Tomboy - A Change in Charlie

Copyright © 2018, 2019 - This is an original work by Zeb Carter and is protected under copyright by U.S. copyright law. It is only submitted at Literotica.com and any submission to any other site has not been authorized by the author.

Warning: This is a story about a cheating wife. You have been warned.

Chapter 1

Josh was sitting in the kitchen with Charlie, his wife's best friend. Charlie, even though she was thirty-four years old, was a tomboy. Yes, a real tomboy. She dressed the part, she acted the part and she spoke like a tomboy. She was a pretty woman but wanted to be one of the boys. Her husband, yes she was married, had been trying to change her for the past ten years. That's how long they had been married.

"Josh, why does Sam keep trying to change what and who I am?" asked Charlie as Josh placed a cup of coffee down in front of her.

"Let me ask you a question first," Josh said.

"Okay, shoot."

"Well, several questions... sorry. How old are you? Have you always been a tomboy? Do you want children?"

"Oh! Really? Ah...I'm thirty-four, but you know that. And I see what you are trying to say, but I'll play along. Yes, I have always been this way, even though Mama tried to put me in dresses. I always threw a fit and ripped them off. So she let me dress in jeans and t-shirts thinking I would outgrow being a tomboy. I haven't so far. Fooled her." Charlie laughed for a few seconds. When she looked at me, she sobered. "Children? Sam and I have talked about them. I don't know if I want any. Sam does one day, then he doesn't the next, so I would say he is undecided."

"Stand up for me Charlie," Josh said.

Shrugging her shoulder, Charlie stood, looking down at Josh.

"Turn around slowly, please."

Charlie turned. When she faced Josh again, he was standing in front of her. She jumped a little, giggling.

"You scared me," said Charlie.

Reaching out Josh took hold of Charlie's chin. He turned her face to the right and then to the left. He pushed her hair out of her eyes. He looked closely at her skin. He looked into her pretty blue eyes. He ran his hands through her hair. He nodded, looking first at her right ear, then her left. He nodded again, looking into her eyes once again.

"You have a very pretty face. Your eyes are absolutely beautiful. Your ears are nicely placed and hardly stick out. Your skin is soft and very nice looking. You could be so gorgeous if you let your hair grow out and did something with it," said Josh still looking her in the eyes.

Reaching out again, Josh took hold of Charlie's t-shirt at her back. He pulled it tight across her chest. She wasn't wearing a bra. He raised his eyebrows. Charlie just smiled at him. Josh walked around behind Charlie. He tugged on her jeans to see how big they were around her waist. He pulled the waist out quite a distance, yet at the hips, they were tight to her skin. Looking down he could see her black panties, which were actually men's black briefs. He let go and came around to her front again.

"Sit," said Josh as he took his seat.

"What was that all about?" Charlie asked taking her seat.

"Well, I just wanted to see what you might look like without the baggy shirts and boy jeans. Unfortunately, it's hard to tell."

"What do you want me to do, strip?" Charlie asked frowning.

"No! No, not at all. Have you ever dressed up to see what you looked like as a girl? A woman?"

"No. Not really. I have a couple of ladies blouses and some pedal pushers with loafers I have worn when Sam and I go out to a nice place to eat and dance. I know I don't look bad in those clothes. It's the real girlie shit that I don't like," said Charlie.

Josh just looked at her, scowling.

"So you have never tried on panties and a bra, nylons, a dress or a skirt and blouse?"

"Not really. I never look at those things... except when I'm out shopping with Barb," Charlie answered.

"Does she ever try to get you to try on some of her clothes?" Josh asked.

"Not really. Every time she asks me, I give her a dirty look and she stops."

"Do you love Sam?" asked Josh, squinting his eyes waiting for the blowup.

"Of course I do," replied Charlie softly. "I love him to death."

"I know. And he loves you as much if not more," Josh told Charlie. She smiled at him.

"Barb really loves you a lot too, Josh."

Josh smiled at Charlie, nodding.

"I know she does. She tells me all the time. I love her too. But I also love you and Sam. You are our closest friends and Barb and I would hate to see anything happen to either of you or your marriage."

"You think my marriage is in trouble?" Charlie asked a perplexed look on her face.

"No, not really, but who's to say that Sam gets tired of waiting for the women he thought he married to come out of her shell," Josh said. "It's been ten years since you two married."

