Owen goes on a date with his girlfriend wearing one of his prettiest camisoles to try to resolve the issues she has in dating another girl
Chapter 4

Owen finished his talk with his new guardian, and it greatly troubled him. He didn't know how much of an impact on his life that made him legally a CIS girl would have on his life. This was something that needed to be corrected. And while he did like Crystal a lot, what she did filled him with fury. She didn't know, but she was a cheerleader, of course.

He wondered if he did want to become a girl. He had to admit that being a girl was a lot of fun, and he learned a new side of things that boys rarely learned about. He didn’t want this to end, but he could be made a trans girl and continue this journey as long as he wished. It would change little in the end. His new friends knew everything, and they fully accepted him. They would stand by him, so he wasn’t worried. There was a certain delight knowing that he was a boy being accepted and experiencing these things. That was something he didn’t want to give up.

There were other problems. Owens girlfriend Cheryl, who he didn’t see in over a week except passing by, or on the squad. She was his girlfriend, but he sensed she was having a problem accepting his current lifestyle. He was afraid that she was going to end it.

Owen prayed that she could accept this. He had called her earlier in the day to set up a date. He was going fully lemme and hoped that she could accept this.

He chose the flirtiest and sexiest things he could find in his wardrobe. The delicate lacy victorias secret pink panties and a pair of sexy nylons and a miniskirt. He simply put on a sexy camisole with floral bra cups built-in. Then he spent some time on his makeup and resolved himself to learning more about doing his own makeup. He did his best and hoped that Megan would help him with the look. He called Megan to come by and help him tonight.

Then he brought out the curling iron to redo his curls on the bottom and approached Megan. She looked him over and smiled. “Can you help me with my makeup. I messed it up.”

Megan looked at his face with her critical eye and responded. “I see you were trying for an exotic look focusing on your eyes. You used too much eyeshadow and mascara. You don't need that much, and it looks stupid if you overdo it. Don't worry, many girls make that mistake. Let's retouch it.

Megan took him to her vanity, and he watched as she used some wipes and skin cleanser and wiped off much of the eyeshadow and the blotted mascara and redid it. Megan took the time to carefully explain how she used very little to make it look better

“See,” Megan explained. “That's how to do it.”

“Thanks,” Owen smiled.

“I never in my wildest dream thought I would be helping my brother with his makeup. That's a first, but just ask me for anything.”

Owen examined his face and retouched his lip gloss. “Considering you are more manly than I am now, I wondered if you had any makeup to help me with.”

Megan started turning red when she saw the mischievous smirk and the twinkle in his eye. Then she laughed and playfully elbowed his ribs. “I have still been doing this longer than you, even if I live as a tomboy most of the time. Keep it up, and I will make you look like a prostitute next time.”

Owen saw her twinkle in her eyes as she smirked. Then he hugged her.

“Owen, what is the occasion, If you don't mind.”

“I am going out with Cheryl tonight,” Owen replied.

Megan rose her eyebrow. “Your girlfriend?” She said seriously. “Don't you think this is a little much.”

“Na,” Owen said. “This is me, and if she cant handle this side of me, then its something we need to know and deal with. I can handle it being over. Some girls can handle this. I will see if Cheryl can handle dating a feminine boy.”

“You look all-girl,” Megan looked at Owen. “That can be a problem if Cheryl does not want to date another girl. And you can't blame her if that's her decision.”

“I won't. I won't be mad if Cheryl breaks it off. I just want to know, and I hope we can still be friends on the squad. I won't be mad in any way. I think I may have a problem dating a girl like you that looks like a boy.” Owen looked into Megan's eyes with a smirk.

“You ass,” Megan said playfully and elbowed him again. “You watch it.”

The two siblings, giggled and Megan dove in tickling Owen. They struggled to get serious, and Megan watched in disbelief as Owen put two small inserts into the cups of his bra.

“Are you serious, Owen,” But Megan knew he was going all out to see if Cheryl could handle this. But there was no longer any boy there. Owen was all girl now.

“I am serious. I am Olivia now.” Owen firmly stated. Then he finished his feminine look with a pair of pink heels and walked down the steps to prepare for his date.

The two had agreed to meet at a local Diner around the corner, and Megan offered to take him there.

Owen walked in, carrying his purse over his shoulder as many girls and sat down in one of the seats and waited for Cheryl.

Cheryl walks in a few minutes later and looks around for Owen. Except Owen wasn't there. Cheryl wondered where own was and stood there by the front waiting.

There were only a few people at the diner at this time in the evening. She saw an older couple eating together in the corner and talking about their children. There was a single man at the table in front of the couple. There were some women on the other side, and she saw a beautiful looking girl around her age sitting alone in front. She was unable to find Owen anywhere.

