they could carry on the trip back to the car.

"Did I pass?"

"I think thar rated an A-. It would have been an A if you had picked up on the pass the shoe salesman made."

"What!"

"Exactly! I thought he would ruin the shoes if he drooled over you any more."

"Really! I just thought he was doing a good job."

"I think he knew your secret. Goodness knows he saw far enough your skirt to verify the fact!"

"No."

"Yes. I'm telling you, if you go back and return some shoes, he will invite into the back room to 'look at some shoes.' I will bet on it.

"He would not! I mean, I would not. What do you think he would want? Oh goodness!"

"You know what. He wants a sexy older woman to kneel down in front of him, unzip his pants and suck him dry."

"Maggie! I am not..."

"Gay? Puh-lease. I've known for a long time. You rarely dated. You always hinted at it. You may not have acted on it —yet— but admit you are at least curious, right?'

"Maggie, don't do this!"

"I won't say anymore. Take a pair back right now. Just see if he asks. Then we will see what you answer is."

"Okay. I will prove you wrong. Hand me the sandals."

###

Val walked back into the shoe store. The clerk, an early 20-something with short brown hair and a killer smile, looked up seemed genuinely pleased to see her return.

"Back so soon? Not that I mind. You either want to buy more, or return something, or..."

She smiled. This could get interesting. She placed the sandals on the counter. His grin diminished.

"So sorry, Do you want cash, store credit or try another pair? I have a few you could look at."

"I think I'd like to try some more."

"I was about to close early because it's so slow. Let me get the front shut down and we can look for what you need in the back room. How's that sound?

"Well, I don't know."

"Come on. We will find what you are looking for."

"And how do you know what I'm seeking?

"Let me finish closing and we can find it together."

He closed the store in record time. He had gotten a handful of married women to do their shopping in the back room. The married ones usually just gave head, saving their pussies for their husbands. This gal was most likely a quick blow and go. That was okay with him. Most of them came back for more, anyway.

Val was nervous for any number of reasons. The man, whose name name she had already forgotten, was, well, a man. It would be a scandal among the readers of his books. Not to mention disease. And what about Cindy, their families, and the fact that this guy may not know she is really male? But one thing she was sure of. She had been curious about sex with men for a while now. She now realized she could only do under it the pretense of being a woman. But was she ready?

"Back here. We have a little break room. Have a seat on the sofa, I'll get some shoes to show you."

"Listen, Brandon," she said, reading his name tag. "You and I both know I didn't come back for shoes."

She moved closer and he wrapped her with his arms and kissed Val. Her mixed feelings floated away. This just felt right.

"My sister is waiting for me, so let's do this."

"Get her in here, then." Brandon flashed his golden smile. "Can't say I've been with sisters before."

"Disabuse yourself of that idea".

As she talked, she sat on the sofa and pulled Brandon to her. She unbuckled his belt, opened his belt and pulled them down to his ankles. Doubt crept in again. As he eased his boxer shorts down, she came face-to-face with his cock. It was beautiful, but she suddenly realized wasn't ready.

"I'm sorry, I can't..."

She was able to go out the door leading to the service corridor before he could pull his pants back up. She hurried as fast as she could without calling attention to herself. She did chuckle slightly as she pictured Brandon trying to run with his pants around his ankles. She then felt bad about running out on him. Would a hand job have been too much to ask? Would he have settled for that? Too late for second guessing now.

Maggie was waiting when she got back to the car.

"Sis, I just meant to see if he would ask. I didn't mean for you to actually..."

She stopped when she saw the look on Val's face.

"Oh dear, he did ask you!"

Val's grin bloomed into a full smile. "Yes, but I didn't go much farther,".

She told Maggie the whole story.

"Face to penis with a handsome young man and you run out. Well, you have to start somewhere. So tell me, Miss Run Away Bride, where are the shoes you went to exchange?

Am I going to have to go back in and drain Brandon to get them back?"

"Oh shit. I forgot. Oh, Maggie, did I do the right thing? Going back to the store, I mean. I never believed he would ask. I was into it, but could't do it."

"It's okay, you are confused. I'm guessing that you have been confused for a long time."

Val didn't answer. She just lowered her head and sobbed gently.

"That was stupid of me to send you back in there," said Maggie, crying. "I'm sorry ... for everything."

"You don't have anything to be sorry about. If you mean putting your clothes on me when I was a kid then don't worry it didn't have anything to do with how I turned out. I suppose if mom and dad had known enough to get me counseling then, things might have turned out differently, I am getting more comfortable pretending to be a woman. If I do fulfill my desire to be with a man, it will be in my time and my choosing. Was I ready to rock Brandon's world? Part of me was, yes. But a big part of me is just not ready."

