Week 1- Courtney

Chris listened to his teacher ramble on about his stupid club. Why was he paying to listen to this guy to talk about his personal life? Why doesn’t he actually let us practice for the play coming up soon? That’s a novel idea. Chris sat slouched in his seat wearing his blue hoodie and blue jeans and his blue sneakers, waiting for class to get started. When Professor Theo finally stopped rambling, class went by quickly. Before Chris left, he decided to swing by Jason’s office to say hey. Jason was the vocal teacher assigned to the drama department. Jason had helped Chris develop a deep, booming voice. Naturally, Chris had a very soft and feminine voice but Jason had taught him how to change that.

Jason saw Chris coming to talk to him.

“Hey Chris. Go meet me in my office buddy. I’ll be right there.”

Chris gave a wave up and went off.

Jason was going have to play a little dirty if he wanted to get his new waitress by the opening of the club. He had been trained to use hypnotism to help coach people into developing a new voice, but he had never tried it for this: feminizing someone. Chris was the perfect candidate as he had a soft, tan skin. His natural voice would be hard to distinguish from a natural woman’s, and he was very short and had a demure demeanor. His long brown hair also would be easy to style. Theo had said anything short of kidnapping was fine and helping Chris get in touch with his feminine side couldn’t hurt, could it?

He went back to his office and met with Chris.

“Hey Chris! How you doing buddy?”

“Can’t complain I guess. Theo is driving me crazy, rambling on about your club. No offense, of course. I just think that class time should be spent doing things for class.”

“I agree with you. That’s why I waited until after class to ask a favor from you. I made some new audio files for my performers to listen to at the club. To help them with their singing voices. You are my best student so I wanted to know if you would take them home and listen to them for me. I will pay you 200 bucks if you listen to them for a week and then get back to me.”

Eager at the chance to help Jason, and to get 200 dollars, Chris eagerly agreed.

Jason told Chris he would e-mail the files to him and sure enough, they were in his inbox when he got home. Chris loaded the files onto his iPod and went about the rest of his day until he went to bed. Right before bedtime, Chris put the earbuds in and went to sleep.

Day 1

Chris woke up in the morning feeling refreshed. He took the earbuds out and got in the shower.

“Whatever those earbuds were supposed to do, they didn’t do it. Oh well, they have a week left. To do whatever it is they are supposed to,” he thought to himself.

As he showered, he looked over his legs and felt a little annoyed by the hair covering them. It seemed like a forest.

“That is going to drive me crazy,” he thought.

He grabbed his razor and began to shave off his leg hair.

“Might as well get everything while I am at it,” he thought.

Many, many minutes later, a nearly hairless Chris left the shower. The only hair left was the flowing brown hair he had on his head.

“That feels much better,”

Chris put on his usual hoodie and blue jeans, but they felt too heavy to him today for some reason. He took them off and put on some of his shorter shorts and put on a sleeveless black shirt he had. He slipped on some flip-flops to show off his newly trimmed legs.

For some reason, Chris felt like going to see Jason today.

“He is paying me to listen to these audio tapes. Might as well tell him I don’t think they are working.”

Chris arrived at Jason’s office and found that he was out for the day.

Chris was annoyed but he found the door cracked and decided to explore Jason’s office.

The office was fairly boring except for a suitcase Chris found. The note on it said that it was for him! 

Chris grabbed the suitcase and went back to his dorm.

Chris opened the case when he got back to the dorm. A note inside read that it was for him to help get into character.

Chris was surprised to fin that the case was filled with… women’s clothing? It was filled with stockings, pantyhose, a few dresses, a short skirt and short shirt, make-up and nail polish.

Chris didn’t know what to think so he did the only thing he could think of: he laughed. It was silly. 

Dressing up like a girl isn’t going to help out with the tapes, he remarked.

He was about to close the case when his hand rubbed across some sheer pantyhose. It felt so soft on his hand. He picked it up and felt it caress his skin.

“Wearing these won’t hurt anybody and it might help with the audio tapes so might as well give it a try”

He also grabbed a pair of fluffy, pink socks from the suitcase and went to the bathroom and tried them on.

He was amazed at the way they felt on his skin. His body got a little too excited, but Chris decided that it was just the sensation of the stockings, nothing more. Chris wore them for the rest of the day.

Chris went to bed with his pantyhose and socks on under his pajamas while he drifted off listening to the next audio file.

Day Two

He woke up and quickly hopped in the shower. He spent a lot of time fretting at the mirror. His face looked so boring today. He decided he couldn’t do anything about it, so he just straightened out his hair and went to class.

Jason was here today so Chris ran over to his office after class.

“Sorry I wasn’t here yesterday Chris. Did you get my suitcase I put together for you?”