Cheryl looked around disappointed for a few minutes and hoped he would arrive. She considered leaving. Then she saw the girl stand up and waved at her. The girl she saw first said, “Cheryl, it's me. I hoped you would notice.”

Cheryl’s frown deepened. That was Owen in the tight pink miniskirt with nylons on her legs, and his pink camisole top with cups and some visible inserts to look like natural breasts and his makeup. It looked like Owen even curled his hair. He was beautiful. In an effort to not look weird, she whispered respectfully.

I guess I should call you Olivia here, so no one notices?”

He nodded. “I would appreciate that, and thank you.”

“Do you know how weird it is to be dating a boy that looks this pretty that I feel I must call him by a feminine name? Sitting there with his breasts looking prettier than I am?” Cheryl whispered.

Owen agreed, “Yes, I can imagine it is difficult, but I want us to work through it. I am still me, Cheryl, and I love you.”

“I love you too,” Cheryl replied. “But I just don't know about this. I noticed things were really weird on Friday when you went in your full cheer outfit and cheered at the game. You were prettier than some of the other cheerleaders. All of the boys were looking at you. They wanted you, Owen. Do you know how that feels for the girl dating you? I just don't know if this is something I can handle. I wanted to date a boy. I don't think I can be with you that way if you are a girl.”

A tear ran down Owens's beautiful face and left a trail of dark eyeshadow lined down his cheek. He sniffled sadly and said, “I understand. I hoped we could get through this. If we cant date, can we still be friends?” Owen asked, hopefully.

“Sure, and I won't let this affect the squad. I intend to remain there. We simply won't be a couple. I will support you in this.” Cheryl said to him.

“That means so much.” Owen exhaled. “I noticed how you were looking at me that day, and how you have distanced yourself from me since I started this. I know this must be very difficult. I am sorry.”

“You haven't done anything wrong,” Cheryl stated. “If this is you, then you must embrace it. It is me who can't handle it.”

“You aren't wrong if you want to date a boy. I am not a boy anymore.” Owen stated. “I am Olivia.”

“None of us are wrong. It's just the way things turned out. I was dating a trans girl who was waiting for a chance to come out. I will support you.”

The waitress appeared, and they ordered their dinners.

Then Cheryl said, “This was one of the reasons why I was against you joining the squad. I figured the girls were making a big mistake. I won't miss this for anything. They really have no clue.”

“Wait!” Owen said. “How could you know I would start dressing like this just to be part of a Squad? I didn't even know about this side.”

“Yes, you did,” Cheryl pointed. “I noticed. Many of us noticed, but you wanted to pretend it wasn't there. But we saw how you loved the girl side of things almost all your life. I noticed it in how you interacted with other girls on a different level than most boys do. There were signs. And you never do anything halfway. When the girls pushed you to join the squad, I figured you would either say no, or go all out and make yourself as feminine as possible to fit in with the squad. And you did that. I am happy for you, Olivia. This is so great for you.”

“I didn't even notice those things,” Owen looked at her. “I guess many other people did. I am glad you want to stay on the squad. You are good, and we will need you.”

Cheryl laughed. “I wouldn't miss this for anything. It's going to be a great show. I love how you maneuvered yourself to be the one in charge. I don't know how you managed that as a new freshmen member. That's just part of what makes you great. And then convinced her to allow you to train a competition squad. Those girls have no clue what's coming there way.” Cheryl laughed louder. A few people looked over. “It's going to be a ride, and if they can't keep up, you will cut them. But I knew you wouldn't be happy just cheering on the sidelines. It's going to be fun.”

“I know they all really want it,” Owen stated. “They are cheerleaders. It's in our nature, they want to go the distance. They just needed someone willing to push them.”

“How did you get the coach to agree?” Cheryl asked.

“I can't believe she wasn't doing this all along,” Owen looked. “Cheryl, she was a cheerleader in high school and a nationally recognized college squad. She competed and placed in nationals. She had the background and the skills. And we will need them, I just can't believe she wasn't pushing for this all along. The squad just needed the motivation.”

Cheryl couldn't believe it. What luck. “I will help you in any way I can. I knew with your background in competing that you wouldn't be happy on the sidelines cheering. You would insist on much more. You will push them to your limits. And I have little doubt you will place in regionals. And by next year, we will probably be competing at the state level.”

Owen shook his head, “No way. I think that's expecting too much. We will be lucky to place in regionals In the fall.” Owen pointed out.

“I have seen you train new students just off the streets to place in regional in NAGA. I seen you push them into the Intermediate divisions within a year when most instructions take two to three years to train a new student to compete in the advanced or intermediate divisions. You have a gift Owen. I put money that we will see the squad competing in state next year.”

“I love your confidence,” Owen giggled a little too girlishly. “Did you all really know I was like this all along? That there was a girl waiting to come out?”