"Oh, Robert I am so..."

"It's Val from now on. That much I am sure of. Over the last three weeks I've learned to embrace my cross dressing full-time. And I still need your help. Do you think you can get Mollie out here as well?"

###

Mollie arrived in two days. Val decided to meet her at the airport. Just as she expected, Mollie walked right past her, never giving the attractive blonde a second glance.

"Tell me I haven't changed so much that my own sister doesn't recognize me!"

Mollie stopped in her tracks and spun around to find the woman calling to her. She was pleasantly surprised at the sight.

'If I didn't know better I would say, 'Maggie, you've changed.' But I do know better. Pleased to meet you, Val."

They hugged a while, not noticing the passing crowd.

"So, I guess this means I do have a new sister. Or should I say sister 'slut?' I heard about your shoe salesman!"

"I'm sure Maggie exaggerated. Nothing happened."

"I wouldn't say that was nothing. Your first blow job was this close! It was your first, wasn't it? Just kidding. We have so much to talk about. You really had his pants down? You are such a slut!"

"If you say so. Yes I had his pants down and I was tempted, but for one thing, I'm married. Cindy doesn't know, but with my talkative sisters around it's only a matter of time."

'We can keep secrets. Speaking of extra-marital sex, Maggie and I are not innocent in that regard."

"What? You have both cheated? Why didn't I know about that? "

"It's because we can keep a secret. In fact, you probably don't know that Maggie went back to the shoe store. Oops, maybe I can't keep a secret!"

"She did WHAT?"

"I wasn't supposed to tell, but she went back to get the shoes you left and to apologize to the shoe boy."

"To apologize for me?"

"She did more than that. She more than made up for you leaving him with his pants down. She told me he reached places Henry couldn't reach."

"That bitch. I can't believe she did that. No, I can. But I can't believe that innocent Mollie has cheated."

"There are lots of things in the family you don' know about.

"I'm sure. Do tell."

As They drove back to the house, Molly filled Val on some of the family secrets. Apparently Robert/Val's preference for women's clothing was a big one. In those. days in the rural South, it would have been a huge scandal. So getting help was never discussed. Just one more way in which he had been let down.

###

Robert finally had a chance to look up. Thankfully the line had dwindled to a handful. His hand was very tired from signing autographs. He was accustomed to signing a lot of autographs at book signings. But he lived near this bookstore and was somewhat of a local celebrity. The turnout had been massive, the line at times snaking around the store. He was glad to see so much support for this new book but he was also glad to see the line coming to an end. The last person in line caught his eye. She returned his glance with a look of adoration. Here was a true fan he thought.

His mystery writer's brain went to work. If she is that much of a fan, then why did she risk missing out on an autograph by hanging back in the line? Obviously, he thought, she was hoping that by being last that she would have more time to talk to him. Very clever girl, exactly the type he had not been able to find.

Her strategy worked. Robert had time to talk to the lady, Cindy, for several minutes before he had to go. Before he did leave, he autographed her copy of his book with his usual scribbled "Robert Preston" plus an added line: "call me" and his phone number.

Pretty smooth for some one who had very few dates in his life.

She did call, they dated a very short time. She loved his writings and he loved her intellect. They married by eloping to Baltimore in honor of Edgar Allen Poe. Cindy remained Robert's greatest fan.

Like most couples the frequency of their love making tapered off drastically after the first year. They were both comfortable with that. Their main attraction to each other remained intellectual more than sexual. They drifted into a routine where Cindy went off to her job each morning and Robert would stay in his home office working on his next book.

A little over a year after they were married, Robert innocently walked by a laundry hamper in front of the laundry room. A long repressed feeling came flooding back as he dug through Cindy's clothes. It was another six years until he was discovered by his wife. In that time, five mystery novels were written while he was dressed in her clothes.

Cindy's initial confusion turned to rage then to compassion then back to rage and finally curiosity. She had known it was not a masculine man. She loved that about him. If he liked doing that, she could be okay with it. She was also aware of the concept of people who developed an aversion to things they loved when they were given too much of the good thing. She hatched the plan to do just that. She call his twin sisters who were all to happy to help. However, they had their own agenda.

It was decided to give him the full treatment: a new name, having him dress up day and night, and getting him to explore sex as a woman. The last part was decided by the sisters, not Cindy, though they got the impression she would be okay if he did. After all, they knew of the yoga instructor who was taking care of her physical needs. A drunken gossip-fest last Christmas had revealed that tidbit.

The sisters also knew of their brother's struggles while trying to date in high school and college. They also agreed that Val's encounter in the shoe store was too much, too soon. He needed more preparation.