“Yes I did. Thank you. I don’t think the tapes are working though,” Chris said as he sat down and crossed his legs.

“Well, that’s too bad. I do have another packed for you if you want to try and see if that helps.”

“Sure why not? he said eagerly.

“Before you go today, I want to teach you how to put on make-up. I know it’s silly, but it might help you with the tapes. You never know.”

“Alright. Might as well.

Jason led Chris back into the area where performers got ready. He gave Chris an overview of make-up and left some dark eye shadow and mascara on his face.

“Here, try on this outfit,”

Jason handed a bag filled with goodies to Chris. Chris went into one of the changing rooms and dug through the bag.

“What am I doing,” he thought as he looked through the bad. “This is silly”

“Earning two hundred bucks” he responded to himself.

That was enough motivation for him. He put on the outfit piece by piece. He started off with the black 

satin underwear, the only reason being his boxers would not work with the daisy duke shorts. Before that, he out on some black pantyhose. He then slipped on the red, pointed toe flats. Last, he put on the red hair band and red necklace along wit the sleek black top.

He left the dressing room to be greeted by a very happy Jason.

“You look fabulous… Courtney,” he laughed.

“Don’t get to use to Courtney,” Chris responded. “She is only here until I am done with the tapes.”

“We could really use someone like you at the club. You would be great for it,” Jason pleaded. I don’t want him to listen to all of the tapes, he thought. If I can stop him now it should be fine. I’m not sure what will happen if he listens to all of them.

“No thanks. I’m not dressing up like a girl for a living. See you later.”

“Well, I think the tapes aren’t working. No need to listen to the rest of them. I’ll pay you the 200 hundred. Don’t worry about it.”

“I’m not one to leave a job undone,” he said as he walked away.

Before he left, Chris changed out of his clothes and took them with him in a bag.

“No way I am being caught walking around like that,” he thought to himself.

The day dragged on until Chris went to bed. Once again wearing his sheer tights and pinks socks, Chris went to bed while the 3^rd nights taped began he to amp up the molding of his subconscious.

Day 3

Chris woke up feeling refreshed once again. Chris had class today so he quickly showered and got ready. He put his long brown hair into a bun and put on some foundation so that his face would look nice.

“No one is going to notice, and it will makes me look prettier. Ur… I mean handsome,” he thought.

Chris decided to wear some black, stay-up stockings under his blue jeans today.

“They feel great and no one will see them. Not that it matters,”

Before Chris left, he decided to wear the black shirt Jason had given him yesterday. It was too soft not too wear, he thought. And you couldn’t tell by looking at it that it was a girl’s shirt.

The day went by quickly. It took a lot of effort for Chris to keep his dick from tearing through his pants as the sensation of the stockings coursed through his body throughout the day.

Chris rushed home after classes, and dropped his pants and ran into the bathroom. It didn’t take much effort before Chris came all over the toilet.

“I don’t know why these clothes are making me feel so good,” he panted. “But I’m enjoying it.”

Chris cleaned up his mess and decided that he wanted to check out the club Jason owned with the other teachers

Chris put his pants back on and walked down to the club. It was about half-way between here and the women’s college on the other side of town.

Chris arrived and went into the club. He found people doing construction still on the stage. 

Chris walked around and found himself in a room with a plethora of outfits all around and several couches. It also had a short, beautiful women walking towards him. On any other day, Chris would have been admiring her face or ass. This time, however, he couldn’t get his eyes to stop from admiring her red blouse and purple tights and black strap heels.

“Hey Chris! Great to see you sweetie! It’s me April from theater.” She said. “Well, you know me as 

Alex. I got hired as a waitress here today so they are letting me play around with the outfits. Sorry 

about my outfit. I was just goofing around with everything.”

Chris remembered Alex from class, but his mind couldn’t connect these two as the same person. Chris started to take all of this in, but his mouth seemed to have a mind of its own.

“I love your blouse and stockings!” he said as his voice reverted to its natural, feminine tone.

“Thanks!” she said as she gave him a hug. “Jason told me you might stop by. He told me you were thinking about joining us here.”

Chris thought to correct her that he wasn’t going to work here, but he decided to just go with it. No harm in pretending.

“Yeah, I’m looking into it.”

“That’s amazing! It will be soooo much fun! Jason told me to give you a makeover to help you get in touch with your feminine side. Come follow me!”

She led him into a closet filled with clothes and told him to strip down. He took off all of his clothes and began to remove his stockings without caring what April would think. April didn’t say anything so no need to worry regardless.

“What am I doing,” he thought as he stood there in just black satin panties. “This is dumb. No point in keeping up this charade.”

