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Rated: 18+ · Interactive · Other · #1971526

The 3rd story in my series of anthologies where guys end up dressing like girls.

This choice: Hair made up like he was going on stage, sunglasses, Bon Jovi tee, white shorts  •  Go Back...
Chapter #11

Hair made up like he was going on stage, sungla...

    by: whodibah Author IconMail Icon
Ashley looked at Sam with her mouth open. Sam had his hair blown out and frizzy. It was really long and reached the middle of his back. He wore 2 diamond earrings. He wore his sunglasses. He had a Bon Jovi concert t shirt on. It was a half cut shirt that revealed his flat hairless stomach. He had white shorts on that showed his short hairless legs.

Ashley didn't want Sam dressed like a kid at her picnic. She at least hoped he wouldn't try and glam himself out like he was getting ready to perform in his band.

"Sam, can we tone it down a little for the picnic?" Ashley nervously asked.

"It's cool Ash, I was thinking..I could bring the guitar and maybe I could play a little for some people while we were waiting for burgers to cook and stuff. You know, maybe someone there would like what they hear and want to hire me." Sam explained.

"Honey, I do love you but we definitely can't have our first outing together at my company picnic with you looking, uhh...looking, this rocking." Ashley tried to watch her words and not hurt Sam's feelings. "Can I just try something when I'm done getting ready?" She asked nicely.

"Yeah, I guess so", Sam replied.

"Ok, I'll be finished in a litle while then when I get things set up, I'll call you in the bathroom, ok?

Sam waited in the tv room. He sat next to the ashtray and lit a cigarette while he put his feet up and watched MTV until Ashley finished 6 cigarettes and 45 minutes later she was finally done.

She finally called Sam into the bathroom.

He walked in and saw Ashley dressed in a blue breezy sundress. It looked beautiful on her. Her face and hair looks as gorgeous as always.

"Wow! You look great!" He said.

"Well thank you. Now it's your turn." She replied.

She had Sam sit on the toilet seat. He sat down and noticed some stuff lined up on the bathroom counter.

"What are we doing?" He asked.

Ashley smiled and turned toward him holding something that was plugged in.

"Well, I was going to flat iron your hair a little. It takes the frizz out and makes your hair look more relaxed and you could do more with it. I promise you'll like it." She explained.

Sam looked disappointed. "I"ll like it, or YOU'LL like it."

Ashley kneeled down to get to Sam's height. Even while he was sitting she still came up taller than him.

"Aww, honey. I just want to make a good impression. This is the first time my work people meeting you, and I just want everything to go perfect."

Sam looked at Ashley and knew this was important to her. He knew their age difference showed in certain situations and there were times he had act and dress a little more mature. Like meeting Ashley's sister Debra for the first time. Debra was very hard to impress. He really tried and dressed nice but Ashley never really took to him. He knew he had to try again today with her work people. He gave in.

"Ok babe, do what you gotta do."

Ashley smiled, "Thank you honey, this means a lot to me."

She started right away sectioning off Sam's hair, she worked at it for awhile until everything was perfect. She approached him with the flat iron and did the first section in the front.

Sam grabbed at his dangling hair and couldn't believe how flat and straight it was. "Are you sure about this Ash?"

"Positive, I promise it will grow on you." She replied.

Section by section Sam felt her run the flat iron through his hair until after about 30 minutes she announced that she was finished.
Sam stood up and looked in the mirror. In the first time since his hair has been so long, he had long straight hair. His hair reached his mid back before but wit the less frizz it looked even longer. He thought it gave him an androgynous look.

"Babe, I look like a chick." He said finally removing his sunglasses.

Ashley looked at his face and saw that he had black eyeliner on. "OH man Sam!! Well, with the eyeliner on you do. What were you thinking? This isn't one of your gigs. This is important to me."

She looked at the time."We're going to be late now, so lets just get moving, but we gotta talk about this later."

Ashley cleaned up the bathroom a little and grabbed the apartment key and her car keys. She told Sam not to forget his cigarettes.
Sam grabbed them but realized that he had no pockets in his white shorts.

"Here just throw them in my purse, and lets go." she replied.

They headed out to the car and drove off in Ashley's Ford Focus. The ride was silent. Ashley was really pissed that Sam was dressed the way he was.

Sam knew that Ashley was upset but was more worried about his hair and what she did to it. Finally after about a 30 minute ride, Ashley pulled into a large park. There were balloons and signs that lined the entrance to the park. Her company had rented out the whole park for their picnic. She drove to the nearest parking lot and got out.

"Babe?" Sam said as Ashley started walking away from him.

"Can I have my cigarettes being you won't let me smoke in the car?"

Ashley threw the purse at him and said, "I have to check us in, I'll be waiting by the BBQ area" As she walked away.

Sam knew he screwed up but thought that he was going to make everything perfect.

He leaned on the hood of the car and unzipped Ashley's purse. He dug for his cigarettes, found them and took one out of the pack and put it up to his lips. His long hair kept getting in the way of his face, so he put his hair behind his ear. He continued to dig through the purse but couldn't find the lighter.

Suddenly a lighter sparked and a hand leaned it forward towards Sam's cigarette and lit it for him. Sam inhaled smoke and immediately began to cough.

He turned and saw a tall muscular man. He extended his hand and said, "I'm Patrick Stevens. I'm the owner of Images advertising."
Sam still coughing said his name, S-Samm."

He put Ashley's purse down on the car hood and shook Mr. Steven's hand. He couldn't believe how tall and big this man was next to him. He looked so little and thin.

"Who are you here with?" He continued.

Sam finally controlling his cough, couldn't raise his voice so he spoke in almost a whisper. "Oh I'm sorry, I'm here with Ashley. She wanted everyone to finally meet me."

"Oh that's great, well we are glad to finally meet some of Ashley's family. I know everyone is meeting over by the BBQ area. I'm going to make a quick speech and then there's all kinds of things for the kids to do and I'm sure there's some other girls here your age.I'll see you over there." and then Patrick walked away.

Same continued to smoke his cigarette recapping the conversation he just had over again in his head. He thought about it and said, "other girls my age?"

Meanwhile Patrick made his way to the BBQ area. Everyone clapped as he waved to everyone. He was a popular boss. He was very down to earth with his employees. He was generous, always having a theme for work like Ice Cream Day, or Pretzel day. Everyone like him so they greeted him with a warm welcome.

He walked around and shook people's hands, made a little small talk. Then he came to Ashley.

"Ah, Ashley, I'm so glad you came, and I just met your lovely daughter Samantha by the car." Ashley stood and looked at him with her mouth in shock and said...
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You have the following choices:

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1. Correct him and tell him that is your boyfriend

2. Yup that's Samantha, my daughter.....

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3. Something else

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