tagTranssexuals & CrossdressersHow I Became a Cheerleader Ch. 05

How I Became a Cheerleader Ch. 05


I woke up Monday morning in time for swim class and dressed in my uniform before leaving for school. I was feeling more confident now and was ready to change into my suit with the rest of the girls. The only difference was the go-go boots that I wore, I packed my school shoes. The white boots showed off my legs to great extent. The three inch heels were chunky and a little hard to drive in, but I got the hang of it pretty quick. The whistles I got as I crossed the senior parking lot proved that I had made the right choice in the boots. My skirt was a little higher on my legs than normal, but with the boots, I thought I looked good. Trent pulled in to the lot and stopped in front of me, blocking my progress.

"Hey sexy, going my way?"

"Sorry mister, but mommy taught me not to accept rides from strangers." I giggled. I leaned down and kissed him on the lips.

"But I've got a nice piece of candy."

"You don't need Candy, you have me." I scowled at him and walked away, working my hips, the boots adding to the allure. I heard a horn going off and thought a car alarm had been set off. Turning I saw Trent banging his head on his steering wheel. Smiling I made my way in to the school.

Swim practice was the usual work out and I felt better than I had in a while when I finished. The girls questioned me about after the party when Trent took me home. I told the truth, I kissed him goodnight on the porch with my Aunt and cousin watching. Candy just would not let it go. She was convinced that we went somewhere and got it on. I simply let her talk and then raised my nose in the air like I was too good for her, saying that what I did with my boyfriend was none of her business. The silence in the locker room was thunderous.

"What do you mean "Boyfriend"?" Chelsea asked suspiciously.

"Just what I said," I told her confidently.

"You mean that you landed the uncatchable Trent McKabe." Candy said shocked.

"Well, he is my boyfriend, so I guess he is not uncatchable." The rest of the day was spent answering questions about my relationship with Trent. No one could believe that we were dating. I solved that problem by walking into the cafeteria, sitting on his lap and kissing him.

The next few days at school were hectic. We had our first football game coming up and we had to get the squad ready. Coach Jacobs worked us like never before. New routines were perfected and polished. Grades were checked to make sure that everyone was eligible to cheer and play. Jason and Heather had even hired a tutor for Trent and they insisted that I study with him at their house. That way, they said, Trent would come home and study.

I was up to date on my homework before Trent and while he was studying with the tutor I surfed the net on his computer. I was looking for ideas about Halloween and couples costumes in the stores. I found the Joker and Harley costumes for the school dance. They were a little pricey, but Trent said that he would handle it; I told him that I would pay for my own. His was a purple jacket and black shirt and pants. Mostly for him it was the makeup that made the costume. For me it was a skintight suit in black and red with white makeup.

We looked at the Cinderella and Prince Charming costumes, but we could not find one for him that we liked. I saw another section of the website and clicked on it, finding the best solution. There was a couple's costume of the Phantom of the Opera and Christine his love.

It was perfect; Trent would look so cool in a tux and cape. The choices for me were almost endless. She wore so many beautiful outfits in the play and the movies I had a hard time. I told Trent what we were wearing and that he should order the tux, cape and mask. I would handle my end with my Aunt.

I rushed home and told Mom and Susan about the costumes. They were thrilled with the idea and we quickly searched the net and narrowed it down to two choices. The first was the one from the movie where she sings for the first time after the diva walks out. The dress was white, off the shoulder, a slight v neck, floor length. It could almost pass as a wedding dress. The bodice was tight and well fitted, flaring into a skirt with what looked like thousands of layers of petticoats and crinoline. The skirt was embroidered with stars at the hem.

The other choice was when the Phantom took her from her dressing room. That outfit was much simpler. A white corset, white house coat with ruffles at the collar, white skirt, thigh high stockings rolled down to the knee and high heeled slippers.

We discussed it endlessly. I finally decided to go with the dressing room outfit. The other was too much like a wedding dress or a formal outfit. We planned a shopping trip for Saturday morning. We had to go to the mall anyway and Mom said that they would get their costumes at the same time. Mom was going as Mae West and Susan was going as Veronica Lake.