Charlie, with a frightened look on her face, stared Josh in the eyes. Josh saw the tears well up in her eyes, then she quickly turned away from him. She went to the paper towels hanging under the cabinets and ripped one off the roll. She blew her nose and wiped her eyes, then tossed the crumpled up mass in the trash bin. Turning back to Josh she looked like someone had just killed her dog.

"Can you help me?" asked Charlie softly.

"Oh, I don't know if I'm the right person..." Josh croaked trying to back away from Charlie.

Reaching out she grabbed his shirt and pulled him back, so he was standing once again in front of her. She didn't let go of his shirt.

"I want you to help me. I want a man's point of view."

"Well, Sam would be better..."

"No. I want to surprise him. Understand?" Charlie growled, pulling Josh even closer.

Josh was looking into her eyes. He wasn't shying away from her, he looked. What he saw, he had never seen in Charlie's eyes before. Passion. Lust. Excitement. He was now scared to death of her. He tried not to let on, but he bet she could smell fear, just like a primal animal could. Josh would bet that Charlie was a beautiful woman when she was naked. He had only seen her in a baggy one-piece bathing suit. She had beautiful legs.

"I understand, Charlie. But listen, I don't think I know all that much about... stuff," Josh stammered.

"Like what stuff?" Charlie asked.

"Like makeup stuff, underwear stuff, all that stuff," Josh croaked.

"Bullshit. I've seen the things that Barb wears and she tells me you love her in that stuff. I have seen her makeup and she tells me how you sometimes do hers when she doesn't have her contacts in, so don't try to tell me you don't know." Charlie was almost shouting now. Her eyes were now full of fire.

"Fine. Fine. Come... come with me," Josh said shying away from her eyes and looking over his shoulder waving her to follow.

Chapter 2

Josh went up to Barb and his bedroom. He threw open the door to Barb's closet. He looked over the dresses. The sexy dresses. Reaching in he pulled a red one that looked fantastic on Barb and with Charlie's body and coloring would look wonderful on her. Then he also pulled a deep blue one out. Charlie would look fantastic in blue. Barb hardly ever wore blue, in fact, she only wore this dress when she let Charlie die her hair the same color and they went out together.

Turning Josh tossed the dresses on the bed. Charlie just looked at them, shaking her head. She didn't say anything, just shook her head. Her gaze came back to Josh's. He nodded as he opened Barb's sexy underwear drawer. The first bra and panty set he pulled out was the same color blue as the dress. Josh also pulled out the blue stockings that went with the dress. He was looking for the garter belt but didn't see it in the drawer.

"Don't bother, Barb never wore a holdup belt with those. They have elastic tops," Charlie said.

Nodding, he pulled the red panties and bra along with the garter belt and a pair of black stockings. He turned and tossed them on the bed.

"Which do you want me to try on first?" asked Charlie eyeing the clothes on the bed.

"I don't care, you can choose," Josh said.

Charlie shrugged her shoulders and started to undress right there in front of Josh. He almost didn't say anything but knew it wouldn't be right.

"Ah... Charlie. Why don't you go to the bathroom to change?" asked Josh.

"What's the difference? You've seen me almost naked before," Charlie said turning to look at him smiling. "Wouldn't you like to see all of me?"

"Sure, but that wouldn't be the right thing to do. Charlie!" Josh shouted as she pulled her t-shirt up over her head. Josh turned away, closing his eyes.

"Oh stop it. We're both adults here. You're not going to rape me are you?" Charlie asked laughing.

Josh thought, 'Fine bitch.' He turned, opened his eyes and gasped at her lovely breasts as she unbuckled her belt and shimmied out of her jeans. There she stood, in just her black briefs. Josh just stared at her. He saw the look on her face. This is what she wanted. She wanted Josh to finally see her naked and he was.

"You're beautiful," whispered Josh. He closed his eyes and shook his head.

"Thank you," replied Charlie smiling at Josh. "You can keep your eyes open."

Josh opened his eyes. Charlie pulled her briefs down her legs and stood. Josh was amazed. Her pussy was shaved bald. Not a hair on it. Barb left a thin landing strip above hers. Josh looked at Charlie with a critical eye. She was thin, but not skinny. She had muscular legs, but not bulging with muscles. Her abdomen was flat. She didn't have a six-pack, but you could tell if you pressed on her stomach, it would be hard muscle you found under the smooth taut skin. Charlie was pulling the bra on now.

"Would you be kind enough to hook me up?" asked Charlie with her back to Josh.

