What are Sisters For?

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Salesman benefits from man's transformation.
8.9k words
4.68
31.4k
14

Part 1 of the 2 part series

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

Robert was in for a big change. He just did not know it yet.

Robert was a cross dresser. That was not the problem. The problem was that his wife did not know. And she was about to find out.

She had missed, or ignored, clues that might have led her to the truth earlier. Had she known earlier, she would not have been ok with her husband strutting around in her underwear and skirts. Fortunately maturity had mellowed her.

Still it was a bit of a shock when she came home earlier than usual one Friday to find her stay-at-home writer husband pounding on the computer keyboard dressed in her new floral print sundress, a blonde wig, and high heel sandals!.

Although Robert knew he would be caught one day, he still panicked when he saw his wife come through the door to his office.

"Cindy? Oh god. You're early, I mean, I can explain."

Cindy was silent, trying to process the scene in front of her. Finally, she was able to gather her thoughts.

"I don't know quite what to say. I kind of suspected that my panty drawer had been rifled through a few times. I thought you had a fetish, but my clothes? Are you gay? Have you gone out of the house like that?" She was more agitated than mad.

"Yes, your clothes. I like wearing them, and I couldn't keep any of my own here, could I? And, no, I've never been outside. I would be mortified if I were to be recognized. Not to mention what my publisher would think."

"How long..."

"Have I been dressing this way? I started by getting into my sisters' panties and training bras. They thought it was cute so they would put their dresses on me, as well. I didn't for a few years during college and after. About a year after we married, I again had the motive and opportunity. The wig is a recent addition. I just felt I looked odd dressed this way with a short haircut."

"And you didn't think you looked odd because of the dress and heels?"

"I suppose that, too. Are you angry? I will stop, if you want me to. You are more important to me than this."

"I'm not mad but I need a few days to sort things out in my head. My underwear, too?

'Uhh, yes. No bra, obviously, and that really cute pink thong with the lace front."

"Not my thong, oooh, just keep it. And any other of my thongs you may have worn!"

"I do launder them. I will stop until you make up your mind."

"Ok. But do keep the thongs."

###

True to her word, Cindy was silent on the subject of Robert's cross dressing but she wasn't idle. First she hit some second-hand shops to find some clothes that would fit him better than hers. She was just over 5'4" and he was a bit taller and 30 pounds heavier than her 130. And he had no breasts. Her clothes fit him well enough for him to piddle around the house, but it wouldn't do for what she had in mind for him. If he were resistant, at least she would not have spent a lot of money. He could still wear them at home. She did buy herself some new panties to replace her thongs.

Among the used clothing were three bras — all padded. She had two blouses and a sweater. Also two skirts. One was knee length, the other was short enough to give him/her pause. Unless Robert learned to walk, sit and bend over correctly, everyone would get an eyeful.

She also bought a basic make-up kit as well as a few specialty items she had researched on the internet. He already had some shoes that fit his larger feet. More shopping would be needed. She hoped that taller heels wouldn't be a problem. A little practice should help avoid a twisted ankle.

Now she was ready to talk.

"Honey, are you home? I have some things for you to try on!"

"In here. What have you bought now? Until we get my next advance we need to cut back. "

"You will approve. It has to do with our little chat last week."

A wave of apprehension washed over him. He was a bit weak in his knees as he walked to join her in their bedroom. What had she bought for me? Did this mean she approved of his 'hobby?'

"First things first. Take your boy clothes off!"

Robert was taken aback by Cindy's authoritarian tone. She normally was not so demanding. It was starting to get him a little excited. He complied. When he removed his pants, he revealed the cream colored panties underneath. Cindy recognized them as one of her favorite pairs. She sighed.

"Really? We will address that later. Take them off for now!"

He complied, not seeing her hit 'send' on her cell phone. Almost immediately the doorbell rang.

"Whoever could that be? Be a dear and go let our visitor in, would you"

"But"

"Yes, you are naked. Answer the door!"

Rather than fight about it, Robert slowly made his way to the front door. He opened it just enough to peep out to see who it was. As soon as he did, the door was shoved open, revealing his older sister, Margaret! He was dumbfounded. Maggie lived three states away.