Friday rolled around and we had the first football game of the season. All was going fine until the second last play of the game. At third and goal at the other team's three yard line, Trent took the handoff and dove over the pile into the end zone. Unfortunately, someone stomped on his hand and dislocated the two middle fingers of his left hand. They led him off the field and Candy had to hold me back from rushing to his side.

I came up behind the bench just as the trainer popped both fingers back into place, the sound nearly made me hurl. The trainer tapped him up and said that he needed to go to the hospital for x-rays.

"I'll call my father to pick me up. I can't drive my car like this."

"I'll take you." I said quickly.

"You can't drive my car. It is a five speed stick."

"Piece of cake," I replied. "My old beetle is four on the floor. I'll get my stuff and meet you at your car." I walked with him to the locker room. I went into the girls and grabbed my gym bag and my purse. All I had brought was a change of clothes for the after party.

I was waiting at his Mustang when Trent came out. He was still in his in his football uniform, his jacket over his shoulders.

"Are you sure, I can just call Dad."

"Give me the keys. I have already called Aunt Carol to pick up my car. I assume you don't want to leave yours here overnight."

"Fine," he grumbled and handed over the keys. I got him settled in the passenger seat and climbed in myself. I had to pull the seat all the way forward just to reach the pedals. The engine started with a roar. I had never driven anything so powerful before and I had to be careful not to scare Trent or myself.

Four hours, three x-rays, two tongue depressors and a roll of adhesive tape and we were on the way home. It was almost three in the morning when we got to his house. Jason and Heather were waiting up for us in their bath robes.

"Are you all right Trent?" Heather asked.

"Just fine Mom." Trent said, raising his hand to show the tape and splints. "They taped me up and sent me home."

"We spoke to Karen," Jason said, looking at me. "Thanks for taking care of Trent. We would have been there, but the charity committee meeting went long. We were supposed to be done by seven, but Mrs. De Haven through a hissy fit about the colours planned for the next gala. It took us till after midnight to calm her down. Karen and Susan picked up your car and took it home. You can spend the night here and we will take you home in the morning."

"I don't want to impose." I said, "I will just call a cab or walk or take the bus home."

"Nonsense," Heather said emphatically. "You will stay here. Now unfortunately, the only space we have is in Trent's bed, so you will have to sleep with him." I stood there stunned. "Just kidding, we have a guest room ready for you. Trent, go and clean up and get to bed. I will make sure that Janie gets to bed."

"Actually, I was planning to..." Jason said smiling.

"You will help Trent." Heather said glowering at Jason. "I will put Janie to bed. Now scoot." She took my arm and led me down the hall to the right. The second door opened to show a large bedroom and en-suite bath. The bed was king size with a canopy. The room was done in dusty rose and the drapes and comforter matched. "Go and clean up and I will find you something to wear to bed."

I went into the en-suite and washed my face getting all the makeup off. I came out and found Heather sitting on my bed. She had a white t-shirt sitting on the bed for me.

"I got you one of Trent's shirts to sleep in. I didn't think you would mind, and I know he won't. Now come and get ready for bed and we can talk. I want to see you."

I was a little nervous, but I had changed in the girl's locker room and made it through that, so this would not be much different. I pulled my sweater over my head and undid my sports bra. I didn't need it, but the sweater tickled my nipples, and I could not focus when they were that hard. I kicked off my shoes and undid my sweater, pushing it, my cheer panties and my thong all down together. They made us wear the white panties under our skirts, and I preferred the thong so I wore both. I sat on the bed and pulled my socks off; Heather motioned for me to lie back on the bed. She spread my legs and looked at my fake vagina.

"Karen was right. It is very realistic, but it could never pass during sex. I understand that it even has a hymen. Are you going to give it to Trent? You can always replace it later."

I was stunned. I knew that Mom and Heather had talked, but I did not know that it was to such an extent.

"Don't forget, your mother and I discussed this on Sunday. I know all about you. I just wanted to see for myself. I want you to know that both Jason and I have no intention of telling Trent anything. We welcome you as you are; you are very good for him. Just let us know before you plan to tell him, so we can be ready when he gets home. Now get some sleep, Trent's room is upstairs on the left, ours is across the hall, so I wouldn't go sneaking through the halls tonight." She gave me cheesy smile. She got off the bed and left me alone in the room. I pulled the shirt off the bed and smelled it. No smell of Trent, too bad. I climbed into the bed and passed out.

