Girls' Night Out Ch. 02

Story Info
"Kylie" steps out.
8.8k words
4.7
16.4k
20
Story does not have any tags

Part 2 of the 21 part series

Updated 06/15/2023
Created 10/26/2022
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

DAY 4

As Cary dressed for work, he wondered what was in store for him.

Angie said something about it being a big day and the fact she wanted him home by 12 meant something. As hard as he thought he couldn't come up with any ideas.

The time at work passed slowly. As it was a Wednesday, which was the usual slow day, there wasn't much to do. He kept checking with Cassie, telling her what she needed to do. She confidently told him she could handle it and not to worry. Beside she said she had his phone number and would call if he was needed. She told him to enjoy his time with his sister and relax.

"Relax!" he thought. "If she only what was going on."

Cary arrived home just before 12. Cassie told him to leave early so he did. He was surprised to see Alexa's car in the driveway. As he walked in the two girls greeted him.

"Quick, take off your clothes and jump in the shower," Angie said helping him get undressed. "Just rinse off and then meet us in the bedroom."

He did as he was told and headed to the bedroom. He was naked but by now he was used to it. The two girls were waiting for him.

"Alright, Kylie here we go," Angie said handing him a pair of panties. "Put these on."

Cary stepped into them and pulled them up. He wasn't really used to this type and they felt tight. Angie stepped up and reached into the front, grabbing his cock. She pushed it down and back between his legs. The tightness of the panties held it snuggly in place. The panties had a satiny front, which felt fantastic against his cock

"Very good. What do you think, Alexa? I found them on line. They call them gaffing"

Alexa walked around him and nodded. She ran her hand over his crotch. "No bulge, good." She then grabbed his butt cheeks. "Very good, just the right amount of padding. Feels right too. Kylie, look in the mirror."

He did what he was told. Looking in the mirror he could see what Alexa meant. His ass had a nice rounded look to it while his front was totally flat.

"Step 2." Angie put the fake breasts on him. They were just like a bra with clear straps and clasped in the back. Of course they were still D size with nipples and areoles. She adjusted the straps. "Take a look."

Again he looked in the mirror. "Wow!" he thought. "They looked so real!"

"You know something, Angie," Alexa said, "I'm getting a little jealous."

Angie laughed. "Me too."

The girls gave him a short sleeve pink polo shirt and a white pair of jeans to wear. A pair of low heel white glittery sandals finished the look. Overall it was an understated look.

Alexa went over to Angie's jewelry box and opened it. "The diamond stud earrings look good but she needs some glitter too." She took the box over to Angie. "Which ones?"

The two sorted through them and picked out two rings, two bracelets, an ankle bracelet, and a small gold necklace. "There, that ought to do it. Let's go.

Cary spoke for the first time. "We are going out, like this?"

"Of course sweetie. You didn't think we dressed you up to leave you home, did you?"

"But, where, where are we going?" he stammered.

Each girl grabbed one of his hands. "Come on sweetie. You'll see."

Alexa drove only a short distance to a nearby town. Cary sat in the backseat without saying a word. The car stopped in front of a hair salon. Under the salon's name, it read, 'Let us make your day better...total make overs.'

"This is it, let's go," Alexa said jumping from the car.

The three girls walked to the front door. Cary stayed in the middle, hoping not to be noticed. He looked cautiously from side to side. As they approached the door, the sign said 'CLOSED' He breathed a sigh of relief. "Now let's get out of here!"

Alexa knocked on the door and after a few seconds the door opened. Standing there to greet them a woman about thirty. She had raven black hair, huge hoop earrings, and tattoos. Her large breasts were barely contained in her top and her leather pants were skintight.

"Alexa, so good to see you," the woman said as she hugged her. "Come in, come in."

The three girls entered the salon.

"Ravenna," Alexa said," Let me introduce Angie and this is Kylie, your client for the day."

Ravenna walked to Cary and took him by the hand. "Let me look at you." She looked him over, head to toe. She ran her fingers through his blonde hair. "I see great possibilities." She turned to Angie and Alexa. "You want the soft look, right. Very feminine. It will take a while but I can do it. Come, Kylie, follow me."

Ravenna led Cary into the backroom where she first washed his hair and then began to style it. Two other girls began to give him a manicure and pedicure. It was going to take time but Alexa and Angie were willing to wait.

Ravenna asked Cary a lot of questions, mostly small talk, to pass the time. He told her he was Cary's sister and was here visiting from Vermont. The rest was easy as the questions were mostly about background, family, and schooling. He told Ravenna he was an illustrator of children's books and that art ran in the family.