"You always answer the door naked, baby boy? Or maybe another nickname may be more appropriate."

He crossed his hands in front of him and stepped away from the door.

"Oh, please, its not like I haven't seen you naked before."

"Maggie, come in before Robert passes out from embarrassment. I hope you are ready to get started." Cindy obviously was not surprised to see Maggie.

"Of course, honey. What can we name her, she said, looking at Robert. She will need a new name."

"I've given it quite a lot of thought and came up with Valerie, or just Val. What do you think?"

"I like it. What do you think about you new name, Val?"

Val had been more aware of her nakedness than of the conversation. She did catch enough, though.

'What the hell are you talking about? My name is..."

"Val, as we said. You want to dress like a woman, then I'm here be sure you do it right. Thats right, Cindy called me about your fetish, or whatever it is. I'm here for however long it takes to teach you a few things like how to walk, talk, and generally be a woman."

Val was still confused, but aware enough to follow.

"You want me to become a woman named Val?"

"Sister, for a well-known mystery writer, you are sure slow on the uptake!"

"Well in that case, skip to the big reveal."

This time it was Cindy who stepped in to answer.

"Starting today, you will not just wear women's clothing. You will be a woman, at least for the time that Maggie will be staying with us. You will be Val, Maggie's sister.

"But..."

'That's the way it will be. I did a lot of thinking since I caught you. This will either get it out of your system or if you keep on with it, you will be good at it. For now I want you good enough to go shopping with us."

Maggie cut in. "Don't worry about the cost. I am taking care of that. You don't know how happy that call from Cindy made me. She told me that she caught you. She said you had mentioned that we sisters had dressed you in our clothes. Mollie couldn't get away. I relished any excuse to get away from Henry for a while."

"So both my sisters know? Thanksgiving should be a blast."

"Five months. We should make good progress by then. Henry and Dave should get a kick out of their new sister-in-law, Val."

Val thought that was all she needed. Her sister's husbands were constantly implying Robert was a wimp because of his slight build and soft features. When they meet Val, they will be unrelenting.

"Let's start by getting her dressed. I bought her some cute outfits to get started with."

Cindy and Maggie sat in the living room sipping wine and watching Val trying on the thrift store clothes. Maggie was close to Val's size, so she brought some of her cast off clothes. Val dutifully tried on all the outfits leaving the denim mini-skirt for last.

"I can't wear this thing. It's so short," said Val as she held it up to her waist. "I would not be able to move in it."

"Try it on," said Maggie. "If anything hangs out it won't be anything we haven't seen before. We're gonna work on how you can move later."

Val disappeared into the bedroom, emerging a few moments later wearing the brief skirt. Just as she thought, with every step she imagined that her ass was showing. It would certainly be a while before she was comfortable wearing something like this outside. The other two women had similar thoughts.

"That's going to take some work," said Maggie, giving Val a critical looking over. Overall I think we got a good start here. You chose your outfits very well, you mixed the separates nicely but you need lots of work in other areas. I hope you have the time to put into this."

"I'm between books right now, but I won't be able to put my publisher off very long on starting the next one."

Cindy chimed in. "I know you're always saying we are not rich. But we are far from destitute. I think the budget could handle it a few months."

"That's it, then" said Maggie. "I won't be a financial burden to you. I've got several of Henry's credit cards. The only thing I like better than being away from Henry is his money. Speaking of which, why don't you let me treat you girls to dinner tonight at the most expensive restaurant you have here. We can get a fresh start on Valerie's training in the morning. But not too early, I had a long drive today."

"What..."

As she is prone to do, Cindy finished Val's sentence. " Will you put on? Go ahead and put your boy clothes back on. Enjoy it because it will be the last time in a while. But you still go by Val. Your book covers will be the only place you'll be known as Robert."

As he turned to walk back to the bedroom, Maggie was giving her a critical going over. Although she was far from masculine, she needed work. Fortunately she did not have coarse body hair but what she did have would have to be addressed. Oh well, Cindy could start on that tonight.