I woke the next morning to the birds singing and the sun shining. The bedside clock said just after nine and I scrambled out of bed. Mom and Susan wanted to go shopping for costumes today. I dressed in my uniform, it was all I had that was acceptable and went out to the kitchen. Jason and Heather were there in their robes and Trent was sitting at the table in a tank top and shorts eating cereal.

"Good morning," Heather said with a smile. "I called Karen when we heard you up and around, so she will be here in about half an hour. Would you care for some breakfast?"

"No thank you, just juice and tea please."

"As you wish," Jason said with a bow. He poured me a glass of orange juice and put the kettle on. We made small talk till my ride showed up, mostly about the upcoming parties. When mom showed up Jason insisted that they join us for coffee. He even made French toast for everyone. We left right after breakfast. Mom and Susan looked at Trent's hand and wished him well. As we left, he walked us out and he pulled me aside.

"Would you like to catch a movie tonight? There is a good double feature on at the drive in." I know, a drive in, how cliché, but looking into his eyes, I could not say no. "I'll pick you up at..."

"How are you going to drive with your hand like that? I'll pick you up at six and we can get something to eat beforehand." I told him, kissing him quickly before jumping into the back seat.

We hit the mall and mom led us directly to Victoria Secrets. Candy was working and she greeted me with a hug. She was full of questions about Trent and was shocked when I told her I spent the night at his place. Mom led us over to the corsets. We could not find what we wanted there and bid goodbye to Candy and headed out of the mall. Mom drove us to a different section of town and found a parking spot right in front of Fredrick's of Hollywood. I was shocked when they both got out and walked straight in.

I followed them in and was surprised at the selection. It was nothing like the seedy slutty lingerie I had imagined, but there were enough strippers' outfits to make sure that any girl in that profession would find what they wanted.

Mom picked out a white corset and thick stockings for me and a black push up corset for her. Susan left us and said that she would be back shortly. My corset fit like a glove and with that and the stockings all I needed was the robe and shoes. Susan found a white silk robe with a ruffled collar. The shoes were high heel slippers with white feathers on the toes.

Susan led me over to the wigs while Mom worked on her outfit. The sales girl helped me pick out a long brunette wig with curls everywhere. I had not planned on a wig, but Susan said that Christine was a brunette, not a blond. I was shocked at the cost of the wig, but Susan said that quality cost. Mom whistled and we turned to look at her.

She was in a black corset, laced way too tight, it pusher her cleavage up and out. She had a long dark skirt and a feather boa. She looked perfect. She even had the swagger and the accent down pat. She was sure to win the best costume prize. We paid for everything and went home. I had a date to get ready for.

Around four Susan pulled me into her bedroom and handed me a black plastic bag.

"What is this?" I asked her looking in the bag.

"It is a dildo for you practice with and a butt plug to keep you open." Susan said confidently. "I know that you and Trent are going to have sex. It has been a while for you since the Coach had a chance with you and you must be getting itchy by now, I would be. This will help you train your butt to take Trent with less pain and pressure. Also make sure you give yourself an enema before your date. Take some lube too, just in case."

I stood there with my mouth hanging open looking into the bag. The plug was larger than I thought it would be, but smaller than Jim's dick, so I knew that practice with it would allow me to take Trent, but still keep me tight. The dildo was about the same size as Jim, so I knew that I would be able to take care of myself anytime. It even vibrated. I just could not believe that Susan would be so casual about it.

I got ready for my movie with Trent. I followed Susan's advice and had an enema and then inserted the plug. It felt a little funny walking around at first, but I got used quickly. I put on a blue chiffon double layered shirred skirt over my black thong. I wore a flower white lace tee on top without a bra. You could see my nipples through the top, so I put on two clear spot band aids over them, to tone matched my flesh and they hid my nipples perfectly. My white boots and a white hair band to hold my hair back completed my outfit. I took a medium size white purse, loaded it with the essentials, extra panties, lube, condoms, lipstick, money, license, extra clear spots and cell phone.