While all this attention was going on Cary felt strangely relaxed. When he entered the salon, he was extremely nervous but now that feeling was long gone. The smell of incense had a very calming effect and he was letting Ravenna do whatever she doing. He was enjoying it and felt strangely relaxed and content. He was actually interested in what the results were going to be. It reminded him of what her older sisters had done long ago.

The girl doing his nails walked over to Alexa and Angie. "What style and color should I do? French style with pink? Or a color?"

Alexa blurted out, "Fuck me red!"

Angie looked at Alexa and sighed. "Ok, red it is."

After almost four hours, it was done. Hair, nails, and make-up, a complete make over. Ravenna brought Kylie out. "Well, what do you think?"

Angie and Alexa were speechless. Everything was perfect. Cary was gone and Kylie stood in his place. Before them wasn't a guy dressed as a girl, Kylie was a woman from head to toe. A totally new person stood in front of them. The transformation was amazing and complete.

Kylie spun around. "What do you think?"

Ravenna explained what she did. "I highlighted the red in her blonde hair and cut it just a little to neaten it up. Added some body and a little flip to it. With the lashes and a little blue mascara, it brought out the blue in her eyes. She has beautiful eyes. Sorry but no red polish. Instead the French style with pink for fingers and toes. The lipstick went with them. It is a better look for her. Bridget even put a little fake tattoo on her ankle. Kylie seemed to like it, didn't you?"

Kylie smiled. "Like it? I love it. I never felt this way."

"Good," Ravenna said with a smile.

"So where are we going next?" Kylie asked from the backseat.

"Whoa, sweetie," Angie said turning around. "What happened to 'I don't want to go out like this?' attitude?"

"I don't know but I've never felt so free and daring. I didn't think I would like this so much. I feel so good," Kylie said leaning back into the seat.

Angie looked over at Alexa who just shrugged her shoulders

They picked a nice restaurant that wasn't too crowded and located in a neighboring town. This kept with their idea to try to go to places where any friends wouldn't see them. The soft lighting was plus as this would aid in Kylie's first time truly out in public. Angie walked behind her as they entered the restaurant. She smiled as she watched her walk. It was perfect and the padding gave Kylie a tight little ass too. Angie was sure it would be difficult for any one not think Kylie was a woman.

The girls talked and laughed about numerous things. The food was good and the wine excellent. It was just three good friends out for dinner.

As they were talking, a man walked to their table. He appeared to be in his early forties with dark hair, streaked with gray. Dressed in a suit, he was extremely handsome. "Excuse me ladies," he said with a slight French accent. "Please don't think me forward but did one of you mention you own a gallery near here?"

"I, rather my brother does," Kylie said correcting herself.

"Very good. Let me introduce myself. I am Michael St. Laurent and I look for artwork to sell in my galleries. I look for unknown or local artists' work. Here is my card." He handed it to Kylie.

"I see, Mr. St.Laurent," Kylie replied.

"Please, mademoiselle call me Michael. And your name?"

Kylie's face turned red as she blushed. She began to breath in short breaths causing her breasts to move. She could feel them rise and fall under her shirt. Recovering, she answered, "Kylie, and these are my two friends, Angie and Alexa."

Michael looked directly into Kylie's eyes and smiled. "Such a pretty name, Kylie. Perhaps I can visit your brother's gallery tomorrow? Do you have his card? I am in town only a short time."

She was about to say no when Angie reached into her pocketbook. "I do. He's my boyfriend so I have one. Here you go." She handed it to Michael.

He took the card and looked it over. "I see it has only one phone number which is his. Mademoiselle, could you put yours on the back, in case I cannot reach your brother?" He handed the card back to Kylie.

Fortunately the number on the card was the business number. She quickly wrote her number on the back and handed it back to him.

"Thank you. Until tomorrow Au revior."

Angie grabbed Kylie's arm. "Holy shit, girl, you just got hit on by a handsome dude. First night out even!"

Alexa added, "I told you I was becoming jealous. Good job sweetie."

Kylie laughed. "Its just for now. Tomorrow I'll be good old Cary and I'll meet with him. No problem."

It was now the girls turn to laugh. "I don't think so. Do you think this make-up, polish, and hair can be undone overnight?" Angie said firmly.

"Yeah, Kylie," Alexa said with a smile. "We paid good money for it and we are going to get our monies worth."