###

"Look at me, I'm a girl." Six-year-old Robert ran through the living room of their family home, wearing nothing but a pair of yellow panties and a white training bra obviously pilfered from Maggie and Molly's room. The twin sisters sat mortified as their younger brother pranced around the room. Mom and dad however thought it was hilarious and laughed out loud. That further added to the girl's discomfort. Just when they thought it couldn't get worse the little panties started to slip down, momentarily hanging up on his penis before falling to his ankles. Maggie and Molly ran to their room crying.

It wasn't until a week later that the girls got a small measure of revenge. Most Saturday nights their parents went to bed early. When they were sound asleep the three kids would sneak down to the TV room. They would drape a blanket over the front of the TV and turn it on with the sound almost all the way off. That way they could watch the weekly scary movie at 11:00 without their mom forbidding it.

The twins were just shy of 10 years old and Robert adored them, very much envying their wealth of worldly knowledge. Information was important to a six-year-old. Chasing after all the red herrings the girls threw at him probably led him to writing mysteries.

On this particular night they had practiced what they were going to say to little Robert.

"Robert, do you know about this movie tonight?"

"No, what," said Robert. Usually the girls had several interesting tidbits about the movie to make it more scary. Things like 'this is real, not a movie.' Or 'this guys head gets chopped off in the end,' things like that. Robert got very little sleep on most Saturday nights.

"Only girls can watch this movie. If a boy tries to watch it his peewee will fall off."

Robert instinctively put his hands in between his legs.

"You mean I can't watch it without my thingie falling off?" He was on the verge of crying.

"That's right you little brat. It won't fall off right away but someday you'll wake up and it won't be there."

"You will have to pee sitting down just like we do."

Robert had seen the girls your urinating sitting down and he didn't think he would like it.

"I want to see it. I don't want to lose my peewee. What we can do?"

"Well there is one thing we can try." As Mollie said this she gave a wink to Maggie. So far so good.

'I'll do anything?"

"You probably won't want to do this but you said anything. So here it goes. Since only girls can see this movie you're going to have to dress like a girl.

"Awww, that's not so bad."

"We will see about that. You have to do more than that. You have to really look like girl with a wig and make-up and everything. Otherwise, well, you know what otherwise is."

"Okay, I will if you are sure I won't lose it."

"Your little wiener will be safe."

While Mollie enlightened him about the mysterious nature of the night's movie, Maggie was getting a bag out their room. In it was a pair of cotton panties with a large cherry imprint on the front, a lacy yellow training bra, a white with yellow trim dress, a blonde wig from mom's closet, lipstick and other make-up items. She showed the stuff to Robert. He looked on it admiringly.

"Do I have to wear the wig and make up?"

"We don't want to take any chances, do we? Besides this will be fun. We will be three girls watching a movie, eating Jiffy Pop. You will be safe then. Go to your room and put the clothes on. We will help you with the rest."

Robert trudged to his room. He did not mind wearing his sisters' clothes. He had done it before and not just once. He liked the feel of woman's clothing. But the wig and make-up was something different. Still, he dutifully peeled off his clothes. He liked the panties with the cherry. He had tried on bras before so putting this one on was no problem. He slid the dress over his head. He needed shoes. He crept into his mom's closet and rummaged through the shoes to find some thee-inch heel white pumps. He realized how much trouble he would be in if he were caught in his parents bedroom. Soft snores reassured him. As soon as he was clear he put on the shoes and wobbled his way to the TV room. The twins were astonished to see the transformation.

"You look real already. But we can't take any chances."

The girls quickly went to work on little brother. Since neither of them had very much experience with make-up, they took the opportunity to experiment. The result was more than a cheap hooker but not as bad a circus clown.

Mollie pulled out a compact camera and snapped two quick shots of Robert. No flash was needed, so Robert didn't notice the faint clicks of the shutter.

The three 'sisters' enjoyed the movie, popcorn, and talking about boys. To keep up the charade, Robert joined the girl talk.

Mollie started it off. "If you could kiss a boy, who would it be? I would pick Jimmy Winston."

Maggie did a fake gag. "Jimmy Winston? He is a slob. I want to kiss Joey Ingram."

Robert startled the girls when he said, "I want to kiss Henry Stevens. He's in my class."

Before the girls could react, Robert whispered, "I'm playing a girl remember?"

"But why him? He's such a little creep," said Maggie.

"I wouldn't really kiss him."