“Many of us noticed many little things about how you presented yourself and spoke. I noticed many of them, and I knew it was just a matter of time. I considered pushing you out myself. I knew it would be terrible if we waited too long. But it still makes me sad to lose my boyfriend Owen. I can't be happier with Olivia. I will remain your friend and stay on the squad to help you.”

The two tightly hugged eachother and went out to meet Megan waiting in the car to take them back.

Megan had to know, “So how did it go, Cheryl?”

“I told Olivia it's too weird dating a boy who is turning into a girl. She understands. We will still be close friends, and I will support her.” Cheryl replied. Then she asked, “How are you dealing with your little brother becoming your little sister?”

“Very weird,” Megan said sarcastically. “I am struggling to deal with the change too. It's going to be difficult.”

“Wait, what!” Cheryl nearly shouted in surprise. “How is it difficult for you?”

“He's my younger brother. He was always so boyish and fighting. Now he's becoming my younger sister. Cant, you see how that is going to be difficult on me?”

“Well yeah, “Cheryl replied. “But I was there when the squad came up with the plan to force Owen to join them. It looked like you were totally on board. You looked happy to force your brother into dresses and see him as a pretty little cheerleader cheering for the boys. It seemed like you were seeing it as a sort of revenge, or something. You were going to enjoy seeing him taken down from a boy getting all of the attention from your father. I just thought it was so funny.”

“Well, That's how I felt until this. What was so funny seeing him forced into being a girl?” Megan challenged hostility.

“That you thought it would change it, and allow you to rise above him or something like that,” Cheryl said to her harshly. “That a boy like Owen, as a girl, won't change what's inside. She has a will of iron and such leadership skills that people gravitate to her. As a girl, she will still rally people, and they will follow her. She will be just the same competitor with an unconquerable drive to succeed at anything she puts her mind too. Make her a cheerleader, and she will soon be on the national stage for the NCA in no time. You should have seen that, Megan. It's funny that you didn't.”

Cheryl added at the end, “And sort of sexist if you ask me.” Cheryl added acidly. “So you were for it until you saw that Olivia would fall into the role and relish it. Now we see, don't we Olivia.”

“She is coming around. Cheryl helped me with my makeup and my hair for the date. But it is funny, I agree,” Owen said, giggling. “She didn’t know what was coming.”

Megan shouted, “Will you two stop making fun of me!”

“You thought making me into a girl would diminish me, and you could use it. Don't be mad at us for thinking its funny,” Owen quipped, giggling like a girl.

They pulled into the Cheryl's driveway and let her out. Then Megan drove them home and got out. Megan watched with an uncomfortable chill as Owen got out of the care and smoothed his skirt and moved her his like any girl would and then walked up to the front door as any girl would. Megan figured that she may as well accept that she now had a little sister. She would miss Owen so much. He took smaller steps and minced his feet, and his hips began swaying with each step as he walked up to his door.

Olivia walked in to see Jane sitting at the Kitchen table with his Coach Crystal Stillwell. He froze, and Megan saw fear flash across his face.

Jane settled him down, “Take it easy Olivia. We are doing fine, and your coach stopped by to apologize and tell me she didn't know the fallout of changing your sex as she did. We are struggling to fix it so it won't impact your future. She gave me a few names of people she knows. One of them is the AG for this state. I have made a call to the Marshals office, and they will be talking to that man very soon.”

Was this supposed to put him at ease? Jane was talking to the United States Marshals, and his records were changed by a corrupt Attorney general? What in this was supposed to help him relax?

“I promise that it will be alright. And Crystal will be fine if she plays along with us. We can make sure its all pinned on the AG and not Crystal. Now we are settling that. We need to make some plans for tomorrow.

“What about Tomorrow?” Owen repeated in a very confused tone.

“You will be taking control of the Junior cheerleaders, remember. You pressured Crystal to make you their coach. They will all be looking to you for guidance so you better have a plan.” Jane said seriously.

“Oh,” Owen said. All of the talk about politics and the marshal's office made him forget everything else. “I have a plan for them. We will update the training. We will work on strength and stamina first and then end with some of the basic cheers and skillsets. And I think I will require them to run half of a mile every other day. Crystal!” Owen said.

Crystal looked up from the chair.

“I would like to try on your old cheer uniform.” Owen smiled.

“Um, we will see.” Crystal replied.

“How can I be a coach and a cheerleader on the squad?” Owen inquired.

“Yes, and you are the assistant coach. But you will the girl in charge there.” Crystal answered.

“Okay, and can you teach me your old cheerleading routine you did at the nationals?” Owen asked, hopefully.

“No,” Crystal replied to him.

Sorry but there is no way. First, that was a routine for the collegiate divisions. They would never allow it in the high school division. You would get so many deductions. And, so many rules have changed since 1989 I dont think we could get away with it in the collegiate divisions today.”