Josh went to where she stood and grabbed the bra and hooked it up. Charlie turned to face Josh. She reached up pulling his lips to hers. Josh froze. Charlie kissed him, opening her mouth and pushing her tongue against his lips. Josh was afraid to move. He was shaking. He didn't know if it was with fear or a hidden passion he had for Charlie. Charlie pulled away from Josh, a look of confusion on her face.

"Don't you like me?" she asked.

"I do." Josh stood there looking into her eyes.

"Then why aren't you kissing me back. We always hug when we see each other socially. Can't we kiss in private?"

"I suppose, but I feel like... Barb... she... oh god, Charlie, we can't." Josh just stood there shivering with anxiety.

"Barb has told me over and over how good a kisser you are. Show me," demanded Charlie.

"What about Sam?" Josh asked.

"Sam? Sam's not here."

"What about your good friend Barbara?"

"Barb? She isn't here either. I wonder where she is though?"

"What do you mean by that? She said she was going shopping. Do you know something I should?"

"Oh, she didn't tell me about going shopping, sorry." Charlie turned away from Josh quickly and was pulling on the panties.

She had chosen the blue outfit, she sat and pulled on the stockings. Once she had them on she stood and posed for Josh. Josh stood there looking at her, his cock was hard as a rock and tented his pants. Charlie looked at his crotch and smiled.

"Did I do that to you dear, sweet Josh?" she asked, her voice husky with arousal.

"You did. Oh my god, you did. Charlie, you look so sexy in those girlie things."

Josh stretched, his joints popping as he did. He shook his head to clear his mind. But all he could see is Charlie on the bed, legs spread and him pounding his cock into her bald pussy. But his love for his wife was keeping him from throwing Charlie down on the bed and ravaging her.

"Try the dress on," said Josh.

Charlie looked at him, a confused look on her face again. She nodded, picked up the dress and stepped into it, pulling it up her body. Turning her back to Josh.

"Zip me up," Charlie said.

Josh did just that, glad that she was now completely covered... yet, she looked even more sexy with the dress on. Josh backed away once the zipper was up and the back of the dress was hooked up. He gasped at how pretty Charlie looked even without the proper makeup on and her short-cropped hair.

"Well?" Charlie asked posing once again.

"You are stunning. Absolutely stunning, Charlie."

Josh gasped as she spun around. The skirt part of the dress flared out showing more of her legs.

"Put the heels on, dear," said Josh.

Charlie slipped on the shoes. She was just a little wobbly at first, with the four-inch heels on. Her legs looked even better with them on. She once again spun around. Once more the dress flared out and up. Josh moaned at just how gorgeous her legs were.

"Charlie?"

"Josh?"

"Why do you hide your body in the clothes you wear? You are a beautiful woman, my dear. Beautiful. Why do you hide under those baggy t-shirts and baggy pants?"

Charlie stood there looking at Josh. Her face changed several times. Josh could see the emotions flash in her eyes. Finally, she looked at him. She was confused once again.

Chapter 3

"Josh?"

Josh just raised his eyebrows.

"Make me more beautiful," said Charlie pointing to her face.

Nodding Josh went to the bathroom, grabbed Barb's terrycloth robe and stood watching Charlie.

"Take the dress off and lay it on the bed. Then put this robe on and sit at Barb's makeup table," said Josh pointing at the place with the mirror and lights.

Charlie turned to allow Josh to unzip the dress for her. She slipped the dress off her shoulders and let it float down her body. Josh watched as she bent, picked it up and put it on the bed, making sure it wasn't all wrinkled. She put the robe on and sat on the short stool. She looked at herself in the mirror.

"You really don't know how to put makeup on?" Josh asked.

"I know lipstick, blush, and mascara."

"Ah, okay, the basics."

Josh was behind her. Reaching over her shoulder he opened the pack of makeup remover sheets and pulled one out.

"Take this and clean your face dear," Josh said.

Charlie took the sheet and started to wipe her face from the forehead down. When she was clean, Josh pulled another sheet out and handed it to her.

"Again. We need your face really clean, without oil or makeup."

Charlie nodded and scrubbed her face with the clean sheet. She tossed it in the small waste container under the table. She sat there waiting for Josh. Josh just looked at her face once again. Even without the little makeup Charlie wore, she was beautiful. Her face was angelic.

"You die your hair?" Josh asked.

"Yes. It's really a mousy brown. I thought a little darker would work better," Charlie explained.