###

The day after Mollie arrived, the twins waited until Cindy left for work to confront Val.

"Okay, baby girl. 'Fess up," said Mollie. "You liked the idea of sucking the shoe clerk, didn't you? You have wanted to be with a man for a long time. Go ahead, your secret is safe with us!"

"Well, I never..."

"Shut up sissy,". Maggie was back to drill sergeant mode. "No more lies. You like being disguised as a woman to be with men without the stigma."

"Alright, yes. I have always wanted to be with men, but I have been afraid. I did want the shoe salesman, but I couldn't. Apparently you don't have that problem!"

Maggie glared at Mollie. "Look, I went back for the shoes, the rest just happened, ok. While we are on the subject, you missed out, baby girl."

Mollie had retrieved a bag from her suitcase. "Bought you a 'coming out gift.'"

Val opened the bag and pulled out an eight inch long realistic dildo. "What am I supposed to do with this thing?"

"Shove it," said Maggie.

It was Mollie's turn to glare. "For you to practice with. Start with your mouth and then get the lube and, you know where."

Val didn't argue, she went to her room with her gift.

It was not the first time Val had tried toys. She had used Cindy's dildos before, but this one was softer and more lifelike. He placed the head in her mouth. It felt good in her mouth, filling her cheek as she pushed in in deeper. A little more and it was bumping the back of her throat. She suddenly gagged forcibly causing her to pull it out. Strings of saliva stretched from her mouth to the fake cock. She was determined to take it all the way. She gagged on it the next several attempts finally taking it all.

She had never tried to use anything in her anus. This dildo was long, but fairly slender so Val decided to give it a try. Took off her knit top and jeans. She had stayed bra-less today. She slid her black boy shorts off. She spread a glob of lube on the head of the dildo and a little more on the shaft. She put more on her finger and coated the tight ring of her ass hole. She laid back on the bed and placed the fake dick at the entrance, probing deeper and deeper until it popped into the opening. She felt some brief pain. That turned into pleasure, as she moved it in deeper. In no time, it was all the way in.and she felt a wonderful fullness. As she moved it in and out there was alternating sensations of full then empty. She loved it. She started to imagine it was Brandon, the shoe clerk working his cock into her ass. She then imagined his cock in Maggie's mouth as his sister sucked him off. Val promised herself she would pay him a visit sometime around closing time.

Another week of training, this time with both sisters, went by fast. Val was getting very good at being a woman. Her walking, talking, mannerisms and even dancing all improved with the constant practice. However, Mollie and Maggie had to go back to their homes and Val was way behind on his newest book. She doubled up on her writing time to get caught up.

Even so, his publisher was impatient. If the book fell too far behind it would miss the Christmas sales window. Luckily he had a successful format. A body was found, the police detectives were stumped, our hero, private dick Anton Grey, stepped in and unraveled several subtle clues to finger a suspect. Val could and did churn out a couple of the novels a year. When pressed he could pound out the pages even faster.

The new book, "The Killer Wore Manolo Blahnik" was flying from Val's manicured fingers to her keyboard. In it, the only clue was a bloody shoe print from a woman's high heel. The victim was a handsome, womanizing shoe salesman. The police spend all their efforts checking the many women he had been involved with to no avail. Anton Gray swoops in, piecing clues together. He deducts it was the victim's brother who had cross dressed to commit the murder. Val had another big seller.

The blistering pace allowed her the finish the final draft on time. She hit 'Send,' and realized she had some time on her hands. She normally took at least a month between projects. She would research current crime statistics, unusual homicides, unsolved crimes and the like. Inspiration was getting harder and harder to find. At least he didn't have to worry about that today. She had an idea, but it wouldn't find its way into a book.

She printed off a segment of the just finished book, put it into a binder. This would get her released from her publisher if he were found out. So would what she planned to do next. Nevertheless, she put the excerpt and a copy of one of her previous novels in a shopping bag. And headed to the mall. Alone.

Her instincts said no and to let the matter rest. But she was determined to do this. Why was a mystery, which guaranteed his interested in playing this out.

If she had a pussy, it would have been wet as she entered the shoe store. The clerk, Brandon, looked up from his short stool where he had been trying to glance up the skirt of a woman trying on shoes. He was visibly shaken to see Val bursting through the door. He spent a few minutes more tending the other lady. She left with out buying.

"You are back. Your sister picked up the shoes you left. She is, let's say, an enthusiastic apologizer."

"Listen, I can give my own, uh, apology."

"I can't close the store this early."

"That wasn't how I wanted to make amends. I brought you these." Val handed the bag to Brandon. Her recognized the book, but not the binder.