"It wasn't part of our plan, sweetie, but it is now. We have to find something for you to wear when you meet Monsieur St. Laurent."

Kylie slumped in her seat. What was a good time had taken a sudden turn.

***

DAY 5

Neither Kylie nor Angie slept well that night. Angie, though excited at the thought of Kylie meeting Mr. St. Laurent, felt there was a bigger problem. What was Kylie going to wearing? Alexa and she planned on clothes shopping Friday, in plenty of time for Saturday. Now it was only Thursday and she needed something fast. So far Kylie fit into Angie's clothes. They were a little snug but wearable. Shoes, stockings, jeans, and even some of the underwear were fine but those damn big breasts! Alexa wanted to give Kylie D cups and that's as far as her thinking went. Angie wanted them to be a little smaller so not to call any attention to them or Kylie. Alexa said they were the only ones she could get. Neither of the girls were that big so they didn't have the bras to fit boobs like those. Yesterday Kylie went without one, which was fine. Today might be a different story.

Kylie worried about other things. Yesterday she was among friends and the lady at the salon was very understanding and discreet. The lighting at the restaurant wasn't very bright but today will be broad daylight. What was she going to wear? How could she explain this to Cassie? She might see right through it. Finally when Mr. St. Laurent discovers what is going on, it could be the end of the biggest deal the gallery could ever see.

Angie rolled over. "Sleep much, sweetie?"

"Nope. You?"

"Me neither," she replied sitting up. "Ok, take your shower. Just rinse off. Don't wash your hair or face. I'll touch up your make-up." She pulled the blanket off. "Let's go, sweetie."

Kylie quickly showered and then returned to the bedroom.

"Ok, Kylie, here's the plan," Angie began. " Here are your boobs."

They looked at them and began to laugh. It broke the tension in the room.

Angie helped Kylie into them and then proceeded to help with the rest. She handed her what appeared to be a body shaper. Kylie slipped it on and pulled it up. It resembled a one-piece bathing suit without a top. It was tight.

"There that will hold you in. Adjust yourself if you need to."

Kylie moved her cock around and tucked it between her legs as Angie looked at her ass.

"It looks good back here. Actually better than yesterday. You have a cute ass."

"Thanks," Kylie said.

"Next the pantyhose we bought last night. It will hold you in even better," Angie said handing them to her.

"So far good, Angie," Kylie said with a half smile. "But what's next?"

Angie went to her closet and took out a white silk blouse. "Here, put this on."

Kylie did. It felt great against her skin. "Can I really wear this? My nipples are pointing out." Even though the blouse had two strategically placed pockets, she was right. "Plus I can't button it up."

Angie came over to help. Kylie was right. It was going to be impossible to button the top three buttons.

"Never mind. Here put this skirt on."

The skirt was black and stopped just short of Kylie's knees. Angie zipped it up and stepped back. It wasn't too short or tight. Kylie looked good. A good business look. Now those boobs. Back to the closet she went.

She returned with a black jacket. "Here put this on. Let's see how this looks."

Kylie put it on and found she could button the center button. It covered her breast perfectly. "That's better," she sighed.

Angie added a small pearl necklace with dropped pearl earrings. She gave Kylie one of her watches and a bracelet to complete the look. After touching up the make-up and a touch of perfume, Angie stepped back. "Damn," she said, "You look simply great. Look in the mirror. One final touch." She handed Kylie the black heels.

Kylie did and agreed. She even turned to look at her backside. "Damn, the heels make my legs look good and my ass too! This just might work," she thought.

Kylie explained everything to Cassie. Cary had another appointment with another dealer, Mr. St. Laurent was coming, she needed Cassie's help, and that she had worked with Cary a while back before she left for Vermont so she knew what to do.

While she sitting there with her, Kylie looked Cassie over, this time with a girl's eye. New clothes, hair, a little different make-up would do wonders for the girl. Perhaps Ravenna could work on her. If Cassie was going to be her ass't. manager, then she was going to have to look the part. Kylie smiled. She was already thinking of changes to the gallery!

"I understand Cary made you the assistant manager, Congratulations," Kylie said to Cassie. "I'm sure you will do a great job."

"Thank you Kylie," Cassie smiled in reply. "Cary didn't tell me he had such a pretty sister. I understand you are twins."

Kylie smiled. "Well, Cassie is on board!" "Why, thank you Cassie. Yes Cary and I are a lot alike."

Mr. St. Laurent arrived promptly at 11 o'clock. He stepped out his Mercedes. No suit today but he did wear his tie.