It was coming up on five thirty when I went downstairs to show my look to Mom and Susan. The both whistled and clapped as I turned in the kitchen.

"You look great," Mom said. "I have not seen that top before."

"Candy and I did a little shopping last week. I thought this would be a good time to try it."

"Don't worry, you are so hot." Susan said. "Now get going, you are going to be late. I will walk you out."

As we left the kitchen, she started. "I don't know what you have planned, but first relax your ass. You look like you are walking with a pickle up there."

"It feels like I am."

"Just relax. Your body will adjust. Now take these." She handed me a small bag and a couple of tampons.

"What are these for?"

"The bag is for the butt plug you are wearing. You will want something to put it in before you put it in your purse. The tampons are for after you too are finished. That will keep you from leaking out all over your skirt and on the car seats."

I drove over to Trent's; picked him up in his car and we went for dinner. The looks we got as I drove up in his car were priceless. The guys were in awe that I was able and allowed to drive it. The girls thought it was sweet that I was taking care of my boyfriend like that. It seemed like everyone was there for dinner and the going to the drive in. It was just a burger joint, but I was able to get a salad.

"Janie, how did you figure out how to drive that car?" Stu asked leering at me.

"Well, the gearing ratio was a little high, but once I re-tuned it and add a new compression seal, it runs like a dream." I left him standing there with his mouth hanging open.

"Where did you learn about things like that?" Trent asked.

"I have taken my car's engine apart more than once. I am not just another pretty face you know."

"I figured that out already, and how did you know I just got a new compression seal installed."

"You left the bill in between the seats."

We ate with the rest of the crowd before heading off to the drive in. I parked us in the last row, near the snack bar. There were not a lot of spaces left back there, all the kids wanted them, for the same reason I did. Trent was not happy sitting in the passenger seat, but I promised him that I would make it up to him. He helped me hook up the speaker wire to the antenna, and run the sound through his speakers. I went with him to the snack bar and we got movie munchies. We left everything in the car and wandered around before it got dark enough to start the movie. Chelsea grabbed me on the way by to check out my outfit.

"I love that top, but how is it that you are not showing anything, I mean I can see that you are not wearing a bra, but you aren't flashing your tits to the world."

I smiled and pulled the band aids from my purse and handed her one. They would do nothing for her black skin, but they matched mine perfectly.

"Clever, very clever," she said smiling and walking away.

We headed back to the car about ten minutes early for the first movie. I had Trent sit in the passenger seat again and I climbed onto his lap. My skirt was tucked beneath me and I was small enough that we had plenty of room to get comfortable. Trent reclined the seat and we snuggled up and watched the movie. The cars around us, full of our friends fogged up very quickly and several were giving their shocks a work out, but I wanted to tease Trent a little before I gave in to him that night. There was still the matter of my fake vagina. I lowered the window a little and we started kissing about half way through the first feature. His good hand was working over my breasts pretty well, and I was grinding into his lap, feeling his cock between my cheeks.

"Trent, there is something I want to discuss with you before we go any further." I said, breaking the kiss.

"Now," he questioned, panting slightly with desire.

"Yes, now. I want you to know that I am a virgin and intend to stay that way for a while yet."

"But you said that you are not a tease."

"I'm not." I said emphatically. "I took care of you in the hot tub and the woods didn't I? I just don't want first time to be in a car or some sleazy motel. I want it to be with someone I love."

"So sex is out of the question."

"No, just my pussy is out of bounds. There are still two other holes you can use." I said as I wiggled my butt on his lap.

"You mean I can..."

"Yes baby, you can fuck my ass, but not just yet. The first movie is almost over. Go the snack bar and get another soda for us while I visit the ladies room and then we'll see during the second movie." I kissed him, driving my tongue into his mouth and rubbing my breasts against him.

I slipped out of the car and into the ladies room before anyone else made it out of their cars. In the stall I took out the plug and applied more lube to my pussy, I had started thinking about my butt as my pussy, since it was the only hole I had to give him. Trent was waiting for me when I got back and we still had a minute or two before everyone else came out so I undid his pants and pushed them to his knees. He sat down on the passenger seat.

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