"If he saw you looking like this, he might want to kiss YOU! Robert and

Henry sitting in a tree, K I S S I N G."

Robert was ashamed but he got over it quickly. He had long ago learned not to take teasing from his sisters too seriously.

On the other hand, when their mother had the film in her camera developed, the girls had to do some explaining.

####

Val woke the next morning, only to see Maggie's stern face glaring at her. There was no telling how long she had been standing there. It would appear that she was taking this Boot Camp concept seriously. Val had went to bed wearing only one of thongs that Cindy had donated to her.

"Just what are you think you're wearing there missy?"

"Well, I, uh."

"That was a rhetorical question Miss Famous Writer. You do know what rhetorical means, don't you? Of course you do, you waste of skin. Who told you to sleep without proper sleepwear? I brought a babydoll nightie for you — use it!"

"Y-yes ma'am!

"You will pick out today's uniform and report for inspection ASAP."

Val did as she was told, opting for a plain white bra and panty set, a short sleeved cream top and a conservative length grey skirt. Not knowing for sure about the hair, she put the one wig that she had available. Never having put make up on herself she did not to even try. That would be for a later lesson.

Maggie had softened from her drill sergeant guise. A low whistle escaped her lips as Val presented herself for inspection. Her thin build, her soft features, and lack of coarse body hair, was a good sign that this might just work.

Step one is to get Val passable enough to go out shopping. The goal is to get her confidence up. Voice lessons, walking in heels lessons, and make-up lessons all were critical to success.

"Nice. I should not be too surprised since.you have been doing this thing for a while now, haven't you? Have you ever thought about trying to pass yourself as a woman? Of course you haven't. You don't have the balls to step out that door. So that will be our first lesson. Open the door."

"But, I ..."

"Do it, or I go home. Open the door and stand there for five minutes. That shouldn't be too hard!"

Val did as she was told, opening the door to the world, and, more importantly, the neighbors. Val kept her eyes shut the entire time, perhaps assuming no one could see her if she couldn't see them. The five minutes seemed like an hour."

"Okay, Sugar, time's up. Get back in here. We have lots of work to do before we can take you out. Let's start on your make-up...

###

After their mom found the photos of Robert dressed as a girl, she was not happy. She knew the girls were behind it, but the expression on his face was a bit disconcerting. He was entirely too happy looking in the dress and bad make-up. Her make-up. She had thought some items had been out of place. She never dreamed this was why.

After mom's tirade over the photos, the twins left Robert pretty much alone. Even when he wanted to be a pirate for Halloween a few years later, the girls refused to help him apply the fake scars that came with the costume.

Things went along just fine until the girls were high school seniors.

Their parents were out on their regular Friday night trip to the bar and would not be back until after closing time. The girls had dates and would also be in late. A perfect opportunity for Robert to play. He went straight to the twins room and their lingerie drawer. He picked out a satiny pair of black panties and a non-matching bra. In the girl's closet he found his favorite red party dress. It was one that each girl had worn on many occasions. It was quite short and flirty. He took his pilfered attire to his room.

Did his fixation with women's clothing stem from his earlier incident with his sisters? Honestly, no. He didn't remember the incident except when the photos we brought out at family gatherings.

He didn't think about why. He just enjoyed the feel of the silky material much more than the coarse feel of his own clothes. He quickly stripped.

He slipped on the bra. He had prepared two small water balloons to help it fit better. He had tried much fuller balloons before with disastrous results. No more burst balloons for him.

He then slipped the dress over his head. He loved the dress. He liked seeing it on his sisters' bodies. But not as much as he liked wearing it himself.

He saved the panties for last. He loved panties. He loved how they looked, how they felt, and how they hugged his body. He slid this pair on slowly, savoring each inch as they rose up his legs before disappearing under the hem of the dress. The smooth fabric felt good against his genitals. . .

He went back to the girl's room to look at himself in the only full length mirror in the house. The dress looked good on him. The balloons gave him the appearance of B cup boobs. The dress was short enough to allow the bottom of his butt cheeks to show if he bent forward at all. He was barefoot because he had no shoes of his own to wear and his sisters' and mom's shoes didn't fit his big feet. He admired himself from every angle.

Cyndi44
Cyndi44
72 Followers