Kylie cheerfully greeted him. "Welcome, Mr. St. Laurent."

"Don't be so formal, Kylie," he replied. "Remember call me Michael."

"Very well, Michael. Right this way." She led him into the gallery. "This is Cassie, our assistant manager."

"Good morning, Cassie." He looked around the gallery at the picture. "Already I'm impressed. Do you mind if I walk around by myself, just to get a feel for the place?"

"No, go right ahead. I'll be here if you have any questions."

Michael walked slowly around, looking at the works on display. He made notes on some index cards as he proceeded. For some works, he stopped and carefully inspected them. Others he just passed by.

"Is there another floor, Kylie?"

"Yes, Mr. err Michael. Actual two more. One upstairs and a small number of paintings downstairs," Kylie quickly replied.

As he went up the stairs, Kylie turned to Cassie, "It appears he likes some of them."

He toured both floors and as he came down the stairs, he motioned to Kylie. She walked over to him, her heels clicking as she crossed the floor.

"Kylie, please walk with me. I would like to discuss some of the paintings." As they walked up the stairs, he put his hand on her back, gently guiding her. Kylie felt a rush through her body. "Whoa!" she thought.

Michael had a number of questions but Kylie handled each one with ease. He had her write down the pictures he was interested in on her clipboard. Stopping at one picture, he pointed out something unusual in it. It was in the lower corner and Kylie, putting on her glasses, bent over to look, Michael gently put his arm around her waist. Again she felt a rush.

After almost two hours, Michael appeared to be satisfied with what he found. "I believe there are seven paintings I would like to purchase. Is that alright, Kylie?"

"Yes Michael that would be wonderful," Kylie replied, hoping to keep the excitement out of her voice.

"Good. Now according my calculations, I believe the total should be around $4,000. With shipping closer to $5,500. I tell you what. You draw up the papers and we will close deal over dinner. What do you say?"

What could she say? $5,500 was more money than the gallery ever made at one time. She couldn't turn him down. But he asked her out for dinner! Now what?

"Of course, Michael, I would be delighted."

He smiled. "Good, around 6 and your choice. Where shall I call on you?"

Kylie thought for a moment. "How about right here. That way I can complete the papers and have them ready for you to sign."

Michael took her hand and kissed it. "Until tonight." He stepped closer and kissed her cheek. She blushed.

As Michael left it gave Kylie time to think. "She had just pulled off the biggest deal the gallery ever had. And she did it as a woman. She was sure if Cary tried it, it wouldn't have gone down. A little flirting and confidence had gone a long way. Now tonight, a dinner will seal it!"

Kylie and Cassie sat in Cary's office at the end of the day. They toasted the day with a Diet Coke.

"Sorry it doesn't seem Cary has any thing stronger. We need to remedy that," Kylie said with a laugh. "We had a very successful day. I want to thank you for all your help."

Cassie smiled back. "I didn't really do anything."

"Yes, you did. You took care of some customers while Mr. St. Laurent was here and then this afternoon you let me complete this paperwork. Congratulations are in order. You sold your first print! You should be pretty excited."

Cassie blushed. "Yes I am. Very much so!"

"Good." Kylie leaned forward, forgetting for moment about her boobs. She had removed her coat as she worked and now showed a lot more. Cassie's eyes grew big. Kylie suddenly realized her mistake. Instead of panicking, she calmly sat back.

"I know Cary has everything in here on consignment. 60-40?" She knew it was more for him than that.

"Sort of," Cassie replied.

"Ok, since this is your first time, and Cary isn't here, I'm going to give you 100%. I'm sure I can convince him."

Cassie gushed with excitement. "Oh thank you, Kylie, thank you, but you really shouldn't."

Kylie waved her hand. "You're worth it. Beside now that you're in management, you are going to have to dress for it. You want to become a successful business woman, don't you?"

Cassie lowered her eyes. "Why, yes, of course. It is just I never thought of myself that way."

Kylie smiled. "I didn't picture that for myself either."

The two girls sat quietly for a moment and then Cassie spoke. She very quietly said, "I know I just met you but I feel like I know you. Maybe its because you are Cary's twin. I don't know."

Kylie stiffened in her seat. "Did Cassie just figure out what is going on?"

"I mean when you told me about this morning and what was going on, you made it seem so easy. And it made my day easier. The way you handled Mr. St. Laurent, that was amazing. So confident yet still so ladylike. I can see why he asked you out."