Josh reached down and lifted the center section of the makeup table. It was hinged and had locking arms on each side. The underside also had a big mirror with lights around the outside of the mirror. Josh flipped a switch and the light blinked into life. Charlie squinted for just a moment as they flashed in her face. Looking in the mirror, Charlie could see her face was bright and without shadows.

"Wow, that's really bright?" said Charlie.

Josh looked up at her. He nodded, reached for dial next to the switch and turned it to the right. The light quickly faded. Leaning over Charlie, he inspected the dial and turned it a little back to the left. The lights became a little brighter. Charlie, kissed his cheek as he moved back. She smiled at him in the mirror. He frowned at her, but inside he was enjoying her closeness and her feelings for him. He was sure she had them from the way she was acting. Would he cheat on Barbara? Of course not. He loved his wife dearly. And Sam was his very close friend. He would never do that to him either.

Josh spun Charlie around to face him as he sat on another small stool in front of her. She smiled at him. He had a pallet of some kind in one hand and a sponge in the other. Not a big, rough sponge, but a small white soft makeup sponge. He was dabbing it on something on the pallet that changed the color of the sponge to a skin tone. Josh started to dab the color on Charlie's face. When he lifted the sponge she went to turn to look in the mirror.

"Ah, ah, ah," Josh said, pulling on her arm to stop her, "not until I'm done. You can always take it off if you don't like it, okay?"

"Fine," Charlie huffed, frowning at Josh.

"Don't frown, it will cause lines on your skin," Josh said chuckling.

Charlie smiled at him, then made a face at him. Josh chuckled again as he continued to dab the foundation on her face. He smoothed and thinned it out. She didn't need much, just a little to feather the color of her skin, which was just a tiny bit mottled from the sun.

"From now on, when you go out in the sun, please use a good SPF sunscreen, it will help the color of your skin and keep it from drying out and winkling," Josh said.

"Really? You can see the difference in my skin tone?" asked Charlie frowning.

"I told you not to frown, now look... the foundation has cracked and caked," Josh complained.

Taking the sponge he smoothed out the foundation where it had cracked and caked.

"Sorry," Charlie said blinking up at him.

"That's okay no problem, it showed me where I had it on too thick, no worries."

"I really need sunscreen every time I go out?" asked Charlie.

"You should. You have beautiful skin, if you want it to stay beautiful you wear sunscreen. Okay?"

"Okay," answered Charlie.

Charlie watched as Josh picked up a big bushy brush. He poked at the tray in his hand and then poked at the top of her cheekbone. He did both sides. Then he took another big brush and started brushing her face like the guy on the PBS station did to his canvas on his painting show. Charlie just calmly sat there letting Josh work on her. Next, he had a lip gloss in his hand and an application thingy. He dabbed at the gloss and then painted Charlie's lips. She went to purse her lips, but Josh shook his head.

Josh took a step back and looked at her. He smiled and came forward. He picked up an eyebrow pencil and started to pencil her eyebrows. She kept them pretty well plucked with Barb's help. Charlie hated bushy eyebrows. Next came the mascara. Josh was gentle as he brushed it on. Charlie tried to keep from blinking. She was somewhat successful. But Josh didn't say anything.

Then he picked up three pens. He looked at me and shook his head. He took one, uncapped it and drew a line on his hand. Nodding he went to the dress on the bed and compared the colors. Nodding he came back to Charlie, tossed the extra pens back in the makeup compartment and carefully drew a line across her top lid just at the lash line. He did that to both eyes. Now he had the eyeshadow. Charlie closed her eyes. She felt him gently brush the shadow onto her lids.

"Keep your eyes closed," Josh said.

Then she heard and felt something sprayed on her face. She felt air moving across her face and figured Josh was fanning her.

"Was that hairspray?" Charlie asked.

"No. It was a makeup fixative. It will wash off in the shower."

"Oh, I..."

"Shhhh," Josh shushed her.

Josh was spraying something again, this time on her hair. He was pushing her hair back on her head. He ran a comb through her hair gently. She sighed at his touch. Again he was fanning her to dry the hairspray. Charlie felt him walk away after he stopped fanning her.

"Keep your eye closed until things set," shouted Josh.

She kept them closed and didn't move a muscle. Josh was back quickly. Charlie felt him put what felt like a hat on her head. Then she felt hair brush her on the back of the neck. It was one of Barb's wigs she had bought when her hair was short. Josh liked long hair. Barb had let hers grow out and stopped needing the wigs.

"Open your eyes please?" Josh asked.