Things changed when April handed him his clothes. A dark blue skirt was among the pile, but that wasn’t what interested him. Red pantyhose, red ballet flats, and a red blouse. The red just glowed in his eyes. All of his worries and objections faded as he quickly snatched the outfit and put it on. He was amazed as he looked in the mirror. Large glasses, a lovely scarf, red blouse, black jacket, dark blue skirt, and red pantyhose and flats.

“You look fabulous!” April squealed.

“I know!” Chris laughed. “It’s a gift”

April took Chris over to get his ears pierced after dress-up. It didn’t hurt too bad. After that, she trimmed up his eyebrows into a feminine brow. She then gave him a bag filled with more make-up and another large, rolling bag filled with more clothing and shoes.

“You are amazing April!” Chris squealed as she rolled out the bag. Chris gave her a kiss on the cheek as they exchanged good-byes.

“Not a problem. Jason also had a video in his office for you.” April went on. “He told me not to give it to you yesterday, but he has just been funny lately. Go ahead and watch it. See you later girl.”

Chris left with the bag in tow, dressed head to tow in his feminine attire.

“See you later girl? I don’t know what April is talking about. Me? A girl?” he thought and began to laugh to himself as he went home.

Chris arrived home and worked on some lines for the upcoming play. Bedtime rolled around and, without a second thought, put on his pajamas and put in his earbuds and went to bed.

Day 4

Chris got up and tip toed over to the shower. He showered off and dried off and got to work on his face. He put foundation on and a dab of blush on the top of his cheeks. He admired himself in the mirror and got to work on his hair. He decided to put his hair back in a bun and use some clips to keep it back.

“I’ll go show off for April today. She will be impressed by how good I have gotten,” he remarked.

“Not that I enjoy looking like this,” he quickly added in the back of his mind.

He grabbed a black blouse with translucent black sleeves from the suitcase April gave him along with black stockings, black satin panties, black satin bra and black skirt.

Chris put everything on, stuffed his bra with inserts April had been kind enough to leave for him. He slipped on some black flats and went back to the club.

“Hey sweetheart! Welcome back!” April ran over to greet Chris with a hug and kiss on the cheek.

“Hey girl! Good to be back.”

“I was actually just about to leave to go shopping,” she said as she grabbed him and pulled him along. 

“You are coming with me. I got some things to teach you.”

Before any objections could be made, they were already out the door.

One shopping montage later, and they were done.

“Let’s go back to your place, sweetie. We can try out those heels and I can show you how to walk in them. Come on Courtney.”

Chris thought about telling her not to call him that.

“Who cares?” he thought. “I’m confident in myself. Courtney isn’t a bad name anyways.”

After a brief walk, they arrived at Chris’ apartment.

“Now that we are in the privacy of your home, you have to let me show you how to walk. You have too much Chris, not enough Courtney.”

“What do you mean?” he asked.

“Sit down,” she commanded. Chris instinctively obeyed.

April took off Chris’ ballet flats and grabbed a shoe and jewelry box from the shopping bags.

“Now, the shoes are just for you to try on. I have to take them back to the club. But this lovely ankle bracelet is yours to keep. A gift from me, my dear!” she said as she put a thin, silver bracelet around her ankle.

“Oh, it’s wonderful!” he cheered as he reached down to hug her.

“Consider it a proactive apology for what I am going to do next.” She said as she slipped on a pair of Annie Klein black 1-inch wedges onto his feet.

“Apologizing for what? These shoes are to die for!” he cheered.

“Well, it’s complicated.” She started as she helped Chris stand up in the heels.

“The main reason is I was hired by Theo and Jason and Charlie to help get the other waitresses ready. I was crossdressing for a while before this whole business so I have experience I am supposed to impart onto you and make you the best girl you can be. Jason originally was grooming you for the waitress role honey, but decided he didn’t feel comfortable doing it this way. So, I’m am taking over where he left off to take you from Chris to Courtney.”

“Doing it what way?” he asked, confused.

“That’s not important honey,” she said as she got Chris to start walking.

Chris ignored his confusion while he attempted to walk across the apartment. His knees wobbled as he tried to bend down to lower his center of gravity.

“No, no” April started. “Keep your knees straight. Treat them like any other shoe. Take small steps. Heel to toe. Keep your feet straight. This going to make your hips swing. Go with it. Show off your feminine side darling. Work with it. Keep your elbows tucked in. And don’t forget to smile.  Girls always look happy.”

Chris tried and tried, but he just couldn’t get a rhythm down. He just wasn’t convincing. He wanted to throw in the towel.

April never grew frustrated. She just cheered him on as he walked around in the heels, even though they were only one inch.

“Come sit down Courtney.” She called as she patted beside her on the bed.

Chris wobbled over, not even thinking of protesting being called Courtney.

“It’s just a cute pet name she has for me. No one would ever mistake me for a women” he thought as he wobbled over in his heels.

“Now, this is part of what I was apologizing for. I am going to take your mind off of the heels. Get on the bed on your knees and bend over. Grab a pillow.”

Slowly, Chris did as he was asked. He bent over as he heard April digging around in the bag. He heard her doing something, and then felt a she reached for his panties and pulled them down.

“Woah!” he protested. “What are you doing?”

“Relax, this will help you. And no one will know, pumpkin. Just our secret.”

Chris wanted to say no, but an odd sense of excitement filled him as he prepared for what was coming. He felt a cold sensation and then a foreign feeling as April shoved something into his ass. He held onto that pillow for dear life as a burning began as she put whatever it was into place.

“All done,” she said. “You did great! Not many people take butt plugs as well as you.”

The pain didn’t go away, but it slowly dimmed into just a soft reminder that it was there.

“Now, get to walking!” she commanded with a laugh.

“This is weird. What the fuck am I doing? I have a ‘butt plug’ in my ass. I need to put a stop to this.” 

Chris thought as he strutted around the room.

As he was thinking, he noticed in the mirror that a woman was walking around his apartment with a sexy strut. He stopped to admire her and after close examination, realized it was him!

“You did it! I knew that would get your mind off of the heels. You come so naturally to it girl!” she cheered as she gave him a kiss on the cheek. “Now, let’s move onto the big boys.”

They went from 2-inch to 3-inch to 5-inch and Chris handled them wonderfully.

Chris glanced at the clock and noticed it was 11.

“Time flies when you are having fun,” April said as she started to pack up.

“It sure does. My dogs are barking,” Chris said as he collapsed on the bed.

“Before I leave, I have something to help you with,” she said as she went over to his computer. “Grab me that disk I gave you the other day.”

Chris got up and grabbed the tape from his bag and walked it over to her.

“Have a seat,” April said as she put the disk in and got it ready. “Kick up your feet and relax. This is to help you loosen up.”

Chris did as he was told. He was worn out so it didn’t take much to get him to anything.

The video opened up and said introduction across a black screen.

“Put on your computer’s headphones.” April said. Chris did so and April hit play.

April wasn’t sure what was playing on the audio, but the screen was a bunch of relaxing colors, blending together and swirling around and around and around.

April snapped out of it when the screen slowly dimmed and the words’ “She is ready” flashed on the screen.

April looked and Chris was glazed out. Staring blankly at the screen

“Can you hear me Chris?” she whispered, unsure what to expect.

“Yes,” he stated blankly.

“Ok,” she began. “You have a different personality in you Chris. Courtney is your feminine side. She is everything that you have done in these past few days. That was all Courtney. Do you understand?”

“Yes”.

“Courtney loves being feminine. She is a party girl and loves to live it up. She loves wearing girly clothing, especially anything black or red. She also loves wearing stockings and showing them off. She is best friends with me and Jennifer, who she will meet later. Courtney loves making everything feminine. Do you understand?”

“Yes”.

“Chris is the same as he was before he began listening to these tapes. He uses his deeper voice and avoids anything feminine. He remembers meeting April and is friends with her, but he doesn’t mind that she is also Alex. Whenever Chris hears someone say,” Go get ready, Courtney”, Chris will get a headache and have to go back to the privacy of his dorm, where Courtney will take over and get dressed. Whenever anyone says, “Go get ready, Chris” to Courtney, the reverse will happen. Neither will ever be aware of the existence of the other. Chris will never question the existence of the female clothes in his apartment and any changes he sees on his body. Do you understand?”

“Yes”.

“Good, go get ready Chris.”

Chris mindlessly stood up and went into the bathroom. He came out many minutes later with Courtney’s clothes, and butt plug, which he went on to put into the closet and the sink to be washed, respectively. He put on his basketball shirts and a plain white shirt and seemed to awaken.

“Hey April. What are you doing in my apartment?”

“We were just hanging out silly. I’ll see you later,” she said as she rolled the bags out the door with her.

“Weird,” he thought. “I guess I can stop listening to the tapes. Jason said he would pay me either way so I guess I’m done.”

Chris got into bed and went to bed without listening to the tapes.

The Rest of Their Life?

Chris woke up to his phone ringing. It was April.

“Uhhhh, its 10 in the morning. What does she want?”

“Hello?”

“Go get ready Courtney! We have an exciting day of shopping today!”

April hung up the phone and set out for Chris’ apartment.

She knocked on the door and was greeted by a feminine voice,” Come right in!”

April opened the door and was greeted by her good friend Courtney.

“Let me put on my heels and we can go on an adventure!” April cheered.

Hope you enjoyed. Next installment, we will get to see April's life and perspective on things.